Terpenoids from rhizomes of Alpinia japonica inhibiting nitric oxide production

Chemistry & Biodiversity
Qiang-Ming LiLing-Yi Kong

Abstract

A new sesquiterpenoid, 1, and three new diterpenoids, 3-5, along with five known compounds, 2 and 6-9, were isolated from rhizomes of Alpinia japonica. The structures of the new compounds were determined as (1R,4R,6S,7S,9S)-4α-hydroxy-1,9-peroxybisabola-2,10-diene (1), methyl (12E)-16-oxolabda-8(17),12-dien-15-oate (3), (12R)-15-ethoxy-12-hydroxylabda-8(17),13(14)-dien-16,15-olide (4), and methyl (11E)-14,15,16-trinorlabda-8(17),11-dien-13-oate (5) by means of spectroscopic data. The absolute configurations at C(4) in 1 and C(12) in 4 were deduced from the circular dichroism (CD) data of the in situ-formed [Rh2 (CF3 COO)4 ] complexes. Inhibitory effects of the isolates on NO production in lipopolysaccharide-induced RAW264.7 macrophages were evaluated, and 2-4, 6, and 7 were found to exhibit inhibitory activities with IC50 values between 14.6 and 34.3 μM.

References

Jan 15, 1998·Journal of Natural Products·B N ZhouD G Kingston
Oct 27, 2001·Journal of Natural Products·D T YoussefP J Scheuer
Apr 24, 2004·Journal of Natural Products·Stefan MüllerIrmgard Merfort
Nov 28, 2006·Journal of Natural Products·Kayo AkiyamaNobuji Nakatani
Apr 14, 2009·Bioorganic & Medicinal Chemistry Letters·Shu-Zhen HuaLing-Yi Kong
May 8, 2010·European Journal of Medicinal Chemistry·Natalia GirónBeatriz de Las Heras
Jun 4, 2011·Organic Letters·Chang-Shui YangLing-Yi Kong

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Citations

Jul 29, 2016·Natural Product Reports·James R Hanson
Jul 14, 2017·Journal of Oleo Science·Yoshinori AsakawaYoshihiro Yaguchi

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