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nomadbrad
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Where do the chemicals come from.
#18048263 - 04/02/13 06:26 PM (11 years, 1 month ago) |
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I have been really trying to wrap my mind around this, maybe it's too much for a layman like me but here it goes....
I've been under the impression that mushrooms have a lot of different chemicals and toxins present in the fruiting bodies. My question is... Do they really just synthesize these from whatever they come across in the substrate they grow in??? Maybe I've been under the wrong impression, maybe they are not as complex in chemical make up as I thought.
Chemistry is not my forte but I would really love it if somebody could break it down a bit for me. That way I don't automatically jump to an alien conspiracy or something from the twilight zone if you know what I mean...
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mentalpatient
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Re: Where do the chemicals come from. [Re: nomadbrad]
#18048328 - 04/02/13 06:38 PM (11 years, 1 month ago) |
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Quite an interesting question. They must convert the nutrients into chemicals or something... The psychoactive compounds must come from somewhere...
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IveBeenRecycled
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Re: Where do the chemicals come from. [Re: mentalpatient]
#18048402 - 04/02/13 06:50 PM (11 years, 1 month ago) |
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Kizzle
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Quote:
Do they really just synthesize these from whatever they come across in the substrate they grow in???
Pretty much. They release enzymes to break down the substrate into basic nutrients they can absorb and then create whatever more complex chemicals they need from those basic building blocks. With the right enzymes they can turn carbohdyrates and amino acids into something like psilocybin.
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mentalpatient
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Re: Where do the chemicals come from. [Re: Kizzle]
#18048690 - 04/02/13 07:45 PM (11 years, 1 month ago) |
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Crazy to think how all this came about naturally in the beginning. The way I can imagine it, all living/growing things had their DNA brewed in some hot cauldron resulting in thousands of different DNA combinations resulting in different forms of living organisms.
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Edited by mentalpatient (04/02/13 07:45 PM)
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Amphibolos
Le bourgeois gentilhomme




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Re: Where do the chemicals come from. [Re: mentalpatient]
#18048705 - 04/02/13 07:49 PM (11 years, 1 month ago) |
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The more plausible hypothesis is that the RNA's are the precursor of complex life
DNA itself cant catalyse its own synthesis, but RNA have sometime the role of an enzyme.
DNA is more like a complex and stable information storage.
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mentalpatient
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Re: Where do the chemicals come from. [Re: Amphibolos]
#18048725 - 04/02/13 07:53 PM (11 years, 1 month ago) |
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Quote:
Amphibolos said: The more plausible hypothesis is that the RNA's are the precursor of complex life
Oh yeah, I remember reading about RNA. Very interesting stuff.
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nomadbrad
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Re: Where do the chemicals come from. [Re: Kizzle]
#18048759 - 04/02/13 07:59 PM (11 years, 1 month ago) |
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Quote:
Kizzle said:
Quote:
Do they really just synthesize these from whatever they come across in the substrate they grow in???
Pretty much. They release enzymes to break down the substrate into basic nutrients they can absorb and then create whatever more complex chemicals they need from those basic building blocks. With the right enzymes they can turn carbohdyrates and amino acids into something like psilocybin.
They restructure the amino acids and basic nutrients into others, I understand that much. I just don't understand why and why so much complexity. It's crazy to really think hard about. Muscimol, ibotenic acid, psilocybin. And on top of that you throw in how they make humans react.
I want to learn how these enzymes really work.
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mentalpatient
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Re: Where do the chemicals come from. [Re: nomadbrad]
#18048829 - 04/02/13 08:11 PM (11 years, 1 month ago) |
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Bet you could spend every night of every day of every week of every month of every year learning about this stuff. It's so complex and multifaceted.
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Edited by mentalpatient (04/02/13 08:11 PM)
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raygle29
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Re: Where do the chemicals come from. [Re: mentalpatient]
#18056211 - 04/04/13 05:32 AM (11 years, 1 month ago) |
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Metabolism can roughly be broken down into two halves: catabolism and anabolism. Catabolism is the process of breaking complex molecules into simpler ones and anabolism is the construction of complex molecules from simple ones. Just about every organism has the same "simple ones" (i.e. intermediates), but what they can build out of those simple molecules is determined by the enzymes that an organism knows how to make.
On the way to catabolizing glucose, various intermediate forms of it get formed. One such intermediate is phosphoenolpyruvate and another common one is erythrose-4-phosphate. We make these constantly in our own bodies, but since humans don't have a lot of cool biosynthetic enzymes available to us we can't do much interesting with them other than send them to the Krebs cycle and eventually oxidize them to CO2 for energy. Plants, fungus, and bacteria, however, have enzymes that can take PEP and E4P and orient them relative to each other in such a way that they can condense into the next intermediate, and through a number of other steps eventually form tryptophan and indole and other cool things. Most of the time, though, they will just oxidize these intermediates for energy like we do.
Basically, whether you are a fungus or a human, you have a lot of the same biochemical intermediates. If you're a fungus, you have some options to turn extra intermediates into cool organic molecules. If you're human, you use those extra intermediates for extra energy, to do some pretty cool feats of physical chemistry - like develop and maintain the ion gradients necessary for consciousness.
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nomadbrad
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Re: Where do the chemicals come from. [Re: raygle29]
#18056523 - 04/04/13 07:54 AM (11 years, 1 month ago) |
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Quote:
raygle29 said: Metabolism can roughly be broken down into two halves: catabolism and anabolism. Catabolism is the process of breaking complex molecules into simpler ones and anabolism is the construction of complex molecules from simple ones. Just about every organism has the same "simple ones" (i.e. intermediates), but what they can build out of those simple molecules is determined by the enzymes that an organism knows how to make.
On the way to catabolizing glucose, various intermediate forms of it get formed. One such intermediate is phosphoenolpyruvate and another common one is erythrose-4-phosphate. We make these constantly in our own bodies, but since humans don't have a lot of cool biosynthetic enzymes available to us we can't do much interesting with them other than send them to the Krebs cycle and eventually oxidize them to CO2 for energy. Plants, fungus, and bacteria, however, have enzymes that can take PEP and E4P and orient them relative to each other in such a way that they can condense into the next intermediate, and through a number of other steps eventually form tryptophan and indole and other cool things. Most of the time, though, they will just oxidize these intermediates for energy like we do.
Basically, whether you are a fungus or a human, you have a lot of the same biochemical intermediates. If you're a fungus, you have some options to turn extra intermediates into cool organic molecules. If you're human, you use those extra intermediates for extra energy, to do some pretty cool feats of physical chemistry - like develop and maintain the ion gradients necessary for consciousness.
Ok, that was really helpful. Way to break it down a little bit easier for me to understand. So basically fungi have a tool chest of enzymes that can break down and then restructure molecules into more complex ones?
This might be a stretch but I am curious as to what the fungi use some of these restructured molecules for. Can anybody point me in that direction? Any links that chime in on this stuff??
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Nobitte
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Re: Where do the chemicals come from. [Re: nomadbrad]
#18056571 - 04/04/13 08:12 AM (11 years, 1 month ago) |
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Raygle1 really nailed it.
Without knowing what molecule in particular you're interested in, and assuming that you want to know about how chemistry works in biological systems, I would suggest getting your hands on some first/second year biology, mycology and biochem texts. They should have most of the answers you're looking for.
Alternatively, you could always try and make it into a career, there are a few universities in the US that im aware of and probably many more that offer courses that might be enlightening, but in light of the fact that you probably can't get public higher education funding, the books might be the better option.
