Desmodinosides A-E: New Flavonoid C-glycosides from Desmodium heterocarpon var. stigosum with hepatoprotective and antifungal activity

• Published in: Fitoterapia 2023-09, Vol.169, p.105609, Article 105609
• Main Authors: Le Dang, Quang, Vu, Hoang Dinh, Nguyen, Van Minh, Choi, Gyung Ja, Hoa, Le Thi Phuong, Dung, Duong Thi, Van Kiem, Phan, Nhiem, Nguyen Xuan, De Tran, Quang, Nguyen, Quoc Cuong, Nghiem, Duc Trong, Quang, Dang Ngoc
• Format: Article
• Language: English
• Subjects: Antifungal activity; Desmodium heterocarpon var. stigosum; Flavonoid C-glycoside; Hepatoprotective activity
• ISSN: 0367-326X
• DOI: 10.1016/j.fitote.2023.105609

Five new flavonoid C-glycosides named desmodinosides A-E (1–5) and one known compound, apigenin 6-C-β-d-xylopyranosyl-2′′-O-β-D-glucopyranoside (6) have been isolated from the methanol extract of the aerial parts of Desmodium heterocarpon var. stigosum. These compounds were determined by 1D and 2D-NMR and HR-MS spectroscopies. The methanol extract of this plant, in particular, demonstrated hepatoprotection and antifungal inhibition. This extract has a remarkable hepatoprotection and activity-dose response with an EC50 of 43.07 μg/mL. The hepatoprotective effect on human liver hepatoma cells (HepG2) of the isolated flavonoid C-glycosides 1–6 was observed. Desmodinosides A-C (1–3) were found to exhibit moderate hepatoprotective activity on HepG2 cells. Of these, compound 2 showed the best hepatoprotective activity with an EC50 value of 74.12 μg/mL. While compounds 1 and 3 displayed EC50 values of 271.21 and 211.99 μg/mL, respectively. Quercetin, a positive control, also caused an EC50 value of 36.42 μg/mL. In addition to having hepatoprotective effect, the methanol extract had an inhibitory effect on the growth of oomycete; it inhibited Phytophthora infestans with IC50 of 13.3 μg/mL and IC90 of 78.7 μg/mL. The oomycete inhibition was directly attributed to compounds 5 and 6, which significantly inhibited P. infestans with IC50 values of 27.4 and 24.7 μg/mL, respectively. Both 5 and 6 and methanol extract were active against P. infestanse in a dose-dependent manner. Our study demonstrated for the first time the new flavonoid C-glycosides from D. heterocarpon var. stigosum and their novel pharmacological properties. The study findings also suggest the plant extract and its metabolites could be used as a new botanical source of bioactive compounds. [Display omitted]