Alkaloid evolution

[Rabaelthazar]

Forgive me if this has been discussed here before, I tried the search engine but couldn't find any hits on the words I searched for. If it has been discussed, if someone could post a link that would be great.

Basically, I've been wondering recently why specific entheogenic alkaloids are found in such diverse plant types.

Psilocybin, for example, is found in a whole lot of different mushrooms. Ok, I can imagine a possible history being something along the lines of one mushroom develops a chemical as a defense mechanism to give animals a message, DO NOT EAT THESE MUSHROOMS AGAIN (until humans came along, that is). That mushroom becomes a successful survivor due to its new defense mechanism and flourishes, mutating and evolving over time into the many different varieties around today.

Here's where I'm stumped. Take our favourite tryptamine... it's found in grasses, succulents, hardwoods... I find it hard to imagine that all these different plants had a common ancestor (although botanists, please feel free to tell me otherwise). Combined with the fact that this chemical is orally inactive, what purpose does it serve other than to give humans profound insight into alternative dimensions? Is the tryptamine molecule just a very natural arrangement of atoms? Did one plant share the secret with another plant of a different genus?

It's one of those things, I guess, that we will never be able to know for sure, but I'm looking here for any theories. Scientific theories through to wacked-out hippy theories and anything in between. Any thoughts?

[naja naja]

Also found in sum corals, fish I beleive and even us. Thats just where we've found it so far. Maybe sumtimes saturation ensures contact. Maybe it's and entity of it's own

[psili sausage]

I think its chemical similarity to tryptophan makes the coincidence more likely. Lots of metabolic pathways in many organisms convert amino acids into neurotransmiters or other chemical messangers etc. An overlap between unrelated species is inevitable.

Another example that comes to mind (not related to alkaloids) is that of chitin. Chitin is a protein found in the cell walls of fungi and also in the exoskeletons of insects, crustaceans etc. It would be unreasonable to conclude that crustaceans and arthropods evolved from fungi... or would it?

Edit: typo

Edited July 3, 2010 by psili sausage

[Max Cady]

I liked to to think when a spot's been picked out or empty that the cows ate them to brighten up they're day a bit.

[Rabaelthazar]

Also found in sum corals, fish I beleive and even us. Thats just where we've found it so far. Maybe sumtimes saturation ensures contact. Maybe it's and entity of it's own

 

Well, maybe it is... and maybe it's such an intelligent and fundamental molecule that all these different life forms (corals, mamals, plants) inherited from a shared ancestor in the single celled organism stage. Hmm.. I don't know.

Sorry, Naja, what do you mean by "saturation ensures contact"?

[Rabaelthazar]

Another example that comes to mind (not related to alkaloids) is that of chitin. Chitin is a protein found in the cell walls of fungi and also in the exoskeletons of insects, crustaceans etc.

 

Thanks Psili, this is the kind of sciency stuff I'm really keen to hear about. More please... and bring on the hippy theories too.

[psili sausage]

If you're keen for more sciency stuff, I found this on wikipedia: KEGG Pathway: Tryptophan metabolism

Tryptophan is in the centre and tryptamine is to the right. Above Tryptamine and to the left is N-Methyltryptamine, but N,N-Dimethyltryptamine is not included (perhaps because there's no conclusive evidence of its role).

You can click on the boxes to get more details on the enzymes and other compounds involved in the reaction. (Heaps of unwanted info here, but wade through it for a bit - perhaps just scroll to the bottom).

That reaction from Tryptamine to N-Methyltryptamine can be repeated to produce N,N-Dimethyltryptamine.

I guess all I was trying to show is that Tryptophan is found in every living thing on the planet and DMT is only 3 small chemical reactions away.

Also, I think what Naja meant is that if you put something everywhere it's sure to be found...

hmm... If it was meant to be our key to communicate with the spirit realm, it would be appropriate to hide it everywhere would it not? Maybe the gods chose such a compound for that reason.

[occidentalis]

Here's where I'm stumped. Take our favourite tryptamine... it's found in grasses, succulents, hardwoods... I find it hard to imagine that all these different plants had a common ancestor (although botanists, please feel free to tell me otherwise).

 

Yep, all these different plants had a common ancestor - in fact, ALL plants had a common ancestor .

