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Yeti101

Hodgkinsonia frutescens

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(Reposted from before the crash, I though it should have been here rather than Ethnobotany as well)

Was looking into something else recently when I came across an interesting sounding alkaloid - Hodgkinsine.

The discovery that alkaloids isolated from Psychotria colorata Muell Arg (RUBIACEAE), a medicinal species traditionally used as an analgesic in the Brazilian Amazon, have a distinctive analgesic profile generated substantial interest. The mechanisms of action by which these alkaloids exert antinociceptive action were investigated by in vivo and in vitro techniques, particularly regarding their involvement with opioid and glutamatergic pathways.We reported that the natural alkaloid hodgkinsine (1) acts dose-dependently as a potent analgesic in mice. Hodgkinsine's effects in thermal models of nociception were naloxone reversible, suggesting that activation of opioid receptors is involved in its mode of action.Indeed, binding data revealed that hodgkinsine binds specifically to opioid receptors. Hodgkinsine also showed a potent dose-dependent analgesic effect in capsaicin-induced pain,suggesting the participation of NMDA receptors in its mode of action. The combination of NMDA antagonists with opioids has been proposed as an alternative in the treatment of neuropathic pain, in part for the analgesic properties of NMDA antagonists, but especially because NMDA antagonists decrease opioid tolerance.
J. Org. Chem., 72 (21), 7909 -7914, 2007. http://pubs.acs.org/cgi-bin/article.cgi/jo.../jo7013643.html

It's also been reported as having antiviral activity against Herpes Simplex type 1 virus. Planta Medica 1995 Aug ;61 (4):313-6

But I was dispointed to find that Psychotria colorata isn't going to be easy for me to get hold of. However, upon looking up Hodgkinsine, I realised that it is found in Hodgkinsonia frutescens AKA the Atherton Turkey Bush. Someone from N QLD could probably provide better distribution info, but as the name suggests, it seems to be around up that way, though it is listed as 'vulnerable'. I found a few nurseries online that look like the stock it, but have not checked availability further. No idea of alkaloid yeilds from this plant. No idea of probable dosage though a better investigation of P. colorata might give some hints as to how much Hodgkinsine is needed for analgesic effect etc.

This paper gives the crude alkaloid extract of Hodgkinsonia frutescens as being 60 g from 10 kg of leaves. http://www.publish.csiro.au/?act=view_file...d=CH9610173.pdf

I have read that Hodgkinsonia ovatiflora, AKA Hodgkinsonia or Golden ash, which has a more southern distribution has tested positive for alkaloids, but I can't find more details (yet).

Hodgkinsine has also been found in Psychotria lyciiflora and Psychotria oleoides along with other interesting related alkaloids.

I can't get the file upload to work right now, but I will put up the structures of Hodgkinsine and some related molecules later.

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having issues with the upload function. should be sorted in a day or two.

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Here are some of the molecules:

post-25-1213873165_thumb.png

jo7013643f00001.gif

jo7013643f00001.gif

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just bumped into this.....trouts notes on aya analogs......

Leal & Elisabetsky 1996b similarly could detect no alkaloid in P. carthaginensis, but interestingly they reported bioactivity.

Interestingly, Elisabetsky et al. 1995 determined a strong opioid analgesic activity in alkaloids present in both flowers and leaves of Psychotria colorata (Willd. ex R.& S.) Muell. Arg.

Flowers were found to be 4X stronger than leaves. This activity was reversed by administration of Naloxone.

Besides Elisabetsky et al. 1995, this species was also analyzed by Verotta et al. 1998 who similarly reported an analgesic activity for the flowers. This species is traditionally used as a treatment for both earache and for abdominal pain. Its common name is Perpétua do mato)

Leal & Elizabetsky 1996a reported the same activity for Psychotria brachypoda (Muell. Arg.) Britton. Both of these species are used as painkillers in ethnomedicine.

Psychotria griffithii is also employed for pain (in Malaya)

t s t .

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It seems that there are several Psychotria sp that either contain Hodgkinsine or related compounds.

Psychotria beccarioides contains Psychotridine, which has u-opioid, but no NMDA antagonist activity (I did have a reference, but it might take me a few days to find it again). Where Hodgkinsine has 3 Nb-Methyltryptamine units, this compound is composed of 5. This sp is found in PNG.

It is also found in Calycodendron milnei which is found "on Pacific Islands" (because that narrows it down!), but since Calycodendron is syn with Psychotria, I'm not sure what this actually is. It might be Psychotria lyciiflora and Psychotria oleoides, because these are apparently found in New Caledonia.

As well as looking at Hodgkinsonia ovatiflora, I think some previously overlooked Psychotria species could be worthwhile. I know that for a long time I was only interested in them if they contained a less obscure tryptamine, but this kind of compound opens up some interesting possibilities.

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Hodgkinsonia ovatiflora - map

Hodgkinsonia frutescens - map

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