Identification and Biological Evaluation of Secondary Metabolites from the Endolichenic Fungus Aspergillus versicolor

A chemical investigation of the endolichenic fungus Aspergillus versicolor (125a), which was found in the lichen Lobaria quercizans, resulted in the isolation of four novel diphenyl ethers, named diorcinols F–H (1–3, resp.) and 3‐methoxyviolaceol‐II (4), eight new bisabolane sesquiterpenoids, named...

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Published inChemistry & biodiversity Vol. 12; no. 4; pp. 575 - 592
Main Authors Li, Xiao-Bin, Zhou, Yan-Hui, Zhu, Rong-Xiu, Chang, Wen-Qiang, Yuan, Hui-Qing, Gao, Wei, Zhang, Lu-Lu, Zhao, Zun-Tian, Lou, Hong-Xiang
Format Journal Article
LanguageEnglish
Published Zürich WILEY-VCH Verlag 01.04.2015
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Abstract A chemical investigation of the endolichenic fungus Aspergillus versicolor (125a), which was found in the lichen Lobaria quercizans, resulted in the isolation of four novel diphenyl ethers, named diorcinols F–H (1–3, resp.) and 3‐methoxyviolaceol‐II (4), eight new bisabolane sesquiterpenoids, named (−)‐(R)‐cyclo‐hydroxysydonic acid (5), (−)‐(7S,8R)‐8‐hydroxysydowic acid (6), (−)‐(7R,10S)‐10‐hydroxysydowic acid (7), (−)‐(7R,10R)‐iso‐10‐hydroxysydowic acid (8), (−)‐12‐acetoxy‐1‐deoxysydonic acid (9), (−)‐12‐acetoxysydonic acid (10), (−)‐12‐hydroxysydonic acid (11), and (−)‐(R)‐11‐dehydrosydonic acid (12), two new tris(pyrogallol ethers), named sydowiols D (13) and E (14), and fifteen known compounds, 15–29. All of the structures were determined by spectroscopic analyses, and a number of them were further identified through chemical transformations and electronic circular dichroism (ECD) calculations. Preliminary bioassays of these isolates for the determination of their inhibitory activities against the fungus Candida albicans, and their cytotoxicities against the human cancer cell lines PC3, A549, A2780, MDA‐MB‐231, and HEPG2 were also evaluated.
AbstractList A chemical investigation of the endolichenic fungus Aspergillus versicolor (125a), which was found in the lichen Lobaria quercizans, resulted in the isolation of four novel diphenyl ethers, named diorcinols F-H (1-3, resp.) and 3-methoxyviolaceol-II (4), eight new bisabolane sesquiterpenoids, named (-)-(R)-cyclo-hydroxysydonic acid (5), (-)-(7S,8R)-8-hydroxysydowic acid (6), (-)-(7R,10S)-10-hydroxysydowic acid (7), (-)-(7R,10R)-iso-10-hydroxysydowic acid (8), (-)-12-acetoxy-1-deoxysydonic acid (9), (-)-12-acetoxysydonic acid (10), (-)-12-hydroxysydonic acid (11), and (-)-(R)-11-dehydrosydonic acid (12), two new tris(pyrogallol ethers), named sydowiols D (13) and E (14), and fifteen known compounds, 15-29. All of the structures were determined by spectroscopic analyses, and a number of them were further identified through chemical transformations and electronic circular dichroism (ECD) calculations. Preliminary bioassays of these isolates for the determination of their inhibitory activities against the fungus Candida albicans, and their cytotoxicities against the human cancer cell lines PC3, A549, A2780, MDA-MB-231, and HEPG2 were also evaluated.
A chemical investigation of the endolichenic fungus Aspergillus versicolor (125a), which was found in the lichen Lobaria quercizans, resulted in the isolation of four novel diphenyl ethers, named diorcinols F-H (1-3, resp.) and 3-methoxyviolaceol-II (4), eight new bisabolane sesquiterpenoids, named (-)-(R)-cyclo-hydroxysydonic acid (5), (-)-(7S,8R)-8-hydroxysydowic acid (6), (-)-(7R,10S)-10-hydroxysydowic acid (7), (-)-(7R,10R)-iso-10-hydroxysydowic acid (8), (-)-12-acetoxy-1-deoxysydonic acid (9), (-)-12-acetoxysydonic acid (10), (-)-12-hydroxysydonic acid (11), and (-)-(R)-11-dehydrosydonic acid (12), two new tris(pyrogallol ethers), named sydowiols D (13) and E (14), and fifteen known compounds, 15-29. All of the structures were determined by spectroscopic analyses, and a number of them were further identified through chemical transformations and electronic circular dichroism (ECD) calculations. Preliminary bioassays of these isolates for the determination of their inhibitory activities against the fungus Candida albicans, and their cytotoxicities against the human cancer cell lines PC3, A549, A2780, MDA-MB-231, and HEPG2 were also evaluated.A chemical investigation of the endolichenic fungus Aspergillus versicolor (125a), which was found in the lichen Lobaria quercizans, resulted in the isolation of four novel diphenyl ethers, named diorcinols F-H (1-3, resp.) and 3-methoxyviolaceol-II (4), eight new bisabolane sesquiterpenoids, named (-)-(R)-cyclo-hydroxysydonic acid (5), (-)-(7S,8R)-8-hydroxysydowic acid (6), (-)-(7R,10S)-10-hydroxysydowic acid (7), (-)-(7R,10R)-iso-10-hydroxysydowic acid (8), (-)-12-acetoxy-1-deoxysydonic acid (9), (-)-12-acetoxysydonic acid (10), (-)-12-hydroxysydonic acid (11), and (-)-(R)-11-dehydrosydonic acid (12), two new tris(pyrogallol ethers), named sydowiols D (13) and E (14), and fifteen known compounds, 15-29. All of the structures were determined by spectroscopic analyses, and a number of them were further identified through chemical transformations and electronic circular dichroism (ECD) calculations. Preliminary bioassays of these isolates for the determination of their inhibitory activities against the fungus Candida albicans, and their cytotoxicities against the human cancer cell lines PC3, A549, A2780, MDA-MB-231, and HEPG2 were also evaluated.
