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Plants of the the Convolvulaceae family and mushrooms

ungelesene_bettlek

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I have read somewhere that Plants of the the Convolvulaceae family and mushrooms are in a symbioitic relationship and the mushrooms belong to the same family or at least order than the ergot fungus. Is that true? Where can I find more scientific papers about that?
 
I think the English word you're looking for is "fungi", not "mushrooms" :). Even though they are the same in German ("Pilze"), the English word "mushroom" generally only refers to basidiomycetes (ex.: psilocybe cubensis, agaricus bisporus, amanita phalloides...), and more specifically their fruiting bodies.

Anyway... convolvulaceae (i.e. morning glories) tend to be associated with epiphytic and endophytic fungi, i.e. ones that symbiotically grow on or inside the plant, and it looks like these are the ones that produce the ergoline-type alkaloids. Indeed the evidence suggests that these are clavicipitaceouss, i.e. closely related to the ergot fungus, claviceps. It's hard to say anything definitive about the taxonomy of these fungi because fungal taxonomy has generally been in a constant state of flux over the past few decades, as molecular biology techniques have become more and more widely available to mycologists.

https://link.springer.com/article/10.1007/s00425-006-0241-0
 
OK, fungi, Pilze in German, thanks for that info!

So does the morning glory Ipomoea tricolor always live in symbosis with a fungus from the family also the Genus Claviceps belongs to? Does this fungus also have a symbiosis with other plants?

I have went to the Springer linkt and read the abstract - thank you a lot for that! But I will DEFINITELY not pay that horrendous amount for the full PDF. INFORMATION MUST BE FREE! Perhaps I go to the university library next week to get it for free.
 
OK, fungi, Pilze in German, thanks for that info!

So does the morning glory Ipomoea tricolor always live in symbosis with a fungus from the family also the Genus Claviceps belongs to? Does this fungus also have a symbiosis with other plants?

I have went to the Springer linkt and read the abstract - thank you a lot for that! But I will DEFINITELY not pay that horrendous amount for the full PDF. INFORMATION MUST BE FREE! Perhaps I go to the university library next week to get it for free.

Try here:

https://www.researchgate.net/public...rring_on_dicotyledonous_plants_Convolvulaceae

you can download a pdf version for free, I've checked and its all there.

Happy reading.
 
OK, fungi, Pilze in German, thanks for that info!

So does the morning glory Ipomoea tricolor always live in symbosis with a fungus from the family also the Genus Claviceps belongs to? Does this fungus also have a symbiosis with other plants?

We do not know much about the exact species of the fungi that live on or inside Ipomea tricolor. However, it looks like they colonize the plant's seeds, which would suggest that the fungus automatically gets passed on to the next generation. I also doubt that these can be cultivated in a petri dish, without a host plant... they might have evolved alongside their hosts for millions of years, possibly making their partnership an obligate one.
No idea whether you can deliberately "infect" other convulvolaceae with these fungi... the German wikipedia article (again, I'm assuming that you're German based on your user name) mentions that at least 23 out of 79 species in the genus Ipomea have been found to contain ergot alkaloids (albeit not necessarily in psychoactive quantities), but I am not sure whether that means that these are all completely different species of fungal symbiotes, too.

Botanists have been aware of the presence of such alkaloids in these plants since the 1960's, but the confirmation that these come not from the plants themselves, but from ergot-like symbiotes, seems to have been a relatively recent one.
 
Try here:

https://www.researchgate.net/public...rring_on_dicotyledonous_plants_Convolvulaceae

you can download a pdf version for free, I've checked and its all there.

Happy reading.
Cool, that worked well!

again, I'm assuming that you're German based on your user name
Yes, I live in the million city most worth living in and study at the Alma Mater Rudolphina. :)

PS: I now read the article you gave me, but I now found this dissertation (in German), which, I hope, will give me more: http://hss.ulb.uni-bonn.de/2007/1060/1060.htm . The epibiotic fungi got the labor names Iasa-F13 in Ipolmoea asarifolia and Tcor-F01 in Turbina corymbosa - you can find more about them by just googleing the labor names.
 
