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 in | Chemistry & biodiversity Vol. 12; no. 4; pp. 575 - 592 |
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Main Authors | , , , , , , , , |
Format | Journal Article |
Language | English |
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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. |
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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 |
Author_xml | – sequence: 1 givenname: Xiao-Bin surname: Li fullname: Li, Xiao-Bin 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) – sequence: 2 givenname: Yan-Hui 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) – sequence: 3 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 – sequence: 4 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) – sequence: 5 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 – sequence: 8 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 – sequence: 9 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) |
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Keywords | Endolichenic fungus Fungi Antifungal activity Aspergillus versicolor Sesquiterpenoids Bisabolane sesquiterpenoid Cytotoxic activity |
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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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