There would be a few posts suggesting decent mycology texts on this website.
Good luck, whatever you do =3.
-------------------- First we must learn... Then... WE CAN TEACH
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Terry M
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Re: Where do the chemicals come from. [Re: Nobitte]
#18056749 - 04/04/13 09:31 AM (11 years, 1 month ago) |
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Great answers here! The short answer is that all living things are biochemical factories.
-------------------- Liberté, égalité, humidité.
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nomadbrad
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Re: Where do the chemicals come from. [Re: Terry M]
#18058641 - 04/04/13 04:50 PM (11 years, 1 month ago) |
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Nobitte, thanks for the advice. I live by a major university and I am sure I could track down some text books on that. That's a great idea.
As far as making a career out of it, we'll, right now I can't. I'm taking over my fathers business so he can retire. I figure that's the least I can do. I certainly could afford it later on in life, so it will probably just end up as an extreme hobby where it is now.
I've never liked chemistry. Now that I love mycology it's just second nature.
I feel like a five year old asking "why? Why? Why?" Ha!
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raygle29
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Re: Where do the chemicals come from. [Re: Terry M]
#18058828 - 04/04/13 05:20 PM (11 years, 1 month ago) |
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Organic chemistry is key if you want to understand how enzymes really work. Its actually pretty dry part of the molecule interacts with a charged atom on the enzyme, which redistributes charge density to allow formation of an otherwise unstable transition state. The transition state is attacked by a pair of electrons from another atom on the enzyme and another molecule is formed... or it all goes in reverse and nothing happens this time, but there are 10^15 tries in a second so something still gets formed. 
Its tough to pin down evolutionary roles for secondary metabolites that aren't antibiotics or hormones/auxins. Its kind of obvious why penicillin grants an evolutionary advantage, given that it kills microorganisms which would otherwise eat the mould's food. Truffles emit a molecule also found in male pig saliva, which makes it attractive to female pigs in heat - which is important since it relies on animals to find it underground and transport its spores in order to reproduce. Its hard to pin down how being psychadelic gives an evolutionary advantage though. Psilocybin is much older than humans, so simply being appealing as an agricultural product isn't a sufficient explanation for its persistence. A lot of stuff in biology and evolution makes sense, but sometimes there are just weird connections that do weird things when they interact with the foundation of something as complex as human consciousness and you just have to marvel at the miracle of it all.
Instead of just being random though, it helps to keep in mind that the tree of life is always changing and more species have gone extinct than we will ever really know about, or be able to understand on the molecular level that we can understand what is going on around us and within us now. Perhaps one of the psilocybes' greatest predators is extinct now, but maybe that predator utilized a distant cousin of our 5HTa receptor for something important and psilocybin happened to exert a particularly toxic effect on its physiology. Most serotonin in our bodies is actually used in neurons in our digestive tract, so maybe it made this proposed predator very ill. Enter our modern day 5HTa receptors, with similar binding properties but part of a much different physiological machine - so instead of our physiology being fatally compromised we just trip. Will we ever find a fossil of that extinct predator? Unlikely, and even if we did would we be able to clone its pseudo-5HTa receptor and find out what effect psilocybin has on its gastric motility? Never! It is gone and lost forever to extinction.
I figure a lot of answers to evolutionary questions like this follow a similar pattern... we weren't there and the actors that were there are gone now. Maybe the psilocybin we enjoy today is the last remnant of a long-forgotten battle between prey and a predator we will never know. It is a loss to be sure, but there is nothing to be done about it now except enjoy the miraculous accident of pharmacology it is to us today!
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nomadbrad
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Re: Where do the chemicals come from. [Re: raygle29]
#18059212 - 04/04/13 06:23 PM (11 years, 1 month ago) |
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Raygle, that seems like a pretty logical hypothesis to me. It certainly would be cool to be able find out what the extinct predator was. Do you suppose that maybe it made a predator feel good and therefore was spreading its spores everywhere??
After sometime I am surprised that the psilocybes would still go through the trouble to produce the toxin. Although because it still has the active component, these mushrooms are cultivated and propagated even further.
Have you seen the documentary "Botany of Desire"? It talks a lot about species using humans for this same reason. It is a well done documentary actually.
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raygle29
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Re: Where do the chemicals come from. [Re: nomadbrad]
#18059682 - 04/04/13 07:58 PM (11 years, 1 month ago) |
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Your guess is as good as mine, nomadbrad. If it was a defense against predators I think it would make them sick and inclined to avoid that species again, providing a survival advantage rather than a reproductive one. If there is a predator today that exhibits some kind of adverse GI response to psilocybin that could be a clue. I'm not sure those studies have been done yet though, but based on the wide distribution of psilocybes across the continents it would have been a long, long time ago. Sometimes things get in there and don't go away though.
I haven't seen the documentary but read the book. Really liked it and made me think about it like that. THC content in cannabis has reached two extremes recently (as in, less than a lifetime) due to strong selection, but psilocybin hasn't had this same artificial selection applied to it. It would be a bad candidate if they wrote a Mycology of Desire.
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kinkaku
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Re: Where do the chemicals come from. [Re: Amphibolos]
#18060681 - 04/05/13 12:05 AM (11 years, 1 month ago) |
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Quote:
Amphibolos said: The more plausible hypothesis is that the RNA's are the precursor of complex life
DNA itself cant catalyse its own synthesis, but RNA have sometime the role of an enzyme.
DNA is more like a complex and stable information storage.
where can I read about this information? sounds like a very interesting read
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Nobitte
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Re: Where do the chemicals come from. [Re: raygle29]
#18060783 - 04/05/13 12:47 AM (11 years, 1 month ago) |
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I've also been similarly of the mind that psilocybin/5HT agonists could be a 'ghost of competition past'.
Their distribution suggests some sort of speciation event before the breakup of Gondwanaland (at least that's what is see when I look at the global patterns of Psilocybe distribution compared to other taxa(that are considered to be relicts) at the genus level).
In my mind at least, this lends credence to the idea that Psilocye is likely to have an ancient origin and to the possibility that it could be at relative equilibrium with its predator species, purely imagination/speculation though.
It had occurred to me previously that it might be a similar selective dispersal mechanism to capsaicin with birds and mammals (causes irritation in mammals but not birds, to facilitate successful dispersal).
I think it would be interesting to see if invertebrates/molluscs (think slugs, snails and gnats for the moment) etc are able to pass viable fungal spores after consuming a sporocarp. I would assume, but I don't know that they would lack some of the receptors necessary for it to have a profound physiological effect on them, thus making them ideal vectors for dispersal in sequestrate species.
Although im not entirely sure on what sort of advantage this would infer on non-sequestrate taxa, as I would guess that they already had anemochory(wind) and hydrochory(water) fairly nailed, do they really need zoochory, facilitated by sporocarp consumption(my only thought is that it increases the chance that the spore finds itself in a suitable substrate, but would that occur if the organism was a mycovore?).
*shrug*
Quote:
kinkaku said:
Quote:
Amphibolos said: The more plausible hypothesis is that the RNA's are the precursor of complex life
DNA itself cant catalyse its own synthesis, but RNA have sometime the role of an enzyme.
DNA is more like a complex and stable information storage.
where can I read about this information? sounds like a very interesting read
Lol sorry to repeat myself, but I would say check out the first chapter of a biochem text and then have a read about nucleotides.
