Structural elucidation, total synthesis, and cytotoxic activity of effphenol A
A highly substituted phenol derivative, effphenol A ( 1 ), was isolated from the deep-sea-derived fungus Trichobotrys effuse FS524. Its complete structural assignment was established through a combination of spectroscopic analysis together with single-crystal X-ray diffraction experiments and furthe...
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Published in | Organic & biomolecular chemistry Vol. 18; no. 44; pp. 935 - 938 |
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Main Authors | , , , , , , , |
Format | Journal Article |
Language | English |
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Royal Soc Chemistry
28.11.2020
Royal Society of Chemistry |
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Abstract | A highly substituted phenol derivative, effphenol A (
1
), was isolated from the deep-sea-derived fungus
Trichobotrys effuse
FS524. Its complete structural assignment was established through a combination of spectroscopic analysis together with single-crystal X-ray diffraction experiments and further unequivocally confirmed by a biomimetic total synthesis. Structurally, effphenol A possesses a poly-substituted 6-5/6/6 tetracyclic ring system, which represents the first case of such a skeleton found in nature. Furthermore, the cytotoxic activity of effphenol A (
1
) toward four human cancer cell lines was assayed.
Effphenol A was isolated and elucidated through spectroscopic analysis together with single-crystal X-ray diffraction experiments and further confirmed by the first biomimetic total synthesis. |
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AbstractList | A highly substituted phenol derivative, effphenol A (1), was isolated from the deep-sea-derived fungus Trichobotrys effuse FS524. Its complete structural assignment was established through a combination of spectroscopic analysis together with single-crystal X-ray diffraction experiments and further unequivocally confirmed by a biomimetic total synthesis. Structurally, effphenol A possesses a poly-substituted 6-5/6/6 tetracyclic ring system, which represents the first case of such a skeleton found in nature. Furthermore, the cytotoxic activity of effphenol A (1) toward four human cancer cell lines was assayed. A highly substituted phenol derivative, effphenol A ( 1 ), was isolated from the deep-sea-derived fungus Trichobotrys effuse FS524. Its complete structural assignment was established through a combination of spectroscopic analysis together with single-crystal X-ray diffraction experiments and further unequivocally confirmed by a biomimetic total synthesis. Structurally, effphenol A possesses a poly-substituted 6-5/6/6 tetracyclic ring system, which represents the first case of such a skeleton found in nature. Furthermore, the cytotoxic activity of effphenol A ( 1 ) toward four human cancer cell lines was assayed. Effphenol A was isolated and elucidated through spectroscopic analysis together with single-crystal X-ray diffraction experiments and further confirmed by the first biomimetic total synthesis. A highly substituted phenol derivative, effphenol A (1), was isolated from the deep-sea-derived fungus Trichobotrys effuse FS524. Its complete structural assignment was established through a combination of spectroscopic analysis together with single-crystal X-ray diffraction experiments and further unequivocally confirmed by a biomimetic total synthesis. Structurally, effphenol A possesses a poly-substituted 6-5/6/6 tetracyclic ring system, which represents the first case of such a skeleton found in nature. Furthermore, the cytotoxic activity of effphenol A (1) toward four human cancer cell lines was assayed.A highly substituted phenol derivative, effphenol A (1), was isolated from the deep-sea-derived fungus Trichobotrys effuse FS524. Its complete structural assignment was established through a combination of spectroscopic analysis together with single-crystal X-ray diffraction experiments and further unequivocally confirmed by a biomimetic total synthesis. Structurally, effphenol A possesses a poly-substituted 6-5/6/6 tetracyclic ring system, which represents the first case of such a skeleton found in nature. Furthermore, the cytotoxic activity of effphenol A (1) toward four human cancer cell lines was assayed. A highly substituted phenol derivative, effphenol A ( 1 ), was isolated from the deep-sea-derived fungus Trichobotrys effuse FS524. Its complete structural assignment was established through a combination of spectroscopic analysis together with single-crystal X-ray diffraction experiments and further unequivocally confirmed by a biomimetic total synthesis. Structurally, effphenol A possesses a poly-substituted 6-5/6/6 tetracyclic ring system, which represents the first case of such a skeleton found in nature. Furthermore, the cytotoxic activity of effphenol A ( 1 ) toward four human cancer cell lines was assayed. |
Author | Zhang, Xiao Liu, Zhaoming Chen, Yuchan Tan, Haibo Chen, Shanchong Dong, Chunmao Liu, Hongxin Zhang, Weimin |
AuthorAffiliation | Guangdong Open Laboratory of Applied Microbiology South China Botanical Garden Chinese Academy of Sciences Central South University Guangdong Provincial Key Laboratory of Applied Botany Key Laboratory of Plant Resources Conservation and Sustainable Utilization Guangdong Provincial Key Laboratory of Microbial Culture Collection and Application Guangdong Institute of Microbiology Guangdong Academy of Sciences State Key Laboratory of Applied Microbiology Southern China Program for Natural Products Chemical Biology Xiangya School of Pharmaceutical Sciences |
AuthorAffiliation_xml | – name: State Key Laboratory of Applied Microbiology Southern China – name: Guangdong Provincial Key Laboratory of Microbial Culture Collection and Application – name: Key Laboratory of Plant Resources Conservation and Sustainable Utilization – name: Guangdong Provincial Key Laboratory of Applied Botany – name: Guangdong Open Laboratory of Applied Microbiology – name: Chinese Academy of Sciences – name: Guangdong Institute of Microbiology – name: Xiangya School of Pharmaceutical Sciences – name: Central South University – name: Program for Natural Products Chemical Biology – name: Guangdong Academy of Sciences – name: South China Botanical Garden |
Author_xml | – sequence: 1 givenname: Hongxin surname: Liu fullname: Liu, Hongxin – sequence: 2 givenname: Shanchong surname: Chen fullname: Chen, Shanchong – sequence: 3 givenname: Xiao surname: Zhang fullname: Zhang, Xiao – sequence: 4 givenname: Chunmao surname: Dong fullname: Dong, Chunmao – sequence: 5 givenname: Yuchan surname: Chen fullname: Chen, Yuchan – sequence: 6 givenname: Zhaoming surname: Liu fullname: Liu, Zhaoming – sequence: 7 givenname: Haibo surname: Tan fullname: Tan, Haibo – sequence: 8 givenname: Weimin surname: Zhang fullname: Zhang, Weimin |
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Notes | For ESI and crystallographic data in CIF or other electronic format see DOI 1974672 10.1039/d0ob01985b Electronic supplementary information (ESI) available: Experimental details, including procedures, syntheses, and the characterization of new products; 1D and 2D NMR, UV, HRESI, as well as a CIF file. CCDC ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
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Snippet | A highly substituted phenol derivative, effphenol A (
1
), was isolated from the deep-sea-derived fungus
Trichobotrys effuse
FS524. Its complete structural... A highly substituted phenol derivative, effphenol A (1), was isolated from the deep-sea-derived fungus Trichobotrys effuse FS524. Its complete structural... |
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SubjectTerms | Biomimetics Chemistry Chemistry, Organic Crystallography Crystals Cytotoxicity Deep sea Fungi NMR Nuclear magnetic resonance Phenols Physical Sciences Science & Technology Single crystals Substitutes Synthesis Tumor cell lines X-ray diffraction |
Title | Structural elucidation, total synthesis, and cytotoxic activity of effphenol A |
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