PMID: 8590637Dec 1, 1995Paper

Antibacterial triterpenoids from Dillenia papuana and their structure-activity relationships

Phytochemistry
A NickO Sticher

Abstract

Two new oleanene-type triterpenoids, dillenic acids D and E, have been isolated from the leaves and stems of Dillenia papuana together with the new natural product 3-oxoolean-12-en-30-oic acid. Together with these compounds, the known compound, betulinic acid (3 beta-hydroxy-20(29)-lupen-28-oic acid) was isolated as the major component of the fractions studied. Dillenic acids D and E were characterized as 2,3-seco-2-oxoolean-12-en-3-methylester-30-oic acid and 1 alpha,3 beta-dihydroxyolean-12-en-30-oic acid and their nuclear magnetic resonance data were unambiguously assigned using two-dimensional nuclear magnetic resonance techniques. A comparison of antibacterial activities of these compounds with the earlier reported dillenic acids A-C indicated that, aside from a double bond in gamma- or delta-position to a carboxylic group, a ketone function in ring A of an oleanene-skeleton may be required for the observed activity.

References

Sep 1, 1994·Journal of Natural Products·A NickT Rali
Jul 1, 1964·Journal of Medicinal Chemistry·A I LASKINJ FRIED

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Citations

Apr 6, 1999·Phytotherapy Research : PTR·J C SteeleM S Simmonds
Jan 10, 2003·Chemical & Pharmaceutical Bulletin·Yoshitaka ToriumiMasao Kikuchi
Mar 5, 2011·Chemical & Pharmaceutical Bulletin·Rene Angelo Sarmiento MacahigHideaki Otsuka
Apr 20, 2014·BioMed Research International·Ping-Chung KuoChi-Chung Peng
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Jan 12, 2016·Journal of Agricultural and Food Chemistry·Sun Woo JinHye Gwang Jeong
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Sep 3, 2013·European Journal of Medicinal Chemistry·Zhiwen ZhouJinyi Xu
Oct 26, 2016·Organic & Biomolecular Chemistry·Ling-Zhi LiShao-Jiang Song
Oct 5, 2019·Natural Product Research·Qinghu MoChengqin Liang
Oct 21, 2009·Journal of Natural Products·Leena PohjalaPäivi Tammela
Jan 10, 2009·Journal of Natural Products·Ian P HollandIan A van Altena

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