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thenilsmeister
Shroomery addict


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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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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.
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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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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.
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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
Sausage

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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
Student


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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
-------------------- First we must learn... Then... WE CAN TEACH
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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
Student


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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.
-------------------- First we must learn... Then... WE CAN TEACH
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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