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I see this thread as super interesting since there's some reports say that FRESH seeds are quite better than old seeds and that's probably because the parasitic/symbiont fungus dies or stops its action once the plant is not "alive", or well, maybe is just because of the cycle, who knows.
The thing is that I've also read that if you consume germinated HBWR seeds the trip is super potent and super clean, so maybe that's because of the fungus reactivating?
it's a really interesting matter and I guess that in a few decades we could try to change some genes in certain plants to create more psychoactive symbionts...
 
I see this thread as super interesting since there's some reports say that FRESH seeds are quite better than old seeds

As has been demonstrated in this study, LSH is a labile compound, and therefore the variances in its concentration may be due to different age and storage conditions of the seeds rather than difference in plant metabolism. Indeed, seeds IT-HB2, which express highest concentration of LSH, were bought directly from the producer, whereas seeds IP-HB1 were purchased in retail stores.

Nowak J, Woźniakiewicz M, Klepacki P, Sowa A, Kościelniak P. Identification and determination of ergot alkaloids in Morning Glory cultivars. Anal Bioanal Chem. 2016 May;408(12):3093-102. doi: 10.1007/s00216-016-9322-5. Epub 2016 Feb 12. PMID: 26873205; PMCID: PMC4830885.
 
Resuscitating this thread...

Apparently the biosynthetic pathway has been established to rely on the epibiotic Clavicipitaceae fungi that colonize the Convolvulaceae species, meaning that the fungi producing LSA and the other various contributors to the psychoactivity in consumption of Morning Glory/HBWR/etc. are in the same fungal family as Claviceps purpurea, the fungus that colonizes rye and can cause ergotism. For more: https://doi.org/10.1016/j.funeco.2011.04.004 (if it is paywalled pop it into scihub).

As for how this can be interpreted to improve the potency of an experience when using the seeds of the plants, I'd think you're right Neuroborean, that the fresher the seeds the less amount of time that whatever symbiosis is going on between the fungus and the plant has been disrupted for. Of course, that also checks out in light of anecdotes of people faring better with fresh seeds. The length of germination drastically affects the seed alkaloid content, with the psychoactivity hard-hitters peaking in concentration around ~48hrs into germination if I remember correctly (there is a peer-reviewed alkaloid analysis study on this that I can't seem to find).

So I wonder if it is the fungal ergoline alkaloid pathway heating up, because that 40/50 hour mark is when they begin to sprout open, which is the plant's first stage of physical exposure to external predators. That would make sense, then, if the fungus were ramping up ergoline production to dissuade animals from eating the seeds. As a lay explanation that checks out, but regardless, 48 hours into germination is the best time to consume for potency, and if anyone knows the study that measured this please link it here.
 
Resuscitating this thread...

Apparently the biosynthetic pathway has been established to rely on the epibiotic Clavicipitaceae fungi that colonize the Convolvulaceae species, meaning that the fungi producing LSA and the other various contributors to the psychoactivity in consumption of Morning Glory/HBWR/etc. are in the same fungal family as Claviceps purpurea, the fungus that colonizes rye and can cause ergotism. For more: https://doi.org/10.1016/j.funeco.2011.04.004 (if it is paywalled pop it into scihub).

As for how this can be interpreted to improve the potency of an experience when using the seeds of the plants, I'd think you're right Neuroborean, that the fresher the seeds the less amount of time that whatever symbiosis is going on between the fungus and the plant has been disrupted for. Of course, that also checks out in light of anecdotes of people faring better with fresh seeds. The length of germination drastically affects the seed alkaloid content, with the psychoactivity hard-hitters peaking in concentration around ~48hrs into germination if I remember correctly (there is a peer-reviewed alkaloid analysis study on this that I can't seem to find).

