scholarly journals A New Trinor-guaiane Sesquiterpene from an Indonesian Soft Coral Anthelia sp

2015 ◽  
Vol 10 (11) ◽  
pp. 1934578X1501001 ◽  
Author(s):  
Novriyandi Hanif ◽  
Anggia Murni ◽  
Marie Yamauchi ◽  
Masahiro Higashi ◽  
Junichi Tanaka
Keyword(s):  
Soft Coral ◽  
Optical Rotation ◽  
2D Nmr ◽  
Planar Structure ◽  
Nmr Data ◽  
Relative Stereochemistry ◽  
Absolute Stereochemistry

A new trinor-guaiane sesquiterpene has been isolated from an Indonesian soft coral Anthelia sp. The planar structure, possessing an octahydroazulene skeleton, and relative stereochemistry were established by analyzing 1D and 2D NMR data, including NOE experiments. Its absolute stereochemistry was elucidated to be 1 S, 4 S, 7 R, and 10 R by comparing observed and calculated optical rotation values. The new compound showed weak cytotoxicity against NBT-T2 cells.

scholarly journals Anti-Neuroinflammatory Agent, Restricticin B, from the Marine-Derived Fungus Penicillium janthinellum and Its Inhibitory Activity on the NO Production in BV-2 Microglia Cells

Marine Drugs ◽  
2020 ◽  
Vol 18 (9) ◽  
pp. 465
Author(s):  
Byeoung-Kyu Choi ◽  
Song-Hee Jo ◽  
Dong-Kug Choi ◽  
Phan Thi Hoai Trinh ◽  
Hwa-Sun Lee ◽  
...  
Keyword(s):  
Inflammatory Mediators ◽  
Inhibitory Activity ◽  
Optical Rotation ◽  
2D Nmr ◽  
Planar Structure ◽  
No Production ◽  
Spectroscopy Data ◽  
Penicillium Janthinellum ◽  
Etoac Extract ◽  
Nmr Data

A new compound containing a triene, a tetrahydropyran ring and glycine ester functionalities, restricticin B (1), together with four known compounds (2–5) were obtained from the EtOAc extract of the marine-derived fungus Penicillium janthinellum. The planar structure of 1 was determined by detailed analyses of MS, 1D and 2D NMR data. The relative and absolute configurations of 1 were established via the analyses of NOESY spectroscopy data, the comparison of optical rotation values with those of reported restricticin derivatives and electronic circular dichroism (ECD). All the compounds were screened for their anti-neuroinflammatory effects in lipopolysaccharide (LPS)-induced BV-2 microglia cells. Restricticin B (1) and N-acetyl restricticin (2) exhibited anti-neuroinflammatory effects by suppressing the production of pro-inflammatory mediators in activated microglial cells.

scholarly journals Restricticin B from the Marine Fungus Penicillium janthinellum and Its Inhibitory Activity on the NO Production in BV-2 Microglia Cells

2020 ◽  
Author(s):  
Byeonung-Kyu Choi ◽  
Shin-Young Park ◽  
Song-Hee Jo ◽  
Dong-Kug Choi ◽  
Phan Thi Hoai Trinh ◽  
...  
Keyword(s):  
Inhibitory Activity ◽  
Optical Rotation ◽  
2D Nmr ◽  
Marine Fungus ◽  
No Production ◽  
Spectroscopy Data ◽  
Penicillium Janthinellum ◽  
Etoac Extract ◽  
Data Comparison ◽  
Nmr Data

A new compound containing a triene, a tetrahydropyran ring and glycine ester functionalities, restricticin B (1), together with four known compounds (2-5) were obtained from the EtOAc extract of the marine fungus Penicillium janthinellum. The planar structure of 1 was determined by detailed analyses of MS, 1D and 2D NMR data. The relative and absolute configurations of 1 were established via analyses of NOESY spectroscopy data, comparison of optical rotation values with those of restricticin derivatives reported and electronic circular dichroism (ECD). All the compounds were screened for their anti-neuroinflammatory effects in lipopolysaccharide (LPS)-induced BV-2 microglia cells. Restricticin B (1) and N-acetyl restricticin (2) exhibited anti-neuroinflammatory effects by suppressing the production of pro-inflammatory mediators in activated microglial cells.

scholarly journals A NEW CYTOTOXIC DOLABELLANE FROM THE INDONESIAN SOFT CORAL Anthelia sp.

