A new 3,4-seco-oleanane-type triterpenoid with an unusual enedione moiety from Hypericum ascyron

Chunmei Chen; Guangzheng Wei; Hucheng Zhu; Yi Guo; Xiao-Nian Li; Jinwen Zhang; Yanfei Liu; Guangmin Yao; Zengwei Luo; Yongbo Xue; Yonghui Zhang

doi:10.1016/j.fitote.2015.04.009

A new 3,4-seco-oleanane-type triterpenoid with an unusual enedione moiety from Hypericum ascyron

Fitoterapia. 2015 Jun:103:227-30. doi: 10.1016/j.fitote.2015.04.009. Epub 2015 Apr 12.

Authors

Chunmei Chen¹, Guangzheng Wei¹, Hucheng Zhu¹, Yi Guo¹, Xiao-Nian Li², Jinwen Zhang³, Yanfei Liu⁴, Guangmin Yao¹, Zengwei Luo¹, Yongbo Xue⁵, Yonghui Zhang⁶

Affiliations

¹ Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, China.
² State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650204, China.
³ Tongji Hospital Affiliated to Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, China.
⁴ The Central Hospital of Wuhan affiliated to Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, China.
⁵ Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, China. Electronic address: [email protected].
⁶ Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, China. Electronic address: [email protected].

PMID: 25870936
DOI: 10.1016/j.fitote.2015.04.009

Abstract

A novel 3,4-seco-oleanane-type triterpenoid named 3,4-seco-olean-13(18)-ene-12,19-dione-3-oic acid (1), bearing an unusual enedione moiety, was isolated from the aerial parts of Hypericum ascyron, together with a known feiedelane-type triterpenoid friedelin (2). The structure of 1 with absolute configuration was elucidated on the basis of spectroscopic methods and a single-crystal X-ray diffraction analysis.

Keywords: 3,4-seco-oleanane; Absolute configuration; Hypericum ascyron; Triterpenoid.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Cell Line, Tumor
Humans
Hypericum / chemistry*
Molecular Structure
Oleanolic Acid / analogs & derivatives*
Oleanolic Acid / chemistry
Oleanolic Acid / isolation & purification
Secosteroids / chemistry
Secosteroids / isolation & purification
Triterpenes / isolation & purification

Substances

Secosteroids
Triterpenes
oleanane
Oleanolic Acid
friedelin