DMT is probably found in trace quantities in many plants - Dennis McKenna has suggested maybe even in all plants at least in very low levels. It's very similar to the hormone auxin and related hormones so may serve as some kind of storage system for those compounds.

As for chitin... basically there are two directions evolution can go which lead to similarities - convergent and divergent

in convergent evolution organisms from separate branches of the evolutionary tree develop the same characteristics to deal with similar environmental pressures (think sharks, dolphins, and penguins - all adapted to fast swimming and hunting under water, yet from three very different groups). This is probably the case with chitin.

In divergent evolution organisms originating from the same branch of the tree may retain the same 'ancestral' characteristics which date back to the time when they were closely related even though they are quite different now - ie many types of distantly related plants (and animals) produce DMT.

[mutant]

Excellent thread

I have been thinking about this for quite some time

What about mesc aline? Cacti were later plants, I think it's one of the relatively recent additions to plantae. And mesc seems to be only occuring in cactacea.

what's the oldest [evolution-wise] plant that features some entheogen substance?

Could we call mesc the newer initiative?

Could this also be the reason why mesc is a 'superior' messenger feat a series of qualities like empathogen, entheogen, psychanalytic/psycholytic etc , that is it's the most recent version of the 'message' ??

[Rabaelthazar]

If you're keen for more sciency stuff, I found this on wikipedia: KEGG Pathway: Tryptophan metabolism

 

Thanks for the link Psili... most of that's too complex for me to grapple, but I can see what you're referring to. Nice.

hmm... If it was meant to be our key to communicate with the spirit realm, it would be appropriate to hide it everywhere would it not? Maybe the gods chose such a compound for that reason.

 

I like this quote. Is the magic of these substances co-incidental or divine? Either way, I'm happy. If they are accidental, then that's almost divine in itself.

Yep, all these different plants had a common ancestor - in fact, ALL plants had a common ancestor .

 

Occidentalis, thank you for your reply. I think your post basically satisfies me in terms of a physical world answer to my question. When you say all plants had a common ancestor, are you speaking about back at the time of the beginning of life on earth? Would you hypothesize that animals, plants and fungi then would also have had a common ancestor, or is that taking it too far?

Thanks for the explanation of convergent and divergent evolution too.

What about mesc aline? Cacti were later plants, I think it's one of the relatively recent additions to plantae. And mesc seems to be only occuring in cactacea.

 

Heya Mutant. I remember reading about some trees that contain mesc. Not sure if that was from that dubious wiki page or somewhere more reliable.... perhaps an acacia or similar?!?

I won't get into the discussion with you of whether mesc. is a superior entheogen or not, otherwise this post will end up 7 pages long

Good questions.

[ThunderIdeal]

dubious wiki page, saying an acacia contains meth, mesc and nicotine..... i've seen it echoed around the web too lol somebody has to fucking do something about that wiki entry.

probably added as a joke/gag/troll or something? is there any reference?

[psili sausage]

Wow, that methamphetamine wiki page indeed reports methamphetamine, mescaline and nicotine in a few texan acacias...

The reference appears legit; it's an article "Toxic amines and alkaloids from acacia rigidula" from the "Phytochemistry" journal. Although, I cannot access the whole article to find what concentrations were found and what techniques were used.

Here's the abstract:

 

 

Acacia rigidula

Benth., blackbrush, is a shrub found growing on rocky ridges in west and southwest Texas and northern Mexico. Consumption of blackbrush and a related species guajillo,

Acacia berlandieri

Benth., has been associated with a locomotor ataxia known as limber leg. In an effort to identify the mechanism of this toxicity, blackbrush was subjected to rigorous chemical analysis. In addition to the four previously detected amines,

N

-methyl-

β

-phenethylamine, tyramine,

N

-methyltyramine, and hordenine, 40 other alkaloids and amines were isolated and identified by GC-MS. These alkaloids and amines included nicotine,

N

,

N

-dimethyltryptamine, mescaline, several tetrahydroisoquinoline alkaloids, and four amphetamines. A significant increase in the number and relative quantities of these compounds was observed in late season foliage.

Interesting...

