Rare new bicyclic cembranoid ethers and a novel trihydroxy prenylated guaiane from the Xisha soft coral Lobophytum sp

Song-Wei Li; Cristina Cuadrado; Xia-Juan Huan; Li-Gong Yao; Ze-Hong Miao; Antonio Hernandez Daranas; Yue-Wei Guo

doi:10.1016/j.bioorg.2020.104223

Rare new bicyclic cembranoid ethers and a novel trihydroxy prenylated guaiane from the Xisha soft coral Lobophytum sp

Bioorg Chem. 2020 Oct:103:104223. doi: 10.1016/j.bioorg.2020.104223. Epub 2020 Aug 26.

Authors

Song-Wei Li¹, Cristina Cuadrado², Xia-Juan Huan³, Li-Gong Yao³, Ze-Hong Miao⁴, Antonio Hernandez Daranas⁵, Yue-Wei Guo⁶

Affiliations

¹ School of Chinese Materia Medica, Nanjing University of Chinese Medicine, 138 Xianlin Road, Nanjing 210023, China; State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, No. 555, Zu Chong Zhi Road, Zhangjiang Hi-Tech Park, Shanghai 201203, China.
² Instituto de Productos Naturales y Agrobiología, Consejo Superior de Investigaciones Científicas (IPNA-CSIC), La Laguna, 38206 Tenerife, Spain.
³ State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, No. 555, Zu Chong Zhi Road, Zhangjiang Hi-Tech Park, Shanghai 201203, China.
⁴ State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, No. 555, Zu Chong Zhi Road, Zhangjiang Hi-Tech Park, Shanghai 201203, China. Electronic address: zhmiao@simm.ac.cn.
⁵ Instituto de Productos Naturales y Agrobiología, Consejo Superior de Investigaciones Científicas (IPNA-CSIC), La Laguna, 38206 Tenerife, Spain. Electronic address: adaranas@ipna.csic.es.
⁶ School of Chinese Materia Medica, Nanjing University of Chinese Medicine, 138 Xianlin Road, Nanjing 210023, China; State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, No. 555, Zu Chong Zhi Road, Zhangjiang Hi-Tech Park, Shanghai 201203, China. Electronic address: ywguo@simm.ac.cn.

PMID: 32891002
DOI: 10.1016/j.bioorg.2020.104223

Abstract

Seven new cembrane-type diterpenes, lobophytolins C-I (3-9), and one new prenylated-guiane-type diterpene, lobophytolin J (10), along with six known related ones (1, 2, 11-14), have been isolated from the soft coral Lobophytum sp. collected off the Xisha Island in the South China Sea. Their structures were elucidated by extensive spectroscopic analysis and quantum mechanical (QM)-NMR methods. The absolute configuration of lobophytolin H (8) was determined by the application of the modified Mosher's method and chemical transformation. Lobophytolin D (4) exhibited promising cytotoxicities in in vitro bioassays against HT-29, Capan-1, A549, and SNU-398 human cancer cell lines with IC₅₀ values of 4.52, 6.62, 5.17, and 6.15 μM, respectively.

Keywords: Cembranoids; Lobophytum; Marine natural products; Quantum mechanical calculations; Soft coral.

Publication types

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

MeSH terms

Animals
Anthozoa / chemistry*
Antineoplastic Agents / chemistry
Antineoplastic Agents / isolation & purification
Antineoplastic Agents / pharmacology*
Cell Line, Tumor
Diterpenes / chemistry
Diterpenes / isolation & purification
Diterpenes / pharmacology*
Drug Screening Assays, Antitumor
Humans
Stereoisomerism

Substances

Antineoplastic Agents
Diterpenes