As previously said by someone clearly a lot smarter than I, RNA is less 'durable' but can form enzymes/catalysts, DNA is more stable making it ideal for the long term storage of information.
-------------------- First we must learn... Then... WE CAN TEACH
Edited by Nobitte (04/05/13 12:50 AM)
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Kizzle
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Re: Where do the chemicals come from. [Re: Nobitte]
#18060914 - 04/05/13 01:44 AM (11 years, 1 month ago) |
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Quote:
Its hard to pin down how being psychadelic gives an evolutionary advantage though.
I know that's the natural assumption but maybe it doesn't. If it were would it make sense to take an extra step to convert psilocin into psilocybin which is inactive until metabolized?
There are other properties to consider. Maybe the blue bruising gave it some kind of advantage. Or maybe the products it breaks down into triggers some kind of response in a damaged area.
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Amphibolos
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Re: Where do the chemicals come from. [Re: raygle29]
#18061204 - 04/05/13 05:43 AM (11 years, 1 month ago) |
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Concerning psilocybin, i saw an old paper that could give us some pointers of the utility of indole alkaloids in fungi.
They found an indole compound that is used by the yeast Malassezia furfur to protect itself from the devastating effects of UV radiation.
Maybe it was the original goal of the pre psilocybin molecules, but it must have evolved with the years.
I personnally think that the fact that psilocybin can be detected through a UV light suggest that it could help the spreading of the spores since some insects have the capacity to see in that wavelength range. They could be attracted by the sporocarp and eat its flesh to spread it further. We have to see if the molusks have also this capacity
Here is the article of the UV protecting indole
Protection from UV's using indole compounds
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Nobitte
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Re: Where do the chemicals come from. [Re: Amphibolos]
#18061465 - 04/05/13 08:01 AM (11 years, 1 month ago) |
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I guess the UV absorption would make sense given that indoles are large aromatic rings. The hydroxyl, its esterified phosphate and the dimethyltryptamine "arm" thingy could be incidental and harmless conserved traits.
Although it seems to me that the extra steps in the (psilocybin) biosynthetic pathway might be energetically unfavourable and not be conserved if they didn't provide some kind of advantage.
Do they contribute markedly to the molecules capacity to absorb uv or any other property that anyone is aware of? precursor to anything else?
-------------------- First we must learn... Then... WE CAN TEACH
Edited by Nobitte (04/05/13 08:10 AM)
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nomadbrad
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Re: Where do the chemicals come from. [Re: Nobitte]
#18062006 - 04/05/13 11:17 AM (11 years, 1 month ago) |
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I think you are on to something there. Insects being the ones thay are attracted to the psilocybin makes more sense to me.
I wonder if the insects of today are attracted in the same way? Maybe we can get a clue from that route. Are flies and their larvae beneficial to the fungi?
Edited by nomadbrad (04/05/13 11:18 AM)
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nomadbrad
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Re: Where do the chemicals come from. [Re: Nobitte]
#18063924 - 04/05/13 07:11 PM (11 years, 1 month ago) |
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Quote:
Nobitte said:
Alternatively, you could always try and make it into a career, there are a few universities in the US that im aware of and probably many more that offer courses that might be enlightening, but in light of the fact that you probably can't get public higher education funding, the books might be the better option.
There would be a few posts suggesting decent mycology texts on this website.
Good luck, whatever you do =3.
I'm just curious why is it that you assume I probably can't afford higher education?? Since we are on the boat of assumptions, has higher education possibly narrowed your view of others?
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Nobitte
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Re: Where do the chemicals come from. [Re: nomadbrad]
#18064521 - 04/05/13 09:11 PM (11 years, 1 month ago) |
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Jeez, it wasn't a comment on your social status or anything, you could be rich for all I know.
More it was a comment on the fact that most of the Pacific Northwest falls within a country where you are expected to privately fund your education, unless of course, you're from Canada(which you don't seem to be with the strong focus on money as a measure of a person, which I always saw as a US trait, correct me if im wrong).
Let me put it this way, I'm an IT tech as well, I made the decision to switch to biology so easily because my government has a higher education funding scheme that means that I don't have to get a private student loan and that I have some form of financial security while I study.
Now, biology as it stands, isn't insanely lucrative, I could probably make more money faster in IT, if my government had not made it easy for me, I probably would have not bothered to retrain and would still just be growing fungi for food and fun rather than looking at them from a scientific perspective.
So don't get offended, im just saying, if the education is expensive, it might be better to go the 'Good Will Hunting' route until you're absolutely certain about wanting to spend your hard earned dollars on higher education.
I should also add that it might not be terribly efficient to study a whole science degree just to find out a few facts, if that is your level of interest.
-------------------- First we must learn... Then... WE CAN TEACH
Edited by Nobitte (04/05/13 09:22 PM)
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nomadbrad
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Re: Where do the chemicals come from. [Re: Nobitte]
#18064683 - 04/05/13 09:40 PM (11 years, 1 month ago) |
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I chose not to go to school. I am the only one out of three siblings that didn't graduate from a university. I chose instead to take over my fathers construction business in order that he may retire soon. I certainly do not consider finances as a measure of a person. At least not in how much they have but, rather how they use their finances.
I have a problem with assumptions that's all, so I thought I would ask.
The university I live by has a great mycology program from what I hear though...
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fastfred
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Re: Where do the chemicals come from. [Re: nomadbrad]
#18065752 - 04/06/13 03:36 AM (11 years, 1 month ago) |
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The basic substrate is tryptophan, a basic amino acid and major building block of all life. The enzymes reponsible are tryptophan decarboxylase, INMT, INMT, and an unknown (AFAIK) hydroxylase.
Since the actives aren't any sort of deterrent the only logical explanation is that they have functioned evolutionarily as an attractant.
-FF
-------------------- It drinks the alcohol and abstains from the weed or else it gets the hose again. -Chemy The difference between the substances doesn't matter. This is a war on consciousness, on our right to the very essence of what we are. With no control over that, we have no need to speak of freedom or a free society. -fireseed "If we are going to have a war on marijuana, the least we can do is pull the sick and the dying off the battlefield." -Neal Levine (MPP) I find the whole "my drug should be legal but yours should be illegal" mindset disgusting and hypocritical. It's what George Bush and company do when they drink a cocktail and debate the best way to imprison marijuana users. -Diploid
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Nobitte
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Re: Where do the chemicals come from. [Re: fastfred]
#18065854 - 04/06/13 04:51 AM (11 years, 1 month ago) |
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Hmmm, I know this subject has been done to death, but I sorta wanna talk about it some more, if yall can indulge me.
Can you think of taxa that are drawn to eat Psilocybe because of their alkaloid content, given that there apparently must have been some reason for it to exist?
It would be interesting to see the food choice of various present day invertebrate groups when presented with sporocarps containing alkaloids and not containing alkaloids.
Im just thinking out loud here, but if hypothetically the speciation event that led to the antecedent of the genus Psilocybe occurred long ago and I say this assuming that the present day range occupied by the genus suggests a wide distribution of the aforementioned antecedent during the Triassic, before the wide scale breakup of Gondwanaland.
Would not the enzymes responsible for transforming tryptophan into other substances have been cast aside at some point? Is it possible that it serves some other purpose, or is it some sort of genetic curio with no conceivable purpose in the present day?
Which leads me to my next question, did this pathway evolve separately in Panaeolus and Psilocybe? or did they share an ancestor at some point that possessed all or some of the enzymes responsible for its synthesis? Do they use different enzymes or sets of enzymes?
