scholarly journals A New Meroterpene, A New Benzofuran Derivative and Other Constituents from Cultures of the Marine Sponge-Associated Fungus Acremonium persicinum KUFA 1007 and Their Anticholinesterase Activities

Marine Drugs ◽  
2019 ◽  
Vol 17 (6) ◽  
pp. 379 ◽  
Author(s):  
Ana J. S. Alves ◽  
José A. Pereira ◽  
Tida Dethoup ◽  
Sara Cravo ◽  
Sharad Mistry ◽  
...  
Keyword(s):  
Marine Sponge ◽  
Nmr Spectra ◽  
2D Nmr ◽  
Electronic Circular Dichroism ◽  
Benzofuran Derivative ◽  
Extensive Analysis ◽  
Stereogenic Centers ◽  
2D Nmr Spectra ◽  
Inhibitory Activities

Previously unreported meroterpene, acremine S (1), and benzopyran derivative, acremine T (2), were isolated, together with lumichrome (3), ergosterol (4) and ergosterol 5,8-endoperoxide, from cultures of the marine sponge-associated fungus Acremonium persicinum KUF1007. The structure of the previously unreported compounds was established based on an extensive analysis of 1D and 2D NMR spectra as well as HRMS data. The absolute configurations of the stereogenic centers of 1 were established, unambiguously, based on NOESY correlations and comparison of calculated and experimental electronic circular dichroism (ECD) spectra. Compounds 1–3 were tested for their in vitro acetylcholinesterase and butyrylcholinesterase inhibitory activities.

scholarly journals Anthraquinones, Diphenyl Ethers, and Their Derivatives from the Culture of the Marine Sponge-Associated Fungus Neosartorya spinosa KUFA 1047

Marine Drugs ◽  
2021 ◽  
Vol 19 (8) ◽  
pp. 457
Author(s):  
Joana D. M. de Sá ◽  
José A. Pereira ◽  
Tida Dethoup ◽  
Honorina Cidade ◽  
Maria Emília Sousa ◽  
...  
Keyword(s):  
Marine Sponge ◽  
Biofilm Formation ◽  
2D Nmr ◽  
Multidrug Resistant ◽  
Stereogenic Centers ◽  
Diphenyl Ethers ◽  
2D Nmr Spectra ◽  
Resistant Strains ◽  
Reference Strains

Previously unreported anthraquinone, acetylpenipurdin A (4), biphenyl ether, neospinosic acid (6), dibenzodioxepinone, and spinolactone (7) were isolated, together with (R)-6-hydroxymellein (1), penipurdin A (2), acetylquestinol (3), tenellic acid C (5), and vermixocin A (8) from the culture of a marine sponge-associated fungus Neosartorya spinosa KUFA1047. The structures of the previously unreported compounds were established based on an extensive analysis of 1D and 2D NMR spectra as well as HRMS data. The absolute configurations of the stereogenic centers of 5 and 7 were established unambiguously by comparing their calculated and experimental electronic circular dichroism (ECD) spectra. Compounds 2 and 5–8 were tested for their in vitro acetylcholinesterase and tyrosinase inhibitory activities as well as their antibacterial activity against Gram-positive and Gram-negative reference, and multidrug-resistant strains isolated from the environment. The tested compounds were also evaluated for their capacity to inhibit biofilm formation in the reference strains.

scholarly journals New Antimalarial and Antimicrobial Tryptamine Derivatives from the Marine Sponge Fascaplysinopsis reticulata

Marine Drugs ◽  
2019 ◽  
Vol 17 (3) ◽  
pp. 167 ◽  
Author(s):  
Pierre-Eric Campos ◽  
Emmanuel Pichon ◽  
Céline Moriou ◽  
Patricia Clerc ◽  
Rozenn Trépos ◽  
...  
Keyword(s):  
Plasmodium Falciparum ◽  
Minimum Inhibitory Concentration ◽  
Marine Sponge ◽  
Nmr Spectra ◽  
Inhibitory Concentration ◽  
Chemical Study ◽  
2D Nmr ◽  
Antimicrobial Activities ◽  
2D Nmr Spectra ◽  
Ic50 Values

