Dimeric Pyranonaphthoquinone Glycosides with Anti-HIV and Cytotoxic Activities from a Soil-Derived Streptomyces

  • J Nat Prod. 2019 Jul 26;82(7):1813-1819. doi: 10.1021/acs.jnatprod.9b00022.
Xin He  1  2 ,  Yongjiang Wang  1 ,  Rong-Hua Luo  3 ,  Liu-Meng Yang  3 ,  Li Wang  1 ,  Dale Guo  2 ,  Jing Yang  1 ,  Yun Deng  2 ,  Yong-Tang Zheng  3 ,  Sheng-Xiong Huang  1
Affiliations
  • 1. State Key Laboratory of Phytochemistry and Plant Resources in West China, CAS Center for Excellence in Molecular Plant Sciences , Kunming Institute of Botany, Chinese Academy of Sciences , Kunming 650204 , People's Republic of China.
  • 2. Key Laboratory of Standardization of Chinese Herbal Medicine, College of Pharmacy , Chengdu University of Traditional Chinese Medicine , Chengdu 611137 , People's Republic of China.
  • 3. Key Laboratory of Animal Models and Human Disease Mechanisms of the Chinese Academy of Sciences , Kunming Institute of Zoology, Chinese Academy of Sciences , Kunming 650204 , People's Republic of China.
PMID: 31310115 DOI: 10.1021/acs.jnatprod.9b00022
Abstract

Eight new sulfur-bridged pyranonaphthoquinone (PNQ) dimers, naquihexcins C-J (1-8), a new PNQ monomer, naquihexcin K (10), and three known analogues (9, 11, and 12) were isolated from Streptomyces sp. KIB3133. The new structures were elucidated by interpretation of spectroscopic data. Dimer 4 was synthesized via a cascade SN2 reactions between two monomers and sodium sulfide, an approach motivated by the proposed biosynthetic pathway of dimeric pyranonaphthoquinones. Naquihexcin E (3) exhibited moderate HIV-1 inhibitory activity. Naquihexcins C (1), E (3), and I (7) showed inhibitory effects against two tumor cell lines (HL-60 and MCF-7) with IC50 values ranging from 1.4 to 16.1 μM.