scholarly journals Butenolide Derivatives with α-Glucosidase Inhibitions from the Deep-Sea-Derived Fungus Aspergillus terreus YPGA10

Marine Drugs ◽  
2019 ◽  
Vol 17 (6) ◽  
pp. 332 ◽  
Author(s):  
Zhongbin Cheng ◽  
Yuanli Li ◽  
Wan Liu ◽  
Lijun Liu ◽  
Jie Liu ◽  
...  
Keyword(s):  
Nuclear Magnetic Resonance ◽  
Magnetic Resonance ◽  
Mass Spectroscopy ◽  
Deep Sea ◽  
Aspergillus Terreus ◽  
Positive Control ◽  
Inhibitory Effects ◽  
Etoac Extract ◽  
Ring Compounds ◽  
Ic50 Values

Three new butenolide derivatives, namely aspernolides N–P (1–3), together with six known analogues (4–9), were isolated from the ethyl acetate (EtOAc) extract of the deep sea-derived fungus Aspergillus terreus YPGA10. The structures of compounds 1–3 were determined on the basis of comprehensive analyses of the nuclear magnetic resonance (NMR) and mass spectroscopy (MS) data, and the absolute configurations of 1 and 2 were determined by comparisons of experimental electronic circular dichroism (ECD) with calculated ECD spectra. Compound 1 represents the rare example of Aspergillus-derived butenolide derivatives featured by a monosubstituted benzene ring. Compounds 6–9 exhibited remarkable inhibitory effects against α-glucosidase with IC50 values of 3.87, 1.37, 6.98, and 8.06 μM, respectively, being much more active than the positive control acarbose (190.2 μM).

scholarly journals Peniginsengins B–E, New Farnesylcyclohexenones from the Deep Sea-Derived Fungus Penicillium sp. YPGA11

Marine Drugs ◽  
2018 ◽  
Vol 16 (10) ◽  
pp. 358 ◽  
Author(s):  
Zhongbin Cheng ◽  
Wei Xu ◽  
Lijun Liu ◽  
Shumin Li ◽  
Wangjun Yuan ◽  
...  
Keyword(s):  
Staphylococcus Aureus ◽  
Nuclear Magnetic Resonance ◽  
Antibacterial Activity ◽  
Magnetic Resonance ◽  
Deep Sea ◽  
Dienoic Acid ◽  
Side Chain ◽  
Chemical Examination ◽  
Etoac Extract ◽  
Penicillium Sp

Chemical examination of the EtOAc extract of the deep sea-derived fungus Penicillium sp. YPGA11 resulted in the isolation of four new farnesylcyclohexenones, peniginsengins B–E (1–4), and a known analog peniginsengin A (5). The structures of compounds 1–4 were determined on the basis of comprehensive analyses of the nuclear magnetic resonance (NMR) and mass spectroscopy (MS) data, and the absolute configurations of 1, 2, and 4 were determined by comparisons of experimental electronic circular dichroism (ECD) with calculated ECD spectra. Compounds 1–5, characterized by a highly oxygenated 1-methylcyclohexene unit and a (4E,8E)-4,8-dimethyldeca-4,8-dienoic acid side chain, are rarely found in nature. Compounds 2–4 exhibited antibacterial activity against Staphylococcus aureus.

scholarly journals Terpenoids from the Deep-Sea-Derived Fungus Penicillium thomii YPGA3 and Their Bioactivities

Marine Drugs ◽  
2020 ◽  
Vol 18 (3) ◽  
pp. 164 ◽  
Author(s):  
Zhongbin Cheng ◽  
Wan Liu ◽  
Runzhu Fan ◽  
Shouye Han ◽  
Yuanli Li ◽  
...  
Keyword(s):  
Deep Sea ◽  
Chemical Study ◽  
Positive Control ◽  
Hydroxyl Group ◽  
Etoac Extract ◽  
The Third ◽  
Ic50 Value ◽  
Ic50 Values ◽  
New Compounds ◽  
First Time