Im high, but im also real curious, thoughts anyone? Might be meat for another thread, ill stop now.
-------------------- First we must learn... Then... WE CAN TEACH
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Amphibolos
Le bourgeois gentilhomme




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Re: Where do the chemicals come from. [Re: Nobitte]
#18065934 - 04/06/13 05:47 AM (11 years, 1 month ago) |
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I think that the psilocybin could be a deviation of the pathway producing other UV resistance pigments (Melanin), if you check its structure you will notice that they are made of indole rings linked together.
Since melanin is a pigment that you can find even in the metazoan and bacterias, you can guess that the enzymes needed to synthetise it are older aswell.
Some mutations might have conducted the pathway to deviate into producing pigments that confer marginal UV resistance and/or attraction of arthropodes and molusks. (psilocybin?)
Quote:
Nobitte said:Which leads me to my next question, did this pathway evolve separately in Panaeolus and Psilocybe? or did they share an ancestor at some point that possessed all or some of the enzymes responsible for its synthesis? Do they use different enzymes or sets of enzymes?
Im high, but im also real curious, thoughts anyone? Might be meat for another thread, ill stop now. 
I suggest that you look up the nucleotide bank on the NCBI genbank site.
If some of the sequences are already there, you could manage to BLAST it and compare the similitude between both sequences to know if the enzymes are similar (but they should be homologues)
Psilocybe cubensis ITS
I can talk about this for a while, but im still not used to express myself in english
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"Homo sum ; humani nihil a me alienum puto"
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fastfred
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Re: Where do the chemicals come from. [Re: Amphibolos]
#18067623 - 04/06/13 03:03 PM (11 years, 1 month ago) |
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Quote:
Can you think of taxa that are drawn to eat Psilocybe because of their alkaloid content, given that there apparently must have been some reason for it to exist?
Homo Sapiens have long been attracted to them. The ~200,000 years we have been around is plenty long enough for one odd enzyme to pop up and affect their evolution.
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Would not the enzymes responsible for transforming tryptophan into other substances have been cast aside at some point? Is it possible that it serves some other purpose, or is it some sort of genetic curio with no conceivable purpose in the present day?
There's no reason to think that psilocybin hasn't been a significant bonus to the mushrooms from the beginning. Only one last enzyme seems to be anything special, and carrying one extra gene isn't going to affect fitness in a negative way.
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Which leads me to my next question, did this pathway evolve separately in Panaeolus and Psilocybe? or did they share an ancestor at some point that possessed all or some of the enzymes responsible for its synthesis? Do they use different enzymes or sets of enzymes?
TDC and INMT are very common. The last enzyme hasn't been characterized AFAIK. Panaeolus and Psilocybe certainly have a common ancestor relatively recently, so it's probably safe to it's a shared pathway.
-FF
-------------------- It drinks the alcohol and abstains from the weed or else it gets the hose again. -Chemy The difference between the substances doesn't matter. This is a war on consciousness, on our right to the very essence of what we are. With no control over that, we have no need to speak of freedom or a free society. -fireseed "If we are going to have a war on marijuana, the least we can do is pull the sick and the dying off the battlefield." -Neal Levine (MPP) I find the whole "my drug should be legal but yours should be illegal" mindset disgusting and hypocritical. It's what George Bush and company do when they drink a cocktail and debate the best way to imprison marijuana users. -Diploid
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Nobitte
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Re: Where do the chemicals come from. [Re: fastfred]
#18070150 - 04/07/13 12:58 AM (11 years, 1 month ago) |
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Thanks for the info, ive got some molecular biology and genetics classes coming up next session, so maybe ill be able to make better sense of it all then.
Im more inclined to see psilocybin as an attractant/deterrent than a UV absorbing molecule (unless of course you can show me a feasible pathway by which one is transformed into the other)
One last question, because ive had coffee and am incredibly curious, although I realise this one probably has a fairly complex answer.
I was thinking over coffee about what mechanisms/processes would account for the variability in psilocybin concentration in species that express it and forgive me for my simplistic approach, im still a newbie at this stuff. Ill pose them as questions, as it seems the easiest way for me.
Do the precursor or enzyme concentrations limit the production of psilocin?
(I saw some post a while back about someone claiming that tryptophan concentrations in the substrate -do- affect the eventual concentration of psilocin/cybin, but I never looked into it, should I?.)
Does the dehydration reaction that esterifies the phosphate to the hydroxyl on psilocin occur non enzymatically(also am I getting that right?)?
(im gonna go -really- out of my league now)
Do genetic/epigenetic factors come into the variability in alkaloid concentrations seen amongst species?
I was having a chat about it to a friend(I think he's a mechatronic engineer) that does pretty much nothing related to biology and came up with the idea that differences in the efficiency of the various homologues of the enzymes responsible could account for it, or that it was related to some (set of?) mechanism(s) or process(s) of gene regulation/expression I am presently unaware of.
Im going to do my own research on it, but I just felt like getting that out in case someone had an 'off the shelf' option or some guidance for me/us ^^.
Nobitte xxx
-------------------- First we must learn... Then... WE CAN TEACH
Edited by Nobitte (04/07/13 01:03 AM)
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fastfred
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Re: Where do the chemicals come from. [Re: Nobitte]
#18070192 - 04/07/13 01:11 AM (11 years, 1 month ago) |
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> Do the precursor or enzyme concentrations limit the production of psilocin?
Tryptophan is an essential amino acid and its concentration is highly regulated. The enzyme concentrations are related by competition. Alternate metabolic pathways and ratios are more important than concentration usually.
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Does the dehydration reaction that esterifies the phosphate to the hydroxyl on psilocin occur non enzymatically(also am I getting that right?)?
For sure.
> Do genetic/epigenetic factors come into the variability in alkaloid concentrations seen amongst taxa?
Everything is "gene x environment" interaction. Kind of a useless and obvious statement to most, but if you control the environment that pretty much narrows down your research.
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Nobitte
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Re: Where do the chemicals come from. [Re: fastfred]
#18070255 - 04/07/13 01:35 AM (11 years, 1 month ago) |
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Oh yeah, duh, bit of an obvious question that one, I guess what I meant was, do you know of any obvious or major factors that limit its production within those terms?
I suppose without having a bunch of species being sequenced for those loci its a bit hard to say one way or the other.
Are there any obvious patterns in terms of mean alkaloid concentration versus substrate/habitat preference, stirpe/clade or anything else, that would suggest a strong environmental or genetic factor one way or the other?
I can see where you're coming from in terms of an experimental approach, one could alter the levels of substituents of the substrate artificially, or interfere with the expression of competing pathways and see what that does to it.
I guess I'm looking for hints in the ecology of the various species first, as its what I know better (if only marginally so).
Thank you for indulging me. Every little bit counts.
On a final note;
Has there been any "serious" research done in this area and do you have any tips for "legitimising" a research proposal for this sort of topic in a fairly stock standard biology faculty, if I was to feel inclined.
Nobitte xxx.
-------------------- First we must learn... Then... WE CAN TEACH
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fastfred
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Re: Where do the chemicals come from. [Re: Nobitte]
#18070300 - 04/07/13 01:58 AM (11 years, 1 month ago) |
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Quote:
Has there been any "serious" research done in this area and do you have any tips for "legitimising" a research proposal for this sort of topic in a fairly stock standard biology faculty, if I was to feel inclined.
