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Author: Subject: Ipomoea pes-caprae
totaljackass
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[*] posted on 25-7-2006 at 13:20
Ipomoea pes-caprae


I was wondering if anyone knew about the alkaloid content of Ipomoea pes-caprae, also known as the railroad vine, or beach morning glory? Of course the only place that would mention this is a place like erowid, which doesn't get specific on which species. Please help.
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Vitus_Verdegast
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[*] posted on 25-7-2006 at 21:31


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 :cool: 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!:D I just fear the journal might be somewhat hard to obtain.


[Edited on 26-7-2006 by Vitus_Verdegast]




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[*] posted on 25-7-2006 at 22:19


This article also mentions ergotamine content (anyone with Athens access?)

Factors Influencing the Reproductive Success of Ipomoea pes-caprae (Convolvulaceae) around the Gulf of Mexico
Margaret S. Devall, Leonard B. Thien
American Journal of Botany, Vol. 76, No. 12 (Dec., 1989) , pp. 1821-1831
http://tinyurl.com/lp9ge

This one ought to mention it too:
Phytotherapy Research
Volume 14, Issue 6 , Pages 401 - 418 (2000)
http://www3.interscience.wiley.com/cgi-bin/abstract/72516788...

Pharmacognostic studies on the Thai medicinal plant Ipomoea pes-caprae (L.) R.Br. (Pak Bung Ta Lae) (Diss., sammanfattning 43 sid., ill., diagr., tab.),
av: Pongprayoon, Ubonwan. Comprehensive summaries of Uppsala dissertations from the Faculty of Pharmacy no 71, Almqvist & Wiksell International, Stockholm, 1990. ISBN 9155426565.

...is all I could locate. The first paper should have more references to the ergotamine content of the leaves of this common vine.




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[*] posted on 25-7-2006 at 23:06


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)
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[*] posted on 25-7-2006 at 23:45


:( 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:
Quote:

Ipomoe_pesCap
Branches have a milk-colored latex in the sap, while leaves produce a compound called indole alkaloid ergotamine (Jirawongse et al. ...
www.sms.si.edu/irlspec/Ipomoea_pesCap.htm - 23k -

JSTOR: Factors Influencing the Reproductive Success of Ipomoea pes ...
Seeds are also protected from most insects by ergotamine (Jirawongse et al., 1979), but bru- chids have apparently evolved the ability to eat seeds ...
[url]links.jstor.org/sici?sici=0002-9122(198912)76:12%3C1821:FITRSO%3E2.0.CO;2-S -[/url]


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

A genetically modified Ipomoea carnea sounds like a great idea! :cool: 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.




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[*] posted on 26-7-2006 at 00:11


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..




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[*] posted on 26-7-2006 at 00:32


Vitus, lucky day. ;)

Here's the American Journal of Botany paper. :D

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 (~_~)




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[*] posted on 26-7-2006 at 11:06


Thanks for the help, i'm very fascinated by ergot alkaloids, and I'm always looking for interesting morning glories to study.

This made me realize, I'm really going to need to do some research on chromatography, it's the only way I'll find anything out for myself.

[Edited on 26-7-2006 by totaljackass]
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[*] posted on 11-12-2016 at 07:59


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 :cool: 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!:D I just fear the journal might be somewhat hard to obtain.


[Edited on 26-7-2006 by Vitus_Verdegast]


JOURNAL OF THE NATIONAL RESEARCH COUNCIL OF THAILAND

http://www.thaiscience.info/journals/view3.asp?sCode=NRCT&sT...

Volume 9, Issue 01 (JANUARY 1977)


The distribution of indole alkaloids in certain genera of convolvulaceae growing in thailand
Vichiara Jirawongse, Tharadol Pharadai, Payom Tantivatana

Attachment: Journal of the National Research Council of Thailand vol 9 p17-24..pdf (1MB)
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[*] posted on 11-12-2016 at 08:39


Inland Occurrence of the Strand Plant Ipomoea pes-caprae (Convolvulaceae) around Lake Nicaragua

Margaret S. Devall and Leonard B. Thien

The Southwestern Naturalist
Vol. 50, No. 3 (Sep., 2005), pp. 380-384

http://www.bio-nica.info/biblioteca/DeVall2005.pdf

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[*] posted on 17-6-2017 at 15:36


As far as symbiosis that is more or less a certainty, although I'm not familiar with the species in question specifically. The plants themselves do not produce the ergoloids, it is depenent upon some obligate endophyte fungi. As I understand it they cannot be cultured in vitro, although an infected plant tissue culture might be possible.