So I wonder if it is the fungal ergoline alkaloid pathway heating up, because that 40/50 hour mark is when they begin to sprout open, which is the plant's first stage of physical exposure to external predators. That would make sense, then, if the fungus were ramping up ergoline production to dissuade animals from eating the seeds. As a lay explanation that checks out, but regardless, 48 hours into germination is the best time to consume for potency, and if anyone knows the study that measured this please link it here.
Really interesting stuff baka, it would be super cool to see that paper; still can't quite get over the fact that the specific periglandula clandestina species (which symbioses with Ipomea Tricolor) wasn't discovered until 2025 even after over half a century of recreational use in the west. It is equally interesting how Hofmann, when he first isolated ergot alkaloids from morning glory, initially believed that they had to have been the result of some fungal biosynthetic pathway but ultimately came to the conclusion that it wasn't because he couldn't find any fungus in the seeds.
 
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Really interesting stuff baka, it would be super cool to see that paper; still can't quite get over the fact that the specific periglandula clandestina species (which symbioses with Ipomea Tricolor) wasn't discovered until 2025 even after over half a century of recreational use in the west.

It was discovered in 2004 that a symbiotic fungus is on Ipomoea asarifolia. A little later on, the same discovery was made for what people usually call Rivea corymbosa.

This is a copy of a post I made on The Shroomery:

An estimated 450 species of morning glory may be colonized by Periglandula fungi.[ 1 ] Periglandula fungi were first described in a 2011 study on Ipomoea corymbosa (the seeds of which are "ololiuhqui") and Ipomoea asarifolia.[ 2 ] The study that kicked off this subject of research was done in 2004[ 3 ]: "The study provides strong evidence that ergoline alkaloids in I. asarifolia are produced by a plant-associated fungus, not the plant itself." (Grok)


1. "an estimated 450 species may be colonized by Periglandula species and thus contain ergot alkaloids."

The Genus Periglandula and Its Symbiotum with Morning Glory Plants (Convolvulaceae). Leistner E, Steiner U. 2018. doi:10.1007/978-3-319-71740-1_5 [Anke T, Schüffler A (eds.). Physiology and Genetics. Cham: Springer International Publishing. pp. 131–147. ISBN 978-3-319-71739-5.] (Abstract)


2. Periglandula, a new fungal genus within the Clavicipitaceae and its association with Convolvulaceae. Steiner, U., Leibner, S., Schardl, C. L., Leuchtmann, A., & Leistner, E. 2011. Mycologia, 103(5), 1133–1145. doi:10.3852/11-03


3. Kucht, S., Gross, J., Hussein, Y., Grothe, T., Keller, U., Basar, S., König, W. A., Steiner, U., & Leistner, E. 2004. Elimination of ergoline alkaloids following treatment of Ipomoea asarifolia (Convolvulaceae) with fungicides. Planta, 219(4), 619–625. doi:10.1007/s00425-004-1261-2
 
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Really interesting stuff baka, it would be super cool to see that paper; still can't quite get over the fact that the specific periglandula clandestina species (which symbioses with Ipomea Tricolor) wasn't discovered until 2025 even after over half a century of recreational use in the west. It is equally interesting how Hofmann, when he first isolated ergot alkaloids from morning glory, initially believed that they had to have been the result of some fungal biosynthetic pathway but ultimately came to the conclusion that it wasn't because he couldn't find any fungus in the seeds.
I mean the fact that none of the Ipomoea or ergoline-producing Convolvulaceae fungal symbionts had been characterized until the 2010s is astonishing itself. Ipomoea tricolor's only recently being discovered and taxonified is particularly crazy because it has been one of the primary species for modern recreational use - which has been a catalyst for a lot of research into the molecular makeup of the plant and its seeds in the 21st century (typically in the name of reducing harm in and increasing info available on "legal highs").

Yes the fungi are only sometimes (and even then, barely) visible to the naked eye, so that is a fair conclusion on Hoffman's part given what resources were available at the time. Plus, while the biosynthesis of the ergolines happens only with the fungus, the resulting alkaloids are translocated across its plant symbiont, so without indication of fungal colonization, it'd be reasonable to conclude the plant synthesizes them itself. Ofc expecting a fungi-plant symbiosis would be equally reasonable so props to him.

