Three New Spongian Diterpenes from the Marine Sponge Dendrilla rosea

2019 ◽  
Vol 72 (12) ◽  
pp. 964
Author(s):  
Joshua B. Hayton ◽  
Gary D. Grant ◽  
Anthony R. Carroll
Keyword(s):  
Staphylococcus Aureus ◽  
Marine Sponge ◽  
2D Nmr ◽  
Nmr Data ◽  
New Metabolites

Three new diterpenes, aplyroseols 20–22 (2–4), were isolated from two specimens of the Australian marine sponge Dendrilla rosea. The structures and relative configurations of the new metabolites were elucidated from analysis of 2D NMR data. The compounds were screened for activity against Staphylococcus aureus, but were inactive at 64µgmL−1.

scholarly journals Isolation and Structure Elucidation of Secondary Metabolites from a Microcystis sp. Bloom Material Collected in Southern Israel

2018 ◽  
Vol 13 (10) ◽  
pp. 1934578X1801301
Author(s):  
Ohad Hasin ◽  
Shmuel Carmeli
Keyword(s):  
Serine Proteases ◽  
Structure Elucidation ◽  
2D Nmr ◽  
Coupling Constants ◽  
Chiral Hplc ◽  
Mass Spectrometric Data ◽  
Spectrometric Data ◽  
Nmr Data ◽  
Hydrophilic Extract ◽  
New Metabolites

The hydrophilic extract of Microcystis sp. bloom material collected from Bror Hayil Reservoir in southern Israel afforded four new metabolites, (2 S,3 S)-3-hydeoxy-1,4-diphenylbutan-2-yl-acetate, aeruginosins BH604, BH462A and BH462B, and two known metabolites cyanopeptolins S and SS. The planar structure of 1–4 was established by analyses of their 1D and 2D NMR data and mass spectrometric data. The absolute configurations of the chiral centers of 1 were established by Mosher method and analysis of the coupling constants between H-2 and H-3, and those of 2–4 by Merfay's method and advanced Merfay's method and chiral HPLC. The compounds do not inhibit the serine proteases trypsin and thrombin.

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.

scholarly journals A New Iridoid from the Aerial Parts of Hedyotis Pilulifera

2016 ◽  
Vol 11 (3) ◽  
pp. 1934578X1601100
Author(s):  
Nguyen Thi Hoai ◽  
Ho Viet Duc ◽  
Nguyen Dinh Quynh Phu ◽  
Takeshi Kodama ◽  
Takuya Ito ◽  
...  
Keyword(s):  
Staphylococcus Aureus ◽  
Antibacterial Activity ◽  
Iridoid Glycosides ◽  
Bacterial Species ◽  
2D Nmr ◽  
Spectral Analyses ◽  
Esi Ms ◽  
Aerial Parts ◽  
Nmr Data ◽  
Mic Value

A new iridoid, 10-acetylborreriagenin (1), and five known iridoid glycosides (2–6), were isolated from the aerial parts of Hedyotis pilulifera. Their structures were elucidated by spectral analyses, including 1D- and 2D-NMR, and HR-ESI-MS, and comparisons with the NMR data reported in the literature. The isolated compounds 1–6 were tested against six bacterial species. Among them, 10-acetylborreriagenin (1) showed antibacterial activity against Staphylococcus aureus, with an MIC value of 100 μg/mL.

scholarly journals New Butenolide and Pentenolide from Dysidea cinerea

2013 ◽  
Vol 8 (12) ◽  
pp. 1934578X1300801
Author(s):  
Phan Van Kiem ◽  
Nguyen Xuan Nhiem ◽  
Ngo Van Quang ◽  
Chau Van Minh ◽  
Nguyen Hoai Nam ◽  
...  
Keyword(s):  
Nmr Spectroscopy ◽  
Marine Sponge ◽  
2D Nmr ◽  
Cd Spectra ◽  
2D Nmr Spectroscopy ◽  
Chemical Methods ◽  
Nmr Data

Two new butenolide and pentenolide derivatives, dysideolides A-B, were isolated from the marine sponge Dysidea cinerea. Their structures were determined by the combination of spectroscopic and chemical methods, including 1D- and 2D-NMR spectroscopy, and CD spectra, as well as by comparing with the NMR data reported in the literature.

scholarly journals Cytotoxic Bromoindole Derivatives and Terpenes from the Philippine Marine Sponge Smenospongia sp.