Chemical study of the CH2Cl2-MeOH (1:1) extract of the sponge Fascaplysinopsis reticulata collected in Mayotte highlighted three new tryptophan derived alkaloids, 6,6′-bis-(debromo)-gelliusine F (1), 6-bromo-8,1′-dihydro-isoplysin A (2) and 5,6-dibromo-8,1′-dihydro-isoplysin A (3), along with the synthetically known 8-oxo-tryptamine (4) and the three known molecules from the same family, tryptamine (5), (E)-6-bromo-2′-demethyl-3′-N-methylaplysinopsin (6) and (Z)-6-bromo-2′-demethyl-3′-N-methylaplysinopsin (7). Their structures were elucidated by 1D and 2D NMR spectra and HRESIMS data. All compounds were evaluated for their antimicrobial and their antiplasmodial activities. Regarding antimicrobial activities, the best compounds are (2) and (3), with minimum inhibitory concentration (MIC) of 0.01 and 1 µg/mL, respectively, towards Vibrio natrigens, and (5), with MIC values of 1 µg/mL towards Vibrio carchariae. In addition the known 8-oxo-tryptamine (4) and the mixture of the (E)-6-bromo-2′-demethyl-3′-N-methylaplysinopsin (6) and (Z)-6-bromo-2′-demethyl-3′-N-methylaplysinopsin (7) showed moderate antiplasmodial activity against Plasmodium falciparum with IC50 values of 8.8 and 8.0 µg/mL, respectively.

scholarly journals Salaramides A and B; Two α-Oxoamides Isolated from the Marine Sponge Hippospongia sp. (Porifera, Dictyoceratida)

2010 ◽  
Vol 5 (2) ◽  
pp. 1934578X1000500
Author(s):  
Julia Bensemhoun ◽  
Amira Rudi ◽  
Yoel Kashman ◽  
Emile M. Gaydou ◽  
Jean Vacelet ◽  
...  
Keyword(s):  
Chemical Transformation ◽  
Marine Sponge ◽  
Mass Spectra ◽  
Nmr Spectra ◽  
2D Nmr ◽  
2D Nmr Spectra

Two novel α-oxoamides, salaramide A (1) and its homologue salaramide B (2), were isolated from the Madagascar marine sponge, Hippospongia sp., collected in Salary Bay, north of Tulear. The structures of 1 and 2 were elucidated by interpretation of mass spectra, 1D and 2D NMR spectra, and confirmed by chemical transformation.

scholarly journals Osirisynes G-I, New Long-Chain Highly Oxygenated Polyacetylenes from the Mayotte Marine Sponge Haliclona sp.

Marine Drugs ◽  
2020 ◽  
Vol 18 (7) ◽  
pp. 350 ◽  
Author(s):  
Pierre-Eric Campos ◽  
Gaëtan Herbette ◽  
Christophe Chendo ◽  
Patricia Clerc ◽  
Florent Tintillier ◽  
...  
Keyword(s):  
Marine Sponge ◽  
Active Compound ◽  
Nmr Spectra ◽  
Proteasome Inhibition ◽  
Chemical Study ◽  
2D Nmr ◽  
Sirtuin 1 ◽  
Fyn Kinase ◽  
2D Nmr Spectra ◽  
Long Chain

Chemical study of the CH2Cl2−MeOH (1:1) extract from the sponge Haliclona sp. collected in Mayotte highlighted three new long-chain highly oxygenated polyacetylenes, osirisynes G-I (1–3) together with the known osirisynes A (4), B (5), and E (6). Their structures were elucidated by 1D and 2D NMR spectra and HRESIMS and MS/MS data. All compounds were evaluated on catalase and sirtuin 1 activation and on CDK7, proteasome, Fyn kinase, tyrosinase, and elastase inhibition. Five compounds (1; 3–6) inhibited proteasome kinase and two compounds (5–6) inhibited CDK7 and Fyn kinase. Osirisyne B (5) was the most active compound with IC50 on FYNB kinase, CDK7 kinase, and proteasome inhibition of 18.44 µM, 9.13 µM, and 0.26 µM, respectively.

scholarly journals Erubescensoic Acid, a New Polyketide and a Xanthonopyrone SPF-3059-26 from the Culture of the Marine Sponge-Associated Fungus Penicillium erubescens KUFA 0220 and Antibacterial Activity Evaluation of Some of Its Constituents

