Nocaviogua A and B: two lipolanthines from root-nodule-associated Nocardia sp

Shanshan Chang; Yajun Luo; Ning He; Xinyue Huang; Mingxu Chen; Lijie Yuan; Yunying Xie

doi:10.3389/fchem.2023.1233938

Nocaviogua A and B: two lipolanthines from root-nodule-associated Nocardia sp

Front Chem. 2023 Aug 3:11:1233938. doi: 10.3389/fchem.2023.1233938. eCollection 2023.

Authors

Shanshan Chang¹, Yajun Luo², Ning He¹, Xinyue Huang¹, Mingxu Chen¹, Lijie Yuan², Yunying Xie¹

Affiliations

¹ CAMS Key Laboratory of Synthetic Biology for Drug Innovation, Institute of Medicinal Biotechnology, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing, China.
² Hebei Key Laboratory for Chronic Diseases, Tangshan Key Laboratory for Preclinical and Basic Research on Chronic Diseases, School of Basic Medical Sciences, North China University of Science and Technology, Tangshan, Hebei, China.

Abstract

Nocaviogua A (1) and B (2), two lipolanthines featuring a non-canonical avionin (Avi)-containing macrocycle and a long acyl chain, were identified from the mutualistic actinomycete Nocardia sp. XZ19_369, which was isolated from the nodules of sea buckthorn collected in Tibet. Their planar structures were elucidated via extensive analyses of 1D and 2D NMR, as well as HRMS data. The absolute configurations were fully elucidated by advanced Marfey's analysis and GIAO NMR calculations, representing the first time that the configurations of this family of lipolanthines have been determined. Nocaviogua A (1) exhibited weak cytotoxicity against human chronic uveal melanoma cells (UM92-1), non-small cell lung cancer (NCI-H2170), and breast cancer (MDA-MB-231). Our work provides valuable information on this burgeoning class of lipolanthines for further investigations.

Keywords: NMR calculations; Nocardia; advanced Marfey’s analysis; cytotoxicity; lipolanthine.

Grants and funding

This work was financially supported by the Program for The National Natural Science Foundation of China (grant nos 81973219 and 82104047), the CAMS Innovation Fund for Medical Sciences (CIFMS, 2021-I2M-1-028), and the National Science Foundation of Hebei Province (grant no. H2021209027).