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Mar. Drugs 2016, 14(11), 215; doi:10.3390/md14110215

Phomopsichin A–D; Four New Chromone Derivatives from Mangrove Endophytic Fungus Phomopsis sp. 33#

1,†
,
2,3,†
,
2,4,* , 1
,
1,* and 3,4,5
1
School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou 510006, China
2
School of Marine Sciences, Sun Yat-sen University, Guangzhou 510006, China
3
Key Laboratory of Functional Molecules from Oceanic Microorganisms (Sun Yat-sen University), Department of Education of Guangdong Province, Guangzhou 510080, China
4
South China Sea Bio-Resource Exploitation and Utilization Collaborative Innovation Center, Guangzhou 510006, China
5
School of Chemistry and Chemical Engineering, Sun Yat-sen University, Guangzhou 510275, China
These authors contributed equally to this work.
*
Authors to whom correspondence should be addressed.
Academic Editor: Russell Kerr
Received: 9 September 2016 / Revised: 20 October 2016 / Accepted: 8 November 2016 / Published: 22 November 2016
(This article belongs to the Special Issue Marine Fungal Natural Products)
View Full-Text   |   Download PDF [2253 KB, uploaded 22 November 2016]   |  

Abstract

Four new chromone derivatives, phomopsichins A–D (14), along with a known compound, phomoxanthone A (5), were isolated from the fermentation products of mangrove endophytic fungus Phomopsis sp. 33#. Their structures were elucidated based on comprehensive spectroscopic analysis coupled with single-crystal X-ray diffraction or theoretical calculations of electronic circular dichroism (ECD). They feature a tricyclic framework, in which a dihydropyran ring is fused with the chromone ring. Compounds 15 showed weak inhibitory activities on acetylcholinesterase as well as α-glucosidase, weak radical scavenging effects on 1,1-diphenyl-2-picrylhydrazyl (DPPH) as well as OH, and weak antimicrobial activities. Compounds 14 showed no cytotoxic activity against MDA-MB-435 breast cancer cells. Their other bioactivities are worthy of further study, considering their unique molecular structures. View Full-Text
Keywords: mangrove endophytic fungi; Phomopsis sp.; secondary metabolites; chromone derivatives mangrove endophytic fungi; Phomopsis sp.; secondary metabolites; chromone derivatives
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    Description: Figure S1: 1H NMR for phomopsichin A (1), Figure S2: 13C-NMR for phomopsichin A (1), Figure S3: 1H-1H COSY for phomopsichin A (1), Figure S4: HSQC for phomopsichin A (1), Figure S5: HMBC for phomopsichin A (1), Figure S6: NOESY for phomopsichin A (1), Figure S7: HR mass spectrometry for phomopsichin A (1), Figure S8: 1H NMR for phomopsichin B (2), Figure S9: 13C-NMR for phomopsichin B (2), Figure S10: 1H-1H COSY for phomopsichin B (2), Figure S11: HSQC for phomopsichin B (2), Figure S12: HMBC for phomopsichin B (2), Figure S13: NOESY for phomopsichin B (2), Figure S14: HR mass spectrometry for phomopsichin B (2), Figure S15: 1H NMR for phomopsichin C (3), Figure S16: 13C-NMR for phomopsichin C (3), Figure S17: 1H-1H COSY for phomopsichin C (3), Figure S18: HSQC for phomopsichin C (3), Figure S19: HMBC for phomopsichin C (3), Figure S20: HR mass spectrometry for phomopsichin C (3), Figure S21: 1H NMR for phomopsichin D (4), Figure S22: 13C-NMR for phomopsichin D (4), Figure S23: 1H-1H COSY for phomopsichin D (4), Figure S24: HSQC for phomopsichin D (4), Figure S25: HMBC for phomopsichin D (4), Figure S26: HR mass spectrometry for phomopsichin D (4), Figure S27: ECD spectrometry for phomoxanthone A (5), Table S1: Crystal data and structure refinement for phomopsichin A (1), Table S2: Fractional atomic coordinates (×104) and equivalent isotropic displacement parameters (Å2×103) for phomopsichin A (1), Table S3: Anisotropic displacement parameters (Å2×103) for phomopsichin A (1), Table S4: Bond lengths for phomopsichin A (1), Table S5: Bond angles for phomopsichin A (1), Table S6: Torsion angles for phomopsichin A (1), Table S7: Hydrogen atom coordinates (Å×104) and isotropic displacement parameters (Å2 × 103) for phomopsichin A (1), Table S8: Inhibitory activities against AchE as well as α-glucosidase, and the radical scavenging effects on DPPH as well as OH of compounds 1-5, Table S9: Antimicrobial activity of compounds 1-5.

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Huang, M.; Li, J.; Liu, L.; Yin, S.; Wang, J.; Lin, Y. Phomopsichin A–D; Four New Chromone Derivatives from Mangrove Endophytic Fungus Phomopsis sp. 33#. Mar. Drugs 2016, 14, 215.

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