Molecules ◽  
2019 ◽  
Vol 24 (1) ◽  
pp. 208 ◽  
Author(s):  
Decha Kumla ◽  
Tida Dethoup ◽  
Luís Gales ◽  
José A. Pereira ◽  
Joana Freitas-Silva ◽  
...  
Keyword(s):  
Antibacterial Activity ◽  
Marine Sponge ◽  
Biofilm Formation ◽  
2D Nmr ◽  
Multidrug Resistant ◽  
Bacterial Biofilm ◽  
X Ray ◽  
Extensive Analysis ◽  
2D Nmr Spectra ◽  
Reference Strains

A new polyketide erubescensoic acid (1), and the previously reported xanthonopyrone, SPF-3059-26 (2), were isolated from the uninvestigated fractions of the ethyl acetate crude extract of the marine sponge-associated fungus Penicillium erubescens KUFA0220. The structures of the new compound, erubescensoic acid (1), and the previously reported SPF-3059-26 (2), were elucidated by extensive analysis of 1D and 2D-NMR spectra as well as HRMS. The absolute configuration of the stereogenic carbon of erubescensoic acid (1) was determined by X-ray analysis. Erubescensoic acid (1) and SPF-3059-26 (2), together with erubescenschromone B (3), penialidin D (4), and 7-hydroxy-6-methoxy-4-oxo-3-[(1E)-3-oxobut-1-en-1-yl]-4H-chromen-5-carboxylic acid (5), recently isolated from this fungus, were assayed for their antibacterial activity against gram-positive and gram-negative reference strains and the multidrug-resistant (MDR) strains from the environment. The capacity of these compounds to interfere with the bacterial biofilm formation and their potential synergism with clinically relevant antibiotics for the MDR strains were also investigated.

scholarly journals Zizaane-Type Sesquiterpenoids and Their Rearranged Derivatives from Agarwood of an Aquilaria Plant

Molecules ◽  
2021 ◽  
Vol 27 (1) ◽  
pp. 198
Author(s):  
Jing-Zhe Yuan ◽  
Yi-Ling Yang ◽  
Wei Li ◽  
Li Yang ◽  
Hao-Fu Dai ◽  
...  
Keyword(s):  
Absolute Configuration ◽  
Ethyl Ether ◽  
Nmr Spectra ◽  
2D Nmr ◽  
Raw264.7 Cells ◽  
No Production ◽  
Ether Extract ◽  
Ic50 Value ◽  
2D Nmr Spectra

Nine new sesquiterpenoids (1–9) were isolated from ethyl ether extract of agarwood originated from Aquilaria sp., including three novel sesquiterpenoids (1–3) derived from zizaane, together with six zizaane-type sesquiterpenoids (4–9). All structures were unambiguously elucidated based on 1D and 2D NMR spectra as well as by HRESIMS data. The absolute configuration of sesquiterpenoids was determined by comparison of the experimental and computed ECD spectra. In vitro anti-inflammatory assessment showed that compound 9 exhibited inhibition of NO production in LPS-stimulated RAW264.7 cells with an IC50 value of 62.22 ± 1.27 μM.

scholarly journals Antioxidant, Cytotoxic, and Acetylcholinesterase Inhibitory Activities of Withanolides from Datura quercifolia

2020 ◽  
Vol 07 (02) ◽  
pp. e68-e72
Author(s):  
Christian Jasso ◽  
Antonio Nieto-Camacho ◽  
MaríaTeresa Ramírez-Apan ◽  
Mahinda Martínez ◽  
Emma Maldonado
Keyword(s):  
Nmr Spectra ◽  
Functional Group ◽  
Antioxidant Activities ◽  
2D Nmr ◽  
Ache Inhibition ◽  
Aerial Parts ◽  
2D Nmr Spectra ◽  
Ic50 Values ◽  
Inhibitory Activities ◽  
Acetylcholinesterase Enzyme

AbstractFive withanolides identified as daturalactone (1) , withanicandrin (2), withanolide B (3), nicandrin B (4), and daturalactone 2 (5) were isolated from the aerial parts (flowers, leaves, and stems) of Datura quercifolia Kunth. Their structures were determined by analysis of the IR, MS, 1D and 2D NMR spectra. All the isolates were evaluated for their cytotoxic and antioxidant activities, as well as for their capacity to inhibit the activity of the acetylcholinesterase enzyme (AChE). As result, the five withanolides showed weak cytotoxic and pro-oxidant activities, however, they displayed a relevant inhibitory activity against AChE, as indicated by the IC50 values ranging from 1.51 to 12.11 µM. The differences in AChE inhibition seem to be related to the functional group at C-12.

