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Ipomoea and Clavine alkaloids Options
 
8-Serpent-Wind
#1 Posted : 7/19/2022 3:17:02 PM

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I intend this to be ongoing and will revise the initial post over times.

To begin I am attaching two PDF files.

One is about Ipomoea nervosa aka Argyreia nervosa known colloquially as Hawaiian Baby Woodrose. This particular paper is a scare piece with a lot of bad information but it also has some accurate chemistry in it and I include it to illustrate the clavine alkaloid content that has been found in the species.

The second paper is about Ipomoea alkaloids as well and shows clavine and lysergic content as well.


It is my hypothesis that the alkaloids in Ipomoea that cause psychedelic effects are the Clavine alkaloids and not LSA, LAH nor any adduct.
I will address this here in an ongoing fashion.
Thank you for your patience.
 

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8-Serpent-Wind
#2 Posted : 7/19/2022 3:22:15 PM

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Some more papers about clavines and animals.

Note that there is not 1 single verified report of pure LSA causing psychedelic effects in any human being. Every single case of ingestion of Pure LSA in isolated form results in sedation.
The papers I include with this post also shows this categorically in animals, that LSA is a sedative.

However the papers also show that some alkaloids cause LSD like effects in animals and those alkaloids are largely clavines.
 
_Trip_
#3 Posted : 7/20/2022 12:44:33 AM

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This is exactly what I've been reading into lately.

Likely why there is a difference reported in trips between HBWR and MG.
Disclaimer: All my posts are of total fiction.



 
brokedownpalace10
#4 Posted : 7/20/2022 11:52:10 AM
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Interesting. Probably likely.

Would the clavines be unstable?
Changing existing seeds' effects with an adduct seems pretty sketchy, but the difference between fresh or immature seeds and old ones seems more supported.

A thread with peoples experiences in the differences between fresh and old might be interesting, actually.
 
benzyme
#5 Posted : 7/21/2022 5:55:48 PM

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The clavines are metabolic intermediates, precursors to lysergic acid derivatives and amides. I don't know whether or not they're centrally active (psychedelic), just that they are known to have vasoconstrictive properties as well, possibly due to adrenergic activity. I had seen alot of them in my experiments analyzing the fermentation broth of claviceps a little over a decade ago.
"Nothing is true, everything is permitted." ~ hassan i sabbah
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Mindlusion
#6 Posted : 7/21/2022 11:41:18 PM

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Very often in the case of natural products, when the natural product chemists isolate and characterize the molecules , very often it is the case that the natural products identified are actually various secondary metabolites, produced via radical oxidation from sunlight and/or catalyzed by oxidative (and reductive in some case) enzymes that are released and activated when the plant cells are broken down. Now it isn't always clear whether these transformations are coincidental, or if they are specifically designed this way, which in the majority of cases, there is plenty of evidence for the latter.

To give an example, a plant produces a molecule that is inactive but a simple transformation spring loads it into an active form. Often the active molecules, depending on their purpose (antibacterial or antifungal, or insecticide, for instance) are quite reactive themselves and have a short half-life and can be damaging to the plant as well, so the plant evolved a mechanism to produce a natural product pro-drug that is only activated when the plant suffers damage to its cells, which release the activating enzyme to convert the molecule to the active form.

Now this does not necessarily mean that these secondary metabolites are not 'natural products' even if they are not even produced by enzymes but instead by oxygen or sunlight, the plant could have intended these just as well, and even if they are not intended, really what's the difference? Currently i'm synthesizing some natural products, a family of which is all related to a commmon precursor, and displays the same behavior, the metabolites however show even more potent activity as anti-inflammatory and anti-cancer than the prodrugs produced by the plant itself.

In the case claviceps and ipomoea, it is very interesting and quite complex. The Ipomoea itself of course does not produce any alkaloids, but some specific species of claviceps have co-evolved and existed this way for such a long period of time, it is difficult for either the plant or fungi to live long without the other, they are like organs for some combinatorial lifeform. Of course, with artifical selection pressures, we can select for adaptions , mutations, that are desirable , for claviceps for example, But even today with modern biotech, these strains cannot sustain more then a few generations before their genetics deteriorate, the only way to really slow this process down and preserve an artificially selected strain is to slow down the replication, with a -80C freezer. Just goes to show how little we really know about genetics, epi-genetics, and the intricate balance of these systems and how even small modifications can cause massive problems downstream that only become apparent after 2-3 generations

Yeah, if you get my point, which is subtly referring to something off topic, that's what I think about scientific 'consensus'
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benzyme
#7 Posted : 7/22/2022 2:59:33 AM

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The ergoline pathway gene cluster is a well studied one, going back to the 1950's. There was also a slew of papers in mid 00's that elucidated the dMAW gene was responsible for initiating the production of clavines and ergolines in a wide range of endophytes and claviceps spp.; that gene activates the expression of dimethylallyl-tryptophan synthase, the enzyme producing the precursor of clavines such as chanoclavine I and II. The seeds are sources of endophytes related to those found in S.robusta, aka "sleepygrass". Arcamone et al. showed in 1961 that C.Paspali with the activated gene (the stevens and hall strain) was a producer of LSH, at around 14-20 days of fermentation.
"Nothing is true, everything is permitted." ~ hassan i sabbah
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Mindlusion
#8 Posted : 7/22/2022 2:46:39 PM

