Looking for any information on psychoactive orchids and/or the action of phenanthrenoids

[Xorkoth]

My girlfriend is very into cultivating orchids. She was reading about a group of orchids which are used as entheogens - a collection of Oncidiums that got reclassified to "Trichocentrum". According to wiki:

The Central and South American species Trichocentrum cebolleta (known formerly as Oncidium cebolleta) has been found to contain a variety of phenanthrenoids.[3] This species is of considerable ethnobotanical interest as one of only a handful of orchids reported to be used as an entheogens. T. cebolleta is used as a substitute for hikuli a.k.a. peyote (the hallucinogenic cactus Lophophora williamsii) by the Tarahumara of Northern Mexico - a tribe noted for the large number of hallucinogenic plants which it uses in various shamanic and running-related practices. The combination of phenanthrenoid content and employment as entheogens in shamanic practices is to be found also in the Asiatic orchids Vanda tessellata and Dendrobium macraei (- known formerly as Ephemerantha macraei and Flickingeria macraei - see page Flickingeria). The orchidaceous genera Trichocentrum, Vanda and Dendrobium are all members of the subfamily Epidendroideae and are also placed currently in the subgroup/clade of Higher Epidendroids within the subfamily.

(emphasis is mine)

I looked into phenanthrenoids, as I had never heard that term before. It's a structural backbone for a variety of compounds, which are found in nature in these orchids. From wiki:

In orchids
Phenanthrenes have been reported in species of Dendrobium, Bulbophyllum, Eria, Maxillaria, Bletilla, Coelogyne, Cymbidium, Ephemerantha and Epidendrum.[3]

3,4,8-Trimethoxyphenanthrene-2,5-diol is one of the 17 phenanthrenes found in the extract of the stems of the orchid Dendrobium nobile.[7][8]

From the stems of the orchid Flickingeria fimbriata, three phenanthrenes can be isolated. The structures are 2,5-dihydroxy-4,9,10-trimethoxyphenanthrene, 2,5-dihydroxy-4-methoxyphenanthrene and 2,5,9-trihydroxy-4-methoxy-9,10-dihydrophenanthrene. These molecules are named plicatol A, B and C.[9]

Nudol is a phenanthrene of the orchids Eulophia nuda, Eria carinata and Eria stricta.[10] 9,10-Dihydro-2,5-dimethoxyphenanthrene-1,7-diol is a phenanthrene from Eulophia nuda. This compound shows cytotoxic activity against human cancer cells.[11]

2,7-Dihydroxy-3,6-dimethoxyphenanthrene is a phenanthrene from Dehaasia longipedicellata.[12]

Bulbophyllum gymnopus produces the phenanthrenediol gymnopusin.[13]

Bulbophyllum reptans contains gymnopusin, confusarin (2,7-dihydroxy-3,4,8-trimethoxyphenanthrene), 2,7-dihydroxy-3,4,6-trimethoxyphenanthrene and its 9,10-dihydro derivative, flavanthrinin (2,7-dihydroxy-4-methoxyphenanthrene) and its 9,10-dihydro derivative (coelonin), cirrhopetalanthrin (2,2′,7,7′-tetrahydroxy-4,4′-dimethoxy-1,1′-biphenanthryl), its 9,9′,10,10′-tetrahydro derivative (flavanthrin) and the dimeric phenanthrenes reptanthrin and isoreptanthrin.[14]

Bulbophyllum vaginatum contains the two phenanthrenes 4,9-dimethoxyphenanthrene-2,5-diol and 4,6-dimethoxyphenanthrene-2,3,7-triol, and the two dihydrophenanthrenes 4-methoxy-9,10-dihydrophenanthrene-2,3,7-triol and 4,6-dimethoxy-9,10-dihydrophenanthrene-2,3,7-triol.[15]

Coelogyne cristata contains coeloginanthridin (3,5,7-trihydroxy-1,2-dimethoxy-9,10-dihydrophenanthrene), a 9,10-dihydrophenanthrene derivative, and coeloginanthrin (3,5,7-trihydroxy-1,2-dimethoxyphenanthrene), the corresponding phenanthrene analogue, coelogin and coeloginin.[16]

Orchinol and loroglossol have a phytoalexin effect and reduce the growth of Cattleya aurantiaca seedlings.[17]

The phenanthrenes 2,5-dihydroxy-3,4-dimethoxyphenanthrene, 9,10-dihydro-2,5-dihydroxy-3,4-dimethoxyphenanthrene, 2,7-dihydroxy-3,4-dimethoxyphenanthrene (nudol), 9,10-dihydro-2,7-dihydroxy-3,4-dimethoxyphenanthrene, 2,5-dihydroxy-3,4,9-trimethoxyphenanthrene and 2,7-dihydroxy-3,4,9-trimethoxyphenanthrene can be isolated from Maxillaria densa.[18]

Cirrhopetalanthrin is a dimeric phenanthrene derivative from Cirrhopetalum maculosum.[19]

Glycosides
Five phenanthrene glycosides, denneanoside A, B, C, D and E and one 9,10-dihydrophenanthrene glycoside, denneanoside F, can be isolated from the stem of Dendrobium denneanum.[20]

If you check the wiki I linked to for phenanthrocenes, it gives links to a lot of what is mentioned above in the quote. Unfortunately I can't seem to find anything about their psychoactivity or pharmacology. Does anyone know anything about this? I'm super curious now. I had never heard of enthegenic orchids, and apparently one species substitutes for peyote for the Tarahumara people. But I am unable to find any written accounts or really much of any information on the effects of this plant. But I'm fascinated by the possibility of a new family of molecules that could be explored for psychoactive or even psychedelic effects.

