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 |
|---|---|
| Main Authors | , , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
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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. |
|---|---|
| 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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| Cites_doi | 10.1039/c6np00124f 10.1021/acs.orglett.9b01754 10.1021/cr900019j 10.1021/acs.jnatprod.9b01285 10.1021/acs.orglett.8b04019 10.1016/j.tetlet.2019.151555 10.1021/acs.orglett.7b00496 10.3390/md18030134 10.1039/c9np00020h 10.1021/acs.jnatprod.9b00834 10.1039/c9qo01365b 10.1021/acs.jnatprod.9b00878 10.1016/j.bmcl.2017.03.010 10.1021/acs.jnatprod.5b01055 10.1039/c9ob02625h 10.1039/c5np00156k 10.1039/c7np00052a 10.1002/anie.201506505 10.1021/acsmedchemlett.8b00368 10.1039/c9np00069k 10.1016/j.bbagen.2013.02.008 10.1021/ja5060302 10.1021/np200906s 10.1016/j.tet.2016.09.011 10.1039/C5NP00156K 10.1039/C9NP00020H 10.1039/C6NP00124F 10.1039/C9QO01365B 10.1039/C7NP00052A 10.1039/C9NP00069K 10.1039/C9OB02625H |
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| Keywords | DERIVATIVES NATURAL-PRODUCTS MEROTERPENOIDS |
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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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