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

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.

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

Marine Drugs ◽

10.3390/md18070350 ◽

2020 ◽

Vol 18 (7) ◽

pp. 350 ◽

Cited By ~ 1

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.

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

Natural Product Communications ◽

10.1177/1934578x1000500218 ◽

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.

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A Green Synthesis and a Chemical Study of the Coumarin, 1-(2-Hydroxy- 2-methyl-2H-chromen-3yl)ethanone

Letters in Organic Chemistry ◽

10.2174/1570178615666180627103639 ◽

2019 ◽

Vol 16 (2) ◽

pp. 128-133

Author(s):

Emerson Teixeira da Silva ◽

Ligia Souza da Silveira Pinto ◽

Solange Maria Silva Veloso Wardell ◽

James Lewis Wardell ◽

Marcus Vinícius Nora de Souza

Keyword(s):

Green Synthesis ◽

Nmr Spectra ◽

Chemical Study ◽

2D Nmr ◽

Mechanistic Study ◽

X Ray ◽

X Ray Crystallography ◽

General Importance ◽

2D Nmr Spectra ◽

Coumarin 1

Coumarins are a class of natural and synthetic products with a wide variety of applications in different fields. Due to the general importance of coumarins, the objective of this work is to further develop the chemistry of 1-(2-hydroxy-2-methyl-2H-chromen-3yl)ethanone, 1, a potentially useful and versatile coumarin but an under-reported compound in the literature. This work describes a green preparation of 1 in the absence of solvents and acids, thereby eliminating byproducts, normally obtained in classical procedures, and a mechanistic study of the reactions of 1 with nucleophiles. In addition, we report the characterisation of 1-(2-ethoxy-2-methyl-2H-chromen-3-yl)ethanone 2, via X-ray crystallography and 2D NMR spectra.

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Stereochemical determination of dictyostatin, a novel microtubule-stabilising macrolide from the marine sponge Corallistidae sp.Electronic supplementary information (ESI) available: copies of 1D and 2D NMR spectra, tables of spectral data and calculated torsion angles. See http://www.rsc.org/suppdata/cc/b3/b316390c/

Chemical Communications ◽

10.1039/b316390c ◽

2004 ◽

pp. 632 ◽

Cited By ~ 57

Author(s):

Ian Paterson ◽

Robert Britton ◽

Oscar Delgado ◽

Amy E. Wright

Keyword(s):

Spectral Data ◽

Marine Sponge ◽

Nmr Spectra ◽

2D Nmr ◽

Supplementary Information ◽

Torsion Angles ◽

2D Nmr Spectra

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New 3-Hydroxyquinaldic Acid Derivatives from Cultures of the Marine Derived Actinomycete Streptomyces cyaneofuscatus M-157

Marine Drugs ◽

10.3390/md16100371 ◽

2018 ◽

Vol 16 (10) ◽

pp. 371 ◽

Cited By ~ 11

Author(s):

Francisco Ortiz-López ◽

Elsa Alcalde ◽

Aida Sarmiento-Vizcaíno ◽

Caridad Díaz ◽

Bastien Cautain ◽

...

Keyword(s):

Nmr Spectra ◽

2D Nmr ◽

Two Dimensional ◽

Amino Acid Residues ◽

Trace Level ◽

One Dimensional ◽

2D Nmr Spectra ◽

Ic50 Values ◽

New Compounds ◽

Tof Ms

Fractionation of the bioactive extract of a culture of the marine derived actinomycete Streptomyces cyaneofuscatus M-157 led to the isolation of the known 3-hydroxyquinaldic acid (4), its amide (5) and three new derivatives (1–3) containing different amino acid residues. The structures of the new molecules (1–3), including their absolute configuration, were determined by the analysis of their ESI-TOF MS and one-dimensional (1D) and two-dimensional (2D) NMR spectra and advanced Marfey’s analysis of their hydrolyzation products. Compound 3 spontaneously dimerized in solution to give the disulfide derivative 6. Unfortunately, none of the new compounds isolated confirmed the antimicrobial activity found in the bacterial extract, perhaps indicating that such antibacterial activity might be due to presence in the extract at the trace level of larger bioactive 3-hydroxyquinaldic acid derivatives from which compounds 1–3 are biosynthetic precursors. Cytotoxicity tests confirmed the moderate and weak IC50 values of 15.6 and 51.5 µM for compounds 5 and 1, respectively.

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A New Megastigmane Glucoside and Other Constituents from Desmodium gangeticum

Journal of Chemistry ◽

10.1155/2020/7416973 ◽

2020 ◽

Vol 2020 ◽

pp. 1-4

Author(s):

Hau Viet Dang ◽

Giang Hoang Do ◽

Phuong Thi Ngo ◽

Tien Dat Nguyen ◽

Ha Minh Le

Keyword(s):

Nmr Spectra ◽

Aerial Part ◽

2D Nmr ◽

Inhibitory Effect ◽

Methyl Benzoate ◽

Raw264.7 Cells ◽

No Production ◽

2D Nmr Spectra ◽

Ic50 Values ◽

Megastigmane Glucoside

A new megastigmane glycoside, gangeticoside (1), and three known compounds leonuriside A (2), methyl benzoate 2-O-β-D-glucopyranoside (3), and tortoside A (4) were isolated from the aerial part of Desmodium gangeticum. Their structures were determined by 1D and 2D NMR spectra. The isolated compounds were evaluated for their inhibitory effect on NO production in LPS-stimulated RAW264.7 cells. Among them, compounds 1, 2, and 3 exhibited strong effect with the IC50 values of 22.3, 15.6, 7.3 μM, respectively.

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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 ◽

10.3390/md17060379 ◽

2019 ◽

Vol 17 (6) ◽

pp. 379 ◽

Cited By ~ 4

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.

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

Planta Medica International Open ◽

10.1055/a-1156-4229 ◽

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.

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