[Auxin]

I'm with occidentalis on the reservoir theory, I've thought for many years that DMT would be a very chemically stable way to store a precursor for indole-3-acetic acid, tryptophan cant be readily stored without complex mechanisms and DMT is metabolically closer to IAA anyway.

Theres a reason there are recurring themes in alkaloids and some alkaloids occur in widely separated groups. Under the western scientific materialism darwinian model plants do not choose to start making a certain new chemical compound to attract/repel/kill insects and animals, rather those secondary metabolites are arrived at by chance as a confluence of pre-existing metabolic/biosynthetic systems and the new chemicals persistence in the species is determined by its ability to increase survival or reproduction rates, or at least a lack of harm to the organism. Thats why if you squint at any alkaloid you can see it was made from an amino acid, or several like how the Heimia alkaloids are fused metabolites of lysine and phenylalanine. Alkaloids are made when some enzyme system, which is there to do some unrelated biochemical process in the plant, acts upon a amino acid or a metabolite thereof and turns it into a new compound.

Decarboxylation and N-methylation enzyme systems are extremely common in life on earth, thats why unrelated organisms can exibit convergent evolution to produce DMT so easily, because its a simple derivative of a common amino acid using very common enzymes. Aryl hydroxylation is also a common functionality of life, both for biosynthesis of amino acids (like tyrosine from phenylalanine) and for steroid synthesis/metabolic removal of aromatic toxins. Thus psilocybin is a possible secondary metabolite produced from native mushroom enzyme systems. Some aryl hydroxylating enzyme systems, like common in plants, are a little bit different in receptor site shape and grabs the indole nucleus at a different angle thus making bufotenine which can be easily methylated to 5-MeO-DMT.

Cacti seem really keen on hydroxylating and methylating too but they seem to mainly have chosen phenylalanine/tyrosine as the object of their affections and thus you get a wealth of phenylalanine derived alkaloids like mescaline and norepinephrine and (mostly) many things in between.

So thats why alkaloids seem to be oddly recurrent.

Edited July 7, 2010 by Auxin

[Rabaelthazar]

So thats why alkaloids seem to be oddly recurrent.

 

Thanks Auxin.

Your whole post was really interesting and informative. I'm glad I posted this topic... I've learned a few nice new tidbits.

[occidentalis]

Occidentalis, thank you for your reply. I think your post basically satisfies me in terms of a physical world answer to my question. When you say all plants had a common ancestor, are you speaking about back at the time of the beginning of life on earth? Would you hypothesize that animals, plants and fungi then would also have had a common ancestor, or is that taking it too far?

 

yes, that's pretty much the scientific consensus - although it's a little more complex than that.

First off - evolution was originally entirely chemical. This is called 'prebiotic life'. Life consisted of replicating polymers (probably RNA first, then DNA). All organisms share the same genetic code (this is why you can transfer a gene from one organism to another and it will work - the code that translates DNA into protein is exactly the same in all organisms). Because it would be extremely unlikely for this code to evolve exactly the same on more than one separate occasion, we can hypothesise that at least at the chemical level, ALL organisms share a common ancestor. The original replicator and its associated molecular mechanisms of replication.

http://en.wikipedia.org/wiki/Abiogenesis

However, once you get into biotic or cellular life, it gets a bit more complex and controversial. It's possible that these chemical replicators went on to become several different types of primitive cell. Or, the cell may have evolved once and then diverged into several different types. Some specialised in producing energy from sunlight - photosynthesis. We might say these were the first plants. Others developed the ability to produce energy from chemicals or heat around undersea vents (some researchers think this may have been the origin of life). Others then developed the ability to prey on the products of the first types, or on the cells themselves - the precurors of animals and fungi.

There are prokaryotes and eukaryotes. Prokaryotes came first: simple cellular organisms like 'blue green algae' (cyanobacteria) and other simple bacteria. What typifies them is a lack of internal cellular organisation - ie, everything in the cell is just floating around in the cytoplasm. Their DNA is in rings called plasmids. Some of these, like cyanobacteria and other prokaryotic algae could be said to be 'plants' because they photosynthesise.

Eukaryotes are all the complex organisms including some types of bacteria but all higher multicelluar organisms - plants, animals, fungi. What typifies them is that their cells contain 'organelles' which are little membrane-bound spaces inside the cell that have specific functions. In animals and fungi, you have mytochondria which break down sugars and produce energy to power the cell. In plants, you have those but also chloroplasts, which are the parts of the cell that contain chlorophyll and do photosynthesis.