A chemical investigation of the endolichenic fungus Aspergillus versicolor (125a), which was found in the lichen Lobaria quercizans , resulted in the isolation of four novel diphenyl ethers, named diorcinols F–H ( 1 – 3 , resp.) and 3‐methoxyviolaceol‐II ( 4 ), eight new bisabolane sesquiterpenoids, named (−)‐( R )‐cyclo‐hydroxysydonic acid ( 5 ), (−)‐(7 S ,8 R )‐8‐hydroxysydowic acid ( 6 ), (−)‐(7 R ,10 S )‐10‐hydroxysydowic acid ( 7 ), (−)‐(7 R ,10 R )‐iso‐10‐hydroxysydowic acid ( 8 ), (−)‐12‐acetoxy‐1‐deoxysydonic acid ( 9 ), (−)‐12‐acetoxysydonic acid ( 10 ), (−)‐12‐hydroxysydonic acid ( 11 ), and (−)‐( R )‐11‐dehydrosydonic acid ( 12 ), two new tris(pyrogallol ethers), named sydowiols D ( 13 ) and E ( 14 ), and fifteen known compounds, 15 – 29 . All of the structures were determined by spectroscopic analyses, and a number of them were further identified through chemical transformations and electronic circular dichroism (ECD) calculations. Preliminary bioassays of these isolates for the determination of their inhibitory activities against the fungus Candida albicans , and their cytotoxicities against the human cancer cell lines PC3, A549, A2780, MDA‐MB‐231, and HEPG2 were also evaluated.
A chemical investigation of the endolichenic fungus Aspergillus versicolor (125a), which was found in the lichen Lobaria quercizans, resulted in the isolation of four novel diphenyl ethers, named diorcinols F–H (1–3, resp.) and 3‐methoxyviolaceol‐II (4), eight new bisabolane sesquiterpenoids, named (−)‐(R)‐cyclo‐hydroxysydonic acid (5), (−)‐(7S,8R)‐8‐hydroxysydowic acid (6), (−)‐(7R,10S)‐10‐hydroxysydowic acid (7), (−)‐(7R,10R)‐iso‐10‐hydroxysydowic acid (8), (−)‐12‐acetoxy‐1‐deoxysydonic acid (9), (−)‐12‐acetoxysydonic acid (10), (−)‐12‐hydroxysydonic acid (11), and (−)‐(R)‐11‐dehydrosydonic acid (12), two new tris(pyrogallol ethers), named sydowiols D (13) and E (14), and fifteen known compounds, 15–29. All of the structures were determined by spectroscopic analyses, and a number of them were further identified through chemical transformations and electronic circular dichroism (ECD) calculations. Preliminary bioassays of these isolates for the determination of their inhibitory activities against the fungus Candida albicans, and their cytotoxicities against the human cancer cell lines PC3, A549, A2780, MDA‐MB‐231, and HEPG2 were also evaluated.
A chemical investigation of the endolichenic fungus Aspergillus versicolor (125a), which was found in the lichen Lobaria quercizans, resulted in the isolation of four novel diphenyl ethers, named diorcinols F-H (1-3, resp.) and 3-methoxyviolaceol-II (4), eight new bisabolane sesquiterpenoids, named (-)-(R)-cyclo-hydroxysydonic acid (5), (-)-(7S,8R)-8-hydroxysydow ic acid (6), (-)-(7R,10S)-10-hydroxysyd owic acid (7), (-)-(7R,10R)-iso-10-hydrox ysydowic acid (8), (-)-12-acetoxy-1-deoxysydonic acid (9), (-)-12-acetoxysydonic acid (10), (-)-12-hydroxysydonic acid (11), and (-)-(R)-11-dehydrosydonic acid (12), two new tris(pyrogallol ethers), named sydowiols D (13) and E (14), and fifteen known compounds, 15-29. All of the structures were determined by spectroscopic analyses, and a number of them were further identified through chemical transformations and electronic circular dichroism (ECD) calculations. Preliminary bioassays of these isolates for the determination of their inhibitory activities against the fungus Candida albicans, and their cytotoxicities against the human cancer cell lines PC3, A549, A2780, MDA-MB-231, and HEPG2 were also evaluated.
