Oxyphyllenone A

Bioorg Med Chem Lett. 2001 Aug 20;11(16):2217-20.

Absolute stereostructures of novel norcadinane- and trinoreudesmane-type sesquiterpenes with nitric oxide production inhibitory activity from Alpinia oxyphylla.[Pubmed: 11514174]

METHODS AND RESULTS:
Novel 14-norcadinane-type sesquiterpenes, oxyphyllenodiols A and B, and 11,12,13-trinoreudesmane-type sesquiterpenes, oxyphyllenones A and B, were isolated from the methanolic extract of kernels of Alpinia oxyphylla.
CONCLUSIONS:
The absolute stereostructures of these norsesquiterpenes were determined on the basis of physicochemical and chemical evidence. In addition, oxyphyllenodiol A and Oxyphyllenone A were found to inhibit the NO production in lipopolysaccharide-activated macrophages..

Yao Xue Xue Bao. 2014 Nov;49(11):1569-73.

The compounds from n-butanol fraction of Alpinia oxyphylla.[Pubmed: 25757283]

METHODS AND RESULTS:
Nine compounds were isolated from the n-butanol fraction of 95% ethanol extract of the fruit of Alpinia oxyphylla Miq. with a combination of various chromatographic approaches, including MDS resin, silica gel, reverse phase C18 and preparative HPLC. On the basis of spectroscopic data analysis, they were elucidated as (1R, 4R, 10R)-1β, 4α-dihydroxy-11, 12, 13-trinor-5, 6-eudesmen-7-one (1), 1β, 4β-dihydroxy-11, 12, 13-trinor-8, 9-eudesmen-7-one (2), Oxyphyllenone A (3), oxyphyllenone B (4), rhamnocitrin (5), staphylionoside D (6), benzyl-1-O-β-D-glucopyranoside (7), 2-O-β-D-glucopyranosyl-(1S)-phenylethylene glycol (8), and (S)-1-phenylethyl-β-D-glucopyranoside (9).
CONCLUSIONS:
Among them, compound 1 is a new sesquiterpene, named as oxyphyllenone C; compounds 8 and 9 are new natural products; compounds 2 and 6 were isolated from the genus Alpinia for the first time, and compound 7 was isolated from A. oxyphylla for the first time.