On a tangent, have you seen this paper: https://pmc.ncbi.nlm.nih.gov/articles/PMC12982482/pdf/41598_2026_Article_39568.pdf
Scientific Report is world-renowned, and open access...the methodology is a bit much for me but I understand enough to see that it does support the Eleusinian Mystery Kykeon hypothesis...
 
Ipomoea tricolor's only recently being discovered and taxonified is particularly crazy because it has been one of the primary species for modern recreational use

It's not surprising at all. Even psychedelic researchers could care less about natural ergolines. Although, with the recent kykeon paper you mentioned, that could be changing.

"In the late 1960s, when I started my research on these matters, I went to Mexico to experiment with morning glory seeds. To begin, I extracted several kilos of seeds using a simple process, purifying an alcoholic extract between organic solvents in the alternating presence of aqueous solutions of ammonia and tartaric acid."

"After a couple days' work, I obtained a nearly colorless syrup that exhibited the bright-blue fluorescence typical of active lysergic acid compounds. A few milligrams of this syrup, taken in a capsule, produced one of the most powerful psychedelic experiences I had known—and by then I had already taken high dose LSD several times, as well as a few other notorious psychedelic agents."

Peter Webster. The Mythology and Chemistry of the Eleusinian Mysteries [lecture]. Jan 13 2006. LSD: Problem Child & Wonder Drug symposium. Basel, Switzerland 
h‍ttps://www.youtube.com/watch?v=uwfkJkvbR-I&t=4125s 1:08:45–1:09:36
 
It's not surprising at all. Even psychedelic researchers could care less about natural ergolines. Although, with the recent kykeon paper you mentioned, that could be changing.
Fair point - I'm saying from the perspective that recognizes how widespread medicinal and modern recreational use is it comes off as wildly surprising. I hope that attention shifts towards them given the increasing tenability of the Kykeon connection, and that that question itself gets more thorough exploration.
 
On a tangent, have you seen this paper: https://pmc.ncbi.nlm.nih.gov/articles/PMC12982482/pdf/41598_2026_Article_39568.pdf
Scientific Report is world-renowned, and open access...the methodology is a bit much for me but I understand enough to see that it does support the Eleusinian Mystery Kykeon hypothesis...
I've skimmed it before, but yeah certainly deserves a full read. On a side note, I would be naturally inclined to believe that the kykeon, assuming it was actually psychoactive in any meaningful sense at all (which is an assumption a lot of people seem to make, not an absurd one, but an assumption nonetheless), was ergotic in nature just based on geographic availability alone.
 
I've skimmed it before,

A good tactic is to give articles to AI agents and ask them to summarize them for you. I had a summary made for that one:

Summary: "Investigating the Psychedelic Hypothesis of Kykeon, the Sacred Elixir of the Eleusinian Mysteries"

Background & Context

The Eleusinian Mysteries were annual religious initiations held for nearly two millennia near Athens, drawing participants from across the Mediterranean. At their heart was the consumption of kykeon (κῠκεών), a ceremonial drink described in the Homeric Hymn to Demeter as made from water, barley, and mint (pennyroyal). Scholars have long debated whether kykeon was merely symbolic or contained a psychoactive ("entheogenic") substance capable of inducing the profound experiences — described as ego dissolution, encounters with death, and spiritual "rebirth" — reported by ancient initiates like Pindar and Cicero.

The Ergot Hypothesis

In 1978, mycologist R. Gordon Wasson, LSD-synthesizer Albert Hofmann, and classicist Carl A. P. Ruck proposed in The Road to Eleusis that ergot (Claviceps purpurea), a parasitic fungus that grows on barley, was the secret psychoactive ingredient. Ergot produces ergot alkaloids (EAs), chemically related to LSD. Archaeological support exists: ergot fragments were found both inside a ceremonial vase and in the dental calculus of a man at a sanctuary dedicated to the Eleusinian goddesses at Mas Castellar de Pontós, near an ancient Greek colony in Spain.

