Show legend Show as text

Structure type: monomer ; 393.1175 [M+Na]+
C₁₇H₂₂O₉
Trivial name: xylarglycoside A, dihydroisocoumarin glycoside
Contained glycoepitopes: IEDB_137485,IEDB_144983,IEDB_152206,IEDB_983930,SB_44,SB_72

• Article ID: 9616
  Gan D, Li C, Shu Y, Wang J, Wang C, Zhu L, Yang Y, Liu J, He B, Cai L, Ding Z "Steroids and dihydroisocoumarin glycosides from Xylaria sp. by the one strain many compounds strategy and their bioactivities" - Chinese Journal of Natural Medicines = Zhongguo Tianran Yaowu 21(2) (2023) 154-160
  

  The fungus Xylaria sp. KYJ-15 was isolated from Illigera celebica. Based on the one strain many compounds (OSMAC) strategy, the strain was fermented on potato and rice solid media, respectively. As a result, two novel steroids, xylarsteroids A (1) and B (2), which are the first examples of C28-steroid with an unusual β- and γ-lactone ring, respectively, along with two new dihydroisocoumarin glycosides, xylarglycosides A (3) and B (4), were identified. Their structures were elucidated by spectroscopic methods, X-ray diffraction and electronic circular dichroism (ECD) experiments. All isolated compounds were evaluated for cytotoxicity, DPPH radical scavenging activity, acetylcholinesterase inhibitory and antimicrobial effect. Compound 1 exhibited potent AChE inhibitory activity with an IC50 value of 2.61 ± 0.05 μmol·L-1. The β-lactone ring unit of 1 is critical for its AChE inhibitory activity. The finding was further confirmed through exploring the interaction of 1 with AChE by molecular docking. In addition, both compounds 1 and 2 exhibited obvious antibacterial activity against Bacillus subtilis with a minimum inhibitory concentration (MIC) of 2 μg·mL-1. Compounds 3 and 4 exhibited antibacterial activities against Staphylococcus aureus with MICs of 4 and 2 μg·mL-1, respectively, which also exhibited DPPH radical scavenging activity comparable to the positive control with IC50 values of 9.2 ± 0.03 and 13.3 ± 0.01 μmol·L-1, respectively.

  bioactivity, secondary metabolite, Xylaria sp., OSMAC strategy

  NCBI PubMed ID: 36871983
  Publication DOI: 10.1016/S1875-5364(23)60394-2
  Journal NLM ID: 101504416
  Publisher: Beijing: Science Press; Elsevier
  Correspondence: L. Cai ; Z. Ding
  Institutions: Functional Molecules Analysis and Biotransformation Key Laboratory of Universities in Yunnan Province, Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, School of Chemical Science and Technology, Yunnan University, Kunming 650091, China
  Methods: 13C NMR, 1H NMR, NMR-2D, X-ray, TLC, composition analysis, HPLC, UV, extraction, CC, fermentation, HR-ESI-MS, antibacterial assay, cytotoxicity assay, molecular docking, ECD, AChE inhibitory assay
  
   
  
  Xylaria sp. KYJ-15
  CSDB ID 41037 (all data & tools)

Show legend Show as text

Structure type: monomer ; 379.1000 [M+Na]+
C₁₇H₂₀O₉
Trivial name: xylarglycoside B, dihydroisocoumarin glycoside
Contained glycoepitopes: IEDB_137485,IEDB_144983,IEDB_152206,IEDB_983930,SB_44,SB_72

• Article ID: 9616
  Gan D, Li C, Shu Y, Wang J, Wang C, Zhu L, Yang Y, Liu J, He B, Cai L, Ding Z "Steroids and dihydroisocoumarin glycosides from Xylaria sp. by the one strain many compounds strategy and their bioactivities" - Chinese Journal of Natural Medicines = Zhongguo Tianran Yaowu 21(2) (2023) 154-160
  

  The fungus Xylaria sp. KYJ-15 was isolated from Illigera celebica. Based on the one strain many compounds (OSMAC) strategy, the strain was fermented on potato and rice solid media, respectively. As a result, two novel steroids, xylarsteroids A (1) and B (2), which are the first examples of C28-steroid with an unusual β- and γ-lactone ring, respectively, along with two new dihydroisocoumarin glycosides, xylarglycosides A (3) and B (4), were identified. Their structures were elucidated by spectroscopic methods, X-ray diffraction and electronic circular dichroism (ECD) experiments. All isolated compounds were evaluated for cytotoxicity, DPPH radical scavenging activity, acetylcholinesterase inhibitory and antimicrobial effect. Compound 1 exhibited potent AChE inhibitory activity with an IC50 value of 2.61 ± 0.05 μmol·L-1. The β-lactone ring unit of 1 is critical for its AChE inhibitory activity. The finding was further confirmed through exploring the interaction of 1 with AChE by molecular docking. In addition, both compounds 1 and 2 exhibited obvious antibacterial activity against Bacillus subtilis with a minimum inhibitory concentration (MIC) of 2 μg·mL-1. Compounds 3 and 4 exhibited antibacterial activities against Staphylococcus aureus with MICs of 4 and 2 μg·mL-1, respectively, which also exhibited DPPH radical scavenging activity comparable to the positive control with IC50 values of 9.2 ± 0.03 and 13.3 ± 0.01 μmol·L-1, respectively.

  bioactivity, secondary metabolite, Xylaria sp., OSMAC strategy

  NCBI PubMed ID: 36871983
  Publication DOI: 10.1016/S1875-5364(23)60394-2
  Journal NLM ID: 101504416
  Publisher: Beijing: Science Press; Elsevier
  Correspondence: L. Cai ; Z. Ding
  Institutions: Functional Molecules Analysis and Biotransformation Key Laboratory of Universities in Yunnan Province, Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, School of Chemical Science and Technology, Yunnan University, Kunming 650091, China
  Methods: 13C NMR, 1H NMR, NMR-2D, X-ray, TLC, composition analysis, HPLC, UV, extraction, CC, fermentation, HR-ESI-MS, antibacterial assay, cytotoxicity assay, molecular docking, ECD, AChE inhibitory assay
  
   
  
  Xylaria sp. KYJ-15
  CSDB ID 41413 (all data & tools)