Marine alkaloids as the chemical marker for the prey-predator relationship of the sponge Xestospongia sp. and the nudibranch Jorunna funebris

Qihao Wu; Song-Wei Li; Nicole J de Voogd; Hong Wang; Li-Gong Yao; Yue-Wei Guo; Xu-Wen Li

doi:10.1007/s42995-021-00096-w

Marine alkaloids as the chemical marker for the prey-predator relationship of the sponge Xestospongia sp. and the nudibranch Jorunna funebris

Mar Life Sci Technol. 2021 Mar 29;3(3):375-381. doi: 10.1007/s42995-021-00096-w. eCollection 2021 Aug.

Authors

Qihao Wu^{1

2}, Song-Wei Li^{1

3}, Nicole J de Voogd^{4

5}, Hong Wang², Li-Gong Yao¹, Yue-Wei Guo^{1

6}, Xu-Wen Li^{1

6}

Affiliations

¹ State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai, 201203 China.
² College of Pharmaceutical Science and Collaborative Innovation Center of Yangtze River Delta Region Green Pharmaceuticals, Zhejiang University of Technology, Hangzhou, 310014 China.
³ Nanjing University of Chinese Medicine, Nanjing, 210023 China.
⁴ National Museum of Natural History, PO Box 9517, 2300 RA Leiden, Netherlands.
⁵ Institute of Environmental Sciences, Leiden University, PO Box 9518, 2300 RA Leiden, Netherlands.
⁶ Open Studio for Druggability Research of Marine Natural Products, Pilot National Laboratory for Marine Science and Technology (Qingdao), Qingdao, 266237 China.

Abstract

The dietary relationship study between marine sponge Xestospongia sp. and its nudibranch predators Jorunna funebris based on the discovery of isoquinolinequinones has long been studied. In this study, chemical investigation of the sponge Xestospongia sp. and nudibranch J. funebris from the South China Sea yielded a new marine alkaloid neopetroside C (1), together with nine known alkaloids (2-10). The chemical structures of all the compounds were elucidated by extensive spectroscopic analysis. Neopetroside C (1) featured a riboside of nicotinic acid with a rare α-N glycosildic linkage and an acyl residue of (Z)-2-methylbut-2-enoic acid attached to C-5'. The plausible chemical ecology relationship between sponge Xestospongia sp. and its nudibranch predator J. funebris was proposed based on the biogenetic relationship of the common marine alkaloids. The observation of two structural fragments, (Z)-2-methylbut-2-enoyloxy and trigonelline groups in both sponge and nudibranch, indicated that nudibranch might uptake chemicals from sponge and then modify and transform them into chemical weapons to defend against predators.

Supplementary information: The online version contains supplementary material available at 10.1007/s42995-021-00096-w.

Keywords: Jorunna funebris; Marine alkaloids; Xestospongia sp. Chemical marker.