Acanthocyclamine A From the Indonesian Marine Sponge Acanthostrongylophora ingens

2014 ◽  
Vol 67 (9) ◽  
pp. 1205 ◽  
Author(s):  
Ariyanti S. Dewi ◽  
Tri A. Hadi ◽  
Nurrahmi D. Fajarningsih ◽  
Joanne T. Blanchfield ◽  
Paul V. Bernhardt ◽  
...  
Keyword(s):  
Absolute Configuration ◽  
Marine Sponge ◽  
National Park ◽  
Biosynthetic Pathway ◽  
Methanolic Extract ◽  
2D Nmr ◽  
X Ray ◽  
X Ray Crystallography ◽  
Dispersion Effects ◽  
Manzamine Alkaloids

A new 3-alkylpiperidine compound (–)-acanthocyclamine A (1) has been obtained from the methanolic extract of Acanthostrongylophora ingens (order Haplosclerida, family Petrosiidae) collected from Wakatobi Marine National Park in South East Sulawesi, Indonesia. The structure of 1 was investigated by extensive 1D- and 2D-NMR experiments. The absolute configuration of 1 was established by X-ray crystallography from anomalous dispersion effects using Cu radiation as C2 (R), C3 (R), C7 (R), and C9 (R). A plausible biosynthetic scheme leading to 1 is presented, and compared with the biosynthetic pathway proposed for the manzamine alkaloids.

scholarly journals Metabolites from the Fungus Phoma sp. 7210, Associated with Aizoon Canariense

2010 ◽  
Vol 5 (8) ◽  
pp. 1934578X1000500
Author(s):  
Jingqiu Dai ◽  
Hidayat Hussain ◽  
Siegfried Dräger ◽  
Barbara Schulz ◽  
Tibor Kurtán ◽  
...  
Keyword(s):  
Solid State ◽  
Absolute Configuration ◽  
Endophytic Fungus ◽  
2D Nmr ◽  
Spectroscopic Methods ◽  
Spectral Measurements ◽  
X Ray ◽  
Mass Spectral ◽  
X Ray Crystallography ◽  
Ray Geometry

A new metabolite, 3,16-diketoaphidicolan (1), was isolated together with four known compounds: aphidicolin (2), 17-acetyl-aphidicolin (3), (+)-eupenoxide (4), and phomoxanthone A (5) from the endophytic fungus Phoma sp. The structure of the new compound 1 was determined by spectroscopic methods (mainly extensive 1D and 2D NMR experiments and by mass spectral measurements) and confirmed by X-ray crystallography. Its absolute configuration was assigned by means of the solid-state CD/TDDFT approach comparing the solid-state CD spectrum with the TDDFT-calculated one on the X-ray geometry.

Sterols from a Vietnamese Wood-Rotting Phellinus sp.

2007 ◽  
Vol 62 (2) ◽  
pp. 289-292 ◽  
Author(s):  
Dang Ngoc Quang ◽  
Dang Dinh Bach ◽  
Yoshinori Asakawa
Keyword(s):  
Nitric Oxide ◽  
Absolute Configuration ◽  
Methanolic Extract ◽  
Uv Spectroscopy ◽  
2D Nmr ◽  
Crystallographic Analysis ◽  
Raw 264.7 Cells ◽  
Raw 264.7 ◽  
X Ray ◽  
Ir And Uv Spectroscopy

Phytochemical examination of the methanolic extract from fruit bodies of an unidentified Vietnamese Phellinus species led to the isolation of four compounds, one of which is a new steroid, 25-hydroxy-ergosta-7,24(28)-dien-3β -ol, named phellinol, together with senexonol, trametenolic acid B and ergosta-4,6,8(14),22-tetraen-3-one. Their structures were determined by 2D NMR, MS, IR and UV spectroscopy. In addition, the absolute configuration of senexonol was established by X-ray crystallographic analysis of its p-bromobenzoate derivative as 22(R)-hydroxy-4(S),14(S)- dimethyl-cholesta-8,24-dien-3-one. All compounds moderately suppressed the lipopolysaccharide (LPS)-induced production of nitric oxide (NO) in RAW 264.7 cells.

Isolation and structure of spongilipid from the Republic of Singapore marine porifera Spongiacf. hispida

1997 ◽  
Vol 75 (6) ◽  
pp. 920-925 ◽  
Author(s):  
George R. Pettit ◽  
Timothy J. Bond ◽  
Delbert L. Herald ◽  
Martin Penny ◽  
Dennis L. Doubek ◽  
...  
Keyword(s):  
Cell Growth ◽  
Absolute Configuration ◽  
Marine Sponge ◽  
Lymphocytic Leukemia ◽  
Biologically Active ◽  
X Ray ◽  
X Ray Crystallography ◽  
Growth Inhibitory ◽  
The Republic

Cell growth inhibitory (P388 lymphocytic leukemia) fractions from the purple marine sponge Spongiacf. hispida were employed to uncover a new biologically active monogalactosyl monoglyceride designated spongilipid (5a). The structure and absolute configuration of spongilipid was established by X-ray crystallography. Spongilipid specifically inhibited growth of the fecal opportunist Enterococcusfaecalis. Keywords: marine sponge, Spongiahispida, spongilipid.

