Isoflavones and Rotenoids from the Leaves of Millettia oblata ssp. teitensis

Abstract

A new isoflavone, 8-prenylmilldrone (1), and four new rotenoids, oblarotenoids A-D (2-5), along with nine known compounds (6-14), were isolated from the CHCl/CHOH (1:1) extract of the leaves of Millettia oblata ssp. teitensis by chromatographic separation. The purified compounds were identified by NMR spectroscopic and mass spectrometric analyses, whereas the absolute configurations of the rotenoids were established on the basis of chiroptical data and in some cases by single-crystal X-ray crystallography. Maximaisoflavone J (11) and oblarotenoid C (4) showed weak activity against the human breast cancer cell line MDA-MB-231 with IC values of 33.3 and 93.8 μM, respectively.

Phytochemical analysis of Ononis arvensis L. by liquid chromatography coupled with mass spectrometry

“…Cuneatin was described in aerial parts of Millettia oblata ssp. teitensis , aerial parts of Retama sphaerocarpa , stem bark of Dalbergia frutescens , Eysenhardtia polystachya , aerial parts and roots of Tephrosia maxima and most importantly, in Cicer species . In his other work, Ingham had shown the chemotaxonomic similarity of genus Ononis and Cicer , and the presence of cuneatin in both genus corroborates this idea.…”

Flavonoids from the stems of Millettia pachyloba Drake mediate cytotoxic activity through apoptosis and autophagy in cancer cells

“…Based on the spectroscopic data and comparisons with the data found in the literature, the known compounds were identified as 8-prenylmilldurone ( 3 ) [22], 6-methoxycalpogonium isoflavone A ( 8 ) [23], durmillone ( 9 ) [24], durallone ( 10 ) [25], ichthynone ( 11 ) [8], millesianin C ( 12 ) [26], toxicarol isoflavone ( 13 ) [27], cladrastin ( 14 ) [28], dalpatein ( 15 ) [29], 7-hydroxy-2′,4′,5′,6-tetramethoxyisoflavone ( 16 ) [30], 3,9-dihydroxypterocarp-6a-en ( 17 ) [31], dehydromaackiain ( 18 ) [32], flemichapparin B ( 19 ) [33], (−)-medicarpin ( 20 ) [34], (−)-maackiain ( 21 ) [35], (−)-variabilin ( 22 ) [36], (−)-pisatin ( 23 ) [37], dalbinol ( 32 ) [38], (−)-sativin ( 25 ) [39], (−)-dehydrodiconiferyl alcohol ( 26 ) [40], (+)-vomifoliol ( 27 ) [41], and dihydrophaseic acid ( 28 ) [42].…”

Hydroxylated Rotenoids Selectively Inhibit the Proliferation of Prostate Cancer Cells

“…No comprehensive study has been made of the inhibitory properties of hydroxylated rotenoids against complex I or their ability to selectively target prostate cancer cells, though a number of reports have been made on the cytotoxicity of certain hydroxylated rotenoids. − Thus, a library of 29 hydroxylated rotenoids was prepared from rotenone ( 1 ) and deguelin ( 2 ) to identify inhibitors of complex I that might be better suited to development as therapeutics than the parent compounds. The inhibitory effect of each hydroxylated rotenoid on complex I was determined and its hydrophobicity predicted.…”