A chemical study of the ethyl acetate (EtOAc) extract from the deep-sea-derived fungus Penicillium thomii YPGA3 led to the isolation of a new austalide meroterpenoid (1) and seven known analogues (2−8), two new labdane-type diterpenoids (9 and 10) and a known derivative (11). The structures of new compounds 1, 9, and 10 were determined by comprehensive analyses via nuclear magnetic resonance (NMR) and mass spectroscopy (MS) data. The absolute configurations of 1, 9, and 10 were determined by comparisons of experimental electronic circular dichroism (ECD) with the calculated ECD spectra. Compound 1 represented the third example of austalides bearing a hydroxyl group at C-5 instead of the conserved methoxy in other known analogues. To our knowledge, diterpenoids belonging to the labdane-type were discovered from species of Penicillium for the first time. Compound 1 showed cytotoxicity toward MDA-MB-468 cells with an IC50 value of 38.9 μM. Compounds 2 and 11 exhibited inhibition against α-glucosidase with IC50 values of 910 and 525 μM, respectively, being more active than the positive control acarbose (1.33 mM).

scholarly journals New Diterpenoids and Isocoumarin Derivatives from the Mangrove-Derived Fungus Hypoxylon sp.

Marine Drugs ◽  
2021 ◽  
Vol 19 (7) ◽  
pp. 362
Author(s):  
Bolin Hou ◽  
Sushi Liu ◽  
Ruiyun Huo ◽  
Yueqian Li ◽  
Jinwei Ren ◽  
...  
Keyword(s):  
Nuclear Magnetic Resonance ◽  
Magnetic Resonance ◽  
Crude Extract ◽  
Mass Spectrometric ◽  
Spectrometric Analysis ◽  
Ic50 Values ◽  
Inhibitory Activities ◽  
The Absolute ◽  
Dpph Scavenging ◽  
New Compounds

Two new diterpenoids, hypoxyterpoids A (1) and B (2), and four new isocoumarin derivatives, hypoxymarins A–D (4–7), together, with seven known metabolites (3 and 8–13) were obtained from the crude extract of the mangrove-derived fungus Hypoxylon sp. The structures of the new compounds were elucidated on the basis of 1- and 2-dimensional (1D/2D) nuclear magnetic resonance (NMR) spectroscopic and mass spectrometric analysis. The absolute configurations of compounds 1, 2, 4, 5, and 7 were determined by comparison of experimental and calculated electronic circular dichroism (ECD) spectra, and the absolute configurations of C-4′ in 6 and C-9 in 7 were determined by [Rh2(OCOCF3)4]-induced ECD spectra. Compound 1 showed moderate α-glucosidase inhibitory activities with IC50 values of 741.5 ± 2.83 μM. Compounds 6 and 11 exhibited DPPH scavenging activities with IC50 values of 15.36 ± 0.24 and 3.69 ± 0.07 μM, respectively.

scholarly journals Benzyl Furanones and Pyrones from the Marine-Derived Fungus Aspergillus terreus Induced by Chemical Epigenetic Modification

Molecules ◽  
2020 ◽  
Vol 25 (17) ◽  
pp. 3927
Author(s):  
Jing-Shuai Wu ◽  
Xiao-Hui Shi ◽  
Ya-Hui Zhang ◽  
Chang-Lun Shao ◽  
Xiu-Mei Fu ◽  
...  
Keyword(s):  
Aspergillus Terreus ◽  
Epigenetic Modification ◽  
2D Nmr ◽  
Etoac Extract ◽  
One Dimensional ◽  
X Ray ◽  
Deacetylase Inhibitor ◽  
Ic50 Values ◽  
First Time ◽  
Mic Value

