Ten new diterpene glycosides virescenosides Z9-Z18 (1-10) together with three known analogues (11-13) and aglycon of virescenoside A (14) were isolated from the marine-derived fungus Acremonium striatisporum KMM 4401. These compounds were obtained by cultivating fungus on wort agar medium with the addition of potassium bromide. Structures of the isolated metabolites were established based on spectroscopic methods. The effects of some isolated glycosides and aglycons 15-18 on urease activity and regulation of Reactive Oxygen Species (ROS) and Nitric Oxide (NO) production in macrophages stimulated with lipopolysaccharide (LPC) were evaluated.

secondary metabolites, Acremonium striatisporum, Diterpene glycosides, Marine fungi, urease activity

NCBI PubMed ID: 31671910
Publication DOI: 10.3390/md17110616
Journal NLM ID: 101213729
Publisher: Basel, Switzerland: Molecular Diversity Preservation International
Correspondence: Zhuravleva OI dvfu.ru>; Antonov AS gmail.com>; Oleinikova GK mail.ru>; Khudyakova YV <161070rambler.ru>; Popov RS mail.ru>; Denisenko VA pidoc.dvo.ru>; Pislyagin EA hotmail.com>; Chingizova EA mail.ru>; Afiyatullov SS piboc.dvo.ru>
Institutions: G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Vladivostok, Russia, School of Natural Science, Far Eastern Federal University, Vladivostok, Russia
Methods: 13C NMR, 1H NMR, NMR-2D, inhibition studies, TLC, biological assays, UV, extraction, gel chromatography, optical rotation measurement, CID-MS, CC, RP-HPLC, cell growth, HR-ESI-MS, determination of NO production, macrophage activity assay, evaporation
 

• Compound ID: 20889
  

  b-D-AltpA-(1-19)-Subst Subst = isopimara-7,15-diene-2α,3β,19-triol = SMILES C[C@@]1(CCC2[C@@](C)(C[C@@H](O)[C@@H]([C@@]3({19}CO)C)O)C3CC=C2C1)C=C

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  Structure type: monomer
  C26H40O9
  Trivial name: virescenoside F
  Compound class: glycoside, diterpene glycoside
  
   
  
  Acremonium striatisporum Kmm 4401
  CSDB ID 49740 (all data & tools)
• Compound ID: 20890
  

  b-D-AltpA-(1-19)-Subst Subst = isopimara-7,15-diene-3β,19-diol = SMILES C[C@](C1)(C=C)CCC2C1=CCC3[C@]2(C)CC{3}C(O)[C@]3(C){19}CO

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  Structure type: monomer
  C26H40O8
  Trivial name: virescenoside G
  Compound class: glycoside, diterpene glycoside
  
   
  
  Acremonium striatisporum Kmm 4401
  CSDB ID 49741 (all data & tools)
• Compound ID: 22020
  

  b-D-Altp-(1-19)-Subst Subst = virescenoside Z9 aglycon = SMILES C=C[C@@]3(C)CC[C@@H]2[C@@]1(C)C{2}[C@@H](O){3}[C@H](O)[C@](C)({19}CO)[C@@H]1{6}[C@@H](O)C(=O)[C@@]2(O)C3

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  Structure type: monomer
  Trivial name: virescenoside Z9
  Compound class: glycoside, diterpene glycoside
  
   
  
  Acremonium striatisporum Kmm 4401
  CSDB ID 49730 (all data & tools)
• Compound ID: 22021
  

  b-D-AltpA-(1-19)-Subst Subst = virescenoside Z10 aglycon = SMILES C=C[C@@]1(C)CC/C2=C(C1)/C(=O)C[C@@H]3[C@]2(C)CC{3}[C@H](O)[C@]3(C){19}CO

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  Structure type: monomer
  Trivial name: virescenoside Z10
  Compound class: glycoside, diterpene glycoside
  
   
  
  Acremonium striatisporum Kmm 4401
  CSDB ID 49731 (all data & tools)
• Compound ID: 22022
  

  b-D-AltpA-(1-19)-Subst Subst = virescenoside Z11, Z15 aglycon = SMILES C=C[C@@]1(C)CC/C2=C(C1)/C(=O)C[C@@H]3[C@]2(C)C{2}[C@@H](O){3}[C@H](O)[C@]3(C){19}CO

