2. Academic Validation
  3. Cytochalasin Derivatives from the Endozoic Curvularia verruculosa CS-129, a Fungus Isolated from the Deep-Sea Squat Lobster Shinkaia crosnieri Living in the Cold Seep Environment

Cytochalasin Derivatives from the Endozoic Curvularia verruculosa CS-129, a Fungus Isolated from the Deep-Sea Squat Lobster Shinkaia crosnieri Living in the Cold Seep Environment

  • J Nat Prod. 2021 Dec 24;84(12):3122-3130. doi: 10.1021/acs.jnatprod.1c00907.
Xue-Yi Hu 1 2,  Chen-Yin Wang 3,  Xiao-Ming Li 1,  Sui-Qun Yang 1,  Xin Li 1,  Bin-Gui Wang 1 2 4,  Shu-Yi Si 3,  Ling-Hong Meng 1 4
Affiliations

Affiliations

  • 1 CAS and Shandong Province Key Laboratory of Experimental Marine Biology, Institute of Oceanology, Chinese Academy of Sciences, and Laboratory of Marine Biology and Biotechnology, Qingdao National Laboratory for Marine Science and Technology, Nanhai Road 7, Qingdao 266071, People's Republic of China.
  • 2 College of Marine Sciences, University of Chinese Academy of Sciences, Yuquan Road 19A, Beijing 100049, People's Republic of China.
  • 3 NHC Key Laboratory of Biotechnology of Antibiotics, and National Center for New Microbial Drug Screening, Institute of Medicinal Biotechnology, Chinese Academy of Medical Sciences & Peking Union Medical College, Tiantanxili No 1, Beijing 100050, People's Republic of China.
  • 4 Center for Ocean Mega-Science, Chinese Academy of Sciences, Nanhai Road 7, Qingdao 266071, People's Republic of China.
PMID: 34846891 DOI: 10.1021/acs.jnatprod.1c00907
Abstract

A new cytochalasin dimer, verruculoid A (1), three new cytochalasin derivatives, including 12-nor-cytochalasin F (2), 22-methoxycytochalasin B6 (3), and 19-hydroxycytochalasin B (4), and 20-deoxycytochalasin B (5), a synthetic product obtained as a natural product for the first time, together with four known analogues (6-9), were isolated and identified from the culture extract of Curvularia verruculosa CS-129, an endozoic fungus obtained from the inner fresh tissue of the deep-sea squat lobster Shinkaia crosnieri, which was collected from the cold seep area of the South China Sea. Structurally, verruculoid A (1) represents the first cytochalasin homodimer containing a thioether bridge, while 12-nor-cytochalasin F (2) is the first 12-nor-cytochalasin derivative. Their structures were elucidated by detailed interpretation of the NMR spectroscopic and mass spectrometric data. X-ray crystallographic analysis and ECD calculations confirmed their structures and absolute configurations. Compound 1 displayed activity against the human pathogenic bacterium Escherichia coli (MIC = 2 μg/mL), while compounds 4, 8, and 9 showed cytotoxicity against three tumor cell lines (HCT-116, HepG-2, and MCF-7) with IC50 values from 5.2 to 12 μM. The structure-activity relationship was briefly discussed.

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