I really haven't been very up to date for a few years, but AFAIK there has been no major papers on the biochemistry. I've posted a fair bit on it before. Tryptophan -> tryptamine is pretty basic, so the real magic happens with the INMT enzyme. It's pretty common, and circulating around your system right now. This leads to DMT, which is interesting enough in itself.
Because tryptophan is common, and tryptamine has shown some interesting effects in increasing production, I suggest that this is probably the rate limiting step.
You have tryptophan --(TDC)--> tryptamine --(INMT)--> NMT --(INMT)--> DMT --(unknown hydroxylase)--> Psilo.

Look at the pathways! Certainly it's not complete, but it is the place to start thinking about the metabolic pathway.
From what I know, TDC is likely the most important enzyme. INMT could be also be important. But because we know that DMT is not found in mushrooms we know the "unknown hydroxylase" is not rate-limiting the rxn.
That leaves two common enzymes TDC and INMT as potential rate-limiters.
The other half of the equation is alternate pathways. Again, alternate pathways of tryptamine and DMT could be a big factor, psilo. pathways could be important too.
I'm probably forgetting stuff and not hitting all your questions, but I took my medicine and hopefully it still helps you figure out the key points.
If you can get my image gallery there are more pics worth looking at BTW, otherwise I can just post them.
-FF
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Nobitte
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Re: Where do the chemicals come from. [Re: fastfred]
#18070390 - 04/07/13 02:41 AM (11 years, 1 month ago) |
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At my present level of understanding, i'm inclined to agree with you, I think I need to sleep on this stuff to take it in.
Was able to go through your gallery.
All great, I especially liked the biosynthetic pathway for ergotamine.
Also the presence of aeruginascin in I. aeruginascens is rather interesting in terms of the conversation we've been having, how closely related are inocybe to psilocybe?
Are NMT, 4HT or 4H-NMT found in Psilocybe, that youre aware of?
From what you've been telling me it would seem that it either goes Tryptamine > NMT > 4H-NMT > Psilo or Tryptamine > 4HT > 4H-NMT > Psilo or some pathway that is not presently known.
Sorry for reiterating, just wanted to make sure I wasn't walking away half cocked.
(I promise ill stop at some point, I have work I should be doing)
-------------------- First we must learn... Then... WE CAN TEACH
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fastfred
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Re: Where do the chemicals come from. [Re: Nobitte]
#18072979 - 04/07/13 04:28 PM (11 years, 1 month ago) |
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I think Tryptamine -> NMT -> DMT -> Psilo. is the way it goes.
You can see from the pathways though that it could proceed in different routes. INMT isn't all that well characterized for our substrates, at least that I've seen. It would be good for someone to do a little more research on that though.
> how closely related are inocybe to psilocybe?
I put up a few phylogenetic trees way back when. Hopefully there's been more work done since then. It would be a good project here for someone to download the sequences and build phylogenetic trees.

You just need to download the sequences from the accession numbers, search for and download new sequences of interest, and run them through a program to generate the tree. Once you do this you can always update it easily when new sequences are added.
> Are NMT, 4HT or 4H-NMT found in Psilocybe, that youre aware of?
It's been some time since I've looked over the literature. IIRC DMT has never been found. So either it's not even remotely rate-limiting or it goes around DMT. You can see that there's different ways to the end, so without knowing the enzyme specificities we can really only guess. If they're not too specific then all routes are probably going on.
-FF
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thenilsmeister
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Re: Where do the chemicals come from. [Re: Nobitte]
#18072996 - 04/07/13 04:31 PM (11 years, 1 month ago) |
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We talked about this a bit in my adaptive theory class. Psilocybin was likely originally a deterrent, much in the same way peppers are. It is easy to see how it is adaptive to disrupt an animals functioning for a period of time rather than being toxic and killing it. Since the animal remains alive to reproduce it learns to avoid that type of fungi, this behavior becomes selected for and spreads across a population faster than if it was lethal. Of course there is going to be different trade offs circumstantially but it is easy to see why an organism would produce such a molecule. However it is interesting that caribou in siberia seek out and eat Amanita muscaria, so it may be likely that at some point these compounds became incentives for specific animals to spread and propagate the germline like fruit.
Great thread btw, I wish I knew more about organic chemistry
Edited by thenilsmeister (04/07/13 05:00 PM)
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fastfred
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It's all biochem! I was never that good at organic, but you can forget all the rules since those enzymes just do their crazy magic as they see fit.
> Psilocybin was likely originally a deterrent,...
I've never bought into that. We have to go with what we know, and it seems that humans have been attracted to mushrooms for as long as we know of. That gives you around 200k years of humans being involved in mushroom evolution, and we know they were attracted to actives just the same as today.
I also don't see the deterrent factor amongst animals. Grazing animals that would likely occasionally accidentally munch them just don't seem like they would be deterred.
Say a grazer ate 20 pounds of grass in a day. They might accidentally eat a handful of mushrooms. But that's maybe a dozen grams going into 20+ pounds of stuff in their stomachs, then going into a 200-1000 pound animal. Likely they would not have noticed they ate the mushrooms, so would have no way to associate any effects. Further the effects take some time to take effect.
I just don't think ruminants could ever make the connection between the effects and something they didn't even know they ate an hour ago. Further, we would be assuming they find the effects unpleasant, which I also somewhat doubt. The effects would probably not be strong enough to be unpleasant to them IMHO.
Of course, it's possible that other animals or insects might be deterred. If a squirrel drags one back to his hole and sits there eating on it he might easily get a negative experience and learn to associate it with the mushroom. Of course some squirrels might like it too!
IME I just see more evidence for attraction than deterrence. But it could also be both. If the actives attract the higher and more powerful species like man, while deterring squirrels and insects, it would be a pretty good strategy.
However I'm just not aware of any evidence that it deters insects, it certainly doesn't deter fruit flies!
It would be really, really easy to do some insect and animal studies. Anyone curious should do an experiment. A simple mouse feeding preference study would probably answer a lot of questions on this frequent topic.
-FF
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thenilsmeister
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Re: Where do the chemicals come from. [Re: fastfred]
#18073292 - 04/07/13 05:41 PM (11 years, 1 month ago) |
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You make some great predictions about insects, especially since insects and fungi predate animals on land we would expect many evolutionary strategies between those clades. Another thing to look into would if psilocybin plays a role in bacteria selection.
"I just don't think ruminants could ever make the connection between the effects and something they didn't even know they ate an hour ago. Further, we would be assuming they find the effects unpleasant, which I also somewhat doubt. The effects would probably not be strong enough to be unpleasant to them IMHO. " You have got to keep in mind that evolution happens over a massive scale of time it probably took several lineages of animals and thousands of years for the psilocybin strategy to develop and for animal behavior to adapt. An animal does not need to be aware of exactly what happened for selection to shape behavior. Energy spent on behavior that does not increase fitness will be out competed and selected out of the gene pool. Even if the effects are pleasant psilocybin disrupts neurological systems from occurring the way they are designed to occur, even if it just makes a deer lie down for a couple hours, over time those deer that did not eat those fungi will out compete those that did.
"I also don't see the deterrent factor amongst animals. Grazing animals that would likely occasionally accidentally munch them just don't seem like they would be deterred." I totally agree with you on this and think that some species such as P. cubensis may have adapted to become coprophilous in such a way, I dont know if there are large bovines indigenous to Equadorian region but that would be a prediction of this line of thought. If that is indeed the area Cubensis originated.
"If the actives attract the higher and more powerful species like man, while deterring squirrels" Researchers are actually finding that squirrels live off a diet of more fungi than nuts so perhaps that is part of it.