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  Structure type: monomer
  Trivial name: virescenoside Z11
  Compound class: glycoside, diterpene glycoside
  
   
  
  Acremonium striatisporum Kmm 4401
  CSDB ID 49732 (all data & tools)
• Compound ID: 22023
  

  b-D-AltpA6Me-(1-19)-Subst Subst = virescenoside Z12, Z18 aglycon = SMILES C=C[C@@]3(C)CC[C@H]1/C(=C\C[C@H]2[C@@](C)({19}CO){3}[C@@H](O)CC[C@]12C)C3

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  Structure type: monomer
  Trivial name: virescenoside Z12
  Compound class: glycoside, diterpene glycoside
  
   
  
  Acremonium striatisporum Kmm 4401
  CSDB ID 49733 (all data & tools)
• Compound ID: 22024
  

  b-D-AltpA6Me-(1-19)-Subst Subst = virescenoside Z13, Z17 aglycon = SMILES C=C[C@@]3(C)CC[C@H]1/C(=C\C[C@H]2[C@@](C)({19}CO){3}[C@@H](O){2}[C@H](O)C[C@]12C)C3

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  Structure type: monomer
  Trivial name: virescenoside Z13
  Compound class: glycoside, diterpene glycoside
  
   
  
  Acremonium striatisporum Kmm 4401
  CSDB ID 49734 (all data & tools)
• Compound ID: 22025
  

  b-D-AltpA6Me-(1-19)-Subst Subst = virescenoside V, Z14 aglycon = SMILES C=C[C@]3(C)/C=C\2C(=O)C[C@H]1[C@@](C)({19}CO){3}[C@@H](O){2}[C@H](O)C[C@]1(C)[C@H]2CC3

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  Structure type: monomer
  Trivial name: virescenoside Z14
  Compound class: glycoside, diterpene glycoside
  
   
  
  Acremonium striatisporum Kmm 4401
  CSDB ID 49735 (all data & tools)
• Compound ID: 22026
  

  b-D-AltpA6Me-(1-19)-Subst Subst = virescenoside Z11, Z15 aglycon = SMILES C=C[C@@]1(C)CC/C2=C(C1)/C(=O)C[C@@H]3[C@]2(C)C{2}[C@@H](O){3}[C@H](O)[C@]3(C){19}CO

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  Structure type: monomer
  Trivial name: virescenoside Z15
  Compound class: glycoside, diterpene glycoside
  
   
  
  Acremonium striatisporum Kmm 4401
  CSDB ID 49736 (all data & tools)
• Compound ID: 22027
  

  b-D-AltpA6Me-(1-19)-Subst Subst = virescenoside Z16 aglycon = SMILES C=C[C@@]3(C)CC[C@H]1/C(=C\C[C@H]2[C@@](C)({19}CO)C(=O)CC[C@]12C)C3

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  Structure type: monomer
  Trivial name: virescenoside Z16
  Compound class: glycoside, diterpene glycoside
  
   
  
  Acremonium striatisporum Kmm 4401
  CSDB ID 49737 (all data & tools)
• Compound ID: 22028
  

  b-D-AltpA6Bu-(1-19)-Subst Subst = virescenoside Z13, Z17 aglycon = SMILES C=C[C@@]3(C)CC[C@H]1/C(=C\C[C@H]2[C@@](C)({19}CO){3}[C@@H](O){2}[C@H](O)C[C@]12C)C3

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  Structure type: monomer
  Trivial name: virescenoside Z17
  Compound class: glycoside, diterpene glycoside
  
   
  
  Acremonium striatisporum Kmm 4401
  CSDB ID 49738 (all data & tools)
• Compound ID: 22029
  

  b-D-ManpA6Me-(1-19)-Subst Subst = virescenoside Z12, Z18 aglycon = SMILES C=C[C@@]3(C)CC[C@H]1/C(=C\C[C@H]2[C@@](C)({19}CO){3}[C@@H](O)CC[C@]12C)C3

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  Structure type: monomer
  Trivial name: virescenoside Z18
  Compound class: glycoside, diterpene glycoside
  
   
  
  Acremonium striatisporum Kmm 4401
  CSDB ID 49739 (all data & tools)