2002 ◽  
Vol 57 (9-10) ◽  
pp. 914-922 ◽  
Author(s):  
Deniz Tasdemir ◽  
Timothy S. Bugni ◽  
Gina C. Mangalindan ◽  
Gisela P. Concepción ◽  
Mary Kay Harper ◽  
...  
Keyword(s):  
Marine Sponge ◽  
Human Colon ◽  
2D Nmr ◽  
Tumor Cell Lines ◽  
Cytotoxic Potential ◽  
Colon Tumor Cell ◽  
Hct 116 ◽  
First Time ◽  
Detailed Chemical ◽  
New Metabolites

A detailed chemical analysis of a Philippine marine sponge Smenospongia sp. has been performed. This study yielded four new metabolites, 5-bromo-l-tryptophan (1), 5-bromoabrine (2), 5,6-dibromoabrine (3) and 5-bromoindole-3-acetic acid (4). The pyrroloiminoquinone alkaloid, makaluvamine O (5) as well as 5,6-dibromotryptamine (6), aureol (7) and furospinulosin 1 (8) were also isolated. Although 1 and 4 have been synthesized previously, this is the first report on the isolation of these compounds from a natural source. The furanosesterterpene furospinulosin 1 (8) was obtained for the first time from the genus Smenospongia. The structures of all compounds were established by spectroscopic methods (UV, IR, 1D and 2D NMR, MS, [α]ᴅ). The cytotoxic potential of 1−8 was evaluated in a panel of isogenic HCT-116 human colon tumor cell lines.

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.

Cytotoxic effects of three new metabolites from Red Sea marine sponge, Petrosia sp.

2014 ◽  
Vol 37 (3) ◽  
pp. 928-935 ◽  
Author(s):  
Ahmed Abdel-Lateff ◽  
Walied M. Alarif ◽  
Hany Z. Asfour ◽  
Seif-Eldin N. Ayyad ◽  
Alaa Khedr ◽  
...  
Keyword(s):  
Red Sea ◽  
Marine Sponge ◽  
Cytotoxic Effects ◽  
New Metabolites

scholarly journals New 9α-Hydroxy-5α,6α-epoxysterols from the Vietnamese Marine Sponge Ircinia echinata

Marine Drugs ◽  
2018 ◽  
Vol 16 (11) ◽  
pp. 424 ◽  
Author(s):  
Thi Trinh ◽  
Bich Truong ◽  
Arlette Longeon ◽  
Thi Doan ◽  
Alexandre Deville ◽  
...  
Keyword(s):  
Marine Sponge ◽  
Breast Cancer Cells ◽  
Mass Spectra ◽  
Human Cancer ◽  
Selective Inhibition ◽  
2D Nmr ◽  
Human Breast ◽  
Hep G2 ◽  
Human Cancer Cell Lines ◽  
Mcf 7

Chemical investigation of the methanol extract of the Vietnamese marine sponge Ircinia echinata led to the isolation of six new 9α-hydroxy-5α,6α-epoxysterols: 5α,6α-epoxycholesta-7,22(E)-dien-3β,9α-diol (1), 5α,6α-epoxycholesta-7,24(28)-dien-3β,9α-diol (2), (24R)-5α,6α-epoxy-24-ethyl-cholesta-7-en-3β,9α-diol (3), 5α,6α-epoxycholesta-7-en-3β,9α-diol (4), (24S)-5α,6α-epoxyergosta-7,22-dien-3β,9α-diol (5), and (24R)-5α,6α-epoxy-24-methyl-cholesta-7-en-3β,9α-diol (6) along with the known 5α-6α-epoxysterols: 5α,6α-epoxystigmasta-7-en-3β-ol (7), 5α,6α-epoxystigmasta-7,22-dien-3β-ol (8), and 5α,6α-epoxyergosta-7-en-3β-ol (9). Their structures and their configurations were established on the basis of high resolution mass spectra and extensive 1D and 2D NMR spectroscopic data and by comparison with the literature. Their cytotoxic activity, evaluated against three human cancer cell lines, MCF-7, Hep-G2 and LU-1, revealed that only compounds 3 and 4 exhibited significant antiproliferative activity and compound 3 showed a selective inhibition towards the MCF-7 human breast cancer cells.

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.

Solution behavior and complete proton and carbon-13 NMR assignments of the coenzyme B12 derivative (5'-deoxyadenosyl)cobinamide using modern 2D NMR experiments, including 600 MHz proton NMR data

1989 ◽  
Vol 111 (4) ◽  
pp. 1484-1491 ◽  
Author(s):  
Thomas G. Pagano ◽  
Paulos G. Yohannes ◽  
Benjamin P. Hay ◽  
Jerry R. Scott ◽  
Richard G. Finke ◽  
...  
Keyword(s):  
Nmr Assignments ◽  
Proton Nmr ◽  
2D Nmr ◽  
Coenzyme B12 ◽  
Solution Behavior ◽  
Nmr Data
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