New Sesquiterpenoids and a Diterpenoid from Alpinia oxyphylla

Abstract

Abstract:The new compounds 2-methyl-6-isopropyl-7-hydroxymethyl naphthalene (1), oxyphyllenone H (2), epi-oxyphyllenone (6), (E)-labda-12,14-dien-15(16)-olide-17-oic acid (3), and two new natural products 4 and 5 were isolated from the ethyl acetate part of 95% ethanol extract of Alpinia oxyphylla, together with six known compounds 7-12. The inhibitory effects of compounds 1-12 on α-glucosidase were evaluated, and compounds 1, 3 and 6 showed moderate bioactive effect, with inhibitory rates of 10.3%, 10.0% and 11.5%, respectively, compared to the positive control acarbose (41.9%) at 20 µg/mL.

An overview of chemical constituents from Alpinia species in the last six decades

“…And 100 exhibited moderate hypoglycemic activity with inhibitory rate of 11.5%, compared to 41.9% of the positive control acarbose (41.9%) at 90 mM. 77 Rhizomes of A. japonica (Thunb.) Miq.…”

“…87 Compound 2-ethyl-6-isopropyl-7-hydroxymethyl naphthalene (149) was a noval naphthalene from A. oxyphylla. 77 It showed bioactive activity with the inhibitory rates of 10.3%, compare to 41.9% of the positive control acarbose at 0.9 mM. 77 Noteworthily, compounds 22-31, 34, 48-56, 58-63, 79-82, 87-89, 117, and 129-136 exerted NO production inhibitory activities at different levels.…”

“…77 It showed bioactive activity with the inhibitory rates of 10.3%, compare to 41.9% of the positive control acarbose at 0.9 mM. 77 Noteworthily, compounds 22-31, 34, 48-56, 58-63, 79-82, 87-89, 117, and 129-136 exerted NO production inhibitory activities at different levels. [58][59][60]65,67,71,73,83,[88][89][90] While (10R)-13-noreudesma-4,6-dien-3,11-dione (46), (5S,8R,10R)-2-oxoeudesma-3,7(11)-dien-12,8-olide (47), (5R,7S,10S)-5-hydroxy-13-noreudesma-3-en-2,11dione (83), and (4S)-10-nor-calamenen-10-one (90) showed potent auxo-action of NO production at 10 mM induced by lipopolysaccharide (LPS) in microglia.…”

Rapid extraction and determination of 25 bioactive constituents in Alpinia oxyphylla using microwave extraction with ultra high performance liquid chromatography with tandem mass spectrometry

“…The analytes A1-A25 were isolated and purified from Fructus Alpinia Oxyphylla in our laboratory, and their identities were confirmed by 1 H and 13 C NMR spectroscopy and MS [15][16][17]. The 13 C and 1 H NMR spectra of the two new compounds are shown in Supporting Information Fig.…”

“…Moreover, most of the constituents were detected for the first time using MS. Furthermore, the compound of oxyphyllenone H and (E)-labda-12,14-dien-15(16)-olide-17-oic acid are two new constituents separated from Fructus Alpinia Oxyphylla for the first time by our laboratory [15]. The structure of all constituents is listed in Supporting Information Fig.…”