Rhazinilam and Quebrachamine Derivatives from Yunnan Kopsia arborea

• Published in: Journal of natural products (Washington, D.C.) D.C.), 2009-02, Vol.72 (2), p.204-209
• Main Authors: Wu, Yuqiu, Suehiro, Mayu, Kitajima, Mariko, Matsuzaki, Takeshi, Hashimoto, Shusuke, Nagaoka, Masato, Zhang, Rongping, Takayama, Hiromitsu
• Format: Article
• Language: English
• Subjects: alkaloids; Alkaloids - chemical synthesis; Alkaloids - chemistry; Alkaloids - isolation & purification; Alkaloids - pharmacology; anticarcinogenic activity; Apocynaceae; Apocynaceae - chemistry; Biological and medical sciences; Cell Proliferation - drug effects; chemical structure; cultured cells; cytotoxicity; Drugs, Chinese Herbal - chemical synthesis; Drugs, Chinese Herbal - chemistry; Drugs, Chinese Herbal - isolation & purification; Drugs, Chinese Herbal - pharmacology; General pharmacology; human diseases; Indole Alkaloids - chemical synthesis; Indole Alkaloids - chemistry; Indole Alkaloids - isolation & purification; Indolizines - chemistry; Indolizines - isolation & purification; Kopsia arborea; Kopsia officinalis; kopsiyunnanine; Lactams - chemistry; Lactams - isolation & purification; Medical sciences; medicinal plants; medicinal properties; Molecular Structure; Nuclear Magnetic Resonance, Biomolecular; Pharmacognosy. Homeopathy. Health food; Pharmacology. Drug treatments; phytochemicals; quebrachamine; rhazinilam; spectral analysis; stereochemistry
• ISSN: 0163-3864; 1520-6025
• DOI: 10.1021/np800489e

Three new rhazinilam-derived alkaloids, kopsiyunnanines C1, C2, and C3, and a new quebrachamine-type alkaloid, kopsiyunnanine D, which possess an unusual methoxymethyl or ethoxymethyl function, were isolated from the aerial parts of Yunnan Kopsia arborea. This is the first report of the presence of these functions in natural alkaloids. The structures and absolute configurations of the alkaloids were determined by spectroscopic methods and confirmed by semisynthesis.