Edited by thenilsmeister (04/07/13 05:42 PM)
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Nobitte
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Im inclined to think that non-sequestrate coprophiles like cubensis rely almost entirely on anemochory to disperse, releasing spores into the environment and having them propagate when a suitable combination of substrate and physical conditions becomes available.
I haven't ever really seen anything to suggest that the propagation starts in the digestive tract, how else would the fungus start colonising new substrates at the start of the vegetating/fruiting season, if it had not already had propagules from last season hanging about.
Im basing this on the fact that rarely if ever have I seen evidence to suggest horse or cow manure from being colonised 'inside-out', rather I usually see the most mature and developed growth on the underside, at the interface of the grass and the manure.
I would certainly love to look at the responses of various taxa to alkaloid infused food and sporocarps, I think it would be interesting as well to do some scatological examination of the species that we believe are consuming the sporocarps to determine the viability of spores leaving their digestive tract and get some strong hints on their life history in that fashion.
In any case, ive never seen animals actively deterred by them, but that remains to be seen, infact, I have noticed that any psilocybe in my rainforest garden are the first targets of fungus gnats and slugs, even when they had the option to eat Lepiota aspera sporocarps.
One thing I have noticed is that there isn't much in the way of ecological models for dispersal and propagation, one thing id like to work on is modelling the dispersal dynamics of coprophiles like cubensis, but as I said previously, im more inclined to think the primary dispersion is anemochorous.
As for south American ruminants, they have a few, various types of pig, deer, horse and camel existed down there before the great American exchange, not entirely sure about bovine organisms though.
-------------------- First we must learn... Then... WE CAN TEACH
Edited by Nobitte (04/07/13 09:51 PM)
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thenilsmeister
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Re: Where do the chemicals come from. [Re: Nobitte]
#18074725 - 04/07/13 10:53 PM (11 years, 1 month ago) |
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Wouldn't that be pretty easy to test? Just inject spores into cow feed which an isolated cow would eat, then incubate the cow pie in a chamber or under something outside and then test it for cubensis mycelium.
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Nobitte
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I suppose it would, i guess ive just never gotten around to it, and i often lack the time or organisation that is required to do it properly at home (and nobody at my uni really works on non-mycorhizal fungi, so theres noone i can come to with the idea)
It sounds like it could be worth a try though.
-------------------- First we must learn... Then... WE CAN TEACH
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piggy
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Re: Where do the chemicals come from. [Re: Nobitte]
#18137115 - 04/19/13 07:15 PM (11 years, 1 month ago) |
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Psilocybin may not be an evolutionary tool, it maybe a loose/dead end. Naturally occurring compounds/chemicals might have no evolutionary advantage to the host plant/animal/fungi but have attractive qualities to Human Beings. Asprin, Ibuprofen, Morphine or to try and get the point across cork trees, Hickory, Oak etc etc etc
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fastfred
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Re: Where do the chemicals come from. [Re: piggy]
#18137619 - 04/19/13 09:06 PM (11 years, 1 month ago) |
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Naturally occurring compounds/chemicals might have no evolutionary advantage to the host plant/animal/fungi but have attractive qualities to Human Beings.
Yeah, compelling the most prolific and powerful animal species on the planet to harvest, possess, and transport your seed couldn't possibly be an evolutionary advantage.
Be sure to send me a book of your compiled wisdom along with my next order of ibuprofen trees.
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nomadbrad
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Re: Where do the chemicals come from. [Re: fastfred]
#18137686 - 04/19/13 09:23 PM (11 years, 1 month ago) |
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Quote:
fastfred said:
Quote:
Naturally occurring compounds/chemicals might have no evolutionary advantage to the host plant/animal/fungi but have attractive qualities to Human Beings.
Yeah, compelling the most prolific and powerful animal species on the planet to harvest, possess, and transport your seed couldn't possibly be an evolutionary advantage.
Be sure to send me a book of your compiled wisdom along with my next order of ibuprofen trees.
Despite the sarcasm I agree. There is no way the process of synthesizing the chemical is done with no apparent reason behind it. Hammering out the why is more interesting then dismissal.
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fastfred
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Re: Where do the chemicals come from. [Re: nomadbrad]
#18138671 - 04/20/13 01:12 AM (11 years, 1 month ago) |
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There's just no evidence out there to even base any decent speculation on. I've done probably the most research here on the genetics and history of cubes, and there is simply no obvious answer.
One of the few things we DO know is that actives have functioned as an attractant over an evolutionary time scale. Humans have eaten, used, associated with, and even worshiped mushrooms through all of recorded history. Countless examples of the significance of mushrooms exist in pre-historical records like cave paintings and sculptures.
Since everything we know points to the fact that humans have always used mushrooms... we can only assume that we have been doing it since we evolved, and probably even prior to actual Homo Sapiens status. That's about 200,000+ years, perhaps even quite a bit longer than that.
That's really ALL we know on the subject. Human preference is certainly a major factor, but there's really no way to know if it is THE most significant factor.
Obviously, if we weren't attracted to actives and the mushrooms had died out, lost the trait, or were simply unknown to us... then we wouldn't be discussing this right now. In that respect humans have been the most important evolutionary factor for the mushrooms.
There's really nothing else worth discussing about this. Fine if people want to throw out idle speculation, but there can't be any discussion on it since there are no facts to consider.
All the steps in the pathway are pretty common. DMT via INMT is common across all sorts of species in the higher kingdoms. So all we have to wonder about is the 4-hydroxylase that converts DMT into psilocin. Hydroxylating some position on an indole ring is plenty common and generic. Any random mutation could produce an enzyme like this from another related enzyme.
What people seem to be asking is why the initial mutation survived in evolutionary terms. Obviously it was non-lethal. But it might or might not have conferred any advantage other than attracting humans. OTOH it might have had some really disappointingly insignificant metabolic advantage that allowed it to become fixed in the species long enough to become a human attractant.
If someone wants to do some experiments we could have at least an interesting discussion. Do spores survive the digestive tract of various animals that might eat it? Are insects or squirrels and other rodents attracted or repelled from it? Fruit flies aren't repelled, so most likely other insects aren't either. Repelling animals doesn't seem to me to be very effective either. From their relative abundance compared to animals they obviously can't really do anything significant to an animal population.
They're not terribly difficult questions to answer. For me attracting humans has been it's only discernable function for as long as I care to worry about. I just don't care enough to wonder if it had any function or even existed 200,000+ years ago.
Once the gene is sequenced it can be compared to other homologs and we can see where it came from, and probably get a rough estimate of when it evolved. If the biochemical pathway is explored further we might even learn if there are any other possible functions.
-FF
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piggy
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Re: Where do the chemicals come from. [Re: fastfred]
#18173968 - 04/26/13 08:43 PM (11 years, 25 days ago) |
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Quote:
fastfred said:
Quote:
Naturally occurring compounds/chemicals might have no evolutionary advantage to the host plant/animal/fungi but have attractive qualities to Human Beings.
Yeah, compelling the most prolific and powerful animal species on the planet to harvest, possess, and transport your seed couldn't possibly be an evolutionary advantage.
Be sure to send me a book of your compiled wisdom along with my next order of ibuprofen trees.
