α-Glucosidase Inhibitors From the Coral-Associated Fungus Aspergillus terreus

Nine novel butenolide derivatives, including four pairs of enantiomers, named (±)-asperteretones A–D (1a/1b–4a/4b), and a racemate, named asperteretone E (5), were isolated and identified from the coral-associated fungus Aspergillus terreus. All the structures were established based on extensive spe...
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Autor*in:	Mengting Liu [verfasserIn] Changxing Qi [verfasserIn] Weiguang Sun [verfasserIn] Ling Shen [verfasserIn] Jianping Wang [verfasserIn] Junjun Liu [verfasserIn] Yongji Lai [verfasserIn] Yongbo Xue [verfasserIn] Zhengxi Hu [verfasserIn] Yonghui Zhang [verfasserIn]

Format:	E-Artikel
Sprache:	Englisch

Erschienen:	2018

Schlagwörter:	coral-associated fungus Aspergillus terreus butenolide derivatives structure reassignments α-glucosidase inhibitors

Übergeordnetes Werk:	In: Frontiers in Chemistry - Frontiers Media S.A., 2014, 6(2018)
Übergeordnetes Werk:	volume:6 ; year:2018

Links:	Link aufrufen Link aufrufen Link aufrufen Journal toc

DOI / URN:	10.3389/fchem.2018.00422

Katalog-ID:	DOAJ046919694

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allfieldsSound	10.3389/fchem.2018.00422 doi (DE-627)DOAJ046919694 (DE-599)DOAJ71856e261e434f1fb0954d8dbd56ba23 DE-627 ger DE-627 rakwb eng QD1-999 Mengting Liu verfasserin aut α-Glucosidase Inhibitors From the Coral-Associated Fungus Aspergillus terreus 2018 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Nine novel butenolide derivatives, including four pairs of enantiomers, named (±)-asperteretones A–D (1a/1b–4a/4b), and a racemate, named asperteretone E (5), were isolated and identified from the coral-associated fungus Aspergillus terreus. All the structures were established based on extensive spectroscopic analyses, including HRESIMS and NMR data. The chiral chromatography analyses allowed the separation of (±)-asperteretones A–D, whose absolute configurations were further confirmed by experimental and calculated electronic circular dichroism (ECD) analysis. Structurally, compounds 2–5 represented the first examples of prenylated γ-butenolides bearing 2-phenyl-3-benzyl-4H-furan-1-one motifs, and their crucial biogenetically related metabolite, compound 1, was uniquely defined by an unexpected cleavage of oxygen bridge between C-1 and C-4. Importantly, (±)-asperteretal D and (4S)-4-decarboxylflavipesolide C were revised to (±)-asperteretones B (2a/2b) and D (4), respectively. Additionally, compounds 1a/1b–4a/4b and 5 were evaluated for the α-glucosidase inhibitory activity, and all these compounds exhibited potent inhibitory potency against α-glucosidase, with IC50 values ranging from 15.7 ± 1.1 to 53.1 ± 1.4 μM, which was much lower than that of the positive control acarbose (IC50 = 154.7 ± 8.1 μM), endowing them as promising leading molecules for the discovery of new α-glucosidase inhibitors for type-2 diabetes mellitus treatment. coral-associated fungus Aspergillus terreus butenolide derivatives structure reassignments α-glucosidase inhibitors Chemistry Changxing Qi verfasserin aut Weiguang Sun verfasserin aut Ling Shen verfasserin aut Jianping Wang verfasserin aut Junjun Liu verfasserin aut Yongji Lai verfasserin aut Yongbo Xue verfasserin aut Zhengxi Hu verfasserin aut Yonghui Zhang verfasserin aut In Frontiers in Chemistry Frontiers Media S.A., 2014 6(2018) (DE-627)742224538 (DE-600)2711776-5 22962646 nnns volume:6 year:2018 https://doi.org/10.3389/fchem.2018.00422 kostenfrei https://doaj.org/article/71856e261e434f1fb0954d8dbd56ba23 kostenfrei https://www.frontiersin.org/article/10.3389/fchem.2018.00422/full kostenfrei https://doaj.org/toc/2296-2646 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ GBV_ILN_11 GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_213 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2003 GBV_ILN_2014 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 6 2018
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callnumber-first	Q - Science
author	Mengting Liu
spellingShingle	Mengting Liu misc QD1-999 misc coral-associated fungus misc Aspergillus terreus misc butenolide derivatives misc structure reassignments misc α-glucosidase inhibitors misc Chemistry α-Glucosidase Inhibitors From the Coral-Associated Fungus Aspergillus terreus
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topic_title	QD1-999 α-Glucosidase Inhibitors From the Coral-Associated Fungus Aspergillus terreus coral-associated fungus Aspergillus terreus butenolide derivatives structure reassignments α-glucosidase inhibitors
topic	misc QD1-999 misc coral-associated fungus misc Aspergillus terreus misc butenolide derivatives misc structure reassignments misc α-glucosidase inhibitors misc Chemistry
topic_unstemmed	misc QD1-999 misc coral-associated fungus misc Aspergillus terreus misc butenolide derivatives misc structure reassignments misc α-glucosidase inhibitors misc Chemistry
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title	α-Glucosidase Inhibitors From the Coral-Associated Fungus Aspergillus terreus
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title_full	α-Glucosidase Inhibitors From the Coral-Associated Fungus Aspergillus terreus
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title_sort	α-glucosidase inhibitors from the coral-associated fungus aspergillus terreus
callnumber	QD1-999
title_auth	α-Glucosidase Inhibitors From the Coral-Associated Fungus Aspergillus terreus
