Ipomoea pes-caprae

Looks quite interesting actually.

According to:

Jirawongse, V., T. Pharadai, and P. Tantivatana. 1979. The distribution of indole alkaloids in certain genera of Convolvulaceae growing in Thailand.
Journal of the National Research Council of Thailand. 9:17-24.

...the leaves produce the indole alkaloid ergotamine that protects the plant from most insects and large grazing mammals such as horses and donkeys.

Ipomoea pes-caprae is one of the most widely distributed beach plants throughout tropical and subtropical areas in the world. It occurs along the beaches, coastal strands and tropical islands of tropical North and South America, east central Africa, west central Africa, India, Asia, and Australia. In North America, I. pes-caprae occurs from Florida, and west through the Gulf of Mexico and the Bahamas. Its range extends from approximately 30° North latitude to 30° South latitude. The extent of these limits are directly determined by climate, as I. pes-caprae does not tolerate prolonged frost conditions.

Aloha! I just fear the journal might be somewhat hard to obtain.


[Edited on 26-7-2006 by Vitus_Verdegast]

I find it very hard to believe that an Ipomea species would produce ergotamine. Ipomea species producing ergine and similar simple lysergic amides is one thing, but to make ergotamine it would be way too much of a coincidence even with all the surprises evolution can prepare us. I do however remember of having read about Ipomea pes-caprae containing lysergamides, but don’t remember which ones (if it was ever even established which ones).
Ergotamine would be plausible, of course, if it is a symbiotic combination like in the cases of Stipa robusta + Acremonium spp. Or the well known parasitic rcombinations of rye + Claviceps sp. (and less known Epichloë typhina parasiting on Lolium perenne, Cynodon dactylon, Festuca arundinaceae, Agrostis perennans…). But of all these hosts for the fungi producing ergotamine or other ergotoxins I never ever heard of Ipomea sp., only various cereals and similar herbs.
Anything is possible however. There is even one species from Columbia, Ipomoea carnea, where lysergic acid ethylamide (N-ethyl-ergine) was claimed to have been identified.* That would be the nearest structure to LSD found in nature. Considering that ergine is often found as its condensation product with acetaldehyde (N-(1-hydroxyethyl)-ergine), the occurrence of N-ethyl-ergine could be explained by enzymes capable of reductive ethylation of ergine with acetaldehyde. Hence it is quite possible that with some genetical manipulation it would be possible to make a strain of Ipomoea carnea being able of a second ethylation and thus to produce LSD itself. Now, that would be an exemplary biochemical achievement! (but I’m diverging from the main topic now)

* at least according to: Ethnobotany : Evolution of a discipline; Edited by Richard Evans Schultes and Simon von Reis (1995).

Vitus, I could get the Phytotherapy Research paper but there is no mention of Ipomea pes-caprae, only some stuff about natural antinociceptives (like opium, cannabis etc.):

Naturally Occurring Antinociceptive Substances from Plants.
Calixto et al.
Phytotherapy Research, 14(6), (2000), 401-418.

Attachment: Naturally Occurring Antinociceptive Substances from Plants.pdf (233kB)
This file has been downloaded 2574 times

I found it using an ipomoea + ergotamine search.

There is some hope for the American Journal of Botany paper, this is a copy of a google search using above terms:

Always that Jirawongse paper though.. Indeed ergine seems much more likely...

A genetically modified Ipomoea carnea sounds like a great idea! As a side-note, apparantely there is "natural intoxication of livestock by the ingestion of Ipomoea carnea (Convolvulaceae) in Brazil and other parts of the world" according to this paper they could be due to the presence of glycosidase inhibitors. I also read somewhere that the calystegine-type alkaloids are of the nortropane type which are also found in datura spp.

What luck!!

I found the Jirawongse paper available online:
http://www.riclib.nrct.go.th/jnrct/pdf/09-1-2.pdf

They analysed leaves and seeds of both Ipomoea pes-caprae subsp. brasiliensis and I. asarifolia using TLC (following the directions of dr. Hofmann, a modification of the Van Urk assay) and compared to standards of ergotamine and ergometrine. Concluding without further analysis that these last two alkaloids, which the authors state themselves have never been found in plants before, are present I find somewhat dodgy and primitive.

In Ipomoea asarifolia 5 indole alkaloids are found in both leaves and seeds, two of them supposedly are ergotamine and ergometrine.

In Ipomoea pes-caprae subsp. brasiliensis 3 indole alkaloids are found, both leaves and seed supposedly containing ergotamine.

The average total alkaloid content was (dired ground plant material):

I. Asarifolia
leaves: 0.0017%
seeds: 0.0037%

I. pes-caprae subsp. brasiliensis
leaves: 0.0011%
seeds: 0.0043%

The concentration of ergot alkaloids in leaves is not as high as that of the seeds because these alkaloids are mostly produced by embryo tissues of the seeds.


Let's hope the American Journal of Botany paper will confirm the presence of ergotamine by more accurate analytical means..

Vitus, lucky day.

Here's the American Journal of Botany paper.

http://rapidshare.de/files/27055799/Reproductive_Success_of_...

Too bad I don't have time to read 'cause I hafta go in a few.

sparky (~_~)

Quote: Originally posted by Vitus_Verdegast

Looks quite interesting actually. According to: Jirawongse, V., T. Pharadai, and P. Tantivatana. 1979. The distribution of indole alkaloids in certain genera of Convolvulaceae growing in Thailand. Journal of the National Research Council of Thailand. 9:17-24. ...the leaves produce the indole alkaloid ergotamine that protects the plant from most insects and large grazing mammals such as horses and donkeys. Ipomoea pes-caprae is one of the most widely distributed beach plants throughout tropical and subtropical areas in the world. It occurs along the beaches, coastal strands and tropical islands of tropical North and South America, east central Africa, west central Africa, India, Asia, and Australia. In North America, I. pes-caprae occurs from Florida, and west through the Gulf of Mexico and the Bahamas. Its range extends from approximately 30° North latitude to 30° South latitude. The extent of these limits are directly determined by climate, as I. pes-caprae does not tolerate prolonged frost conditions. Aloha! I just fear the journal might be somewhat hard to obtain. [Edited on 26-7-2006 by Vitus_Verdegast]