I would love to browse a book of your compiled wisdom. Your sweeping statements have no basis in fact. Maybe you should omit from discounting blind evolution because you "reckon" whatever, and try to incorporate how evolution takes place with regard to the genesis for the production of 'visionary' compounds as an evolutionary advantage, as you stipulate. How many plants/animals contain psychoactive compounds?? More than we could fit on this page. They evolved without selective breeding/interference by ourselves because we weren't around. Their particular chemical composition ,whether recognized/used by us or not, has no relation to how their biology evolved. Psylocybe mushrooms have been around a damn site longer than the "blink of an eye" time scale of Homo sapiens or any of our ancestors. Read 'The origin of species' Darwin; or much more recently 'Climbing Mount Improbable' Dawkins or ' The Blind Watchmaker' Dawkins etc. Instead of hyperbole and unfounded personal opinion some considered facts would be more than welcome than speculation. No offense
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matsc
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Most secondary metabolites (like the hallucinogens) arose out of a combination of gene duplication events, random mutation, horizontal gene transfer, and pure blind luck.
Basically, some gene that codes for something essential, an amino acid or something, gets changed a little and ends up making a slightly different product. This product can then be acted on by some other enzyme. Several steps like this and you end up with.... something. In rare cases this "something" gives the organism some advantage. Maybe it tastes bad so animals wont eat it. Maybe it absorbs UV so the thing doesnt get sun burned. Doesnt matter, if it gives the thing an advantage over its environment, its gonna keep it.
These pathways can be mindblowingly complex, but they almost always have a first step that siphons off the precursor of some essential product. For example, here is what the biosynthesis of caffeine looks like:

It starts with a nucleotide (DNA/RNA) recycling pathway product, and uses enzymes that are all modifications of enzymes that plants had some time in history.
Edited by matsc (04/27/13 12:05 AM)
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fastfred
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Re: Where do the chemicals come from. [Re: matsc]
#18179836 - 04/28/13 02:44 AM (11 years, 23 days ago) |
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Quote:
Most secondary metabolites (like the hallucinogens) arose out of a combination of gene duplication events, random mutation, horizontal gene transfer, and pure blind luck.
That's the case with ALL organic molecules and genes, not just secondary metabolites. Considering that, it's kind of a pointless statement. (no offense)
> Your sweeping statements have no basis in fact.
Kind of pointless to argue against such a vague and completely unsupported assertion.
Quote:
Maybe you should omit from discounting blind evolution because you "reckon" whatever, and try to incorporate how evolution takes place with regard to the genesis for the production of 'visionary' compounds as an evolutionary advantage, as you stipulate.
I don't think you're grasping what I've said. You have to have a basic framework of understanding to even discuss the subject. Evolution is a natural force that acts upon genetic variation generated by random mutation of genetic material.
> They evolved without selective breeding/interference by ourselves because we weren't around.
Really? I'm glad you have pinpointed when the actives arose.
Humans have been around about 200,000 years. You have no basis to speculate on what mushrooms were up to +200K years ago.
Quote:
Their particular chemical composition ,whether recognized/used by us or not, has no relation to how their biology evolved.
More baseless speculation flying in the face of the evidence right in front of you.
> Psylocybe mushrooms have been around a damn site longer than the "blink of an eye" time scale of Homo sapiens or any of our ancestors.
+200K years is not a "blink of an eye" by any measure. It's not even a evolutionary timescale, more on the order of geologic. (200K puts you back into the Pleistocene epoch)
Evolution happens every day. It's a continuous process that you can witness with your own eyes if you just open them a little once in awhile. Whole species can change in just a few generations. Available variation x selective pressure determines the speed of evolution. You can find examples anywhere from millions of years to a few weeks.
Humans obviously couldn't have caused the mutation to a pathway that produces actives any more than some metabolic need could have caused it. Just not how things work.
> Instead of hyperbole and unfounded personal opinion some considered facts would be more than welcome than speculation.
Humans spread, propagate, and cultivate active mushrooms. It's the main reason they are so widespread and successful today. That's just basic fact, not personal opinion and hyperbole.
There's evidence as far back as we can dig up that humans have used and had a religious association with mushrooms. What more do you want? What more evidence do you think could ever possibly be produced?
Are you going to argue for some completely unsupported theory against all the evidence and clear proof of long term human interaction?
It just doesn't matter. Humans have been the reason for the evolutionary success of mushrooms for the past +200K years. Nothing can change that and it's obviously the largest influence they've experienced.
-FF
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piggy
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Re: Where do the chemicals come from. [Re: fastfred]
#18192036 - 04/30/13 01:18 PM (11 years, 21 days ago) |
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"It just doesn't matter. Humans have been the reason for the evolutionary success of mushrooms for the past +200K years. Nothing can change that and it's obviously the largest influence they've experienced"
Excellent. You've got my vote...
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Nobitte
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Re: Where do the chemicals come from. [Re: piggy]
#18194408 - 04/30/13 09:30 PM (11 years, 21 days ago) |
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Right-o, lets be civil ladies and gents.
And this is why paleobiogeography is important, be careful, im about to be reeeeallly boring.
Im more inclined to think that the present day proliferation is the result of humans, but the genus and the psilocybin pathway genotype are the result of a far more ancient evolutionary history.
FF, i can totally see where you're coming from in terms of the profound impact that alkaloid producing fungi and humans have on each other and im certain that humans assisted somewhat in their present day distribution, due to the presence of psychoactive alkaloids and our desire to imbibe them. We may have even brought some speciation events to occur where there have been very close associations, but not generally across alkaloid producing taxa.
There has to be something else involved. Some sort of competition or selective pressure, now, im aware that not all speciation events are the result of pressure altering a genotype (I've been reading papers that suggest allopatry and random genetic drift could account for some cases, i can dig them up if you want), but im inclined to think that in this case its a definite possibility.
Speculation and supposition is great while were toying with ideas, but im not incredibly inclined to just say that it is impossible to find out.
I was musing on this the other day and i came to thinking that we could do molecular analysis of preserved spores, and get some sense of a date of them with sediment analysis, if such a thing was possible and in so doing determine the species that were present in their current form back then. Perhaps even with some tricky dispersion modeling and knowledge of the geo-history of the areas in question we might be able to determine where the source of them(the spores) could be.
I agree that 200000 is no paltry number of years and that dramatic changes could take place over those timescales, but im also inclined to believe that the genus could be much older and that its possible that these traits arose earlier than hominid proliferation.
How much about ancient basidiomycete species do we know?(i really should research that given how much i go on about them) is there a known timeline for diversification of basids or and Dikarya? If the genus psilocybe and panaeolus are indeed older than us as modern humans, what would that say about the presence of alkaloids, would they also be just as 'old'?
Surely the pathway could not have evolved independently 20-30 times world wide(given that it could have been present in a number of ancestral species and didnt do so independently in all past and present species, which would imply it happening 100s of times), purely as the result of human interaction, id be willing to accept it, but id need more evidence than archeology and inference.
If for instance, you were able to show that (if you are inclined to believe in 'OoA theory') the present day distribution of psilocybe across the world and the diversity of species could be correlated with the spread of hominids from Africa and that alkaloid producing genus' spread from there in a similar means to us, i would probably side with you(given careful consideration of the evidence), but as of yet i am still inclined to believe that we as a species or as a broader hominid taxa would only account for a small portion of the present day species.
I sorta... steam of consciousness'd this one, because im kinda busy, so y'all gotta tell me if you think its hogwash.
I like that this conversations still going, but lets keep the ad hominem to our pets, partners/spouses and workmates =3.
