Daphniyunnines A−E, Alkaloids from Daphniphyllum yunnanense

• Published in: Journal of natural products (Washington, D.C.) D.C.), 2006-04, Vol.69 (4), p.553-557
• Main Authors: Zhang, Hua, Yang, Sheng-Ping, Fan, Cheng-Qi, Ding, Jian, Yue, Jian-Min
• Format: Article
• Language: English
• Subjects: alkaloids; Alkaloids - chemistry; Alkaloids - isolation & purification; Alkaloids - pharmacology; Animals; anticarcinogenic activity; Biological and medical sciences; chemical constituents of plants; chemical structure; Crystallography, X-Ray; cultured cells; cytotoxicity; Daphniphyllaceae; Daphniphyllum; Daphniphyllum yunnanense; daphniyunnines; Drug Screening Assays, Antitumor; Drugs, Chinese Herbal - chemistry; Drugs, Chinese Herbal - isolation & purification; Drugs, Chinese Herbal - pharmacology; General pharmacology; Heterocyclic Compounds, 4 or More Rings - chemistry; Heterocyclic Compounds, 4 or More Rings - isolation & purification; Heterocyclic Compounds, 4 or More Rings - pharmacology; Humans; Leukemia P388; Medical sciences; Molecular Structure; Nuclear Magnetic Resonance, Biomolecular; Pharmacognosy. Homeopathy. Health food; Pharmacology. Drug treatments; phytochemicals; plant extracts; Plants, Medicinal - chemistry; Saxifragaceae - chemistry; spectral analysis; stereochemistry
• ISSN: 0163-3864; 1520-6025
• DOI: 10.1021/np050490e

The first chemical study on the stems and leaves of Daphniphyllum yunnanense led to the isolation of five new alkaloids, daphniyunnines A−E (1−5). Daphniyunnines B−E (2−5) are four unusual C-22 nor-Daphniphyllum alkaloids. The structures of these alkaloids were characterized by spectroscopic methods, especially 2D NMR techniques. A single-crystal X-ray diffraction analysis was used to confirm the structure of 1. Daphniyunnine D (4) showed cytotoxicity against two tumor cell lines, P-388 and A-549, with IC50 values of 3.0 and 0.6 μM, respectively.