Spongian Diterpenes Including One with a Rearranged Skeleton from the Marine Sponge Spongia officinalis

  • J Nat Prod. 2019 Jun 28;82(6):1714-1718. doi: 10.1021/acs.jnatprod.9b00270.
Qian Chen  1 ,  Qiqi Mao  1 ,  Miao Bao  1 ,  Yongxiao Mou  1 ,  Chengyan Fang  1 ,  Min Zhao  1 ,  Wei Jiang  2 ,  Xia Yu  3 ,  Chaojie Wang  1 ,  Lishang Dai  1 ,  Wenfei He  1 ,  Jianyong Dong  1 ,  Jianzhang Wu  1 ,  Pengcheng Yan  1
Affiliations
  • 1. School of Pharmaceutical Sciences , Wenzhou Medical University , Wenzhou , Zhejiang 325035 , People's Republic of China.
  • 2. School of Environmental Science and Engineering , Yangzhou University , Yangzhou , Jiangsu 225127 , People's Republic of China.
  • 3. Xiangya School of Pharmaceutical Sciences , Central South University , Changsha , Hunan 410013 , People's Republic of China.
PMID: 31095383 DOI: 10.1021/acs.jnatprod.9b00270
Abstract

Five new diterpenes, including an unprecedented 5,5,6,6,5-pentacyclic diterpene, sponalactone (1), two new spongian diterpenes, 17- O-acetylepispongiatriol (2) and 17- O-acetylspongiatriol (3), and two new spongian diterpene artifacts, 15α,16α-dimethoxy-15,16-dihydroepispongiatriol (4) and 15α-ethoxyepispongiatriol-16(15 H)-one (5), were isolated from a South China Sea collection of the marine Sponge Spongia officinalis, together with three known analogues (6-8). The structures of the new diterpenes were elucidated by extensive spectroscopic analysis. The absolute configurations were established on the basis of ECD data. Compounds 1-5 and 7 exhibited moderate inhibition against LPS-induced NO production in RAW264.7 macrophages with IC50 values of 12-32 μM.