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Prostratin (Molecule of the Month for April 2012)



Prostratin is a protein kinase C activator found in the bark of the mamala tree of Samoa, Homalanthus nutans (Euphorbiaceae). While prostratin was originally isolated and identified as a new phorbol from species of the genus Pimelea (Thymelaceae) in Australia, the antiviral activity of prostratin was discovered during research on the traditional knowledge of Samoan healers in Falealupo village by ethnobotanist Paul Alan Cox and a team at the U.S. National Cancer Institute. Samoan healers use the mamala tree to treat hepatitis. Research indicated that prostratin has potential to be useful in the treatment of HIV as it could flush viral reservoirs in latently infected CD4+ T-cells.

Prostratin is of interest because of its unique ability to activate latent viral reservoirs, while preventing healthy cells from infection, as well as its discovery through ethnobotany.

Pioneering agreements to protect indigenous intellectual property rights of the Samoan people were established between the Samoan government and the AIDS Research Alliance, with 20% of ARA's profits to be returned to the Samoan people, and between the Samoan Government and the University of California, Berkeley where a team led by Jay Keasling is trying to isolate the gene sequence responsible for prostratin biosynthesis. Samoa and UC Berkeley agreed to share equally in any commercial proceeds from the gene product.

Formal Chemical Name (IUPAC)
(1aR,1bS,4aR,7aS,7bR,8R,9aS)-4a,7b-dihydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-5-oxo-1,1a,1b,4,4a,5,7a,7b,8,9-decahydro-9aH-cyclopropa[3,4]benzo[1,2-e]azulen-9a-yl acetate

References

http://en.wikipedia.org/wiki/Prostratin

Picture of Prostratin

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Prostratin structure
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Picture of Prostratin

C22H30O6



Update by Karl Harrison
(Molecule of the Month for April 2012 )