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Anti‐inflammatory effect of isopimarane diterpenoids from Kaempferia galanga
Author(s) -
Tungcharoen Pattreeya,
Wattanapiromsakul Chatchai,
Tansakul Pimpimon,
Nakamura Seikou,
Matsuda Hisashi,
Tewtrakul Supinya
Publication year - 2020
Publication title -
phytotherapy research
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.019
H-Index - 129
eISSN - 1099-1573
pISSN - 0951-418X
DOI - 10.1002/ptr.6549
Subject(s) - nitric oxide , chemistry , nitric oxide synthase , diol , terpenoid , lipopolysaccharide , anti inflammatory , ic50 , cyclooxygenase , stereochemistry , in vitro , pharmacology , biochemistry , medicine , enzyme , immunology , organic chemistry
Two new isopimarane diterpenes, 1α‐hydroxy‐14α‐methoxyisopimara‐8(9),15‐diene ( 7 ) and 1α,14α‐dihydroxyisopimara‐8(9),15‐diene ( 9 ) and eight known isopimarane diterpenes including (‐)‐sandaracopimaradiene ( 1 ), 6β‐acetoxysandaracopimaradiene‐9α‐ol ( 2 ), sandaracopimaradiene‐7β,9α‐diol ( 3 ), sandaracopimaradiene‐1α,9α‐diol ( 4 ), 6β‐acetoxysandaracopimaradiene‐9α‐ol‐1‐one ( 5 ), 6β‐acetoxysandaracopimaradiene‐1α,9α‐diol ( 6 ), 6β,14α‐dihydroxyisopimara‐8(9),15‐diene ( 8 ), and 6β,14β‐dihydroxyisopimara‐8(9),15‐diene ( 10 ) were isolated from hexane fraction of Kaempferia galanga ethanol extract. Compounds 5 , 6 , 8 , and 9 exerted the good anti‐inflammatory effect on lipopolysaccharide‐stimulated nitric oxide production from RAW264.7 cells with IC 50 of 11.2, 7.7, 14.3, and 12.1 μM, respectively. These four compounds inhibited nitric oxide synthase (iNOS) mRNA expression. Compounds 5 and 6 also suppressed cyclooxygenase 2 (COX‐2) mRNA expression; in addition, compound 6 had mild inhibitory effect on TNF‐α mRNA. Among these compounds, 5 dramatically inhibited iNOS and COX‐2 mRNA expression. The influential structures were proposed to be oxygen substitute at C‐1, C‐6, and α‐OH at C‐14.