Chemical epigenetic modification on a marine-derived fungus Aspergillus terreus RA2905 using a histone deacetylase inhibitor, suberoylanilide hydroxamic acid (SAHA), resulted in a significantly changed metabolic profile. A chemical investigation of its ethyl acetate (EtOAc) extract led to the isolation of a racemate of benzyl furanone racemate (±)-1, which further separated chirally as a pair of new enantiomers, (+)- and (−)-asperfuranone (1), together with two new benzyl pyrones, asperpyranones A (2) and B (3). Their structures were elucidated by analysis of the comprehensive spectroscopic data, including one-dimensional (1D) and two-dimensional (2D) NMR, and HRESIMS. The absolute configurations were determined by electronic circular dichroism (ECD) calculation and single-crystal X-ray crystallographic experiment. The structures with benzyl furanone or benzyl pyrone skeletons were discovered from natural products for the first time. Compounds (±)-1, (+)-1, (−)-1, and 2 displayed the antifungal activities against Candida albicans with MIC values of 32, 16, 64, and 64 μg/mL and PTP1B inhibitory activities with the IC50 values of 45.79, 17.32, 35.50, and 42.32 μM, respectively. Compound 2 exhibited antibacterial activity against Pseudomonas aeruginosa with the MIC value of 32 μg/mL.

scholarly journals Two New Cytotoxic Compounds from a Deep-Sea Penicillum citreonigrum XT20-134

Marine Drugs ◽  
2019 ◽  
Vol 17 (9) ◽  
pp. 509 ◽  
Author(s):  
Xi-Xiang Tang ◽  
Shun-Zhi Liu ◽  
Xia Yan ◽  
Bo-Wen Tang ◽  
Mei-Juan Fang ◽  
...  
Keyword(s):  
Tumor Cell ◽  
Deep Sea ◽  
Cytotoxic Activities ◽  
Ionization Mass ◽  
Human Hepatoma ◽  
Etoac Extract ◽  
Deep Sea Sediment ◽  
Cytotoxic Compounds ◽  
Ic50 Values ◽  
New Compounds

Penicillum citreonigrum XT20-134 (MCCC 3A00956) is a fungus with cytotoxic activity, derived from deep-sea sediment. Five new compounds, adeninylpyrenocine (1), 2-hydroxyl-3-pyrenocine-thio propanoic acid (2), ozazino-cyclo-(2,3-dihydroxyl-trp-tyr) (3), 5,5-dichloro-1-(3,5-dimethoxyphenyl)-1,4-dihydroxypentan-2-one (4), and 2,3,4-trihydroxybutyl cinnamate (5), together with 19 known compounds (6–24), were isolated from an ethyl acetate (EtOAc) extract of its fermentation. The structures of the new compounds were comprehensively characterized by high-resolution electrospray ionization-mass spectrometry (HR-ESI-MS), 1D and 2D nuclear magnetic resonance (NMR). All isolates were evaluated for their cytotoxic activities. The heteroatom-containing new compounds 2 and 4 showed potent cytotoxicity to the human hepatoma tumor cell Bel7402 with IC50 values of 7.63 ± 1.46, 13.14 ± 1.41 μM and the human fibrosarcoma tumor cell HT1080 with IC50 values of 10.22 ± 1.32, 16.53 ± 1.67 μM, respectively.

scholarly journals A systematic review of the small molecule studies of osteoarthritis using nuclear magnetic resonance and mass spectroscopy

2019 ◽  
Vol 27 (4) ◽  
pp. 560-570 ◽  
Author(s):  
M.K.J. Jaggard ◽  
C.L. Boulangé ◽  
P. Akhbari ◽  
U. Vaghela ◽  
R. Bhattacharya ◽  
...  
Keyword(s):  
Systematic Review ◽  
Nuclear Magnetic Resonance ◽  
Magnetic Resonance ◽  
Small Molecule ◽  
Mass Spectroscopy ◽  
Nuclear Magnetic

Immunosuppressive activity of cyclosporine metabolites compared and characterized by mass spectroscopy and nuclear magnetic resonance

