Ent-kauren-19-oic acid derivatives from the stem bark of Croton pseudopulchellus Pax |
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| Authors: | Moses K. Langat Neil R. Crouch Leena Pohjala Päivi Tammela Peter J. Smith Dulcie A. Mulholland |
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| Affiliation: | 1. Division of Chemical Sciences, Faculty of Health and Medical Sciences, University of Surrey, Guildford, GU2 7XH Surrey, UK;2. School of Chemistry, University of KwaZulu-Natal, Durban 4041, South Africa;3. Ethnobotany Unit, South African National Biodiversity Institute, PO Box 52099, Berea Road 4007, Durban, South Africa;4. Centre for Drug Research, Faculty of Pharmacy, University of Helsinki, F1-00014 Helsinki, Finland;5. Division of Pharmaceutical Biology, Faculty of Pharmacy, University of Helsinki, FI-00014 Helsinki, Finland;6. Department of Medicine, Division of Clinical Pharmacology, University of Cape Town, K45 Old Main Building, Groote Schuur Hospital, Observatory, 7925 Cape Town, South Africa |
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| Abstract: | 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. |
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