DEHATRINE, AN ANTIMALARIAL BISBENZYLISOQUINOLINE ALKALOID FROM THE INDONESIAN MEDICINAL PLANT BEILSCHMIEDIA MADANG, ISOLATED AS A MIXTURE OF TWO ROTATIONAL ISOMERS

• Published in: Chemical & pharmaceutical bulletin Vol. 41; no. 5; pp. 997 - 999
• Main Authors: KITAGAWA, Isao, MINAGAWA, Kazuyuki, ZHANG, Ru-song, HORI, Kazuyuki, DOI, Mitsunobu, INOUE, Masatoshi, ISHIDA, Toshimasa, KIMURA, Masatsugu, UJI, Tahan, SHIBUYA, Hirotaka
• Format: Journal Article
• Language: English
• Published: Tokyo The Pharmaceutical Society of Japan 1993; Maruzen; Japan Science and Technology Agency
• Subjects: Alkaloids - chemistry; Alkaloids - isolation & purification; Alkaloids - pharmacology; Animals; antimalarial substance; Antimalarials - chemistry; Antimalarials - isolation & purification; Antimalarials - pharmacology; Beilschmiedia madang; Biological and medical sciences; bisbenzylisoquinoline; dehatrine; Erythrocytes - parasitology; General pharmacology; Humans; In Vitro Techniques; Indonesia; Indonesian medicinal plant; Isoquinolines - chemistry; Isoquinolines - isolation & purification; Isoquinolines - pharmacology; Medical sciences; Models, Molecular; Pharmacognosy. Homeopathy. Health food; Pharmacology. Drug treatments; Plants, Medicinal - chemistry; Plasmodium falciparum - drug effects; rotational isomer; Stereoisomerism; Asia; Indonesia; Antimalarial; Isoquinoline derivatives; Molecular structure; Isomer; Medicinal plant; Alkaloid; Folk medicine; Dicotyledones; Angiospermae; Plant origin; Isolation; Spermatophyta; Lauraceae
• ISSN: 0009-2363; 1347-5223
• DOI: 10.1248/cpb.41.997

Through bioassay-guided separations of the chemical constituents of the Indonesian medicinal plant Beilschmiedia madang BL. a bisbenzylisoquinoline alkaloid was obtained as the major antimalarial principle. The physicochemical properties of the alkaloid were consistent with the proposed structure of dehatrine (1). However, the alkaloid isolated by us was shown to be a mixture of two rotational isomers. The X-ray crystallographic analysis of 1 has shown that two rotamers are incorporated in a single crystal in 1 : 1 ratio. The complex NMR spectrum of 1 has also been defined as a mixture of two rotamers by extensive use of 2D (COSY and COLOC) techniques. Dehatrine (1) has been shown to significantly inhibit the growth of cultured Plasmodium falciparum K1 strain (cholorquine resistant) with similar activity to quinine.