perrottetinenic acid

[Turing Machine]

I cannot find any information on the structure or possible activity of this cannabinoid (perrottetinenic acid) discovered in the New Zealand liverwort in 2002. Does anyone have this available?

 

[nuke]

Well, the research paper about it's discovery is free: http://cpb.pharm.or.jp/cpb/200210/c10_1390.pdf

See also: Perrottetinene

It doesn't look like anyone has done any research as to its activity, but you could always just purchase the plant and make some extract yourself.

 

[Turing Machine]

Thanks! The links are very appreciated.

I do have one more question though. It was said in the pdf file that decarboxylation was thought to have occurred in the gc/ms at 250C. Would it be safe to assume that if one could decarboxylate the cannabinoid acid(s) found in this species with the same procedures as on uses to decarboxylate the cannabinolic acids found in herbal cannabis i.e. hanging and drying?

 

[tamtoot]

f.ckin awesome!
Does it mean that scientists discovererd a new nature made cannabiod that is made by plants of non-cannabecea family?

 

[(zonk)]

very interesting... I just looked at a pic of liverwort, kinda looks like lichen which shulgin mentioned as having a chem with a partial structure to thc

 

[Turing Machine]

f.ckin awesome!
Does it mean that scientists discovererd a new nature made cannabiod that is made by plants of non-cannabecea family?

Yes, although it is not for sure that it is active and I don't know the SAR of cannabinoids enough to say one way or the other. To be perfectly fair this is not the first occasion of such a discovery, although it is the first occasion of one being discovered with a decent chance of recreational potential. Beta caryophyllene is a CB2 agonist found in multiple species including cannabis. There's also a few fatty acid amide (anandamide type) cannabinoids which have been found in plants but afaik fatty acid amide cannabinoids don't have much in the way of recreational potential. Perrottetine on the other hand is the only cannabinoid I know of which is found in non cannabis plants and has potential to be qualitatively similar to THC.

very interesting... I just looked at a pic of liverwort, kinda looks like lichen which shulgin mentioned as having a chem with a partial structure to thc

Yes, liverworts are a fascinating class of plants. Since they aren't as sexy as bromeliads and epiphytic orchids I never studied them much aside from the taxonomy and basics I was taught in school but this will give me a good excuse.

 

[fryingsquirrel]

Are these even flowering plant? If they are something far more primitive I wonder what light this sheds on the evolution of drugs in plants? First impression is it supports turing machine's statements that cannabinoids serve as anti-biotic/anti-virals.

 

[vecktor]

According to the current SAR, the Perrottetinene compound is almost certainly an active CB2 agonist with a lower activity and affinity for CB1, the CB2 and CB1 active site both tolerate terminal aromatic rings on the sidechain with the CB2 receptor being much more tolerant. see levonantradol for a very potent example of a aromtic ring substituted CB1/2 agonist. unlike levonantradol the side chain in Perrottetinene is not forced out of the phenyl ring plane so potency is not going to be great.

There are probably other natural classical cannabinoids out there undiscovered, olivetol and orcinol (litmus) and other 3-alkyl resorcinols half of the structure are rather widely distributed in lower plants and the other part of the cannabinol structure is just made from ubiquitous terpines. That FWIW, was what shulgin was referring to.

V

 

[fastandbulbous]

Are these even flowering plant? If they are something far more primitive I wonder what light this sheds on the evolution of drugs in plants? First impression is it supports turing machine's statements that cannabinoids serve as anti-biotic/anti-virals.

Well you get lysergamide derivatives in both flowering plants (morning glory) and in fungi (ergot) and fungi aren't even plants in the strictest definition, more a halfway housae between plants & animals (they store carebohydrates in the form of glycogen rather than starch, do not have a strict cell/nucleus relationship a bit like muscle tissue yada yada yada)

 

[Turing Machine]

Are these even flowering plant? If they are something far more primitive I wonder what light this sheds on the evolution of drugs in plants? First impression is it supports turing machine's statements that cannabinoids serve as anti-biotic/anti-virals.

