PMID- 34600094
OWN - NLM
STAT- MEDLINE
DCOM- 20211222
LR  - 20211222
IS  - 1873-6971 (Electronic)
IS  - 0367-326X (Linking)
VI  - 155
DP  - 2021 Nov
TI  - Antimicrobial and cytotoxic phenolic bisabolane sesquiterpenoids from the fungus 
      Aspergillus flavipes 297.
PG  - 105038
LID - S0367-326X(21)00213-6 [pii]
LID - 10.1016/j.fitote.2021.105038 [doi]
AB  - Phenolic bisabolane-type sesquiterpenoids (PBS) represent a rare class of natural 
      products with diverse biological activities. In this study, chemical 
      investigations of the fungus Aspergillus flavipes 297 resulted in the isolation 
      and identification of seven PBS, including a pair of new enantiomers (+)-1a and 
      (-)-1b, a new derivative 2, and five previously reported ones 3-7. The chemical 
      structures of the isolated PBS were determined by extensive NMR and HRESIMS 
      spectroscopic analysis. The absolute configurations of the separated enantiomers 
      (+)-1a and (-)-1b were solved by comparison of the experimental ECD spectra with 
      those of the TDDFT-ECD calculated spectra. The new compounds 1 and 2 represent 
      rare cases of PBS bearing a methylsulfinyl group, which was distinct from the 
      commonly-observed PBS structurally. All the isolated compounds 1-7 were evaluated 
      their antimicrobial and cytotoxic activities. As a result, the tested compounds 
      showed selective antimicrobial activity against several pathogenic bacteria and 
      fungi with the MIC (minimum inhibiting concentrations) values ranging from 2 to 
      64 mug/mL. Moreover, enantiomers (+)-1a and (-)-1b, together with compound 2, 
      exhibited promising cytotoxicity against MKN-45 and HepG2 cell lines, 
      respectively, indicating that the methylsulfinyl substituent enhanced 
      cytotoxicity to a certain degree.
CI  - Copyright (c) 2021 Elsevier B.V. All rights reserved.
FAU - Chen, Yu
AU  - Chen Y
AD  - Department of General Surgery, the First Affiliated Hospital of Soochow 
      University, Suzhou 215006, China; Department of General Surgery, Suqian First 
      Hospital, Suqian 223800, China.
FAU - Zhu, Hong-Yan
AU  - Zhu HY
AD  - Department of General Surgery, the First Affiliated Hospital of Soochow 
      University, Suzhou 215006, China; Department of General Surgery, South China 
      Hospital, Health Science Center, Shenzhen University, Shenzhen 518116, China.
FAU - Xu, Lian-Cheng
AU  - Xu LC
AD  - Department of General Surgery, Suqian First Hospital, Suqian 223800, China.
FAU - Wang, Shi-Ping
AU  - Wang SP
AD  - Department of General Surgery, Suqian First Hospital, Suqian 223800, China.
FAU - Liu, Shan
AU  - Liu S
AD  - Department of General Surgery, Suqian First Hospital, Suqian 223800, China.
FAU - Liu, Guo-Dong
AU  - Liu GD
AD  - Department of General Surgery, Suqian First Hospital, Suqian 223800, China.
FAU - Luo, Wei-Huan
AU  - Luo WH
AD  - Department of General Surgery, Suqian First Hospital, Suqian 223800, China.
FAU - Cao, Guan-Yi
AU  - Cao GY
AD  - Department of General Surgery, Suqian First Hospital, Suqian 223800, China.
FAU - Zhang, Zi-Xiang
AU  - Zhang ZX
AD  - Department of General Surgery, the First Affiliated Hospital of Soochow 
      University, Suzhou 215006, China. Electronic address: zhangzxzmed@163.com.
LA  - eng
PT  - Journal Article
DEP - 20210930
PL  - Netherlands
TA  - Fitoterapia
JT  - Fitoterapia
JID - 16930290R
RN  - 0 (Anti-Infective Agents)
RN  - 0 (Antineoplastic Agents)
RN  - 0 (Biological Products)
RN  - 0 (Monocyclic Sesquiterpenes)
RN  - 0 (Phenols)
RN  - Aspergillus flavipes
SB  - IM
MH  - Anti-Infective Agents/isolation & purification/*pharmacology
MH  - Antineoplastic Agents/isolation & purification/*pharmacology
MH  - Aspergillus/*chemistry
MH  - Biological Products/isolation & purification/pharmacology
MH  - Cell Line, Tumor
MH  - China
MH  - Humans
MH  - Microbial Sensitivity Tests
MH  - Molecular Structure
MH  - Monocyclic Sesquiterpenes/isolation & purification/*pharmacology
MH  - Phenols/isolation & purification/*pharmacology
MH  - Seawater/microbiology
OTO - NOTNLM
OT  - Antimicrobial activity
OT  - Aspergillus flavipes
OT  - Cytotoxic activity
OT  - Phenolic bisabolane sesquiterpenoids
OT  - Secondary metabolites
EDAT- 2021/10/03 06:00
MHDA- 2021/12/24 06:00
CRDT- 2021/10/02 20:11
PHST- 2021/08/23 00:00 [received]
PHST- 2021/09/17 00:00 [revised]
PHST- 2021/09/23 00:00 [accepted]
PHST- 2021/10/03 06:00 [pubmed]
PHST- 2021/12/24 06:00 [medline]
PHST- 2021/10/02 20:11 [entrez]
AID - S0367-326X(21)00213-6 [pii]
AID - 10.1016/j.fitote.2021.105038 [doi]
PST - ppublish
SO  - Fitoterapia. 2021 Nov;155:105038. doi: 10.1016/j.fitote.2021.105038. Epub 2021 
      Sep 30.