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InvisibleAmphibolos
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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)

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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OfflineNobitte
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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)

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?


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Then... WE CAN TEACH :weirdeyes:

Edited by Nobitte (04/05/13 08:10 AM)

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Offlinenomadbrad
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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)

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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Offlinenomadbrad
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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)

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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OfflineNobitte
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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)

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.

:awehigh:


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Then... WE CAN TEACH :weirdeyes:

Edited by Nobitte (04/05/13 09:22 PM)

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Offlinenomadbrad
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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)

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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Re: Where do the chemicals come from. [Re: nomadbrad]
    #18065752 - 04/06/13 03:36 AM (11 years, 1 month ago)



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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OfflineNobitte
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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)

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. :awehigh:


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Then... WE CAN TEACH :weirdeyes:

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InvisibleAmphibolos
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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)

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. :awehigh:




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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Invisiblefastfred
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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)

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.

Quote:

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.

Quote:

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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OfflineNobitte
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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)

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


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Then... WE CAN TEACH :weirdeyes:

Edited by Nobitte (04/07/13 01:03 AM)

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Invisiblefastfred
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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)

> 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.

Quote:

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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OfflineNobitte
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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)

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.


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Invisiblefastfred
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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)

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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OfflineNobitte
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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)

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)


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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)

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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Re: Where do the chemicals come from. [Re: Nobitte]
    #18072996 - 04/07/13 04:31 PM (11 years, 1 month ago)

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 :tongue2:


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Edited by thenilsmeister (04/07/13 05:00 PM)

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Re: Where do the chemicals come from. [Re: thenilsmeister] * 1
    #18073097 - 04/07/13 04:54 PM (11 years, 1 month ago)

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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Re: Where do the chemicals come from. [Re: fastfred]
    #18073292 - 04/07/13 05:41 PM (11 years, 1 month ago)

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.


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Edited by thenilsmeister (04/07/13 05:42 PM)

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OfflineNobitte
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Re: Where do the chemicals come from. [Re: thenilsmeister]
    #18074335 - 04/07/13 09:45 PM (11 years, 1 month ago)

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 :weirdeyes:

Edited by Nobitte (04/07/13 09:51 PM)

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