The key problem with this hypothesis has always been ergot's toxicity. Unprocessed ergot causes ergotism ("Saint Anthony's Fire"), with symptoms including hallucinations, burning sensations, convulsions, gangrene, and death — it killed 50,000 people in a 1418 Paris epidemic alone. How could ancient priestesses have administered it safely to thousands of initiates?

The Study's Central Question

The authors tested a previously proposed but never experimentally verified solution: that Eleusinian priestesses may have used lye (alkaline water made from wood ash) to chemically transform the toxic ergot compounds into safer, psychedelic ones. Ancient Greeks were known to use alkali-based medicines, making this plausible. Specifically, the hypothesis was that boiling ergot in lye would hydrolyze the toxic ergopeptides (like ergocristine and ergokryptine) into the psychedelic lysergamides — primarily LSA (lysergic acid amide) and its epimer iso-LSA — compounds structurally related to LSD and known to cause euphoria and hallucinations.

Experimental Methods

The team collected Claviceps purpurea ergot sclerotia, confirmed by molecular (ITS rDNA) and microscopic analysis. They prepared wood ash lye solutions (burning oak and olive wood) at initial pH levels of 10.5, 11.5, and 12.5. A full factorial experimental design tested 48 combinations of three variables: lye pH, ergot concentration (5%, 10%, 20% w/v), and reaction time (15, 30, 60, 120 minutes at 100°C). Products were analyzed by TLC, NMR spectroscopy, and UHPLC/Q-TOF-HRMS (high-resolution mass spectrometry). LSA and iso-LSA reference compounds were first isolated and fully characterized from Argyreia nervosa seeds.

Key Results

The critical finding was that complete hydrolysis of toxic ergopeptides occurred under specific conditions: 5% w/v ergot, initial lye pH 12.5, refluxed for 120 minutes. Under these conditions:

• All six major toxic ergopeptides (ergotamine, ergocristine, ergokryptine, ergosine, ergocornine, ergometrine) and their epimers were completely undetectable by mass spectrometry.

• The products were LSA and iso-LSA at yields of 0.54 mg/g and 0.48 mg/g of ergot used, respectively.

• NMR confirmed the disappearance of the amide bonds characteristic of toxic ergopeptides and the appearance of spectral signatures matching LSA and iso-LSA.

• Only trace amounts of ergometrine (a simpler, far less toxic lysergamide) persisted, which poses no significant danger.

• Statistical modeling confirmed lye pH was the sole significant predictor of yield, with a quadratic relationship (R² ~0.83 for LSA).

Practicality for Ancient Use

The authors addressed the concern that a pH >11.5 solution would be caustic to drink. They demonstrated that natural atmospheric CO₂ exposure over days, combined with the addition of ergot powder itself, neutralized the initial pH to safe levels. Adding the resulting solution to a slightly acidic barley-mint preparation would reduce it further, making it drinkable.

Regarding quantities: with roughly 0.54 mg LSA per gram of ergot, and a minimum effective dose of ~0.5 mg LSA, approximately 1 gram of ergot per initiate would suffice. For up to 2,000 initiates, priestesses would have needed only a few kilograms of ergot sclerotia — a manageable and concealable amount. This need may have been even lower given the nine-day fast observed by initiates before drinking kykeon (fasting amplifies psychedelic sensitivity), and the intense ritual setting.

Ergot sourcing was plausible: every Greek city-state contributed grain offerings to Eleusis, and the fertile, marshy Thriasian Plain surrounding Eleusis provided suitable conditions for localized C. purpurea infection of barley.

Psychoactivity of LSA and Iso-LSA

[I'm replacing Cluade's text in this section with the text in the document (from the middle of page 14).]

