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Sesquiterpenoids and tirucallane triterpenoids from the roots of Scorzonera divaricata.

Abstract
A sulfated guaiane sesquiterpene lactone, an unusual pyridinium alkaloid with a sulfated guaiane sesquiterpene lactone nucleus, an amino conjugate of a sulfated guaiane sesquiterpene lactone, a bisabolane sesquiterpene, three tirucallane triterpenes, and six known compounds, were isolated from roots of Scorzonera divaricata. Their structures and absolute configurations were established based on chemical and spectroscopic methods, X-ray single crystal crystallography, and also by comparison with experimental and calculated ECD spectra. One of the tirucallane triterpenes exhibited significant cytotoxic activities against four human cancer cell lines (HL60, HeLa, HepG2, and SMMC-7721) in vitro. Two of sulfated guaiane sesquiterpenoids also exhibited antioxidant activities by scavenging ABTS cation free radicals. Tirucallane-type and dammarane-type triterpenes were not previously known in the genus Scorzonera. The study suggests that sulfated guaiane-type sesquiterpenoids are a valuable marker for systematic chemical studies in the Lactuceae tribe of the Asteraceae.
AuthorsYong-Jin Yang, Juan Yao, Xiao-Jie Jin, Zhuan-Ning Shi, Tian-Fei Shen, Jian-Guo Fang, Xiao-Jun Yao, Ying Zhu
JournalPhytochemistry (Phytochemistry) Vol. 124 Pg. 86-98 (Apr 2016) ISSN: 1873-3700 [Electronic] England
PMID26832425 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)
CopyrightCopyright © 2016 Elsevier Ltd. All rights reserved.
Chemical References
  • Antineoplastic Agents, Phytogenic
  • Sesquiterpenes
  • Sesquiterpenes, Guaiane
  • Triterpenes
  • guaiane
  • tirucallane
  • dammarane
Topics
  • Antineoplastic Agents, Phytogenic (chemistry, isolation & purification, pharmacology)
  • Crystallography, X-Ray
  • Drug Screening Assays, Antitumor
  • HL-60 Cells
  • HeLa Cells
  • Hep G2 Cells
  • Humans
  • Molecular Conformation
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Plant Roots (chemistry)
  • Scorzonera (chemistry)
  • Sesquiterpenes (chemistry, isolation & purification, pharmacology)
  • Sesquiterpenes, Guaiane
  • Triterpenes (chemistry, isolation & purification, pharmacology)

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