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

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).

A new flavonoid from Cudrania cochinchinensis.

Chemical investigation of the ethanol extract of the roots of Cudrania cochinchinensis led to the isolation of a new flavonoid, (6S,12S,13R)-1-methoxy cyanomaclurin (1), together with seven known compounds, 1,3,5-trihydroxy-4-(3'-hydroxy-3'-methylbutyl)xanthone (2), 1,3,6-trihydroxy-4-prenylxanthone (3), 1,3,6,7-tetrahydroxyxanthone (4), 1,3,5,6-tetrahydroxyxanthone (5), 1,3,6-trihydroxy-5-methoxyxanthone (6), resveratrol (7) and oxyresveratrol (8). The structure of compound 1 was elucidated on the basis of 1D and 2D NMR spectra and the HR-ESI-MS data. The absolute stereochemistry was deduced via Rh2(OCOCF3)4-induced CD and NOESY spectra.

Two new flavonols from Cudrania cochinchinensis.

Two new flavonols, 6-p-hydroxybenzyl kaempferol (1) and 6-p-hydroxybenzyl quercetin (2), together with six known compounds were isolated from the roots of Cudrania cochinchinensis and their structures elucidated on the basis of spectroscopic methods. Their antioxidant capacities were evaluated by 1,1-diphenyl-2-picryl-hydrazyl and 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) radical-scavenging assays. The results suggested that compounds 2, 4, and 7 showed significant radical-scavenging activities.

A New Prenylated Xanthone from Root Barks of Cudrania cochinchinensis / 中草药·英文版

Objective: To study the chemical constituents from the root barks of Cudrania cochinchinensis. Methods: The chemical constituents were isolated and purified by silica gel column chromatography. The structures of the compounds were identified on the basis of spectral data (MS, 1H-NMR, 13C-NMR, and 2D NMR) and by the comparison of spectroscopic data with the reported values in the literatures. Results: A new xanthone, 1,6,7-trihydroxy-4-(1,1-dimethylallyl)-3-methoxyxanthone (1) and a known prenylated xanthone 1,5,6-trihydroxy-4-(1,1-dimethylallyl)-3-methoxyxanthone (isocudraniaxanthone B, 2) were isolated from the root barks of C. cochinchinensis. Conclusion: Compound 1 is a new prenylated xanthone. Isomers 1 and 2 are obtained from this plant for the first time. © 2013 Tianjin Press of Chinese Herbal Medicines.

Isolation of two benzopyran isoflavones from fruits of Cudrania cochinchinensis and their antitumor activities / 中草药

Objective: To study the chemical constituents from the fruits of Cudrania cochinchinensis. Methods: The ethanol extract from the fruits of C. cochinchinensis was separated by silica column chromatography, and the structures were elucidated based on spectroscopy and X-ray diffraction. Results Two known benzopyran isoflavones were isolated and elucidated as 4'-O-methylalpinmumisoflavone (1) and isoderrone (2). The crystal structures showed compounds 1 and 2 belonged to monoclinic system, the space group was P2 (1)/c, and the 3D-supramolecular structures were accumulated by hydrogen bond in intra-and inter-molecule, π-π deposition, and Van der Waals force. The in vitro inhibition on BEL-7404 and SGC-7901 carcinoma cell lines was investigated and the results showed compound 2 had a distinct antiproliferative activity. Conclusion: Compound 1 is isolated from this plant and compound 2 from the plants in this genus for the first time. The plane crystal structures of compounds 1 and 2 are determined by X-ray crystal diffraction, and the 3D stack structures are also reported for the first time.