New 4',5'-methylenedioxyflavone derivatives from the whole plant of sarcandra glabra

• Published in: Natural product research Vol. 38; no. 2; pp. 177 - 185
• Main Authors: Qin, Ya-Qiu, Liu, Wei, Yin, Rui, Xiao, Ping-Ting, Wang, Zi-Yuan, Huang, Tian-Qing, Liu, E-Hu
• Format: Journal Article
• Language: English
• Published: England Taylor & Francis 2024; Taylor & Francis Ltd
• Subjects: Animals; Anti-inflammatory activity; Anti-Inflammatory Agents - chemistry; Anti-Inflammatory Agents - pharmacology; Chromatography; Cytotoxicity; cytotoxicity; Sarcandra glabra; Drugs, Chinese Herbal - chemistry; Hexadecane; Humans; Inflammation; Macrophages; Magnoliopsida - chemistry; Mice; Natural products; NMR; Nuclear magnetic resonance; Quercetin; RAW 264.7 Cells; structural elucidation; Anti-inflammatory activity; structural elucidation; cytotoxicity; Sarcandra glabra
• ISSN: 1478-6419; 1478-6427
• DOI: 10.1080/14786419.2022.2111562

Two new natural products named 5,7-dihydroxy-3,3',6,8-tetramethoxy-4',5'-methylenedioxyflavone (1) and 3,3',5,7-tetramethoxy-4',5'-methylenedioxyflavone (2), along with thirteen known compounds, β-sitosterol (3), desmethoxyyangonin (4), hexadecane (5), 3,9-bis(2,4-di-tert-butylphenoxy)-2,4,8,10-tetraoxa-3,9-diphosphaspiro [5.5] undecane 3,9-dioxide (6), 2'6'-dihydroxy-4'-methoxydihydrochalcone (7), cardamonin (8), 3,3',5,6,7,8-hexamethoxy-4',5'-methylenedioxyflavone (9), isofraxidin (10), aniba dimer A (11), 3,3',4',5,5',8-hexamethoxy-6,7-methylenedioxyflavone (12), quercetin (13), quercitrin (14) and isoquercitrin (15) were isolated from Sarcandra glabra (Thunb.) Nakai by various chromatographic methods. Compounds 1, 2, 4, 6, 11, and 12 were isolated from S. glabra for the first time. Their chemical structures were identified through the analysis of NMR and HR-MS spectra. The anti-inflammatory and cytotoxic activities of compounds 1-15 were evaluated in cell assays. The results indicated that compounds 1, 7, 8, 10, 14, and 15 significantly inhibited the NO production in LPS-induced RAW 264.7 murine macrophage cells. Moreover, compounds 1, 3, 4, 7, 8, 9, 10 and 12 exhibited a cytotoxic effect on the human HepG2 cell line.