Antiproliferative Homoisoflavonoids and Bufatrienolides from Urginea depressa

Abstract

Investigation of the South African plant Urginea depressa Baker (Asparagaceae Juss.) for antiproliferative activity against the A2780 ovarian cancer cell line led to the isolation of the six new homoisoflavonoids urgineanins A-F (1 - 6), the two known bufatrienolides 7 and 9, and the new bufatrienolides urginins B and C (8 and 10). Structures were elucidated based on analysis of their 1D and 2D NMR spectra, electronic circular dichroism, and mass spectrometric data. Five of the six new homoisoflavonoids had good antiproliferative activity against the A2780 ovarian cancer, A2058 melanoma, and H522-T1 human non-small cell lung cancer cells, and urgineanin A (1) had submicromolar activity against all three cell lines. The four bufatrienolides 7 – 10 had strong antiproliferative activity against the same cell line, with IC50 values of 24.1, 11.2, 111 and 40.6 nM, respectively.

Ethnobotanical survey of medicinal plants used in the Maseru district of Lesotho

“…D. depressa has long been known to be toxic to sheep and cattle (Kellerman et al, 2005;Pooley, 2003;Van Wyk et al, 2002), but it is reported in the current study to cure diseases such as cancer, liver problems, HIV and mental illness. Recent studies have confirmed that five homoisoflavonoids urgineanins A-E (1-5), isolated from D. depressa showed strong antiproliferative activity against the A2780 ovarian cancer cell line (Dai et al, 2013). Similarly, P. heptandra is reported in the current study to cure cancer.…”

Sappanin-type homoisoflavonoids from Sansevieria trifasciata Prain

“…homoisoflavonoid (Yan et al, 2012;Dai et al, 2013). It also showed a singlet of two protons at d 5.91 ppm suggesting a methylenedioxyl moiety (Teponno et al, 2013b) and a singlet of three protons at d 3.81.…”

Phytochemical Investigations of Three Rhodocodon (Hyacinthaceae Sensu APG II) Species

“…The unusual 3S-configuration has been reported once from the Urginiodeae subfamily, from Urginea depressa. 25 The isolation of compound 3 was facilitated by acetylation yielding two products, the 3'-acetate, (3A) and the 5,7-diacetate, (4) has been isolated previously from Urginea altissima, 26 Helleborus orientalis, and H. thibetanus (Ranunuclaceae). 27,28 Gamabufotalin-3-O-α-L-rhamnoside (5) has been isolated previously from Urginea altissima.…”