Cytotoxic Isoflavans from Eysenhardtia polystachya

Abstract

Two new cytotoxic isoflavans, (3S)-7-hydroxy-2',3',4',5', 8-pentamethoxyisoflavan (1) and (3S)-3',7-dihydroxy-2',4',5', 8-tetramethoxyisoflavan (2), were isolated from the bark and trunks of Eysenhardtia polystachya (Leguminosae), together with the known constituents stigmasterol, isoduartin, cuneatin, 7-hydroxy-2',4', 5'-trimethoxyisoflavone, and 3,4-dimethoxy-8, 9-(methylenedioxy)pterocarpan. The structures of 1 and 2 were elucidated on the basis of spectroscopic methods. The antimicrobial, cytotoxic, and insecticidal potential of some of these compounds were evaluated. The isoflavans 1, 2, and isoduartin (2', 7-dihydroxy-3',4',8-trimethoxyisoflavan) displayed moderate cytotoxic activity against KB cell lines.

Colutin, new antifungal isoflavan from Colutea armata

“…This was further supported by the UV spectrum, which exhibited bands at 218 and 284 nm [13]. The 1 H NMR spectrum of 1 also revealed four aromatic protons at G 6.61 (d, J = 8.5 Hz), 6.38 (d, J = 8.5 Hz), 6.79 (d, J = 8.5 Hz), and 6.57 (d, J = 8.5 Hz), in addition to singlets of three methoxyl groups at G 3.47, 3.86, and 3.87.…”

“…Identification of the NOE interaction between H-6 and the methoxyl group at G 3.47 linked to C-7 (at G 152.2 by HMBC), between H-4c and the methoxyl group at G 3.86 linked to C-5c (at G 146.5, by HMBC), between the methoxyl at G 3.87 linked to C-6c (at G 145.2, by HMBC) and the methoxyl group at C-5c, and between H-3c and the aldehydic moiety at G 10.30 linked to C-2c (at G 138.8, by HMBC) further allowed us to confirm the positions of various substituents. The CD curve of 1 indicating the 3S configuration showed a negative Cotton effect in the 262-290 nm region [13]. Thus, on the basis of these evidences, colutin (1) was assigned the structure (3S)-8-(6cc-methyl-5cc-heptenyl)-2c-aldehyde-5c,6c,7-trimethoxyisoflavan.…”

Synthesis and functionalization of silica-based nanoparticles with fluorescent biocompounds extracted from Eysenhardtia polystachya for biological applications

“…This tree gained attention due to its blue fluorescence as a result of its infusion in water, and by its biological properties, including antidiabetic, antibacterial, antioxidant, among others [36,37]. Many studies have reported the principal components of EP extracted using methanol, ethanol and water as solvents [35,36,38,39]. In this way, the responsible compounds for the fluorescence of EP are Coatline A and Coatline B,…”

Antioxidant Evaluation of Eysenhardtia Species (Fabaceae): Relay Synthesis of 3-O-Acetyl-11.ALPHA.,12.ALPHA.-epoxy-oleanan-28,13.BETA.-olide Isolated from E. platycarpa and Its Protective Effect in Experimental Diabetes

“…12) Previous studies on Eysenhardtia species have highlighted the hypoglycemic activity of E. polystachya 13) and the antihyperglycemic activity of E. platycarpa, 14) as well as the isolation of cytotoxic flavonoids 15,16) and 3-O-acetyloleanolic acid [which displayed antihyperglycemic activity in streptozotocin (STZ)-induced diabetic rats 14) ]. As part of our screening of plants for the isolation of substances with antioxidant and antihyperglycemic potential, 14,17) this study was conducted to A) assess the antioxidant effects of extracts from E. platycarpa, E. punctata, and E. subcoriacea, as well as of compounds 1-8, natural constituents isolated from E. platycarpa (Chart 1), in a rat pancreas model and in a 1,1 diphenyl-2-picrylhydrazyl (DPPH) radical scavenger assay; B) synthesize 1, which displayed a protective effect against 2,2-azo-bis(2-amidinopropane)dihydrochloride (AAPH)-induced damage in pancreatic homogenate; and C) evaluate the protective effect of 1 in STZinduced diabetic rats.…”