Jellynolide A, pokepola esters, and sponalisolides from the aquaculture sponge Spongia officinalis L

Tianyun Jin; Pinglin Li; Cili Wang; Xuli Tang; Xiaoli Yu; Fengqing Sun; Lianzhong Luo; Huilong Ou; Guoqiang Li

doi:10.1016/j.phytochem.2021.113006

Jellynolide A, pokepola esters, and sponalisolides from the aquaculture sponge Spongia officinalis L

Phytochemistry. 2022 Feb:194:113006. doi: 10.1016/j.phytochem.2021.113006. Epub 2021 Nov 25.

Authors

Tianyun Jin¹, Pinglin Li², Cili Wang¹, Xuli Tang³, Xiaoli Yu¹, Fengqing Sun¹, Lianzhong Luo⁴, Huilong Ou⁵, Guoqiang Li⁶

Affiliations

¹ Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy Department, Ocean University of China, Qingdao, 266003, People's Republic of China; Laboratory of Marine Drugs and Biological Products, National Laboratory for Marine Science and Technology, Qingdao, 266235, People's Republic of China.
² Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy Department, Ocean University of China, Qingdao, 266003, People's Republic of China; Laboratory of Marine Drugs and Biological Products, National Laboratory for Marine Science and Technology, Qingdao, 266235, People's Republic of China. Electronic address: lipinglin@ouc.edu.cn.
³ College of Chemistry and Chemical Engineering, State-Province Joint Engineering Laboratory of Marine Bioproducts and Technology, Ocean University of China, Qingdao, 266003, People's Republic of China.
⁴ Engineering Research Center of Marine Biopharmaceutical Resource, Xiamen Medical College, Xiamen, 361023, People's Republic of China.
⁵ Department of Aquaculture, College of Marine Sciences, Hainan University, Haikou, Hainan, 570228, People's Republic of China.
⁶ Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy Department, Ocean University of China, Qingdao, 266003, People's Republic of China; Laboratory of Marine Drugs and Biological Products, National Laboratory for Marine Science and Technology, Qingdao, 266235, People's Republic of China. Electronic address: liguoqiang@ouc.edu.cn.

PMID: 34837765
DOI: 10.1016/j.phytochem.2021.113006

Abstract

Jellynolide A, an unreported bicyclic diterpenoid with an unprecedented penta-substituted carbon skeleton which implied an irregular biogenic pathway, together with four pairs of rare phosphate triesters, (±)-pokepola ester B-E, one undescribed related racemic furanoterpenoid, (±)-sponalisolide C, one undescribed furanoterpenoid, (-)-sponalisolide D, and two known (±)-sponalisolide B and dendrolasin carboxylic acid were isolated from the aquaculture Spongia officinalis L. Their structures were elucidated by comprehensive spectroscopic analysis, quantum chemical calculation of NMR parameters, and electronic circular dichroism (ECD). The plausible biosynthetic pathway of jellynolide A was proposed. (±)-Pokepola ester C exhibited significant inhibition against Wnt, HIF1 signaling pathways. (+)-Pokepola ester B and (-)-pokepola ester D showed moderate cytotoxicity activities.

Keywords: Aquaculture sponge; Biological activity; Phosphate triester; Spongia officinalis L.; Spongidae; Terpenoids.

MeSH terms

Aquaculture
Carbon*
Circular Dichroism
Esters*
Magnetic Resonance Spectroscopy

Substances

Esters
Carbon