Highly Oxygenated Caryophyllene-Type Sesquiterpenes from a Plant-Associated Fungus, Pestalotiopsis hainanensis, and Their Biosynthetic Gene Cluster
Seven new β-caryophyllene derivatives, pestalotiphains A-G (1-7), along with six known analogues (8-13), were isolated from the plant-associated Pestalotiopsis hainanensis. Compound 1 represents the first example of a caryophyllene-adenine hybrid, and 2 contains a novel oxatricyclo[4.3.1.0] system. Their structures and absolute configurations were assigned by interpretation of a combination of spectroscopic data and electronic circular dichroism calculations. Compound 8 exhibited moderate inhibition of HL-60 and THP-1 cell lines (IC50, 6.2 and 2.0 μM, respectively). A candidate biosynthetic gene cluster responsible for these compounds was uncovered by bioinformatics analyses and confirmed by a biochemical approach.
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2020 |
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| Erschienen: |
2020 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:83 |
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| Enthalten in: |
Journal of natural products - 83(2020), 11 vom: 25. Nov., Seite 3262-3269 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Zhang, Yalong [VerfasserIn] |
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| Links: |
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| Themen: |
BHW853AU9H |
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| Anmerkungen: |
Date Completed 27.10.2021 Date Revised 27.10.2021 published: Print-Electronic Citation Status MEDLINE |
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| doi: |
10.1021/acs.jnatprod.0c00501 |
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| funding: |
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| Förderinstitution / Projekttitel: |
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| PPN (Katalog-ID): |
NLM316339679 |
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| 500 | |a published: Print-Electronic | ||
| 500 | |a Citation Status MEDLINE | ||
| 520 | |a Seven new β-caryophyllene derivatives, pestalotiphains A-G (1-7), along with six known analogues (8-13), were isolated from the plant-associated Pestalotiopsis hainanensis. Compound 1 represents the first example of a caryophyllene-adenine hybrid, and 2 contains a novel oxatricyclo[4.3.1.0] system. Their structures and absolute configurations were assigned by interpretation of a combination of spectroscopic data and electronic circular dichroism calculations. Compound 8 exhibited moderate inhibition of HL-60 and THP-1 cell lines (IC50, 6.2 and 2.0 μM, respectively). A candidate biosynthetic gene cluster responsible for these compounds was uncovered by bioinformatics analyses and confirmed by a biochemical approach | ||
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| 700 | 1 | |a Yan, Daojiang |e verfasserin |4 aut | |
| 700 | 1 | |a Liu, Bingyu |e verfasserin |4 aut | |
| 700 | 1 | |a Zhang, Le |e verfasserin |4 aut | |
| 700 | 1 | |a Zhang, Chen |e verfasserin |4 aut | |
| 700 | 1 | |a Chen, Minghua |e verfasserin |4 aut | |
| 700 | 1 | |a Mou, Yanhua |e verfasserin |4 aut | |
| 700 | 1 | |a Hu, Youcai |e verfasserin |4 aut | |
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