Three new flavonol glycosides from Fissistigma pallens

Abstract

Three new flavonol glycosides, fissflavosides A-C (1–3), together with six known flavonol glycosides, kaempferol 3-O-α-L-rhamnopyranosyl-(1→2)-β-D-galactopyranoside (4), kaempferol 3-O-α-L-rhamnopyranosyl-(1→6)-β-D-galactopyranoside (5), kaempferol 3-O-α-L-rhamnopyranosyl-(1→6)-β-D-glucopyranoside (6), rhamnetin 3-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranoside (7), rutin (8), and isorhamnetin 3-O-α-L-rhamnopyranosyl-(1→2)-β-D-galactopyranoside (9) were isolated from the methanol extract of the Fissistigma pallens leaves. Their chemical structures were determined by 1D-, 2D-NMR, and MS data as well as in comparison with reported data in the literature. Compounds 1–9 showed weak cytotoxic activity on three human cancer cell lines, HT-29, A-2058, A-549 with IC50 ranging from 134.6 to 162.6 µM. In addition, the antioxidant capacities of compounds were also tested by ORAC assay. All compounds showed significant antioxidant with trolox equivalents ranging from 4.4 to 8.6 µM at the concentration of 1.0 µM. The results indicated 7 and 8 having meaningful reducing capacity of copper (I) ions of 2.7 to 6.9 µM at the concentrations of 1 and 2 µM.

FLAVONOL GLYCOSIDES FROM THE LEAVES OF FISSISTIGMA PALLENS (FIN. & GAGN.) MERR.

“…However, a few phytochemical investigations of Fissistigma pallens have been studied [6,7]. Previously, we reported flavonol glycosides and sesquiterpene glycosides from this plant [8,9]. In this continuous study, we report the structural elucidation of five flavonol glycosides from the leaves of F. pallens (Fig.…”

Chemical constituents of the leaves of Fissistigma balansae

“…In Vietnam, there were 23 Fissistigma species, and several species are used in traditional medicine to treat many different diseases such as traumatic injuries, hepatomegaly, rheumatism and arthritis. [1] Phytochemical investigations of Fissistigma species revealed the presence of alkaloids, [2][3][4] sesquiterpenes, [5] flavonoids, [6] and chalcones. [7] Some of these compounds showed bioactivities such as cytotoxic, anti-inflammatory, and antitumor effects.…”

“…Rutin (quercetin 3-O-rutinoside, 6)Yellow solid; ESIMS: m/z 611 [M+H] + , C27H30O16 1. H NMR (CD3OD, 500 MHz): 6.20 (d, 2.0 Hz, H-6),6.40 (d, 2.0 Hz, H-8), 7.99 (d, 2.0 Hz, H-2′), 7.56 (dd, d, 2.0, 8.0 Hz, H-6′), 6.94 (d, 8.0 Hz, H-5′), Glc: 5.13 (d, 7.5 Hz, H-1′′), 3.68 (dd, 7.5, 9.5 Hz, H-2′′), 3.63 (t, 9.5 Hz, H-3′′), 3.31 (dd, 9.5, 9.0 Hz, H-4′′), 3.27 (m, H-5′′), 3.57 (dd, 11.8, 4.6 Hz, Ha-6′′), 3.77 (dd, 11.8, 2.4 Hz, Hb-6′′), Rha: 4.54 (brs, H-1′′′), 3.68 (brd, 3.2 Hz, H-2′′′), 3.52 (dd, 9.0, 3.2 Hz, H-3′′′), 3.26 (dd, 9.0, 9.5 Hz, H-4′′′), 3.43 (m, H-5′′′), 1.15 (d, 6.4 Hz, H-6′′′).2.3.7. Acanthoside B (7)Colorless solid.…”