A new antifungal and cytotoxic C-methylated flavone glycoside from Picea neoveitchii

• Published in: Bioorganic & medicinal chemistry letters Vol. 22; no. 18; pp. 5819 - 5822
• Main Authors: Chen, Wei-Quan, Song, Zhi-Jun, Xu, Han-Hong
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 15.09.2012; Elsevier
• Subjects: Alternaria; Alternaria mali; Animals; Antibiotics. Antiinfectious agents. Antiparasitic agents; Antifungal activity; Antifungal agents; Antifungal Agents - chemistry; Antifungal Agents - isolation & purification; Antifungal Agents - pharmacology; antifungal properties; apigenin; Biological and medical sciences; branches; C-Methylated flavone glycoside; Cell Survival - drug effects; Chemistry; Chemistry, Medicinal; Chemistry, Organic; Cytotoxicity; Data processing; Dose-Response Relationship, Drug; Flavones; Flavones - chemistry; Flavones - isolation & purification; Flavones - pharmacology; Fungi - drug effects; Fungi - growth & development; glycosides; Glycosides - chemistry; Glycosides - isolation & purification; Glycosides - pharmacology; Kaempferol; Leaves; Life Sciences & Biomedicine; Magnaporthe grisea; Medical sciences; Microbial Sensitivity Tests; Molecular Structure; Pathogens; Pharmacology & Pharmacy; Pharmacology. Drug treatments; Physical Sciences; Picea; Picea - chemistry; Picea neoveitchii; Pinaceae; plant pathogens; Pyricularia grisea; Science & Technology; Sclerotium; spectroscopy; Spodoptera - cytology; Spodoptera - drug effects; Spodoptera litura; Stereoisomerism; Structure-Activity Relationship; Antifungal activity; Cytotoxicity; C-Methylated flavone glycoside; Picea neoveitchii; Pinaceae; PINUS-DENSIFLORA; TRITERPENOIDS; BARK; HEARTWOOD; MORRISONICOLA; JEZOENSIS VAR. HONDOENSIS; GLUCOSIDES; CUTICLE; EPOXYSERRATANES; Flavonoid; Biological activity; Polyphenol; Antifungal agent; Gymnospermae; Phenols; Flavone derivatives; Coniferales; Spermatophyta; C-Glycoside; Methylation; Picea
• ISSN: 0960-894X; 1464-3405
• DOI: 10.1016/j.bmcl.2012.07.089

A new C-methylated flavone glycoside, 5,7-dihydroxy-3-methoxy-6-C-methylflavone 8,4′-di-O-β-d-glucopyranoside (1), together with seven known compounds (2–9) were isolated from the twigs and leaves of Picea neoveitchii Mast. The cytotoxicities of the isolated compounds on Spodoptera litura Fabricius cell were evaluated by MTT assay and their antifungal activities were evaluated by disc diffusion method. Three of these compounds were isolated from the Pinaceae family for the first time. A new C-methylated flavone glycoside, 5,7-dihydroxy-3-methoxy-6-C-methylflavone 8,4′-di-O-β-d-glucopyranoside (1), was isolated from the twigs and leaves of Picea neoveitchii Mast, together with eight known compounds, 5,7,8,4′-tetrahydroxy-3-methoxy-6-methylflavone 8-O-β-d-glucopyranoside (2) kaempferol 3,4′-di-O-β-d-glucopyranoside (3), apigenin 7-O-β-d-glucopyranoside (4), tiliroside (5), massonianoside B (6), umbeliferone 7-O-β-d-glucopyranoside (7), dihydroconiferin (8) and gleditschiaside A (9). Their structures were elucidated on the basis of analyses of spectroscopic data. Compound 1 showed moderate antifungal activity against tested plant pathogens (Pyricularia grisea (Cooke) Sacc., Sclerotium rocfsii Sacc. and Alternaria mali Roberts), however, compounds 2 and 5 had obvious inhibitory effect against S. rocfsii and A. mali, respectively. Compounds 1, 2, 3 and 9 also exhibited potent cytotoxicity against Spodoptera litura Fabricius cells.