New nitrogenous sesquiterpenes based on alloaromadendrane and epi-eudesmane skeletons from the marine sponge Axinellacannabina

1987 ◽  
Vol 65 (3) ◽  
pp. 518-522 ◽  
Author(s):  
Patrizia Ciminiello ◽  
Ernesto Fattorusso ◽  
Silvana Magno ◽  
Luciano Mayol
Keyword(s):  
Spectral Data ◽  
Marine Sponge ◽  
Structure Elucidation ◽  
Nmr Spectra ◽  
2D Nmr ◽  
Relative Stereochemistry ◽  
Complete Assignment

Six new nitrogenous sesquiterpenes (1–6), which form two new isocyanide-isothiocyanate-formamide series, have been isolated from the marine sponge Axinellacannabina. The structure elucidation of these compounds is based upon spectral data, including 2D-nmr, and chemical interconversions. The complete assignment of all proton and carbon resonances in nmr spectra of axisonitrile-2 (7), an isonitrile previously isolated from the same source, is also reported, along with its complete relative stereochemistry.

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.

E-Homolupane Derivatives Substituted in Position 17 and 22a. 1H NMR, 13C NMR and IR Spectra

1995 ◽  
Vol 60 (4) ◽  
pp. 619-635 ◽  
Author(s):  
Václav Křeček ◽  
Stanislav Hilgard ◽  
Miloš Buděšínský ◽  
Alois Vystrčil
Keyword(s):  
Nmr Spectra ◽  
2D Nmr ◽  
Coupling Constants ◽  
Side Chain ◽  
Oxidation Reactions ◽  
H Nmr ◽  
Complete Assignment ◽  
Nmr Techniques ◽  
Intramolecular Association ◽  
C Nmr

A series of derivatives with various oxygen functionalities in positions 17,22a or 19,20 was prepared from diene I and olefin XVI by addition and oxidation reactions. The structure of the obtained compounds was confirmed by 1H NMR, 13C NMR and IR spectroscopy. The kind of intramolecular association of the 17α-hydroxy group was studied in connection with modification of the side chain and substitution in position 22a. Complete assignment of the hydrogen signals and most of the coupling constants was accomplished using a combination of 1D and 2D NMR techniques. The 1H and 13C NMR spectra are discussed.

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 Three New Aaptamines from the Marine Sponge Aaptos sp. and Their Proapoptotic Properties

2010 ◽  
Vol 5 (12) ◽  
pp. 1934578X1000501 ◽  
Author(s):  
Larisa K. Shubina ◽  
Tatyana N. Makarieva ◽  
Sergey A. Dyshlovoy ◽  
Sergey N. Fedorov ◽  
Pavel S. Dmitrenok ◽  
...  
Keyword(s):  
Detailed Analysis ◽  
Spectral Data ◽  
Marine Sponge ◽  
2D Nmr ◽  
Human Leukemia ◽  
Mass Spectral Data ◽  
Mass Spectral ◽  
Induced Apoptosis

Three new aaptamine-type alkaloids, 2,3-dihydro-2,3-dioxoaaptamine (1), 6 -( N-morpholinyl)-4,5-dihydro-5-oxo-demethyl(oxy)aaptamine (2) and 3-(methylamino)demethyl(oxy)aaptamine (3), along with known aaptamines were isolated from the sponge Aaptos sp. Their structures were determined on the basis of detailed analysis of their 1D and 2D NMR spectroscopic and mass spectral data. The isolated compounds induced apoptosis in human leukemia THP-1 cells.

scholarly journals Mumunine - A New Carbazole Alkaloid from Murraya koenigii (Linn.) Spreng

2020 ◽  
Vol 12 (4) ◽  
pp. 665-672
Author(s):  
M. Chakraborty
Keyword(s):  
Data Analysis ◽  
Spectral Data ◽  
Structure Elucidation ◽  
2D Nmr ◽  
Rich Source ◽  
Murraya Koenigii ◽  
Spectral Data Analysis ◽  
Carbazole Alkaloids

The plant Murraya koenigii, commonly known as curry leaf tree is a rich source of carbazole alkaloids. A number of monomeric as well as dimeric carbazoles with C13, C18 and C23 skeleton have been isolated from the plant. In my present work, a new carbazole alkaloid, designated as mumunine, was isolated from the bark of Murraya koenigii (Linn) Spreng, along with a known carbazole alkaloid, viz. mahanimbine. The structure of the new alkaloid 1 was elucidated on the basis of 1D and 2D NMR spectral data analysis. In this paper, the isolation and structure elucidation of the new compound will be discussed in detail.

scholarly journals Ferulol and epi-Samarcandin, Two New Sesquiterpene Coumarins from Ferula Sinaica

2007 ◽  
Vol 2 (5) ◽  
pp. 1934578X0700200
Author(s):  
Ahmed A. Ahmed ◽  
Abou El-Hamd H. Mohamed ◽  
Mohamed H. Abd El-Razek ◽  
Mohamed-Elamir F. Hegazy
Keyword(s):  
Spectral Data ◽  
Structure Elucidation ◽  
Methylene Chloride ◽  
2D Nmr ◽  
Carbon Skeleton ◽  
Methylene Chloride Extract

Re-investigation of the methylene chloride extract of the root of Ferula sinaica gave a sesquiterpene coumarin with a rare carbon skeleton and 3′,9′-di- epi-samarcandin. The structure elucidation was determined by MS; 1H- and 13C- 1D and 2D NMR spectral data.

scholarly journals A New Antiplasmodial Compound from the Papuan Marine Sponge Xestospongia sp.

2018 ◽  
Vol 4 (1) ◽  
pp. 1-6 ◽  
Author(s):  
Murtihapsari Murtihapsari ◽  
Amir M Suruwaky ◽  
Kadarusman Kadarusman ◽  
Dikdik Kurnia ◽  
Tati Herlina ◽  
...  
Keyword(s):  
Plasmodium Falciparum ◽  
Marine Sponge ◽  
Structure Elucidation ◽  
2D Nmr ◽  
Antiplasmodial Activity ◽  
Nmr Analysis ◽  
Ic50 Value

A new antiplasmodial compound, 2-(3H-diazirine-3-yl)benzaldehyde (1), has been isolated from the Papuan marine sponge Xestospongia sp. The structure elucidation of compound 1 was determined by spectroscopic evidences including UV, IR, MS, 1D and 2D-NMR analysis. Compound 1 showed moderate antiplasmodial activity against Plasmodium falciparum with IC50 value of 1.08 x 10-6 mM. DOI:http://dx.doi.org/10.15408/jkv.v4i1.6735

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