Flavans with potential anti-inflammatory activities from Zephyranthes candida

Bioorg Med Chem Lett. 2016 Dec 15;26(24):5967-5970. doi: 10.1016/j.bmcl.2016.10.081.

Guanqun Zhan ¹, Junfei Zhou ¹, Tingting Liu ¹, Guijuan Zheng ¹, Haji Akber Aisa ², Guangmin Yao ³

Affiliations

1 Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, People's Republic of China.
2 The Key Laboratory of Plant Resources and Chemistry of Arid Zone and State Key Laboratory Basis of Xinjiang Indigenous Medicinal Plants Resource Utilization, Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Urumqi 830011, People's Republic of China.
3 Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, People's Republic of China. Electronic address: gyap@mail.hust.edu.cn.

PMID: 27825545 DOI: 10.1016/j.bmcl.2016.10.081

Abstract

Three new flavans, (2R,3R)-7-methoxy-flavan-3-ol (1), (2S)-7,3'-dihydroxy-4'-methoxyflavan 3'-O-β-d-glucopyranoside (2), (2S)-7,3'-dihydroxy-4'-methoxyflavan 7-O-β-d-glucopyranoside (3), and one known flavan (4) were isolated from the whole Plants of Zephyranthes candida (Amaryllidacea). The structures of the new flavans 1-3 were determined by extensive spectroscopic analyses including HRESIMS, NMR, and electronic circular dichroism (ECD), and the absolute configuration of 1 was confirmed by single-crystal X-ray diffraction analysis with Cu Kα irradiation. Flavans 1-3 displayed significant inhibitory effects on the LPS-induced NO production in RAW264.7 mouse macrophages with IC₅₀ values of 17.34, 16.14, and 21.52μM, respectively, suggesting their potentials for anti-inflammatory agents.

Keywords

Amaryllidacea; Anti-inflammatory activities; Flavans; Zephyranthes candida.

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