Polysubstituted Isoflavonoids from Spatholobus suberectus, Flemingia macrophylla, and Cudrania cochinchinensis

Abstract

Four hitherto unknown polysubstituted isoflavonoids, including three isoflavans: 7,4′-dihydroxy-8,2′,3′-trimethoxyisoflavan (1), 7,2′,4′-trihydroxy-8,3′-dimethoxyisoflavan (2), and 7,2′,4′-trihydroxy-5-methoxyisoflavan (3), and one prenylated isoflavone cudraisoflavone M (4) were isolated from the ethanol extracts of Spatholobus suberectus (for 1 and 2), Flemingia macrophylla (for 3), and Cudrania cochinchinensis (for 4), respectively. Their structures were established on the basis of extensive spectroscopic analysis. Compounds 1 and 4 exhibited weak cytotoxic activity against five human cancer cell lines (HL-60, A-549, SMMC-7721, MCF-7, and SW-480).Graphical Abstract Electronic supplementary materialThe online version of this article (doi:10.1007/s13659-017-0121-2) contains supplementary material, which is available to authorized users.

A Review of the Pharmacological Potential of Spatholobus suberectus Dunn on Cancer

“…It seems that flavonoids have hydroxyl radical-scavenging capacity that is connected to their antimutagenic properties [ 126 ]. 7,4′-dihydroxy-8,2′,3′-trimethoxyisoflavan extracted from SSD has significant cytotoxicity in preventing human cancer cell lines, viz., HL-60, SMMC-7721, SW-480 MCF-7, and A-549 [ 41 ]. The ethanolic extract of SSD contains four novel isoflavanes, which exert potential cytotoxicity activities in MCF-7 and MDA-MB-231 BC cell lines.…”

Ethnopharmacology, Phytochemistry, and Pharmacological Activities of Spatholobus suberectus Vine Stem

“…According to empirical rules, a positive Cotton effect at ∼240 nm and a negative Cotton effect at ∼280 nm are the signs of 3 S -isoflavane, 13 while the 3 R -isomer should show a negative Cotton effect in the 215 to 240 nm region. 14 For complex derivatives, electronic CD simulation is required to assign the absolute configuration of compounds. 9 Pterocarpan-type isoflavonoids were also found in S suberectus stems ( 46 – 48 ).…”

Antibacterial and cytotoxic activities of phenolic constituents from the stem extracts of Spatholobus parviflorus

“…A water decoction of the stems and leaves (Mahidol University 1996) of S. parviflorus is used in traditional medicine by tribal communities in the North of Thailand to treat indigestion, gastritis, menstrual pain, and other diseases. Plants of the genus Spatholobus are a major source of flavonoids (Yoon et al 2004;Tang et al 2012;Wang et al 2017). Recently, Sichaem and co-workers reported the isolation of flavonoids and phenolic derivatives and their cholinesterase activity from the extracts of the stems of S. parviflorus (Sichaem et al 2018).…”