Author Zhu, Rong-Xiu
Yuan, Hui-Qing
Gao, Wei
Lou, Hong-Xiang
Zhang, Lu-Lu
Li, Xiao-Bin
Zhou, Yan-Hui
Chang, Wen-Qiang
Zhao, Zun-Tian
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  surname: Zhou
  fullname: Zhou, Yan-Hui
  organization: Department of Natural Products Chemistry, Key Lab of Chemical Biology of Ministry of Education, School of Pharmaceutical Science, Shandong University, No. 44 West Wenhua Road, Jinan 250012, P. R. China (phone: +86-531-88382012; fax: +86-531-88382019)
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  givenname: Rong-Xiu
  surname: Zhu
  fullname: Zhu, Rong-Xiu
  organization: School of Chemistry and Chemical Engineering, Shandong University, No. 27 Shanda Nanlu, Jinan 250100, P. R. China
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  givenname: Wen-Qiang
  surname: Chang
  fullname: Chang, Wen-Qiang
  organization: Department of Natural Products Chemistry, Key Lab of Chemical Biology of Ministry of Education, School of Pharmaceutical Science, Shandong University, No. 44 West Wenhua Road, Jinan 250012, P. R. China (phone: +86-531-88382012; fax: +86-531-88382019)
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  givenname: Hui-Qing
  surname: Yuan
  fullname: Yuan, Hui-Qing
  organization: Department of Biochemistry and Molecular Biology, School of Medicine, Shandong University, No. 44 West Wenhua Road, Jinan 250012, P. R. China
– sequence: 6
  givenname: Wei
  surname: Gao
  fullname: Gao, Wei
  organization: College of Life Sciences, Shandong Normal University, No. 88 East Wenhua Road, Jinan 250014, P. R. China
– sequence: 7
  givenname: Lu-Lu
  surname: Zhang
  fullname: Zhang, Lu-Lu
  organization: College of Life Sciences, Shandong Normal University, No. 88 East Wenhua Road, Jinan 250014, P. R. China
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  givenname: Zun-Tian
  surname: Zhao
  fullname: Zhao, Zun-Tian
  organization: College of Life Sciences, Shandong Normal University, No. 88 East Wenhua Road, Jinan 250014, P. R. China
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  givenname: Hong-Xiang
  surname: Lou
  fullname: Lou, Hong-Xiang
  email: louhongxiang@sdu.edu.cn
  organization: Department of Natural Products Chemistry, Key Lab of Chemical Biology of Ministry of Education, School of Pharmaceutical Science, Shandong University, No. 44 West Wenhua Road, Jinan 250012, P. R. China (phone: +86-531-88382012; fax: +86-531-88382019)
BackLink https://www.ncbi.nlm.nih.gov/pubmed/25879502$$D View this record in MEDLINE/PubMed
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Issue 4
Keywords Endolichenic fungus
Fungi
Antifungal activity
Aspergillus versicolor
Sesquiterpenoids
Bisabolane sesquiterpenoid
Cytotoxic activity
Language English
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Kropf H. (e_1_2_1_16_2) 1983; 11
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Huang Y.‐F. (e_1_2_1_40_2) 2012; 31
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Snippet A chemical investigation of the endolichenic fungus Aspergillus versicolor (125a), which was found in the lichen Lobaria quercizans, resulted in the isolation...
A chemical investigation of the endolichenic fungus Aspergillus versicolor (125a), which was found in the lichen Lobaria quercizans , resulted in the isolation...
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SubjectTerms Acids
Antifungal activity
Antifungal Agents - chemistry
Antifungal Agents - isolation & purification
Antifungal Agents - pharmacology
Antineoplastic Agents, Phytogenic - chemistry
Antineoplastic Agents, Phytogenic - pharmacology
Aspergillus - chemistry
Aspergillus - metabolism
Aspergillus versicolor
Bioassays
Bisabolane sesquiterpenoid
Candida albicans
Candida albicans - drug effects
Cell Line, Tumor - drug effects
Circular Dichroism
Cytotoxic activity
Dichroism
Drug Evaluation, Preclinical - methods
Endolichenic fungus
Ethers
Fungi
Humans
Lichens - microbiology
Lobaria quercizans
Magnetic Resonance Spectroscopy
Metabolites
Molecular Structure
Phenyl Ethers - chemistry
Phenyl Ethers - pharmacology
Pyrogallol
Secondary Metabolism
Secondary metabolites
Sesquiterpenes - chemistry
Sesquiterpenes - isolation & purification
Sesquiterpenoids
Structure-Activity Relationship
Tumor cell lines
Title Identification and Biological Evaluation of Secondary Metabolites from the Endolichenic Fungus Aspergillus versicolor
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https://www.ncbi.nlm.nih.gov/pubmed/25879502
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https://www.proquest.com/docview/1680462714
Volume 12
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