Flavonoid glycosides from the rhizomes of Pronephrium penangianum. (November 2020)

• Record Type: Journal Article
• Authors: Shen, Bingbing; Chen, Shenghuang; Zhou, Qi; Jian, Yuqing; Daniyal, Muhammad; Sheng, Wenbing; Gong, Limin; Luo, Dixian; Liu, Bin; Xu, Guangming; Wang, Wei
• Is Part Of: Phytochemistry. Volume 179(2020)
• Publication Date: 2020-11
• Subjects: Pronephrium penangianum (Thelypteridaceae) -- Flavonoid glycosides -- Pigment -- Jixueqi -- Biosynthetic pathways -- Cytotoxicity; Botanical chemistry -- Periodicals; Biochemistry -- Periodicals; Botany -- Periodicals; Chimie végétale -- Périodiques; 572.2
• DOI: 10.1016/j.phytochem.2020.112500
• Languages: English
• ISSNs: 0031-9422

Abstract

Abstract: Six flavonoid glycosides jixueqisus A-F, together with nine known flavonoids, were isolated from the rhizomes of the fern Pronephrium penangianum . Among them, two red pigments jixueqisus A and B possess the same rare 6, 8-dimethyl-2-phenyl-7 H -1-benzopyran-7-one skeleton (a long conjugated system). Jixueqisu Cwas a dihydrochalcone glycoside, jixueqisu D was a chalcone glycoside, jixueqisu E was an aurone glycoside, and jixueqisu F was a flavonone glycoside. Interestingly, jixueqisus D-F, (2 S )-5, 2′, 5′-trihydroxy-7-methoxyflavanone and 5, 2′, 5′-trihydroxy-7-methoxyflavone possessed a 2, 5-dihydroxy substituted benzene ring (B-ring). Their structures were elucidated by various spectroscopic and chemical methods. Furthermore, the plausible biosynthetic pathways of jixueqisus A-F were discussed, respectively. All isolated compounds were evaluated for their activities against the proliferation of MCF-7, HepG-2, HCT-116 and BGC-823 tumor cell lines, four known flavane-4-ol glycosides, abacopterins A and C, eruberin B and triphyllin A, exhibited moderate activities to various cell lines. Graphical abstract: Image 1 Highlights: Six previously undescribed flavonoid glycosides with nine known flavonoids were isolated from Pronephrium penangianum. Jixueqisus A (1 ) and B (2 ), red color, which possess rare 6, 8-dimethyl-2-phenyl-7 H -1-benzopyran-7-one skeleton. Flavonoids 4 –8 possessed a 2, 5-dihydroxy substituted benzene ring (B-ring). Plausible biosynthetic pathways of 1 –3 and 4 –8 were discussed, respectively. Some known flavane-4-ol glycosides shown moderate activities to various tumor cell lines.