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1. (Article ID: 9645)
Ma ZL, Yu ZP, Zheng YY, Han N, Zhang YH, Song SY, Mao JQ, Li JJ, Yao GS, Wang CY
Bioactive Alpha-Pyrone and Phenolic Glucosides from the Marine-Derived Metarhizium sp. P2100
Journal of Fungi 9(1) (2023)
28
Glycoside compounds have attracted great interest due to their remarkable and multifarious bioactivities. In this study, four hitherto unknown 4-methoxy-β-D-glucosyl derivatives were obtained and identified from the marine-derived fungus Metarhizium sp. P2100, including three α-pyrone glycosides (1-3) and one phenolic glycoside (4). Their planar structures were elucidated by comprehensive spectroscopic analysis, including 1D/2D NMR and HRESIMS. The absolute configurations of 1-3 were determined by a single-crystal X-ray crystallographic experiment, a comparison of the experimental, and a calculated electronic circular dichroism (ECD) spectra, respectively. Compounds 2 and 3 are a pair of rare epimeric pyranoside glycosides at C-7 with a core of aglycone as 2H-pyrone. Compounds 1-4 exhibited weak anti-inflammatory activities. In particular, compounds 1-3 displayed inhibitory activities against α-amylase, showing a potential for the development of a new α-amylase inhibitor for controlling diabetes.
marine-derived fungus, 4-O-methyl-β-D-glucose, α-amylase inhibitor, Metarhizium
NCBI PubMed ID: 36675849Publication DOI: 10.3390/jof9010028Journal NLM ID: 101671827Publisher: Basel, Switzerland: MDPI AG
Correspondence: G.S. Yao <2616
mju.edu.cn or ygshan
126.com>; C.Y. Wang
ouc.edu.cn>
Institutions: Key Laboratory of Marine Drugs, The Ministry of Education of China, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, China, Fujian Key Laboratory on Conservation and Sustainable Utilization of Marine Biodiversity, Institute of Oceanography, Minjiang University, Fuzhou 350108, China, Laboratory for Marine Drugs and Bioproducts, Qingdao National Laboratory for Marine Science and Technology, Qingdao 266237, China, Institute of Evolution & Marine Biodiversity, Ocean University of China, Qingdao 266003, China
Methods: 13C NMR, 1H NMR, IR, X-ray, TLC, UV, extraction, optical rotation measurement, CC, fermentation, HR-ESI-MS, antibacterial assay, determination of NO production, cell proliferation assay, ECD, bioassay
The publication contains the following compound(s):
- Compound ID: 23526
|
b-D-Glcp4Me-(1-4)-Subst
Subst = 4-hydroxy-6-pentyl-2-pyrone = SMILES O=C1C={4}C(O)C=C(CCCCC)O1 |
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Structure type: monomer
; 381.1531 [M+Na]+
C17H26O8
Trivial name: 4-(4'-methoxy-b-D-glucopyranosyl)-6-pentyl-2-pyrone
- Compound ID: 23527
|
b-D-Glcp4Me-(1-7)-Subst
Subst = 6-(7R-hydroxypentyl)-4-methoxy-6-pentyl-2-pyrone = SMILES O=C1C=C(OC)C=C({7}[C@H](O)CCCC)O1 |
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Structure type: monomer
; 389.1807 [M+H]+
C18H28O9
Trivial name: 7(R)-(4'-methoxy-b-D-glucosyl)-4-methoxy-6-pentyl-2-pyrone
- Compound ID: 23528
|
b-D-Glcp4Me-(1-7)-Subst
Subst = 6-(7S-hydroxypentyl)-4-methoxy-6-pentyl-2-pyrone = SMILES O=C1C=C(OC)C=C({7}[C@@H](O)CCCC)O1 |
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Structure type: monomer
; 389.1767 [M+H]+
C18H28O9
Trivial name: 7(S)-(4'-methoxy-b-D-glucosyl)-4-methoxy-6-pentyl-2-pyrone
- Compound ID: 23529
|
b-D-Glcp4Me-(1-4)-Subst
Subst = lecaniside D aglycon = SMILES CC(C1=CC(OC)={4}C(C=C1)O)=O |
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Structure type: monomer
; 365.1199 [M+Na]+
C16H22O8
Trivial name: lecaniside D
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