scholarly journals New Aromatic Bisabolane Derivatives with Lipid-Reducing Activity from the Marine Sponge Myrmekioderma sp.

Marine Drugs ◽  
2019 ◽  
Vol 17 (6) ◽  
pp. 375 ◽  
Author(s):  
Margarida Costa ◽  
Laura Coello ◽  
Ralph Urbatzka ◽  
Marta Pérez ◽  
Margret Thorsteinsdottir
Keyword(s):  
Spectral Analysis ◽  
Spectral Data ◽  
Marine Sponge ◽  
Metabolic Disorders ◽  
Fat Metabolism ◽  
Nile Red ◽  
2D Nmr ◽  
Reducing Activity ◽  
New Compounds ◽  
Related Compounds

The previously reported 1-(2,4-dihydroxy-5-methylphenyl)ethan-1-one (1), (1’Z)-2-(1’,5’-dimethylhexa-1’,4’-dieny1)-5-methylbenzene-1,4-diol (2), and 1,8-epoxy-1(6),2,4,7,10-bisaborapentaen-4-ol (5) together with four new structures of aromatic bisabolane-related compounds (3, 4, 6, 7) were isolated from the marine sponge Myrmekioderma sp. Compounds 1, 2, and 5 were identified based on spectral data available in the literature. The structures of the four new compounds were experimentally established by 1D and 2D-NMR and (−)-HRESIMS spectral analysis. Cytotoxic and lipid-reducing activities of the isolated compounds were evaluated. None of the isolated compounds were active against the tested cancer cell lines; however, lipid-reducing activity was found for compounds 2–5 and 7 in the zebrafish Nile red fat metabolism assay. This class of compounds should be further explored for their suitability as possible agents for the treatment of lipid metabolic disorders and obesity.

scholarly journals Flavonoid Glycosides and their p-Coumaroyl Esters from Campylospermum calanthum Leaves

2012 ◽  
Vol 67 (5-6) ◽  
pp. 233-243 ◽  
Author(s):  
Savio S. Elo Manga ◽  
Anastasie E. Tih ◽  
Bintou Abderamane ◽  
Raphael T. Ghogomu ◽  
Alain Blond ◽  
...  
Keyword(s):  
Spectral Data ◽  
Spectroscopic Analysis ◽  
Methanol Extract ◽  
2D Nmr ◽  
Flavonoid Glycosides ◽  
Flavonoid Aglycones ◽  
New Compounds ◽  
Related Compounds ◽  
Chemical Evidence

Six new compounds, comprising three flavonoid glycosides and their respective coumaroyl esters, have been isolated and characterized from the methanol extract of the leaves of Campylospermum calanthum, along with three known flavonoid aglycones, 7-O-methyl apigenin (1), 7-O-methyl luteolin (2), and 7-O-methyl quercetin (3). Their structures were elucidated based on chemical evidence as well as spectroscopic analysis including 1D and 2D NMR (1H-1H COSY, HSQC, HMBC, and NOESY) spectroscopy and by comparing their spectral data with those reported for related compounds

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.

scholarly journals Conjugated Polyene Ketones From the Marine Sponge Clathria (Thalysias) Reinwardti (Vosmaer, 1880) and Their Cytotoxic Activity

2021 ◽  
Vol 16 (9) ◽  
pp. 1934578X2110437
Author(s):  
Bui H. Tai ◽  
Dan T. Hang ◽  
Do T. Trang ◽  
Pham H. Yen ◽  
Phan T. T. Huong ◽  
...  
Keyword(s):  
Cytotoxic Activity ◽  
Marine Sponge ◽  
Human Cancer ◽  
2D Nmr ◽  
Ionization Mass ◽  
Hep G2 ◽  
Human Cancer Cells ◽  
Resolution Electron ◽  
New Compounds ◽  
First Time

