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Planta Med 2014; 80(11): 949-954
DOI: 10.1055/s-0034-1382840
Natural Product Chemistry
Original Papers
Georg Thieme Verlag KG Stuttgart · New York

Four Phragmalin Orthoesters from the Chinese Mangrove Xylocarpus granatum

Zhen-Fang Zhou   *
1   Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai, China
,
Ling-Yi Kong   *
2   State Key Laboratory of Natural Medicines, Department of Natural Medicinal Chemistry, China Pharmaceutical University, Nanjing, China
,
Tibor Kurtán
3   Department of Organic Chemistry, University of Debrecen, Debrecen, Hungary
,
Hai-Li Liu
1   Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai, China
,
Attila Mándi
3   Department of Organic Chemistry, University of Debrecen, Debrecen, Hungary
,
Jia Li
1   Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai, China
,
Yu-Cheng Gu
4   Syngenta Jealottʼs Hill International Research Centre, Berkshire, United Kingdom
,
Yue-Wei Guo
1   Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai, China
› Author Affiliations
Further Information

Publication History

received 26 September 2013
revised 06 June 2014

accepted 12 June 2014

Publication Date:
16 July 2014 (online)

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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.


Supporting Information

 

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