Four Phragmalin Orthoesters from the Chinese Mangrove Xylocarpus granatum

Abstract

Four new 8,9,30-phragmalin orthoesters (1–4), along with six related known compounds, namely xyloccensins O–S (5–9) and V (10), were isolated and characterized from the twigs and leaves of the Chinese mangrove Xylocarpus granatum. The structures of the new compounds were determined on the basis of extensive spectroscopic analysis and by comparison with those of related known compounds in the literature. The absolute configuration of xyloccensin Q (7) was revised as its enantiomer by X-ray diffraction analysis employing graphite monochromated Cu Kα radiation (λ = 1.54 178 Å) with a Flack parameter of − 0.04 and was further secured by a time-dependent density functional theory electronic circular dichroism (TDDFT ECD) calculation. Consequently, the absolute configurations of xyloccensins O (5), P (6), R (8), S (9), and V (10) were all corrected as their corresponding enantiomers, respectively. Xyloccensin S (9) exhibited inhibitory activity against protein tyrosine phosphatase 1B, a potential drug target for the treatment of type II diabetes and obesity, with an IC₅₀ value of 8.72 µg/mL.

Key words

Meliaceae - Xylocarpus granatum - phragmalin orthoesters - configuration determination - biological activity

^* These two authors contributed equally to this work.

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