Chemical Constituents of Glycosmis arborea:  Three New Carbazole Alkaloids and Their Biological Activity

Abstract

As part of the phytochemical studies of the plant genus Glycosmis, the constituents of the plant Glycosmis arborea were investigated. Three new carbazole alkaloids named glybomines A (1), B (2), and C (3), along with known monomeric alkaloids belonging to the carbazole, quinazoline, furoquinoline, quinolone, and acridone classes, were isolated from stems of the plant collected at Mymensing in Dhaka, Bangladesh. Glybomine A (1) is the first example of a 2,5-oxygenated carbazole alkaloid from natural sources. As a primary screening test for anti-tumor promoters, nine alkaloids isolated from this plant have been tested for their inhibitory effects on Epstein-Barr virus early antigen (EBV-EA) induction by the tumor promoter 12-O-tetradecanoylphorbol-13-acetate (TPA). All alkaloids tested showed inhibitory activity.

Wound healing activity of Glycosmis arborea leaf extract in rats

“…Hepatoprotective activity of butanol extract of aerial parts is reported (Gomes et al, 2003). The carbazole and acridine alkaloids isolated from Glycosmis arborea were reported to have inhibitory activity over Epstein-Barr virus (Ito et al, 2004) and anti-tumor activity (Quader et al, 1999).…”

Glycosmis pentaphylla (Retz.) DC arrests cell cycle and induces apoptosis via caspase-3/7 activation in breast cancer cells

“…The present study was aimed at studying the effect of the leaves of the plant on breast cancer cell lines. Previous studies on the plant reported the presence of acridone and carbazole alkaloids (Ito et al, 2004;Quader et al, 1999). Carbazole alkaloids also can intercalate the DNA due to their polycyclic and aromatic nature (Asche and Demeunynck, 2007).…”

Synthesis, anticonvulsant, antioxidant and binding interaction of novel N-substituted methylquinazoline-2,4(1H,3H)-dione derivatives to bovine serum albumin: A structure–activity relationship study

“…They possess a variety of biological effects; viz the acridone alkaloids from G. arborea including atalaphyllidine, 5-hydroxy-N-methylseverifoline, atalaphyllinine, and des-N-methylnoracrony-cine showed potent antiproliferative activity against tumor cell lines [22]. Along with acridones, monomeric alkaloids belonging to the carbazole, quinazoline, furoquinoline and quinolone exhibited significant anti-tumor-promoting activity on Epstein-Barr virus early antigen activation [23]. Glycosmicine, one derivative of quinazolinedione has been isolated from the G. arborea.…”