Five conjugated polyene ketones (1-5) were isolated from the methanol extract of the marine sponge Clathria ( Thalysias) reinwardti (Vosmaer, 1880) living in the coastal waters of Vietnam. Their structures were determined to be 8-(2′,3′,4′-trimethylphenyl)-6-methyl-oct-3( E),5( E),7( E)-trien-2-one (1), 13-apoastaxanthinone (2), 9-apoastaxanthinone (3), 2,3-dehydro-4-oxo- β-ionone (4), and 4-(2′,3′,4′-trimethylphenyl)-but-3( E)-en-2-one (5), by extensive analysis of high-resolution electron spray ionization mass spectrum (HR-ESI-MS), one-dimensional, and two-dimensional (2D) nuclear magnetic resonance (NMR) spectra, as well as by comparison of the spectral data with those reported in the literature. Compound 1 was new, compounds 2 to 4 were isolated from nature for the first time, and the chemical structure as well as the NMR assignments, of 5 were indicated by 2D NMR for the first time. Additionally, compound 5 exhibited cytotoxic activity against the human cancer cells SK-LU-1, SK-Mel-2, MCF-7, and Hep-G2 with half-minimal inhibitory concentration (IC50) values of 15.12 ± 3.43, 17.41 ± 2.83, 33.12 ± 3.39, and 34.38 ± 3.52 µM, respectively, but displayed only a weak cytotoxic effect on the normal HEK-239A cells (IC50 64.67 ± 3.67 µM). Compound 5 also significantly increased Caspase-3 activity in SK-LU-1 cells at concentrations of 10, 15, and 20 µM.

scholarly journals Cyclic Peroxides from a Two-Sponge Association of Plakortis communis-Agelas mauritiana

2013 ◽  
Vol 8 (6) ◽  
pp. 1934578X1300800
Author(s):  
Pinus Jumaryatno ◽  
Lynette K. Lambert ◽  
John N. A. Hooper ◽  
Joanne T. Blanchfield ◽  
Mary J. Garson
Keyword(s):  
2D Nmr ◽  
Side Chain ◽  
Relative Configuration ◽  
Carboxylic Acid Groups ◽  
Rp Hplc ◽  
Chemical Shift Data ◽  
New Compounds ◽  
Cyclic Peroxide ◽  
Related Compounds ◽  
Shift Data

A cyclic peroxide 1 with an unusual phenethenyl side chain, together with the known peroxide 2 with a C4-sidechain have been isolated from a two-sponge association of Plakortis communis – Agelas mauritiana (Carter, 1883) collected near Mooloolaba, South-East Queensland, Australia. Metabolite purification was complicated by the presence of the free carboxylic acid groups in 1 and 2; therefore, diazomethane treatment was undertaken to afford methyl ester 3. Following RP-HPLC purification, the ring-opened analogues 4 and 5 were also obtained. The structures of the new compounds were elucidated on the basis of their 1D and 2D NMR and MS data, and by comparison with literature data. The relative configuration of the isolated peroxides was determined by the interpretation of JH-H values and comparison of the 13C chemical shift data with literature data for related compounds. The bromopyrrole alkaloid longamide (6) was also isolated.

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 New ent–Kaurane type Diterpene Glycoside, Pulicaroside-B, from Pulicaria Undulata L

2008 ◽  
Vol 3 (2) ◽  
pp. 1934578X0800300 ◽  
Author(s):  
Nasir Rasool ◽  
Viqar Uddin Ahmad ◽  
Naseem Shahzada ◽  
Muhammad A. Rashida ◽  
Aman Ullah ◽  
...  
Keyword(s):  
Spectral Data ◽  
Plant Extract ◽  
Soluble Fraction ◽  
2D Nmr ◽  
Spectroscopic Techniques ◽  
Spectral Evidence ◽  
Whole Plant ◽  
Derivatives Of ◽  
Related Compounds

