Isoflavanones from Desmodium oxyphyllum and their cytotoxicity

Abstract

Two new isoflavanones, (3R)-7-hydroxy-4'-methoxy-5-methoxycarbonyl-isoflavanone (1) and (3R)-8-hydroxy-4'-methoxy-7-methoxycarbonyl-isoflavanone (2), together with seven known isoflavanones (3-9) were isolated from Desmodium oxyphyllum of the Leguminosae family. Their structures were elucidated by spectroscopic methods, including extensive 1D and 2D NMR techniques. Compound 1 showed good cytotoxicity against NB4 and SHSY5Y cell lines with IC50 values of 3.1 and 2.5 μM; compound 2 exhibited cytotoxicity against PC3 cell lines with a IC50 value of 3.6 μM; compound 4 showed cytotoxicity against A549 and SHSY5Y cell lines with IC50 values of 3.6 and 2.8 μM; and compound 5 displayed cytotoxicity against NB4, SHSY5Y, and MCF7 cell lines with IC50 values of 2.6, 3.8, and 2.8 μM, respectively. Other compounds also showed moderate cytotoxicity for some tested cell lines with IC50 values between 5.4 and 8.8 μM.

New Isoflavanes from Spatholobus suberectus and Their Cytotoxicity against Human Breast Cancer Cell Lines

“…It can be speculated that the substituents on the aromatic rings in isoflavanes play an important role in inhibiting the proliferation of breast cancer cells. Although several natural isoflavones showed strong antiproliferative effects on breast cancer cells [15,16,17], the two isoflavones 7 and 8 isolated from S. suberectus were inactive in this study (IC 50 > 100 μM). It is worth investigating whether other isoflavanes and isoflavones of S. suberectus have anti-breast cancer effects.…”

“…Isoflavanes and isoflavones are two subclasses of isoflavonoids, which are plant secondary metabolites characterized by a B-ring attached at the C-3 position of the C-ring. They are known for their significant estrogen-like activity, and modern research suggests that they also have antiproliferation in many kinds of human cancer cell lines [12,13,14,15,16,17]. However, there are few reports on the cytotoxic isoflavanes and isoflavones of S. suberectus .…”

Isoflavonoids from Desmodium heterophyllum Aerial Parts

“…The inhibitory effects of the isolated compounds against α-amylase and α-glucosidase were evaluated in comparison with the antidiabetic acarbose. As indicated in Table 1, dalbergioidin (2) and genistein (5) were the most active, which inhibited both α-amylase and α-glucosidase. Compounds 1 and 3 only showed inhibitory effects against α-glucosidase activity while compound 4 was inactive.…”

“…In our ongoing research for antidiabetic agents from the traditional herbs, a methanol extract of D. heterophyllum aerial parts was found to show significant inhibitory activity against α-amylase and α-glucosidase (68.3 and 75.6% inhibition at 20 µg/mL, respectively). A phytochemical investigation of this extract led to the isolation of a new isoflavanone (1), together with dalbergioidin (2), 4',5,7-trihydroxy-3'-methoxyisoflavone (3), 2',4',5,7tetrahydroxyisoflavone (4), and genistein (5). 162.6) as well as H-8 to C-6 ( C 105.2), C-7 ( C 165.8), C-9, and C-10 ( C 103.7).…”

“…In order to establish the absolute configuration at C-3, the CD curve of 1 was recorded. The configuration at C-3 was determined as R from the fact that the CD spectrum of 1 indicated a positive Cotton effect at 310 nm [5]. Consequently, compound 1 was elucidated as (3R)-2',4',5,7-tetrahydroxy-6-methylisoflavanone.…”