Crokonoids A-C, A Highly Rearranged and Dual-Bridged Spiro Diterpenoid and Two Other Diterpenoids from Croton kongensis

Yao-Yue Fan; Shu-Qin Shi; Guo-Zhen Deng; Hong-Chun Liu; Cheng-Hui Xu; Jian Ding; Guan-Wu Wang; Jian-Min Yue

doi:10.1021/acs.orglett.9b04484

Crokonoids A-C, A Highly Rearranged and Dual-Bridged Spiro Diterpenoid and Two Other Diterpenoids from Croton kongensis

Org Lett. 2020 Feb 7;22(3):929-933. doi: 10.1021/acs.orglett.9b04484. Epub 2020 Jan 9.

Authors

Yao-Yue Fan¹, Shu-Qin Shi², Guo-Zhen Deng^{1

3}, Hong-Chun Liu¹, Cheng-Hui Xu¹, Jian Ding¹, Guan-Wu Wang^{2

4}, Jian-Min Yue¹

Affiliations

¹ State Key Laboratory of Drug Research , Shanghai Institute of Materia Medica, Chinese Academy of Sciences , 555 Zuchongzhi Road , Shanghai 201203 , People's Republic of China.
² Nano Science and Technology Institute , University of Science and Technology of China , Suzhou , Jiangsu 215123 , People's Republic of China.
³ University of Chinese Academy of Sciences , No.19A Yuquan Road , Beijing 100049 , People's Republic of China.
⁴ Department of Chemistry , University of Science and Technology of China , Hefei , Anhui 230026 , People's Republic of China.

PMID: 31916776
DOI: 10.1021/acs.orglett.9b04484

Abstract

Crokonoid A (1), a highly rearranged diterpenoid featuring a dual-bridged tricyclo[4.4.1.1^1,4]dodecane-2,11-dione ring system and its two possible ent-kaurene diterpenoid precursors (2 and 3), was isolated and structurally characterized by solid data from Croton kongensis. Compound 1 exhibited significant cytotoxicity against HL-60 and A-549 cell lines with IC₅₀ values of 1.24 ± 0.56 and 1.92 ± 0.60 μM, respectively.

Publication types

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

MeSH terms

A549 Cells
Antineoplastic Agents, Phytogenic / chemistry
Antineoplastic Agents, Phytogenic / isolation & purification
Antineoplastic Agents, Phytogenic / pharmacology*
Cell Line, Tumor
Cell Proliferation / drug effects
Croton / chemistry*
Diterpenes / chemistry
Diterpenes / isolation & purification
Diterpenes / pharmacology*
Drug Screening Assays, Antitumor
HL-60 Cells
Humans
Molecular Structure
Stereoisomerism

Substances

Antineoplastic Agents, Phytogenic
Diterpenes