2013 ◽  
Vol 13 (3) ◽  
pp. 216-220 ◽  
Author(s):  
Anggia Murni ◽  
Novriyandi Hanif ◽  
Junichi Tanaka
Keyword(s):  
Mass Spectrometry ◽  
Drug Development ◽  
Ethyl Acetate ◽  
Spectroscopic Data ◽  
Soft Coral ◽  
Ethyl Acetate Extract ◽  
2D Nmr ◽  
Cancer Drug ◽  
Nmr Data ◽  
Anti Cancer

One new dolabellane (1) and two known diterpenoids stolonidiol (2) and clavinflol B (3) have been isolated from the ethyl acetate extract of the Indonesian soft coral Anthelia sp. A new compound 1 exhibited a moderate cytotoxicity against NBT-T2 cells at 10 µg/mL, while known compounds 2 and 3 showed cytotoxicity at 1 and 0.5 µg/mL, respectively. Structure of the new compound 1 was elucidated by interpretation of NMR spectroscopic data (1D and 2D NMR data) and mass spectrometry (ESIMS data) as well as comparison with those of related ones. This finding should be useful for anti cancer drug development of the promising dolabellane-types compound.

scholarly journals Additional New Tetracyclic Tetraterpenoid: Methyl Tortuoate D from Soft Coral Sarcophyton tortuosum

2009 ◽  
Vol 4 (9) ◽  
pp. 1934578X0900400 ◽  
Author(s):  
Wen-Jian Lan ◽  
Shou-Liang Wang ◽  
Hou-Jin Li
Keyword(s):  
Mass Spectrometry ◽  
South China Sea ◽  
Electrospray Ionization ◽  
South China ◽  
Soft Coral ◽  
2D Nmr ◽  
Ionization Mass ◽  
Spectroscopic Techniques ◽  
Direct Infusion ◽  
Relative Stereochemistry

Under the guidance of chemical prescreening by direct infusion electrospray ionization mass spectrometry (DI ESI-MS), a new tetracyclic tetraterpenoid, methyl tortuoate D (1) was isolated from the soft coral Sarcophyton tortuosum collected from the South China Sea. Its structure and relative stereochemistry were established by MS, and 1D- and 2D-NMR spectroscopic techniques.

Studies of Australian Soft Corals .XXXVII. The Structure Determination of 2 Cembranolide Diterpenes From Soft Corals of the Genus Efflatounaria (Coelenterata, Octocorallia, Alcyonacea)

1986 ◽  
Vol 39 (1) ◽  
pp. 123 ◽  
Author(s):  
BF Bowden ◽  
JC Coll ◽  
LM Engelhardt ◽  
GV Meehan ◽  
GG Pegg ◽  
...  
Keyword(s):  
Structure Determination ◽  
Soft Coral ◽  
Soft Corals ◽  
X Ray ◽  
X Ray Crystallography ◽  
Coral Genus ◽  
Relative Stereochemistry ◽  
Chemical Correlation ◽  
Absolute Stereochemistry

Two isomeric 7,8-epoxycembra-3,11,15-trien-16,2-olides have been isolated from different species of the soft coral genus Efflatounaria. The structure of each was deduced spectroscopically , and the relative stereochemistry of one was determined by X-ray crystallography. The absolute stereochemistry of each cembranolide was obtained by chemical correlation with known compounds.

