Prostratin

Prostratin
Names
	Preferred IUPAC name (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
	Other names 12-Deoxyphorbol-13-acetate
Identifiers
CAS Number	60857-08-1 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL170518 ;
ChemSpider	399975 ;
PubChem CID	454217;
UNII	KO94U6DIQ6 ;
CompTox Dashboard (EPA)	DTXSID10893788 ;
	InChI InChI=1S/C22H30O6/c1-11-6-16-20(26,18(11)25)9-14(10-23)7-15-17-19(4,5)21(17,28-13(3)24)8-12(2)22(15,16)27/h6-7,12,15-17,23,26-27H,8-10H2,1-5H3/t12-,15+,16-,17-,20-,21+,22-/m1/s1 Key: BOJKFRKNLSCGHY-HXGSDTCMSA-N ; InChI=1/C22H30O6/c1-11-6-16-20(26,18(11)25)9-14(10-23)7-15-17-19(4,5)21(17,28-13(3)24)8-12(2)22(15,16)27/h6-7,12,15-17,23,26-27H,8-10H2,1-5H3/t12-,15+,16-,17-,20-,21+,22-/m1/s1 Key: BOJKFRKNLSCGHY-HXGSDTCMBJ;
	SMILES O=C1\C(=C/[C@H]2[C@]3(O)[C@@H](/C=C(/CO)C[C@]12O)[C@H]4[C@@](OC(=O)C)(C[C@H]3C)C4(C)C)C;
Properties
Chemical formula	C22H30O6
Molar mass	390.47 g/mol
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

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 ester 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.^[1]

As a modulator of protein kinase C, it has been shown to exhibit promising therapeutic potential against other diseases such as cancer and Alzheimer's disease. In 2015, study showed that orally administrated prostratin repressed human pancreatic tumor.^[2]

^ Prostratin and the AIDS Research Alliance, AIDS Research Alliance, 2006
^ Wang, Man-Tzu; Holderfield, Matthew; Galeas, Jacqueline; Delrosario, Reyno; To, Minh D.; Balmain, Allan; McCormick, Frank (2015). "K-Ras Promotes Tumorigenicity through Suppression of Non-canonical Wnt Signaling". Cell. 163 (5): 1237–1251. doi:10.1016/j.cell.2015.10.041. PMID 26590425.

[1] Prostratin and the AIDS Research Alliance, AIDS Research Alliance, 2006

[2] Wang, Man-Tzu; Holderfield, Matthew; Galeas, Jacqueline; Delrosario, Reyno; To, Minh D.; Balmain, Allan; McCormick, Frank (2015). "K-Ras Promotes Tumorigenicity through Suppression of Non-canonical Wnt Signaling". Cell. 163 (5): 1237–1251. doi:10.1016/j.cell.2015.10.041. PMID 26590425.

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