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benzyme wrote:
The ergoline pathway gene cluster is a well studied one, going back to the 1950's. There was also a slew of papers in mid 00's that elicidated the dMAW gene was responsible for initiating the production of clavines and ergolines in a wide range of endophytes and claviceps spp.; that gene activates the expression of dimethylallyl-tryptophan synthase, the enzyme producing the precursor of clavines such as chanoclavine I and II. The seeds are sources of endophytes related to those found in S.robusta, aka "sleepygrass". Arcamone et al. showed in 1961 that C.Paspali with the activated gene (the stevens and hall strain) was a producer of LSH, at around 14-20 days of fermentation.


Yes indeed, this is exactly what I was referring to. Lab strains of claviceps fungi (stevens and hall) that have been selected for production, have managed to artificially select and culture strains of the fungi with a mutation in that gene, so that LSH production is increased and can persist outside the normal life cycle of the fungi, and within a liquid culture medium instead of within the plant and seeds of the Ipomoea. The wild strain of the fungi does not produce any LSH or any ergot alkaloids when it is cultivated outside of its natural environment, it reverts to a dormant state where it can continue to thrive as a mycelium but never sexually reproduce or produce any alkaloids.

But unfortunately, these kinds of artificial selections that we can do in the lab, are not stable across time, the genetic mutations that are selected for tend to hurt the viability of the organism to reproduce. Like the bananas you eat. If you were to obtain a production strain of C Paspali today, it is a direct transfer from that original 1961 strain. The only way to keep is to keep a culture tube frozen at -80C and limit the number of transfers made. So the strain itself when used for production will only last a number of cycles before it needs to be thrown out

Expect nothing, Receive everything.
"Experiment and extrapolation is the only means the organic chemists (humans) currrently have - in contrast to "God" (and possibly R. B. Woodward). "
He alone sees truly who sees the Absolute the same in every creature...seeing the same Absolute everywhere, he does not harm himself or others. - The Bhagavad Gita
"The most beautiful thing we can experience, is the mysterious. The source of all true art and science."
 
benzyme
#9 Posted : 7/22/2022 2:55:46 PM

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Yeah, I definitely saw that after five generations of transfers, and read about that phenomenon in the attached paper.
That dMAW gene is the on-switch for the entire ergoline pathway, it is a effectively a promoter gene. It is normally a dormant pathway, as tryptophan is typically used for structural protein synthesis.

There have been some studies which have shown that histone acetyltransferase inhibitors (post-translation modifiers) induced promotion of ergoline production, but I've never experimented with them. A peer on another forum had experimented with garcinol, and did get phenotypic differences on the morphology which indicated some change in the growth cycle had occurred, but he lacked the ability to screen the samples for secondary metabolite production.
"Nothing is true, everything is permitted." ~ hassan i sabbah
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benzyme
#10 Posted : 7/22/2022 4:37:57 PM

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For those wondering why I'm posting about claviceps instead of ipomoea, it's because the gene cluster is the same. Periglandula Ipomoeae is the endophyte in Ipomoea spp.

Quote:
Clavicipitaceous fungi isolated from the two different plant species could be distinguished by their atp6 and rpbA sequences, and nuclear genes for γ-actin (actG), translation elongation factor 1–α (tefA), and 4–(γ,γ-dimethylallyl)tryptophan synthase (dmaW), the determinant step in ergoline (i.e. ergot) alkaloid biosynthesis. Based on these findings we propose a new fungal genus, Periglandula, gen. nov., and describe two new species, Periglandula ipomoeae sp. nov., from host plant I. asarifolia, and Periglandula turbinae sp. nov., from T. corymbosa.


https://www.tandfonline....1-031?journalCode=umyc20
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benzyme
#11 Posted : 7/28/2022 3:42:37 PM

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Excellent read, probably the most comprehensive on this thread.

Diversification of ergot alkaloids and heritable fungal symbionts in morning glories
https://doi.org/10.1038/s42003-021-02870-z
"Nothing is true, everything is permitted." ~ hassan i sabbah
"Experiments are the only means of attaining knowledge at our disposal. The rest is poetry, imagination." -Max Planck
 
downwardsfromzero
#12 Posted : 7/31/2022 3:21:23 PM

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Beaulieu et al. 2021 is indeed great.

What is known of the pharmacology of these other clavine alkaloids?




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benzyme
#13 Posted : 8/2/2022 5:45:24 AM

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Chanoclavine is apparently a D2 agonist. I'm not sure about agroclavine or elymoclavine; I wouldn't be surprised if they had norepinephrine/a-adrenergic activity
"Nothing is true, everything is permitted." ~ hassan i sabbah
"Experiments are the only means of attaining knowledge at our disposal. The rest is poetry, imagination." -Max Planck
 
 
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