At some point, someone (haha, great science history lesson here) noticed that the chloroplasts and mitochondria contained their own DNA. And that their DNA was in a plasmid (a ring, rather than a coiled chromosome) just like prokaryotic bacteria. And that these organelles, which had previously been considered just 'organs' of the cells, were actually very similar to free living prokaryotic cells like bacteria. The conclusion was that at some point in evolutionary history these primitive prokaryotic bacteria got together with some other cellular machinery such as a nucleus and ribosomes, somehow wrapped themselves all up in a membrane, and entered into a symbiotic relationship with each other. They traded autonomy for stability, lost all the DNA they no longer needed, and lived happily ever after. The emphasis is definitely on the 'somehow' and no one has really been able to give a very good demonstration of how it could have happened. But the reality is, the cells of all complex organisms contain 'organelles' which are very closely related to free living prokaryotic organisms.

http://en.wikipedia.org/wiki/Endosymbiotic_theory

So it is complex because the tree of life doesn't only branch, it also recombines. Basically - you had plants first, if your definition of plants includes prokaryotic algae. Then came animals and fungi.

Animals and fungi are more closely related to each other than either are related to plants (both live by breaking down the energy produced by plants rather than making their own energy). So the first ancestor of animals and fungi came along and started eating plants, then at some point diverged - animals are the ones that started moving around and hence needed a nervous system, and fungi are the ones that decided ubiquity was more effective than locomotion and didn't bother with the whole nervous system thing but instead reproduced by spores which can easily be disseminated far and wide.

[mutant]

I won't get into the discussion with you of whether mesc. is a superior entheogen or not, otherwise this post will end up 7 pages long

that was 'superior' not superior. I don't like football mentality and tools are different not better or worse. So I don't believe mesc is superior. ;)

Interesting thread.

do did mesc really came up later, as did cactacea, like I said?

Edited July 7, 2010 by mutant

[occidentalis]

I don't know of mescaline occurring in any plants outside of the Cactaceae. Related compounds such as essential oils like elemicin are found in many species and mescaline is only a methyl away... but perhaps that methyl is something only the cactaceae can do.

[Rabaelthazar]

yes, that's pretty much the scientific consensus - although it's a little more complex than that.

 

Occidentalis... thankyou, thankyou, thankyou. That was a very tasty meal of brain-food. Got a big smile on my face after that one.

[Rabaelthazar]

that was 'superior' not superior.

 

[Magicdirt]

Forgive me if this has been discussed here before, I tried the search engine but couldn't find any hits on the words I searched for. If it has been discussed, if someone could post a link that would be great.

 

Fuck the search engine

Try this in your search engine - google/yahoo etc

site:shaman-australis.com whatever you're looking for

[Auxin]

I don't know of mescaline occurring in any plants outside of the Cactaceae. Related compounds such as essential oils like elemicin are found in many species and mescaline is only a methyl away... but perhaps that methyl is something only the cactaceae can do.

 

The problem is its not a methyl group off, a methylene group would need to be removed and replaced with an amino group, a trickier biochemical move. But backing up a bit, the real problem in those instances are those essential oil compounds which resemble MDMA and mescaline were not biosynthesized from amino acids, rather they were pieced together from acetyl-CoA, pyruvate, and glyceraldehyde IIRC, so they didnt have the amine group to work with from the start and would have to incorporate it at some point. It is conceivable, for example, that a route could easily mutate to form 4-(3,4,5-trimethoxyphenyl)propanone instead of elemicin and that could pose as a deaminated amino acid and be aminated thus producing the amphetamine analog of mescaline... but no ones found a plant that did that lol, alkaloids are much easier to form when the precursor is an amino acid rather than an isoprenoid or something, some authors even regard it as being a defining factor that alkaloids must have as their origin some amino acid. I am not of that more extremist school of thought, but it does show just how nearly universal it is that amino acids are the precursors of alkaloids. Edited July 7, 2010 by Auxin

[occidentalis]

ah yeah, thanks Auxin. How could I forgot about the amine?

That's why I'm a biologist and you're a chemist ;)