1H-Naphtho[2,1-b]pyran,3-ethenyldodecahydro-3,4a,7,7,10a-pentamethyl-, (3R,4aR,6aS,10aS,10bR)- (9CI)

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CAS: 596-84-9
MF: C20H34O
MW: 290.48336
Synonyms: 1H-Naphtho[2,1-b]pyran,3-ethenyldodecahydro-3,4a,7,7,10a-pentamethyl-, (3R,4aR,6aS,10aS,10bR)- (9CI)

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Jeroen S. Dickschat

Technical University of Braunschweig
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Dulcie A. Mulholland

University of KwaZulu-Natal
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Co-reporter: Moses K. Langat, Neil R. Crouch, Leena Pohjala, Päivi Tammela, Peter J. Smith, Dulcie A. Mulholland
pp: 414-418
Publication Date(Web):September 2012
DOI: 10.1016/j.phytol.2012.03.002
Two new ent-kauren-19-oic acid derivatives, ent-14S*-hydroxykaur-16-en-19-oic acid and ent-14S*,17-dihydroxykaur-15-en-19-oic acid together with eleven known compounds ent-kaur-16-en-19-oic acid, ent-kaur-16-en-19-al, ent-12β-hydroxykaur-16-en-19-oic acid, ent-12β-acetoxykaur-16-en-19-oic acid, 8R,13R-epoxylabd-14-ene, eudesm-4(15)-ene-1β,6α-diol, (−)-7-epivaleran-4-one, germacra-4(15), 5E,10(14)-trien-9β-ol, acetyl aleuritolic acid, β-amyrin, and stigmasterol were isolated from the stem bark of Croton pseudopulchellus (Euphorbiaceae). Structures were determined using spectroscopic techniques. Ent-14S*-hydroxykaur-16-en-19-oic acid, ent-kaur-16-en-19-oic acid, ent-12β-hydroxykaur-16-en-19-oic acid, ent-12β-acetoxykaur-16-en-19-oic acid and 8R,13R-epoxylabd-14-ene were tested for their effects on Semliki Forest virus replication and for cytotoxicity against human liver tumour cells (Huh-7 strain) but were found to be inactive. Ent-kaur-16-en-19-oic acid, the major constituent, showed weak activity against the Plasmodium falciparum (CQS) D10 strain.Graphical abstractImage for unlabelled figureHighlights► Two novel ent-diterpenoids have been isolated along with a range of known ent-diterpenoids, sesquiterpenoids and triterpenoids. ► Following ethnomedicinal usage, compounds were tested for anti-viral activity against the Semliki virus but were found to be inactive. ► The major constituent showed moderate antiplasmodial activity against the chloroquine resistant strain of the malarial parasite Plasmodium falciparum.

Moses Langat

University of Surrey
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ChengZhi Gu

Shihezi University
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Ikhlas Khan

University
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