They are not flowering plants, but they are capable of reproducing sexually in the same manner as mosses. They obviously cann't produce seeds but they can produce a new diploid offspring with combined genetic information from an ovum an sperm that grows to a mature point and releases spores.

 

[nuke]

Many of the enzymes required to synthesize these compounds are found within fungi and even bacterial, so it's not all that surprising to find cannabinoid compounds in a liverwort. In cannabis they seem to have some function in regards to reproduction that's not entirely well understood; after you isolate the genes responsible (probably not hard; there are some reported from cannabis sativa and they're a pretty strong chance they're present in this plant as well), a study of expressed RNA in different parts of the plant along with a study of RNA during different life-cycles of the plant may help elucidate the function of this compound. Would be a fun little project if you had a year or two to dedicate to it.

They are not flowering plants, but they are capable of reproducing sexually in the same manner as mosses. They obviously cann't produce seeds but they can produce a new diploid offspring with combined genetic information from an ovum an sperm that grows to a mature point and detaches itself.

That's correct, the reproduction is similar to mosses and ends with spores, which could be thought of as sporopollenin-encased pseudoseeds I suppose. Interesting too is that sperm from the plant propel themselves with flagella a la mammalian sperm -- there are parallels everywhere if you look deep. M. Polymorpha is a well studied ancestor to many plants, from a bioactivity perspective and a genetic perspective.

 

[Phener]

Is it me of does that benzene ring on the end look quite out of place, like it would complicate the pharmacological profile.

*Disclaimer: I know nothing about the SAR of cannabinoids*

 

[fryingsquirrel]

Well you get lysergamide derivatives in both flowering plants (morning glory) and in fungi (ergot) and fungi aren't even plants in the strictest definition, more a halfway housae between plants & animals (they store carebohydrates in the form of glycogen rather than starch, do not have a strict cell/nucleus relationship a bit like muscle tissue yada yada yada)

Yes, I was aware of this. Any ideas on how such relatively complex molecules would arise in two totally unrelated species? Perhaps from the production of much simpler tryptamines?

 

[Turing Machine]

Yes, I was aware of this. Any ideas on how such relatively complex molecules would arise in two totally unrelated species? Perhaps from the production of much simpler tryptamines?

If I were to guess I'd say it was a simple case of "convergent evolution"

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

Also, can any chemists tell me if they'd expect perrottetenic acid to decarboxylate from simple hanging and drying the plant in the same way cannabinolic acids in cannabis decarboxylate to form cannabinoids?

 

[tryp2fun]

Yes, I was aware of this. Any ideas on how such relatively complex molecules would arise in two totally unrelated species? Perhaps from the production of much simpler tryptamines?

The ergot alkaloids found in ergot and in convolvulaceae are both due to fungi. In the case of convolvulaceae the fungus is an endophyte. Ergot alkaloids are also found in some grasses, such as tall fescue, due to an endophyte. There's no mystery or convergent evolution required.

 

[egor]

I have been looking into Perrottetinene for a year, but unfortunately the only place I have seen it will not sell to private individuals. Finding Radula Marginata is no easier...

 

[Turing Machine]

Fascinating, I remember reading about some lysergamide producing endophytic fungi but am quite shocked to hear this is the case with morning glories.

 

[Turing Machine]

I have been looking into Perrottetinene for a year, but unfortunately the only place I have seen it will not sell to private individuals. Finding Radula Marginata is no easier...

I'm pretty sure I can get Radula Marginata to work with. I have no experience growing mosses, but have the tools and resources to do so. Unfortunately I'm moving from the perfect climate for cultivation of it to a new more desert like climate in the few months.

 

[nuke]

I have been looking into Perrottetinene for a year, but unfortunately the only place I have seen it will not sell to private individuals. Finding Radula Marginata is no easier...

The following species also contain Perrottetinene:
Radula perrotettii
Radula laxiramea

 

[fryingsquirrel]

Fascinating, I remember reading about some lysergamide producing endophytic fungi but am quite shocked to hear this is the case with morning glories.

+ 1
I was aware endophytic fungi were found in certain grasses but morning glories came as a total surprise.