A new benzofuran derivative, pumiloside (1), together with seven known flavonoid glycosides, afzelin (2), astragalin (3), quercitrin (4), isoquercitrin (5), kaempferol 3-O-rutinoside (6), rutin (7) and kaempferol 3-O-sophoroside (8) were isolated from the leaves of Ficus pumila. Their structures were established by spectroscopic data and comparison with the literature values.
Cassia grandis is used for the treatment of skin disorders, back pain, aches, etc. in Vietnamese traditional medicine. In this paper, phytochemicals of the leaves were investigated. A new naphthalene derivative (1, cassgranon D) and, seven known compounds rutin (2), afzelin (3), quercitrin (4), epicatechin (5), (-)-epiafzelechin (6), isoquercitrin (7) and aloe emodin (8) were isolated from the ethyl acetate and methanol extracts. Their structures were elucidated by spectral evidences (UV, IR, MS, H,C, DEPT, HSQC and HMBC NMR), as well as by comparing with published data.
In the present study, phenolic constituents from the rhizomes of D. bonii were isolated and their antibacterial and antioxidant activities were determined. A new compound and eight known phenolic compounds were isolated from the ethanol extract of D. bonii. The structure of the new compound was characterized by spectroscopic analysis as 3-(5-hydroxymethyl)furan-2-yl)-2-phenylacrylaldehyde (9), along with chrysophanol (1), nobiletin (2), protocatechuic acid (3), protocatechualdehyde (4), isoliquiritigenin (5), rutin (6), nicotiflorin (7), and linocaffein (8). These compounds were isolated from this plant for the first time. Most of the compounds demonstrated antibacterial and antioxidant activities, with compound 4 demonstrating especially potent antioxidant effects (SC 50 4.87 Pg/mL) in the DPPH test. Keyword: Drynaria bonii, phenolic compound, antioxidant, antibacterial. The genus Drynaria is comprised of 19 species [1], of which seven are found in Vietnam [2]. Drynaria bonii Christ, a Vietnamese medicinal plant, has been traditionally used to heal bone fractures, stimulate the growth of hair, and treat tinnitus or deafness [2,3]. Until now, there has been no literature on the chemical constituents isolated from this plant. In our continuing studies on the Drynaria species in Vietnam [4-6], this paper describes the isolation and structural determination of nine secondary metabolites from the ethanol fraction of the rhizomes of Drynaria bonii Christ. Bioassays showed that most of the metabolites had antibacterial activity using the disc diffusion method and antioxidant activity using the 2,2-diphenyl-1-picrylhydrazyl (DPPH) free radical scavenging test.After a primary separation by column chromatography with silica gel (normal and reversed phase), the ethanol extract of D. bonii was partitioned successively with petroleum ether, chloroform, ethyl acetate, and methanol. After purifying by Sephadex LH-20 and ODS column chromatography, the petroleum ether, chloroform, ethyl acetate, and methanol fractions of D. bonii yielded nine compounds (1-9), one of which was a new compound (9).Compound 9 was obtained as a dark brown powder. It reacted positively with FeCl 3 , proving that 9 was a phenolic compound. The molecular formula was established as C 14 H 12 O 3 using HR-ESI-MS (the mass spectrum showed a pseudomolecular ion peak [M + Na] + at m/z 251.0679; calcd for C 14 H 12 O 3 Na, 251.0684). The PMR spectrum of 9 displayed two doublet olefinic signals at G 6.12 (1H, d, J = 3.5 Hz, H-3) and 6.35 (1H, d, J = 3.5 Hz, H-4), suggesting the presence of a 2,5-disubstituted furan ring, six aromatic protons at G [7.16 (2H, m, H-2c, 6c), 7.45 (2H, m, H-3c, 5c), 7.44 (1H, m, H-4c), and 7.50 (1H, s, H-6)]. The singlet signal at G 9.66 (1H, s, H-E) indicated the existence of an aldehyde in its structure. The 13 C NMR spectrum showed 14 carbon signals, of which there was a carbonyl at G 192.6 (C-E), two oxyaryl carbons at G 149.2 (C-2) and 159.3 (C-5), eight methine aromatic carbons, and two quaternary aromatic carbons.
In Vietnam, the medicinal plant Drynaria bonii H. Christ is used for the treatment of osteoporosis, bone fractures, and stimulate the growth of hair, treat tinnitus (Ho 2002; Loi 2004). In this article, experiments were designed to investigate the proliferation activity of ethanol, n-hexane, chloroform, ethyl acetate and methanol extracts from D. bonii rhizomes on MG-63 human osteoblast-like cells. The results showed that methanol and hexane extracts had the ability to proliferate MG-63 cells at the concentration varying from 0.1 to 0.01 μg/mL. In particular, at the concentration of 0.01 μg/mL, hexane and methanol extracts illustrated the highest proliferation ratio with 9.31% and 6.16%, respectively. By column chromatography, a new compound named drynaether A (1) and five known compounds uracil (2), 4'-hydroxy-7-methoxyflavan (3), kaempferol (4), indole-3-carboxylic acid (5) and protocatechuic acid (6) were isolated and identified from the methanol extract.
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