Bicyclic lactones and racemic mixtures of dimeric styrylpyrones from the leaves of Miliusa velutina

A unique class of eight bicyclic lactones with a C 18 carbon architecture, named velutinones A–H ( 1–8 ), three new dimeric styrylpyrones, velutinindimers A–C ( 9–11 ), five known compounds, the kawapyrone, yangonin ( 12 ), three flavonoids ( 13–15 ), and an acetogenin, cananginone H ( 16 ) were iso...

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Published inRSC advances Vol. 7; no. 41; pp. 25285 - 25297
Main Authors Wongsa, N., Kanokmedhakul, K., Boonmak, J., Youngme, S., Kanokmedhakul, S.
Format Journal Article
LanguageEnglish
Published 01.01.2017
Subjects
Biotechnology
Carbon
Flavonoids
Lactones
Optical properties
Optical rotation
Toxicity
X rays
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Summary:A unique class of eight bicyclic lactones with a C 18 carbon architecture, named velutinones A–H ( 1–8 ), three new dimeric styrylpyrones, velutinindimers A–C ( 9–11 ), five known compounds, the kawapyrone, yangonin ( 12 ), three flavonoids ( 13–15 ), and an acetogenin, cananginone H ( 16 ) were isolated from the leaves of Miliusa velutina . The absolute configurations of 2 and 5 were assigned by Mosher's method, whereas ECD, optical rotations, and X-ray crystallographic analysis indicated the racemic nature of compounds 10 and 11 . Compounds 2–4 and 7–11 showed antimalarial activity with IC 50 values in the range of 5.4–10.0 μM. Moreover, 1–4 and 6–8 displayed cytotoxicity against the KB, MCF7, and NCI-H187 cancer cell lines and Vero cell lines with IC 50 values in the range of 4.0–24.1 μM.
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ISSN:2046-2069
2046-2069
DOI:10.1039/C7RA01609C