دورية أكاديمية
Isolation and stereospecific synthesis of indole alkaloids with lipid-lowering effects from the marine-derived fungus Colletotrichum gloeosporioides BB4.
| العنوان: | Isolation and stereospecific synthesis of indole alkaloids with lipid-lowering effects from the marine-derived fungus Colletotrichum gloeosporioides BB4. |
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| المؤلفون: | Huang Q; School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou, 510006, People's Republic of China; School of Pharmacy, Guangdong Pharmaceutical University, Guangzhou, 510006, People's Republic of China. Electronic address: m15202884285@163.com., Hao MJ; School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou, 510006, People's Republic of China. Electronic address: m15202884285@163.com., Wang LY; School of Pharmacy, Guangdong Pharmaceutical University, Guangzhou, 510006, People's Republic of China; Department of Clinical Pharmacy, Guangdong Provincial People's Hospital, Guangdong Academy of Medical Sciences, Guangzhou, 510080, People's Republic of China. Electronic address: laiyouwang@hotmail.com., Wu F; School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou, 510006, People's Republic of China. Electronic address: wufeng35@mail2.sysu.edu.cn., Li HJ; School of Chemistry, Sun Yat-sen University, Guangzhou, 510006, People's Republic of China. Electronic address: ceslhj@mail.sysu.edu.cn., Yuan J; Zhongshan School of Medicine, Sun Yat-sen University, Guangzhou, 510080, People's Republic of China. Electronic address: yuanjie@mail.sysu.edu.cn., Xu J; School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou, 510006, People's Republic of China. Electronic address: xujun9@mail.sysu.edu.cn., Mahmud T; Department of Pharmaceutical Sciences, Oregon State University, Corvallis, OR, 97331, United States. Electronic address: Taifo.mahmud@oregonstate.edu., Lan WJ; School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou, 510006, People's Republic of China. Electronic address: lanwj@mail.sysu.edu.cn. |
| المصدر: | Phytochemistry [Phytochemistry] 2023 May; Vol. 209, pp. 113612. Date of Electronic Publication: 2023 Feb 21. |
| نوع المنشور: | Journal Article |
| اللغة: | English |
| بيانات الدورية: | Publisher: Elsevier Country of Publication: England NLM ID: 0151434 Publication Model: Print-Electronic Cited Medium: Internet ISSN: 1873-3700 (Electronic) Linking ISSN: 00319422 NLM ISO Abbreviation: Phytochemistry Subsets: MEDLINE |
| أسماء مطبوعة: | Publication: 2003- : London : Elsevier Original Publication: 1961-2003: Oxford : Pergamon Press. |
| مواضيع طبية MeSH: | Indole Alkaloids*/pharmacology , Colletotrichum*, Magnetic Resonance Spectroscopy ; Lipids ; Molecular Structure |
| مستخلص: | Seven undescribed compounds, colletotrichindoles A-E, colletotrichaniline A, and colletotrichdiol A, as well as three known compounds, (-)-isoalternatine A, (+)-alternatine A and 3-hydroxybutan-2-yl 2-phenylacetate were isolated from the marine-derived fungus Colletotrichu gloeosporioides BB4. The racemic mixtures colletotrichindole A，colletotrichindole C, and colletotrichdiol A were further separated by chiral chromatography to give three pairs of enantiomers (10S,11R,13S)/(10R,11S,13R)-colletotrichindole A, (10R,11R,13S)/(10S,11S,13R)-colletotrichindole C, and (9S,10S)/(9R,10R)-colletotrichdiol A, respectively. The chemical structures of seven undescribed compounds and the known compounds, (-)-isoalternatine A, and (+)-alternatine A were determined using a combination of NMR, MS, X-ray diffraction, ECD calculations, and/or chemical synthesis. All possible enantiomers of colletotrichindoles A-E were synthesized and used to determine the absolute configurations of the natural products by comparing their spectroscopic data and HPLC retention times on a chiral column. In addition, the X-ray crystal structures of the known compounds (-)-isoalternatine A and (+)-alternatine A were also obtained to confirm their absolute configurations. (10S,11R,13S)-Colletotrichindole A, colletotrichindole B, and (+)-alternatine A significantly reduced triglyceride levels in 3T3-L1 cells with EC Competing Interests: Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper. (Copyright © 2023 Elsevier Ltd. All rights reserved.) |
| فهرسة مساهمة: | Keywords: Colletotrichum gloeosporioides; Lipid-lowering effects; Marine-derived fungus; Stereospecific synthesis |
| المشرفين على المادة: | 0 (Indole Alkaloids) 0 (Lipids) |
| SCR Organism: | Colletotrichum gloeosporioides |
| تواريخ الأحداث: | Date Created: 20230222 Date Completed: 20230331 Latest Revision: 20230331 |
| رمز التحديث: | 20231215 |
| DOI: | 10.1016/j.phytochem.2023.113612 |
| PMID: | 36813220 |
| قاعدة البيانات: | MEDLINE |
Full Text Finder | تدمد: | 1873-3700 |
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| DOI: | 10.1016/j.phytochem.2023.113612 |