perrottetinenic acid

[tryp2fun]

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

Here are some references:

Molecular characterization of a seed transmitted clavicipitaceous fungus occurring on dicotyledoneous plants (Convolvulaceae). Steiner U, Ahimsa-Müller MA, Markert A, Kucht S, Gross J, Kauf N, Kuzma M, Zych M, Lamshöft M, Furmanowa M, Knoop V, Drewke C, Leistner E. Planta. 2006 Aug;224(3):533-44. Epub 2006 Mar 9.

Clavicipitaceous fungi associated with ergoline alkaloid-containing convolvulaceae. Ahimsa-Müller MA, Markert A, Hellwig S, Knoop V, Steiner U, Drewke C, Leistner E. J Nat Prod. 2007 Dec;70(12):1955-60.

Biosynthesis and accumulation of ergoline alkaloids in a mutualistic association between Ipomoea asarifolia (Convolvulaceae) and a clavicipitalean fungus. Markert A, Steffan N, Ploss K, Hellwig S, Steiner U, Drewke C, Li SM, Boland W, Leistner E. Plant Physiol. 2008 May;147(1):296-305.

 

[Astavats]

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*

It might actually work well. Compare it to AM-411's structure - they're almost identical, with minor differences, and a adamantane group tacked in place of the phenylethyl group. Of course in the end receptor preferences might not fit this comparison.

 

[Hammilton]

Almost identical? Not close. there's a huge difference between a big bulky and bulbous adamantane vs. a flat, aromatic phenyl ring.

 

[fastandbulbous]

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.

OK 5-methoxytryptamine being found in various plant species and also Bufo marines (cane toad) - OK that's clutching at straws

Oh wait, morphine in Paperver somniferum and trace amounts being found in the mammalian brain that can only have come from synthesis as opposed to ingesting morphine

I'm getting into Fortean Times territory here...

 

[vecktor]

Almost identical? Not close. there's a huge difference between a big bulky and bulbous adamantane vs. a flat, aromatic phenyl ring.

see my earlier post, the structure is very similar to levonatradol indicating that both CB1 and CB2 can accept a terminal phenyl on the sidechain.
I for one would not bet aginst this being an active CB1 CB2 agonist.

 

[Turing Machine]

fftopic:

I'm getting into Fortean Times territory here...

Have I found a fellow Discordian and Keeper of the Sacred Chao perhaps? "We Discordians Have To Stick Apart!" RAW was one of the great losses of the last few years but in good company with Evel Knievel, George Carlin, James Brown, Dennis Hopper and others I'm sure to be missing.

 

[Astavats]

Almost identical? Not close. there's a huge difference between a big bulky and bulbous adamantane vs. a flat, aromatic phenyl ring.

Agreed, though this is irrelevant as you misunderstood my post. What I said was "they're almost identical, with minor differences, and a adamantane group tacked in place of the phenylethyl group." By this I meant the majority of the structure is essentially the same, aside the stereo and double bond being moved over, which I implied with 'minor differences'. With this similarity granted it becomes only a issue of substitution - if adamantane worked phenylethyl might fit as well.

A side note English is not my first language and my articulation is weak. I tried to express it as clear as possible though apparently not clear enough. Hope this cleared things up.

 

[Hammilton]

see my earlier post, the structure is very similar to levonatradol indicating that both CB1 and CB2 can accept a terminal phenyl on the sidechain.
I for one would not bet aginst this being an active CB1 CB2 agonist.

right, if it weren't, this isn't one I'd be persuing, but I am, and will continue to do so. That and growing liverworts seems like an interesting challenge.

finding it has been a much larger challenge, though.

 

[Turing Machine]

That and growing liverworts seems like an interesting challenge.

I don't know about this genus particularly but cultivation might not be very challenging. Some liverworts are considered greenhouse pests in some regions.

 

[Hammilton]

Cultivation turns out to be extremely difficult. Attempting to keep it alive indoors or anywhere is very difficult, even by taking the bark off the tree it's growing on. I tried varying the humidity, the light, nothing I tried managed to keep it alive.

After consulting with a number of researchers in the area, I've concluded that growing this plant is not feasible. It grows too slow, and worse, it's next to impossible to get started.

The best advice I've received yet would be to try growing it in M&S culture media. I would like to do this, but at the same time, I don't know that the tiny return (ie, a very slow growing plant) would be worth the extensive effort necessary to produce it.

If anyone is interested in attempting it, I'd try to obtain the closely related Radula complanata first. It's widely available throughout the world, at least all of Europe and as far as I can tell, all of the US. I found it in Wisconsin after a lot of work. After finding it the first time, I suspect it wouldn't be that hard to repeat. It's just finding it that first time. Clue: Look at logs that are really rotting away lying on the ground in a pine forest. That's where I found all of my samples.






It wasn't mentioned in this thread, but the problem with perrottetinene is not the 3-phenethyl group, but the cis-isomerism. trans- is far more desirable. Just need to convert it from one to the other.

Does anyone here have experience with converting this particular compound? It has been mentioned at other forums, I'm posting here hoping that someone from one of the forums I'm not a member who has tried this reads this and can comment.

 

[bloodshed344]

OP, go here and click on reference #2:
http://en.wikipedia.org/wiki/Radula_marginata

it links to a guy with the same interest as you.