1990 ◽  
Vol 36 (2) ◽  
pp. 225-229 ◽  
Author(s):  
K R Copeland ◽  
R W Yatscoff ◽  
R M McKenna
Keyword(s):  
Nuclear Magnetic Resonance ◽  
Magnetic Resonance ◽  
Mass Spectroscopy ◽  
Proton Nuclear Magnetic Resonance ◽  
Therapeutic Monitoring ◽  
Potency Ratio ◽  
Transplant Patients ◽  
In Vitro Systems ◽  
Nuclear Magnetic

Abstract Eight cyclosporine (CsA) metabolites were isolated from the urine of renal-transplant patients by high-pressure liquid chromatography. Structure and purity of the metabolites were assessed by fast atomic bombardment/mass spectroscopy, by proton nuclear magnetic resonance (NMR), and, when the quantity of metabolites permitted, by 13C-NMR. The immunosuppressive activities (I) of the metabolites were tested in three separate in vitro systems: primary and secondary mixed lymphocyte reactions as well as by a mitogen-stimulated system. The I, as measured by comparing the concentration of each metabolite required for 50% inhibition of incorporation of [3H] thymidine, varied among the assay systems, as did the ranking of I among the test systems. In general, the I of most metabolites in all assay systems were less than 10% of that for CsA. Metabolites with single modifications exhibited the greatest I; e.g., that of M-17 was congruent to 16% of that of CsA (potency ratio 0.16) in a secondary mixed lymphocyte reaction. The significance of these findings in relation to therapeutic monitoring of CsA is discussed.

scholarly journals Two New AChE Inhibitors Isolated from Li Folk Herb Heilaohu “Kadsura coccinea” Stems

Molecules ◽  
2019 ◽  
Vol 24 (19) ◽  
pp. 3628
Author(s):  
Sheng Zhuo Huang ◽  
Lin Ping Duan ◽  
Hao Wang ◽  
Wen Li Mei ◽  
Hao Fu Dai
Keyword(s):  
Mass Spectrometry ◽  
Nuclear Magnetic Resonance ◽  
Magnetic Resonance ◽  
Spectroscopic Data ◽  
Positive Control ◽  
Ache Inhibitors ◽  
Activity Test ◽  
Ache Inhibitory Activity ◽  
Kadsura Coccinea ◽  
Ellman’S Method

Two new triterpenoids, named kadsuricoccins A and B, together with three known ones, were isolated from the Li folk herb Heilaohu, the stems of Kadsura coccinea (Lem.) A. C. Smith, which was used for food and as a healthy supplement. Their structures were elucidated by comprehensive analyses of mass spectrometry (MS) and nuclear magnetic resonance (NMR) spectroscopic data. To search healthy components, an acetylcholinesterase (AChE) inhibitory activity test by Ellman’s Method was conducted, kadsuricoccins A and B showed activity with the AChE inhibit index (AII) up to 68.96% ± 0.19% and 57.8% ± 0.11% at 94 nM (compared with positive control tacrine AII 79.80% ± 0.20%, 9.4 nM), respectively.

scholarly journals Applications D'Intelligence Artificielle Dans La Chimie Organique. XVII. Nouveaux Programmes Du Projet SISTEMAT

1994 ◽  
Vol 12 (2) ◽  
pp. 91-98 ◽  
Author(s):  
Vincente de Paulo Emerenciano ◽  
Gilberto do V. Rodrigues ◽  
Patricia A. T. Macari ◽  
Sandra A. Vesti ◽  
Joao H. G. Borges ◽  
...  
Keyword(s):  
Nuclear Magnetic Resonance ◽  
Natural Products ◽  
Magnetic Resonance ◽  
Data Base ◽  
Mass Spectroscopy ◽  
Nmr Spectra ◽  
Heuristic Rules ◽  
Structure Generation ◽  
Natural Products Chemistry ◽  
C Nmr

This work describes the new improvements of the SISlEMAT project, one system for structural elucidation mainly in the field of Natural Products Chemistry. Some examples of the resolution of problems using13C Nuclear Magnetic Resonance and Mass Spectroscopy are given. Programs to discover new heuristic rules for structure generation are discussed. The data base contains about 100013C NMR spectra.

Sign in / Sign up

Export Citation Format

Share Document