Flavans with potential anti-inflammatory activities from Zephyranthes candida.
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 IC50values of 17.34, 16.14, and 21.52μM, respectively, suggesting their potentials for anti-inflammatory agents.
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.
Guanqun
G
Zhan
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.
Junfei
J
Zhou
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.
Tingting
T
Liu
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.
Guijuan
G
Zheng
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.
Haji Akber
HA
Aisa
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.
Guangmin
G
Yao
D000070378:Amaryllidaceae / Q000737:chemistry*; D000818:Animals; D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D004305:Dose-Response Relationship, Drug; D005419:Flavonoids / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D008070:Lipopolysaccharides / Q000037:antagonists & inhibitors / Q000494:pharmacology; D051379:Mice; D015394:Molecular Structure; D009569:Nitric Oxide / Q000037:antagonists & inhibitors / Q000096:biosynthesis; D000067996:RAW 264.7 Cells; D013329:Structure-Activity Relationship
D000894:Anti-Inflammatory Agents, Non-Steroidal; D005419:Flavonoids; D008070:Lipopolysaccharides; D009569:Nitric Oxide
Amaryllidacea; Anti-inflammatory activities; Flavans; Zephyranthes candida