Diocollettines A, an unusual tricyclic diarylheptanoid derivative from the rhizomes of Dioscorea collettii

• Published in: Tetrahedron letters Vol. 57; no. 29; pp. 3215 - 3217
• Main Authors: Jing, Song-Song, Wang, Ying, Yan, Yong-Ming, Li, Xia, Li, Xue-Jiao, Zhao, Cheng-Cheng, Sun, Jia-Chen, Qiu, Pei-Yu, Man, Shu-Li, Gao, Wen-Yuan
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 20.07.2016; Elsevier
• Subjects: Absolute configuration; Chemistry; Chemistry, Organic; Cytotoxicity; Dioscorea collettii; Physical Sciences; Science & Technology; Tricyclic diarylheptanoid; ZIMUTSMRSAMDQO-BIRZXAFVSA-N; Dioscorea collettii; Cytotoxicity; Tricyclic diarylheptanoid; XMQSLAYELOPKEA-DFIADLHWSA-N; Absolute configuration; CELLS; VILLOSA WILD YAM; SAPONINS; PHENOLIC-COMPOUNDS; BULBIFERA; CONSTITUENTS
• ISSN: 0040-4039; 1873-3581
• DOI: 10.1016/j.tetlet.2016.06.047

[Display omitted] •A new diarylheptanoid with 6/5/5 fused rings was isolated from D. collettii.•The structures were elucidated by spectroscopic analysis and ECD calculation.•The structure of new compound was confirmed by single-crystal X-ray diffraction.•The cytotoxic activities of the compounds were tested against NCL-H460. An unprecedented diarylheptanoid derivative with 6/5/5 fused rings, diocollettines A (1), together with five known compounds (2–6) were isolated from the rhizomes of Dioscorea collettii. The structures were elucidated by extensive NMR spectroscopic analysis, together with HR-ESI-MS techniques. The absolute configuration of compound 1 was unambiguously confirmed by comparison of experimental data with calculated electronic circular dichroism (ECD) spectra and single-crystal X-ray diffraction analysis. Compound 1 exhibited moderate cytotoxicity against NCL-H460.