A rare isoflavone-quinone and a new flavanone from the roots of Dalbergia stipulacea Roxb.

Abstract

Two previously undescribed compounds, namely dalpulapans F and G (1 and 2), along with 11 known compounds were isolated from the MeOH crude extract of the roots of Dalbergia stipulacea. Dalpulapan F was found as a rare isoflavone-quinone derivative. Their structures and absolute configurations were supported by extensive spectroscopic data analysis, including 1D and 2D NMR, HRESIMS data, specific rotation data, and comparison of the experimental and calculated ECD data. Cytotoxicity evaluation of the isolated compounds against HepG2 and KKU-M156 cell lines revealed that isoflavonoid 9 and rotenoid 13 exhibited the most activity against the two cell lines.

Structural modification of olibergin A, an isoflavonoid, from Dalbergia stipulacea Roxb. and its cytotoxicity

“… 9 (−)-12α-hydroxyrotenone from the methanol extract of D. stipulacea roots displayed cytotoxicity against HepG2 cell line with an IC 50 value of 18.01 ± 1.51 mM. 10 It was found that (−)-vestitol from the stems of this plant displayed the strongest antifungal activity against Pythium insidiosum and had higher activity than the amphotericin-B standard. 11 …”

“…8 The chemical constituents from the stems and the roots of this plant are chalcones, isoflavonoids, flavonoids, pterocarpans, diterpenes and coumarins. 9–11 R , R -Velucarpin A, a pterocarpan, from the roots of this plant showed cytotoxicity against HeLa cells with an IC 50 value of 10.9 ± 0.42 μM (Posri et al , 2021). 9 (−)-12α-hydroxyrotenone from the methanol extract of D. stipulacea roots displayed cytotoxicity against HepG2 cell line with an IC 50 value of 18.01 ± 1.51 mM.…”