The endoophyte is of the clavicipitaceous family, at least the other ergoloid-producing plants are host to clavicipitalean endophytes, although some of the higher plants of the grasses are host to balansioid species, a group of microfungi closely related to the Clavicipitales.
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[*] posted on 25-6-2017 at 11:03


Also, I forgot to mention, animal toxicity in Ipomoea species cannot solely be attributed to ergoloids. At least one species (argentinian) produces a lethally toxic glycoprotein, in the days where wars were fought on horseback, the natives would often apparently outrun the foreign invaders being fought by leading their mounts into stands of the Ipomoea species and preventing their feeding. The newcomers of course lack such native knowledge of the area, and the result was their horses dropping dead shortly after and the natives thus being able to evade pursuit.

Also, I.serocophylla, I.carnea and I.reidellii contain calystegeine type alkaloids as well as something much nastier, swainsonine, which causes, if not acutely fatal, a degenerative neurological disease resembling the mannosidoses in which glycosylated garbage builds up in lysosomes resulting in a broad spectrum of neurological damage. And also causes degeneration of striated muscle tissue. Its the same toxin as found in 'locoweed', Swainsonia spp. Nasty stuff, swainsonine is a potent inhibitor of lysosomal
a-mannosidase and Golgi mannosidase I, and the calystegines share similar activity apparently, according to this paper.
https://naldc.nal.usda.gov/download/22144/PDF

I.fistulosa is also toxic, probably due to swainsonine, causing a very similar or identical toxidrome in affected animals. The genus contains both a fair few ergoloid-producing species and a significant number of toxic species, in some cases potentially lethal or permanently impairing. It would be well to bone up on any specific species if venturing out of the usual garden-varieties as ergoloid sources lest some stain positive with Van Urk reagent and contain such unpleasant substances.. Given the presence in higher plants, such as the morning glories, hawaiian baby woodrose and ololiuqi is universally as far as thus known, a result of Clavicipitalean endophytes (with good enough support to this being given by the fact that there are multiple reports of hawaiian baby woodrose seeds sourced from india being biologically inactive, it stands to reason that production will be variable, according to the strain of the fungus.

If its anything like Claviceps then 'variable' isn't even close to being adequate. The propensity for problems with those fungi such as senescence or mutation to non-productive strains, and degeneration of productive ones, most active producers of ergoloids lacking production of ascospores causing a high intraspecies variability.

If culturing the fungi within Ipomoea species is what your thinking (to the OP) just forget it. It appears to be an obligate symbiote and that I am aware of it has never been successfully cultured in vitro. Culture in undifferentiated callus tissue might be doable, but don't expect to get anything growing on a normal agar plate.

It would be interesting to see if the requirement is for a plant constituent or, as with alkaloid production in Claviceps spp, dependent upon a specific living biological structure within the plant to serve as host. I've never heard of any attempts to encapsulate the Ipomoea endophytes within a matrix (in the case of the ergots, this, such as via electrospraying a fine dispersion of a productive culture in alginate/perflurocarbon emulsion (the primary problem with encapsulation like this, is that the productivity is stabilized, the alginate microspheres acting as pseudo-sclerotia and protected against mechanical buffeting and battering, general wear and tear, at the expense of oxygen transport.

The use of a perfluorocarbon emulsion up to about 50-60%, if the right one is chosen assists in that respect acting similarly to liquid-breathing technology and IIRC some synthetic blood plasma experiments were done using emulsified perfluorocarbons. This serves to enable O2 transport much deeper into the body of the alginate microspheres and enable production of higher ergot alkaloids, whereas if this is neglected, in the more anoxic zones, the higher ergot alkaloids such as ergine and the ergopeptides suffer a decrement in production that is quite severe, with the product of the inner zone of encapsulated Claviceps being mainly clavines, as one of the final steps in the biosynthetic ergot alkaloid pathway (in Claviceps) involves an oxidation step to form the full ergoline ring structure.

Hope this is helpful. I'm extrapolating based on the relation of the endophyte to Clavicipitaceous fungi, I'm not a specialist in knowledge of this endophyte, but do know a fair bit about Claviceps if you can benefit from it, ask.
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