A New Dimeric Carbazole Alkaloid from Glycosmis stenocarpa Roots

• Published in: Chemical & Pharmaceutical Bulletin Vol. 52; no. 10; pp. 1175 - 1178
• Main Authors: Cuong, Nguyen Manh, Hung, Tran Quang, Sung, Tran Van, Taylor, Walter Chacles
• Format: Journal Article
• Language: English
• Published: TOKYO The Pharmaceutical Society of Japan 01.10.2004; Pharmaceutical Society of Japan; Pharmaceutical Soc Japan; Japan Science and Technology Agency
• Subjects: Alkaloids - chemistry; Alkaloids - isolation & purification; bis-pyranocarbazole; bisisomahanine; Carbazoles - chemistry; Carbazoles - isolation & purification; Chemistry; Chemistry, Medicinal; Chemistry, Multidisciplinary; chirality; dimer; Dimerization; Glycosmis stenocarpa; Life Sciences & Biomedicine; Magnetic Resonance Spectroscopy; murrayafoline-A; Pharmacology & Pharmacy; Physical Sciences; Plant Roots; Rutaceae; Science & Technology; Stereoisomerism; bisisomahanine; MURRAYA-KOENIGII; bis-pyranocarbazole; chirality; dimer; Glycosmis stenocarpa; murrayafoline-A; CONSTITUENTS
• ISSN: 0009-2363; 1347-5223
• DOI: 10.1248/cpb.52.1175

A new dimeric pyranocarbazole alkaloid, bisisomahanine (1), was isolated from the roots of Glycosmis stenocarpa (DRAKE) TAN., along with two known monomeric carbazole alkaloids, murrayafoline-A (2) and murrayanine (3). The planar structure of bisisomahanine was determined to be 9,9″-dihydroxy-3,3″,8,8″-tetramethyl-3,3″-bis-(4-methyl-3-pentenyl)-3,3″,11,11″-tetrahydro-10,10″-(bipyrano[3,2-a]carbazole) from the combination of spectroscopic and chemical evidence. Bisisomahanine is the first dimeric prenylated pyranocarbazole alkaloid with a 1,1′ type of linkage; the NMR and CD spectroscopic data indicated it to be a mixture of diastereomers having a dominant configuration at the axis of chirality. 1H- and 13C-NMR assignments of murrayafoline-A were made on the basis of 2D-experiments.