Bioactive macrolides and polyketides from marine dinoflagellates

2003 ◽  
Vol 75 (2-3) ◽  
pp. 337-342 ◽  
Author(s):  
J. Kobayashi ◽  
K. Shimbo ◽  
Takaaki Kubota ◽  
M. Tsuda
Keyword(s):  
2D Nmr ◽  
X Ray Diffraction ◽  
Marine Dinoflagellate ◽  
Feeding Experiments ◽  
Nmr Data ◽  
Structure Activity ◽  
Marine Dinoflagellates ◽  
Relationship Of ◽  
Absolute Stereochemistry ◽  
C Nmr

Absolute stereochemistry of amphidinolides G and H, potent cytotoxic 27- and 26-membered macrolides, respectively, isolated from a marine dinoflagellate Amphidinium sp., was determined by X-ray diffraction analysis, synthesis of a degradation product, and chemical interconversion. Six new macrolides, amphidinolides H2~H5, G2, G3, and W, have been isolated from a marine dinoflagellate Amphidinium sp. (strain Y-42), and the structures were elucidated by 2D NMR data and chemical means. The structure-activity relationship of amphidinolide H-type macrolides for cytotoxicity was examined. The biosynthetic origins of amphidinolides B, C, H, J, T1, and W were investigated on the basis of 13C NMR data of 13C-enriched samples obtained by feeding experiments with [1-13C], [2-13C], and [1,2-13C2] sodium acetates in cultures of the dinoflagellates. Five novel long-chain polyhydroxyl compounds, colopsinols A~E, were obtained from the Amphidinium sp. (strain Y-5).

scholarly journals Synthesis of Cyclobutane Analogue 4: Preparation of Purine and Pyrimidine Carbocyclic Nucleoside Derivatives

Molecules ◽  
2019 ◽  
Vol 24 (18) ◽  
pp. 3235 ◽  
Author(s):  
Noha Hasaneen ◽  
Abdelaziz Ebead ◽  
Muhammad Murtaza Hassan ◽  
Hanan Afifi ◽  
Howard Hunter ◽  
...  
Keyword(s):  
2D Nmr ◽  
Major Product ◽  
Trans Orientation ◽  
Charge Delocalization ◽  
Pyrimidine Nucleosides ◽  
Nmr Data ◽  
Relative Stereochemistry ◽  
Steric Factors ◽  
Nmr Techniques ◽  
Carbocyclic Nucleoside

The coupling of 2-bromo-3-benzoyloxycyclobutanone with purine under basic conditions produces two regioisomers consisting of the N-7 and N-9 alkylated products in equal amounts in their racemic forms. The distribution of the isomers is consistent with the charge delocalization between the N-7 and N-9 positions of the purinyl anion. The structural assignments and relative stereochemistry of each regioisomer were based on 1 and 2D NMR techniques. The relative stereochemistry of the C-2 and C-3 substituents in each regioisomer was the trans orientation consistent with steric factors in the coupling step. The N-9 regioisomer was reduced with sodium borohydride to give the all trans cyclobutanol as the major product in a stereoselective manner. The alcohol was debenzoylated with sodium methoxide in a transesterification step to give the nucleoside analogue. The regioisomeric pyrimidine nucleosides were prepared by Vorbrüggen coupling of the 3-hydroxymethylcyclobutanone triflate with either thymine or uracil followed by stereoselective hydride addition. Regiospecificity of the coupling at the N-1 position was observed and stereoselective reduction to the trans-disubstituted cyclobutanol structure assignments was based on NMR data.

scholarly journals STRUCTURE ELUCIDATION OF FOUR STEROIDS FROM THE SOFT CORAL SINULARIA NANOLOBATA

2017 ◽  
Vol 55 (3) ◽  
pp. 258
Author(s):  
Ninh Thi Ngoc ◽  
Nguyen Van Thanh ◽  
Nguyen Xuan Cuong ◽  
Nguyen Hoai Nam ◽  
Do Cong Thung ◽  
...  
Keyword(s):  
Detailed Analysis ◽  
Structure Elucidation ◽  
Soft Coral ◽  
2D Nmr ◽  
Chromatographic Methods ◽  
Nmr Data