abstract	Nine novel butenolide derivatives, including four pairs of enantiomers, named (±)-asperteretones A–D (1a/1b–4a/4b), and a racemate, named asperteretone E (5), were isolated and identified from the coral-associated fungus Aspergillus terreus. All the structures were established based on extensive spectroscopic analyses, including HRESIMS and NMR data. The chiral chromatography analyses allowed the separation of (±)-asperteretones A–D, whose absolute configurations were further confirmed by experimental and calculated electronic circular dichroism (ECD) analysis. Structurally, compounds 2–5 represented the first examples of prenylated γ-butenolides bearing 2-phenyl-3-benzyl-4H-furan-1-one motifs, and their crucial biogenetically related metabolite, compound 1, was uniquely defined by an unexpected cleavage of oxygen bridge between C-1 and C-4. Importantly, (±)-asperteretal D and (4S)-4-decarboxylflavipesolide C were revised to (±)-asperteretones B (2a/2b) and D (4), respectively. Additionally, compounds 1a/1b–4a/4b and 5 were evaluated for the α-glucosidase inhibitory activity, and all these compounds exhibited potent inhibitory potency against α-glucosidase, with IC50 values ranging from 15.7 ± 1.1 to 53.1 ± 1.4 μM, which was much lower than that of the positive control acarbose (IC50 = 154.7 ± 8.1 μM), endowing them as promising leading molecules for the discovery of new α-glucosidase inhibitors for type-2 diabetes mellitus treatment.
abstractGer	Nine novel butenolide derivatives, including four pairs of enantiomers, named (±)-asperteretones A–D (1a/1b–4a/4b), and a racemate, named asperteretone E (5), were isolated and identified from the coral-associated fungus Aspergillus terreus. All the structures were established based on extensive spectroscopic analyses, including HRESIMS and NMR data. The chiral chromatography analyses allowed the separation of (±)-asperteretones A–D, whose absolute configurations were further confirmed by experimental and calculated electronic circular dichroism (ECD) analysis. Structurally, compounds 2–5 represented the first examples of prenylated γ-butenolides bearing 2-phenyl-3-benzyl-4H-furan-1-one motifs, and their crucial biogenetically related metabolite, compound 1, was uniquely defined by an unexpected cleavage of oxygen bridge between C-1 and C-4. Importantly, (±)-asperteretal D and (4S)-4-decarboxylflavipesolide C were revised to (±)-asperteretones B (2a/2b) and D (4), respectively. Additionally, compounds 1a/1b–4a/4b and 5 were evaluated for the α-glucosidase inhibitory activity, and all these compounds exhibited potent inhibitory potency against α-glucosidase, with IC50 values ranging from 15.7 ± 1.1 to 53.1 ± 1.4 μM, which was much lower than that of the positive control acarbose (IC50 = 154.7 ± 8.1 μM), endowing them as promising leading molecules for the discovery of new α-glucosidase inhibitors for type-2 diabetes mellitus treatment.
abstract_unstemmed	Nine novel butenolide derivatives, including four pairs of enantiomers, named (±)-asperteretones A–D (1a/1b–4a/4b), and a racemate, named asperteretone E (5), were isolated and identified from the coral-associated fungus Aspergillus terreus. All the structures were established based on extensive spectroscopic analyses, including HRESIMS and NMR data. The chiral chromatography analyses allowed the separation of (±)-asperteretones A–D, whose absolute configurations were further confirmed by experimental and calculated electronic circular dichroism (ECD) analysis. Structurally, compounds 2–5 represented the first examples of prenylated γ-butenolides bearing 2-phenyl-3-benzyl-4H-furan-1-one motifs, and their crucial biogenetically related metabolite, compound 1, was uniquely defined by an unexpected cleavage of oxygen bridge between C-1 and C-4. Importantly, (±)-asperteretal D and (4S)-4-decarboxylflavipesolide C were revised to (±)-asperteretones B (2a/2b) and D (4), respectively. Additionally, compounds 1a/1b–4a/4b and 5 were evaluated for the α-glucosidase inhibitory activity, and all these compounds exhibited potent inhibitory potency against α-glucosidase, with IC50 values ranging from 15.7 ± 1.1 to 53.1 ± 1.4 μM, which was much lower than that of the positive control acarbose (IC50 = 154.7 ± 8.1 μM), endowing them as promising leading molecules for the discovery of new α-glucosidase inhibitors for type-2 diabetes mellitus treatment.
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title_short	α-Glucosidase Inhibitors From the Coral-Associated Fungus Aspergillus terreus
url	https://doi.org/10.3389/fchem.2018.00422 https://doaj.org/article/71856e261e434f1fb0954d8dbd56ba23 https://www.frontiersin.org/article/10.3389/fchem.2018.00422/full https://doaj.org/toc/2296-2646
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up_date	2024-07-03T23:14:07.130Z
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All the structures were established based on extensive spectroscopic analyses, including HRESIMS and NMR data. The chiral chromatography analyses allowed the separation of (±)-asperteretones A–D, whose absolute configurations were further confirmed by experimental and calculated electronic circular dichroism (ECD) analysis. Structurally, compounds 2–5 represented the first examples of prenylated γ-butenolides bearing 2-phenyl-3-benzyl-4H-furan-1-one motifs, and their crucial biogenetically related metabolite, compound 1, was uniquely defined by an unexpected cleavage of oxygen bridge between C-1 and C-4. Importantly, (±)-asperteretal D and (4S)-4-decarboxylflavipesolide C were revised to (±)-asperteretones B (2a/2b) and D (4), respectively. 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