Investigation of the n-butanol-soluble fraction of the whole plant extract of Pulicaria undulata yielded a new ent–kaurane type diterpene glycoside, pulicaroside-B (1), together with three known compounds, paniculoside-IV (2), roseoside (3), and corchoionol C (4). Compounds 3 and 4 are derivatives of α-ionol. The structures of the new and known compounds were elucidated by 1D- and 2D-NMR spectroscopic techniques, along with other spectral evidence, and by comparison of the spectral data with those of closely related compounds.

scholarly journals New Acyclic Cytotoxic Jasplakinolide Derivative from the Marine Sponge Jaspis splendens

Marine Drugs ◽  
2019 ◽  
Vol 17 (2) ◽  
pp. 100
Author(s):  
Sherif Ebada ◽  
Werner Müller ◽  
Wenhan Lin ◽  
Peter Proksch
Keyword(s):  
Spectral Analysis ◽  
Marine Sponge ◽  
Parent Compound ◽  
2D Nmr ◽  
Chemical Structures ◽  
Nmr Data ◽  
Ic50 Values ◽  
Nanomolar Range ◽  
Mouse Lymphoma

A new acylic jasplakinolide congener (2), another acyclic derivative requiring revision (4), together with two jasplakinolide derivatives including the parent compound jasplakinolide (1) were isolated from the Indonesian marine sponge Jaspis splendens. The chemical structures of the new and known compounds were unambiguously elucidated based on HRESIMS and exhaustive 1D and 2D NMR spectral analysis as well as a comparison of their NMR data with those of jasplakinolide (1). The isolated jasplakinolides inhibited the growth of mouse lymphoma (L5178Y) cells in vitro with IC50 values in the low micromolar to nanomolar range.

Avarol and Related Compounds from the New Zealand Marine Sponge Dysidea sp.

1997 ◽  
Vol 50 (4) ◽  
pp. 341 ◽  
Author(s):  
Michael Stewart ◽  
Patrick M. Fell ◽  
John W. Blunt ◽  
Murray H. G. Munro
Keyword(s):  
New Zealand ◽  
Marine Sponge ◽  
Spectroscopic Methods ◽  
New Compounds ◽  
Related Compounds

Bioassay and t.l.c. guided separation of extracts from the New Zealand marine sponge Dysidea sp. has led to the isolation of avarol (1), six other known compounds (2)–(4) and (6)–(8), and seven new compounds (9)–(15). All but one of these, compound (8), are related to avarol. The structures of all the compounds have been established by spectroscopic methods.

New lupan-type triterpenoids

2016 ◽  
Vol 71 (11-12) ◽  
pp. 381-386 ◽  
Author(s):  
Pierre Mkounga ◽  
Hermine L.D. Maza ◽  
Blandine M.W. Ouahouo ◽  
Lydie N. Tyon ◽  
Hayato Ishikawa ◽  
...  
Keyword(s):  
Spectral Data ◽  
Manihot Esculenta ◽  
2D Nmr ◽  
Antimicrobial Activities ◽  
Wide Range ◽  
New Compounds ◽  
Chemical Evidence

Abstract Three new lupan-type triterpernoid derivatives, namely globimetulin A (1), B (2) and C (3), were isolated from the shoot of Globimetula dinklagei (Loranthaceae), a hemiparasitic plant growing on Manihot esculenta, along with five known compounds: friedelin (4), friedelan-3-ol (5), 28-hydroxyfriedelin (6), 4-hydroxy-3,5-dimethoxybenzoic acid (7) and (1R,5S,7S)-7-[2-(4-hydroxyphenyl)ethyl]-2,6-dioxabicyclo[3.3.1]nonan-3-one (8). The structures of the new compounds were elucidated by detailed analyses of their MS, IR, 1D and 2D NMR spectral data and chemical evidence. Some of these compounds were evaluated in vitro for their antimicrobial activities against a wide range of microorganisms, but none of them exhibited noticeable activity.

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