Inflammation Modulatory Phorbol Esters from the Seeds of Aquilaria malaccensis

The tree Aquilaria malaccensis is a valuable source of agarwood, which is used in herbal medicinal preparations. Phytochemical research on A. malaccensis seeds has led to the isolation of four new phorbol esters (1–4), two known phorbol esters (5, isolated from Nature for the first time, and 6), and...

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Published in:Journal of natural products (Washington, D.C.) D.C.), 2017-05, Vol.80 (5), p.1421-1427
Main Authors: Wagh, Vitthal D, Korinek, Michal, Lo, I-Wen, Hsu, Yu-Ming, Chen, Shu-Li, Hsu, Hsue-Yin, Hwang, Tsong-Long, Wu, Yang-Chang, Chen, Bing-Hung, Cheng, Yuan-Bin, Chang, Fang-Rong
Format: Article
Language:English
Subjects:
Anti-Inflammatory Agents - chemistry
Anti-Inflammatory Agents - isolation & purification
Anti-Inflammatory Agents - pharmacology
Glycerides - chemistry
Glycerides - isolation & purification
Glycerides - pharmacology
Humans
Molecular Structure
Neutrophils - chemistry
Neutrophils - drug effects
Phorbol Esters - chemistry
Phorbol Esters - isolation & purification
Phorbol Esters - pharmacology
Seeds - chemistry
Thymelaeaceae - chemistry
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Summary:The tree Aquilaria malaccensis is a valuable source of agarwood, which is used in herbal medicinal preparations. Phytochemical research on A. malaccensis seeds has led to the isolation of four new phorbol esters (1–4), two known phorbol esters (5, isolated from Nature for the first time, and 6), and two known glycerides (7 and 8). The structures of these isolates were elucidated by means of spectroscopic data interpretation. The inflammation-modulatory activities of the isolates on elastase release and superoxide anion generation in human neutrophils were evaluated. Interestingly, phorbol esters 1, 5, and 6 showed potent inhibitory activity on elastase release in human neutrophils, with IC50 values of 2.7, 0.8, and 2.1 μM, respectively. All isolated phorbol esters exerted enhancing activity on superoxide anion generation. The results indicated that phorbol esters may play a bilateral modulatory role in the processes of inflammation. In addition, the compounds were evaluated for their cytotoxic properties against HepG2 (hepatoma), MDA-MB-231 (breast), and A549 (lung) cancer cells, but all compounds were inactive for all cell lines used (IC50 > 10 μM).
ISSN:0163-3864
1520-6025
DOI:10.1021/acs.jnatprod.6b01096