scholarly journals Triterpenoids From Kadsura coccinea With Their Anti-inflammatory and Inhibited Proliferation of Rheumatoid Arthritis-Fibroblastoid Synovial Cells Activities

2021 ◽  
Vol 9 ◽  
Author(s):  
Yu-pei Yang ◽  
Yu-qing Jian ◽  
Yong-bei Liu ◽  
Muhammad Ismail ◽  
Qing-ling Xie ◽  
...  
Keyword(s):  
Rheumatoid Arthritis ◽  
Nmr Spectra ◽  
2D Nmr ◽  
Raw 264.7 Macrophages ◽  
Tnf Α ◽  
2D Nmr Spectra ◽  
Kadsura Coccinea ◽  
Lanostane Triterpenoid ◽  
C Nmr

One new 3,4-seco-17,13-friedo-lanostane triterpenoid heilaohuacid A (1), one new 3,4-seco-17,14-friedo-lanostane triterpenoid heilaohuacid B (2), five new 3,4-seco-lanostane triterpenoids heilaohuacids C-D (3–4) and heilaohumethylesters A-C (7–9), one new 3,4-seco-cycloartane triterpenoid heilaohuacid E (5), and one new intact-lanostane triterpenoid heilaohuacid F (6), together with twenty-two known analogues (10–31), were isolated from heilaohu. Their structures were determined using HR-ESI-MS data, 1D and 2D NMR spectra, 13C NMR calculations, and electronic circular dichroism (ECD) calculations. Heilaohuacids A and B (1 and 2) contain a 3,4-seco ring A and unprecedented migration of Me-18 from C-13 to C-17 or C-14 to C-18. This type of lanostane triterpenoid derivatives was rarely reported so far. More importantly, all compounds against inflammatory cytokines IL-6 and TNF-α levels on LPS-induced RAW 264.7 macrophages were evaluated, and compounds 4 and 31 significantly inhibited the release level of IL-6 with IC50 values of 8.15 and 9.86 μM, respectively. Meanwhile, compounds 17, 18, and 31 significantly inhibited proliferation of rheumatoid arthritis-fibroblastoid synovial (RA-FLS) cells in vitro with IC50 values of 7.52, 8.85, and 7.97 μM, respectively.

scholarly journals Chemical Constituents of the Marine Sponge Aaptos aaptos (Schmidt, 1864) and Their Cytotoxic Activity

2021 ◽  
Vol 16 (2) ◽  
pp. 1934578X2199334
Author(s):  
Do Thi Trang ◽  
Bui Huu Tai ◽  
Dan Thuy Hang ◽  
Pham Hai Yen ◽  
Phan Thi Thanh Huong ◽  
...  
Keyword(s):  
Cytotoxic Activity ◽  
Spectral Data ◽  
Absolute Configuration ◽  
Marine Sponge ◽  
Chemical Constituents ◽  
2D Nmr ◽  
Extensive Analysis ◽  
First Time ◽  
Tddft Method ◽  
Mcf 7

Seven compounds (1-7) were isolated from the marine sponge Aaptos aaptos living in the Vietnamese sea. Their structures were determined as 2 hours, 5 H,7 H,9 H-9 S-hydroxy-imidazo[1,5- α]pyridine-1,3-dione (1), 3-([9-methylhexadecyl]oxy)propane-1,2-diol 2, 2,3-dihydro-2,3-dioxoaaptamine (3), indol-3-aldehyde (4), methyl indole-3-carboxylate (5) 4-hydroxy-5-(indole-3-yl)−5-oxo-pentan-2-one (6), and thymidine (7) by extensive analysis of HR-ESI-MS, 1D, and 2D NMR spectral data, as well as by comparison of the spectral data with those reported in the literature. In addition, the absolute configuration of 1 was determined from the experimental ECD spectrum and comparison of this with the theoretical ECD calculations using the TDDFT method. Compounds 1 and 2 were isolated from nature for the first time. Compound 3 induced cytotoxic activity against SK-LU-1, MCF-7, HepG2, and SK-Mel-2 cell lines with IC50 values of 41.27 ± 2.63, 40.70 ± 2.65, 34.31 ± 3.43, and 36.63 ± 1.40 µM, respectively.

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