[ … ] in a β-arrestin2 recruitment assay, LSA exhibited approximately 100-fold lower potency than LSD at both the 5-HT₂A and 5-HT₂B receptors, while remaining notably active, with EC₅₀ values of 58 nM and 54 nM, respectively46. Regarding iso-LSA, it has demonstrated measurable affinity for central 5-HT binding, as reported in early QSAR studies47. Notably, it displaced both 3Hserotonin and 3HLSD from rat cerebral cortex membranes with pIC50 values of 7.00 and 6.70, respectively and exhibits a log P of 0.95, consistent with moderate lipophilicity and potential for blood-brain barrier permeability47. In vivo studies further support its central activity48. Iso-LSA administered intraperitoneally to rats reached measurable concentrations in the brain correlating with behavioral effects such as decreased conditioned avoidance response, indicating that the parent compound, rather than a metabolite, acts as the psychoactive agent48. Therefore, despite its isomeric difference from LSA, iso-LSA (being the C-8 (S) epimer, which are usually considered inactive)39 may retain central serotonergic activity relevant to psychedelic potential. Additionally, the result of each of the kykeon preparations was an equilibrium mixture of LSA and iso-LSA, which may be more psychoactive than either pure alkaloid alone28. However, further pharmacological and toxicological evaluations are necessary to define the exact safety profile and receptor affinities of the resulting mixtures. Another key factor is that "set and setting" predominantly shape the experience, the substances merely acting as tools2. In an ancient ritual framework, marked by botanical synergism, fasting, and heightened expectancy, their psychedelic potential would have been amplified. At Eleusis, optimal ceremonial conditions gave these entheogens a meaningful role, showing that their effects must be understood within a religious context, rather than purely pharmacological terms.

The Role of Pennyroyal

The authors propose that pennyroyal (Mentha pulegium), the mint ingredient in kykeon, may have played a synergistic role. Its main compound, pulegone, interacts with CNS pathways involved in sedation and psychotropic activity, and its rosmarinic acid content modulates MAO-A (which breaks down neurotransmitters). This suggests an "entourage effect" analogous to terpene–THC synergy in cannabis or the DMT–β-carboline interaction in ayahuasca, potentially prolonging and deepening the entheogenic state.

Conclusion

The study provides the first experimental demonstration that crude ergot sclerotia can be detoxified into psychoactive lysergamides using only wood ash lye and heat — a technique accessible to ancient priestesses. The authors conclude this strongly supports the Wasson-Hofmann-Ruck hypothesis that ergot was the entheogenic agent in kykeon, and that the Eleusinian Mysteries were built around a genuinely psychedelic experience. They call for future organic residue analysis of archaeological vessels from the Eleusis site to provide material confirmation.

Written by Claude
 
The hydroxyethylamide long thought to be psychoactive actually can never reach the brain, since this compound is a labile adduct of ergine and acetaldehyde. It is therefore transformed into ergine and isoergine rapidly, even by mild extraction methods.

vbest regards,
peter


Peter Webster. Quoted by @tregar, https://drugs-forum.com/threads/lucid-visual-morning-glory-extract-theory.30919/#post-184703 2006-09-04



LAHydroxyethylamide was not discovered right away since even gentle extractions tended to convert it all to ergine/isoergine, so this would indicate that the equilibrium lies far toward the ergine/isoergine side of the equation. And it suggests strongly that to produce LAH from ergine you would need some special conditions, which are probably not just having it in the presence of even higher concentrations of acetaldehyde, amounts that you wouldnt at all want to ingest!

Also, since LAH->>ergine in mild conditions, you must assume that it would happen in the bloodstream, even if LAH were able to pass the digestive tube. So there is anotherdoubt about whether it could actually arrive at brain receptors.

Of course, there may be some complicating factors here that aren't described in the papers I've read, That's possible with a great many aspects of LA chemistry (there are still a couple of quite important and unexplained results I got in certain experiments - I even asked Sasha and he couldn't clarify!) but for me, the odds of LAH getting to receptors and causing the initial reaction leading to psychedelic experience are quite low.


Peter Webster, 2016-01-05, personal correspondance
 
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