Four steroids namely 3β-hydroxyergosta-5,24(28)-diene-7-one (1), dissesterol (2), 16α-hydroxysarcosterol (3), and sarcophytosterol (4) were isolated form the soft coral Sinularia nanolobata using various chromatographic methods. Their structures were elucidated by detailed analysis of the 1D and 2D NMR data and comparison with the reported values.

scholarly journals Cherbonolides M and N from a Formosan Soft Coral Sarcophyton cherbonnieri

Marine Drugs ◽  
2021 ◽  
Vol 19 (5) ◽  
pp. 260
Author(s):  
Chia-Chi Peng ◽  
Tzu-Yin Huang ◽  
Chiung-Yao Huang ◽  
Tsong-Long Hwang ◽  
Jyh-Horng Sheu
Keyword(s):  
Superoxide Anion ◽  
Cytochalasin B ◽  
Soft Coral ◽  
2D Nmr ◽  
Human Neutrophils ◽  
Cd Spectra ◽  
Ether Linkage ◽  
Relative Configuration ◽  
Nmr Data ◽  
New Compounds

Two new isosarcophine derivatives, cherbonolides M (1) and N (2), were further isolated from a Formosan soft coral Sarcophyton cherbonnieri. The planar structure and relative configuration of both compounds were established by the detailed analysis of the IR, MS, and 1D and 2D NMR data. Further, the absolute configuration of both compounds was determined by the comparison of CD spectra with that of isosarcophine (3). Notably, cherbonolide N (2) possesses the unique cembranoidal scaffold of tetrahydrooxepane with the 12,17-ether linkage fusing with a γ-lactone. In addition, the assay for cytotoxicity of both new compounds revealed that they showed to be noncytotoxic toward the proliferation of A549, DLD-1, and HuCCT-1 cell lines. Moreover, the anti-inflammatory activities of both metabolites were carried out by measuring the N-formyl-methionyl-leucyl-phenylalanine/cytochalasin B (fMLF/CB)-induced generation of superoxide anion and elastase release in the primary human neutrophils. Cherbonolide N (2) was found to reduce the generation of superoxide anion (20.6 ± 6.8%) and the elastase release (30.1 ± 3.3%) in the fMLF/CB-induced human neutrophils at a concentration of 30 μM.

scholarly journals Targeted Isolation of Xenicane Diterpenoids from Taiwanese Soft Coral Asterospicularia laurae

Marine Drugs ◽  
2021 ◽  
Vol 19 (3) ◽  
pp. 123
Author(s):  
Yu-Chi Lin ◽  
Yi-Jen Chen ◽  
Shu-Rong Chen ◽  
Wan-Ju Lien ◽  
Hsueh-Wei Chang ◽  
...  
Keyword(s):  
Cytotoxic Effect ◽  
Soft Coral ◽  
Ethanol Extract ◽  
2D Nmr ◽  
Ionization Mass ◽  
Spectroscopic Analyses ◽  
Potential Source ◽  
First Case ◽  
The Family ◽  
Mcf 7

Application of LC-MS/MS-based molecular networking indicated the ethanol extract of octocoral Asterospicularia laurae is a potential source for the discovery of new xenicane derivatives. A natural product investigation of this soft coral resulted in the isolation of four new xenicane diterpenoids, asterolaurins O‒R (1‒4), together with six known compounds, xeniolide-A (5), isoxeniolide-A (6), xeniolide-B (7), 7,8-epoxyxeniolide-B (8), 7,8-oxido-isoxeniolide-A (9), and 9-hydroxyxeniolide-F (10). The structures of isolated compounds were characterized by employing spectroscopic analyses, including 2D-NMR (COSY, HMQC, HMBC, and NOESY) and high-resolution electrospray ionization mass spectrometry (HRESIMS). Asterolaurin O is the first case of brominated tricarbocyclic type floridicin in the family Xeniidae. Concerning bioactivity, the cytotoxic activity of those isolates was evaluated. As a result, compounds 1 and 2 demonstrated a selective cytotoxic effect against the MCF-7 cell line at IC50 of 14.7 and 25.1 μM, respectively.

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