 

[sekio]

Given the lack of a basic nitrogen and the high logP due to the planar aromatic nature of these, I womder if they are paychoactive at all. Some of them could be carcinogenic, like dioxins, thanks to their planar.aromatic shape.

I recall reading once that oxycodone was found in an orchid of some sort...

 

[Xorkoth]

Oh wow, really?

I find it interesting that the tribe mentioned in the quote above uses a species of orchid "to substitute for peyote". It's a tribe known to use a wide variety of psychoactive plants. That's the part that really piqued my curiosity. Although for all I know, they use it to substitute for a really low dose of peyote that is used to heighten the senses for hunting or something. There really is very little detail to go on.

 

[allone]

so thats all there is?? man, im starving for more information regarding some supposedly psychoactive orchids. it reminds me of "Adaptation" where Maryl Streep character gets high on ghost orchids

 

[allone]

there is one with some reported use as possible psychoactive; https://en.wikipedia.org/wiki/Vanda_tessellata
it contains both pain relieving and aphrodisiac qualities in the roots.

 

[mp44god]

Given the lack of a basic nitrogen and the high logP due to the planar aromatic nature of these, I womder if they are paychoactive at all. Some of them could be carcinogenic, like dioxins, thanks to their planar.aromatic shape.

I recall reading once that oxycodone was found in an orchid of some sort...

How could a synthetic opioid be found in a plant?

 

[polymath]

How could a synthetic opioid be found in a plant?

Conversion of morphine to oxycodone can happen biosynthetically. There's even an artificial strain of yeast that does this.

A microbial biomanufacturing platform for natural and semi-synthetic opiates

Opiates and related molecules are medically essential, but their production via field cultivation of opium poppy Papaver somniferum leads to supply inefficiencies and insecurity. As an alternative production strategy, we developed baker's yeast Saccharomyces ...

www.ncbi.nlm.nih.gov

 

[sekio]

Ref for oxycodone in orchids: [paper].

It's possible it comes from soil contamination, but also possible that it could be biosynthesized... I recall codeinone can be converted to 14-hydroxycodeinone (dehydrooxycodone) by simple action of metal ions and oxygen.

 

[G_Chem]

I still think that analysis had to of been a cross contamination or something... I’d need to see multiple analysis to believe Oxycodone appears in some random orchid.

-GC

 

[Skorpio]

I'm really leery of that oxycodone finding. There aught to be precursors in non-negligable amounts for anybody to be able to claim plant production of a compound.

At least it wasn't as bad as the gcms paper that found Prozac in plants and suggested that they had a novel finding and not environmental contamination. Like if anybody found a plant enzyme that could produce trifluoromethyl groups they would get like a nobel or at least a news and views in a top tier journal.

 

[allone]

^ what about when they found amphetamines in those trees in texas.... https://en.wikipedia.org/wiki/Senegalia_berlandieri
i wonder if that was also contamination...

but anyway back on topic. i hope someone helps me find out more about the OP's original interest finding out if those are for real or not!

 

[G_Chem]

^ what about when they found amphetamines in those trees in texas.... https://en.wikipedia.org/wiki/Senegalia_berlandieri
i wonder if that was also contamination...

but anyway back on topic. i hope someone helps me find out more about the OP's original interest finding out if those are for real or not!

Lol didn’t that one have like meth, Mescaline and other shit.. Quite obviously another example of cross contamination.

-GC

 

[allone]

yeah. i feel soooo stupid back then when i read this article i went nuts!!! i wanted that shit so bad, i ordered some as powder over the net, but it was probably another acacia species so i was already fucked anyway. but yea, such BS lol!!

 

[polymath]

There was also diazepam found in potatoes, allegedly as a result of traces of it in water supply.

 

[allone]

There was also diazepam found in potatoes, allegedly as a result of traces of it in water supply.

but the creator of diazepam does admit he got the idea originally from something to do with potatoes. so they might contain something similar and it was probably mistaken for diazepam

 

[Anonymous Dissident]

There was also diazepam found in potatoes, allegedly as a result of traces of it in water supply.

I thought it was diazepam found in lettuce??

 

[allone]

I thought it was diazepam found in lettuce??

lol maybe it was all over the place. were those scientists based in some empoverished indian compound pharmacy?