Xxxx
Nobitte
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matsc
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Re: Where do the chemicals come from. [Re: Nobitte]
#18194595 - 04/30/13 10:19 PM (11 years, 21 days ago) |
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Quote:
Nobitte said:
Surely the pathway could not have evolved independently 20-30 times world wide(given that it could have been present in a number of ancestral species and didnt do so independently in all past and present species, which would imply it happening 100s of times), purely as the result of human interaction, id be willing to accept it, but id need more evidence than archeology and inference.
It is entirely possible it did arise several times in history. So far as I know (feel free to correct me here if im wrong), all the currently known psilocin/psilocybin containing fungi are in the order Agaricales, but are from different families. So lets say that it has arisen at least twice, once each for the Gymnopilus and Psilocybe (Strophariaceae) family, and once for the Panaeolus family (Psathyrellaceae). Its more likely that it came about independently in the Gym genus and Psilocybe genus, but for simplicities sake we can group them together.
Biosyntheitcally speaking , psilocin and psilocybin arent complicated. Start with tryptophan (an amino acid), decarboxylate, methylate, and oxidize and boom, psilocin. Toss on a phosphate and you got psilocybin. There are hundreds of enzymes that carry out these types of reactions. The chances of them mutating a bit to accept tryptophan and tryptophan like molecules into their active sites is not a huge stretch of the imagination. (A note: This is just one biosynthetic pathway I found, its possible its theoretical rather than found in nature)
To use the example of caffeine again, it appears in dozens of plants, from all across the globe, and with only tenuous relations between them. Its an easy pathway to mutate into, and it gives the thing an advantage. Nature loves those 
Edit: Oh and you might find this interesting: http://blog.mycology.cornell.edu/2009/05/13/paleomycology-discovering-the-fungal-contemporaries-of-dinosaurs/
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Edited by matsc (04/30/13 10:28 PM)
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Nobitte
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Re: Where do the chemicals come from. [Re: matsc]
#18195355 - 05/01/13 02:10 AM (11 years, 20 days ago) |
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Im not saying that i think its impossible that it couldnt have arisen several times, infact i would say that is likely, CAM/C4 photosynthesis did, so i dont see why this couldnt.
Im just saying i dont think it would have arisen independantly in Psilocybe, Panaeolus and Gyms(we were also talking about inocybes potentially possessing some of the pathways involved, so they might be in there too) on a species level, i sort of meant to imply that the development of this pathway would be around or before their family level differentiation, thus setting the development of the compound back a long time (relative to the human-driven hypothesis), making it seem unlikely that humans had a role in its initial development, but more in its proliferation.
I know the process seems simple, but if it was so easy and advantageous to be magic, would not have more species with the requisite precursor pathways have gotten to this point.
I guess what i wanted to point to is that given the fact that it is in multiple families, you would need to determine the evolutionary relationship of these pathways before setting any sort of timeline as to when they came about (allowing us to speculate on the means of speciation/differentiation).
I do actually really like where your going with this and i think were thinking along similar lines. I guess it is rather difficult for us to construct these things, but it might be important to determine whether this is actually the case, so that we can formulate more informed hypotheses on its genesis. And that the answers we seek might be in an indepth molecular/genetic analysis of the taxa, pathways and how they relate to eachother, sounds hell laborious)
On a less related note, i am often asked why researching alkaloid biosynthesis would be important or even worth funding, but for enthusiasts like us i would say its more out of sheer curiosity rather than anything terribly pragmatic. Can anyone think of a good reason that they want to share for looking into this stuff, apart from the old chestnut of adding to humanities collective knowledge.
Im not a Biotech major, so once we start getting smaller than physiological scales i get a bit muddled, im doing my best =3.
PS Thank you muchly for the link, greatly appreciated, i did a research internship on entomopathogenic fungal control agent(Metarhizium acridum) ecotoxicity(relative to organohalides)^^. So anything with evil, insect munching fungi pleases me greatly.
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Edited by Nobitte (05/01/13 02:21 AM)
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matsc
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Re: Where do the chemicals come from. [Re: Nobitte]
#18195395 - 05/01/13 02:34 AM (11 years, 20 days ago) |
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I actually was/am a biotech major (Technically Biochemisty with a focus in molecular biophysics). My intention in school was pharmaceutical focused, my activity of choice is the lifting of whole pathways from one organism (plants and fungi mostly) and inserting it whole into another organism (bacteria or biomass plants.) Teaching soybeans to make medicines, making complex plant-origin metabolites by the litre in cell culture, that sorta thing.
Unfortunately the whole rampant anti-GMO lobby has made this field hellish. Cant even plant a seed without a phonebooks worth of paperwork and more oversight than the manhattan project -_-.
Plants can do things with chemistry that humans wouldnt have even thought possible. Drugs that would never make it past the note pad in a big pharma lab that somehow miraculously work in humans (Im looking at you taxol!). I love this stuff
Molecular evolution is a relatively young field, but its growing quickly. There are certain "molecular clock" sequences in organisms that you can use to identify rates of mutation, and comparatively, how far back it diverged from its relatives. I doubt this has been done in any extensive degree with active specimens like Psilocybe, but the theory is the same. Similarly the gene sequences of various proteins can be compared across species/genera to see how close/different they are from one another to try and infer degrees of relatedness, and how far back they diverged (Say, 1 stable mutation per 1000 generations, 1 generation is a month, so something that is different by 1 amino acid diverged ~80 years ago. Massive oversimplification by the way)
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fastfred
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Re: Where do the chemicals come from. [Re: matsc]
#18200681 - 05/02/13 02:22 AM (11 years, 19 days ago) |
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> It is entirely possible it did arise several times in history.
I think this is quite possible. DMT is present in mammals and quite a few different plant species. Psilocin is just one step away.
Serotonin is also present in many organisms, from algae and other unicellular organisms all the way up to humans. Serotonin is 5-hydroxylated tryptamine, while psilocin is 4-hydroxylated tryptamine with two extra methyl branches at the end of the chain.
It's not difficult to imagine that the serotonin hydroxylation enzyme might be easily mutated to also accept DMT, which could easily change the 5 position to the 4.
Quote:
In drying seeds, serotonin production is a way to get rid of the buildup of poisonous ammonia. The ammonia is collected and placed in the indole part of L-tryptophan, which is then decarboxylated by tryptophan decarboxylase to give tryptamine, which is then hydroxylated by a cytochrome P450 monooxygenase, yielding serotonin.
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This means serotonin secretion not only serves to increase the spread of enteamoebas by giving the host diarrhea, but also to coordinate their behaviour according to their population density, a phenomenon known as quorum sensing.
I guess that's two new theories for potential biochemical utility for psilocin. Ammonia metabolism and quorum sensing. Both would be important to mushrooms.
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you would need to determine the evolutionary relationship of these pathways before setting any sort of timeline as to when they came about
The data is out there. Quite a few species have ITS/LSU regions sequenced, so we can build phylogenetic trees from them.

You can build your own trees and add whatever sequences you can find to see if there is a common ancestor. You can also analyze for genetic drift and get a pretty rough timeline for the different species. Without sequence of the actual unknown 4-hydroxylase though you won't be able to say much about the timeline of actives unless you get lucky and find a good common ancestor with a clear lineage of the gene.
> my activity of choice is the lifting of whole pathways
If you get bored some day whip up some DMT producing Pischia or brewing yeast. TDC and INMT are sequenced and available ready to go for $50 or so each.
While you're at it throw those into a few mushroom species. TDC is probably the rate limiting step, so that would produce some mega-potent strains.
-FF
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