scholarly journals Phenylhydrazone and Quinazoline Derivatives from the Cold-Seep-Derived Fungus Penicillium oxalicum

Marine Drugs ◽  
2020 ◽  
Vol 19 (1) ◽  
pp. 9
Author(s):  
Ya-Ping Liu ◽  
Sheng-Tao Fang ◽  
Zhen-Zhen Shi ◽  
Bin-Gui Wang ◽  
Xiao-Nian Li ◽  
...  
Keyword(s):  
Deep Sea ◽  
Spectroscopic Data ◽  
2D Nmr ◽  
Penicillium Oxalicum ◽  
Marine Phytoplankton ◽  
Cold Seep ◽  
Phytoplankton Species ◽  
X Ray ◽  
X Ray Crystallography ◽  
Quinazoline Derivatives

Three new phenylhydrazones, penoxahydrazones A–C (compounds 1–3), and two new quinazolines, penoxazolones A (compound 4) and B (compound 5), with unique linkages were isolated from the fungus Penicillium oxalicum obtained from the deep sea cold seep. Their structures and relative configurations were assigned by analysis of 1D/2D NMR and mass spectroscopic data, and the absolute configurations of 1, 4, and 5 were established on the basis of X-ray crystallography or ECD calculations. Compound 1 represents the first natural phenylhydrazone-bearing steroid, while compounds 2 and 3 are rarely occurring phenylhydrazone tautomers. Compounds 4 and 5 are enantiomers that feature quinazoline and cinnamic acid units. Some isolates exhibited inhibition of several marine phytoplankton species and marine-derived bacteria.

scholarly journals Fusarins G–L with Inhibition of NO in RAW264.7 from Marine-Derived Fungus Fusarium solani 7227

Marine Drugs ◽  
2021 ◽  
Vol 19 (6) ◽  
pp. 305
Author(s):  
Guangyuan Luo ◽  
Li Zheng ◽  
Qilin Wu ◽  
Senhua Chen ◽  
Jing Li ◽  
...  
Keyword(s):  
Fusarium Solani ◽  
2D Nmr ◽  
Inflammatory Activity ◽  
Raw264.7 Cells ◽  
Spectroscopic Methods ◽  
X Ray ◽  
X Ray Crystallography ◽  
Structure Activity ◽  
Ic50 Values ◽  
New Compounds

Six new fusarin derivatives, fusarins G–L (1–6), together with five known compounds (5–11) were isolated from the marine-derived fungus Fusarium solani 7227. The structures of the new compounds were elucidated by means of comprehensive spectroscopic methods (1D and 2D NMR, HRESIMS, ECD, and ORC) and X-ray crystallography. Compounds 5–11 exhibited potent anti-inflammatory activity by inhibiting the production of NO in RAW264.7 cells activated by lipopolysaccharide, with IC50 values ranging from 3.6 to 32.2 μM. The structure–activity relationships of the fusarins are discussed herein.

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 Secondary Metabolites with Nitric Oxide Inhibition from Marine-Derived Fungus Alternaria sp. 5102

Marine Drugs ◽  
2020 ◽  
Vol 18 (8) ◽  
pp. 426 ◽  
Author(s):  
Senhua Chen ◽  
Yanlian Deng ◽  
Chong Yan ◽  
Zhenger Wu ◽  
Heng Guo ◽  
...  
Keyword(s):  
Secondary Metabolites ◽  
2D Nmr ◽  
X Ray ◽  
X Ray Crystallography ◽  
Spectroscopic Analyses ◽  
Structure Activity ◽  
Ic50 Values ◽  
Alternaria Sp ◽  
Modified Mosher’S Method ◽  
Oxide Inhibition

Two new benzofurans, alternabenzofurans A and B (1 and 2) and two new sesquiterpenoids, alternaterpenoids A and B (3 and 4), along with 18 known polyketides (5−22), were isolated from the marine-derived fungus Alternaria sp. 5102. Their structures were elucidated on the basis of extensive spectroscopic analyses (1D and 2D NMR, HR-ESIMS, and ECD) and X-ray crystallography, as well as the modified Mosher’s method. Compounds 2, 3, 5, 7, 9–18, and 20–22 exhibited potent anti-inflammatory activity by inhibiting the production of NO in RAW264.7 cells activated by lipopolysaccharide with IC50 values in the range from 1.3 to 41.1 μM. Structure-activity relationships of the secondary metabolites were discussed.

scholarly journals Am I seeing double? Absolute configuration and X-ray crystallography

2017 ◽  
Vol 73 (a1) ◽  
pp. a103-a103
Author(s):  
Bruce C. Noll ◽  
Holger Ott ◽  
Michael Ruf ◽  
Tobias Stuerzer
Keyword(s):  
Absolute Configuration ◽  
X Ray ◽  
X Ray Crystallography

scholarly journals Absolute Configuration of Cembrane Diterpenoids from Bursera multijuga

2014 ◽  
Vol 9 (9) ◽  
pp. 1934578X1400900 ◽  
Author(s):  
Juan D. Hernández-Hernández ◽  
Hugo A. García-Gutiérrez ◽  
Luisa U. Román-Marín ◽  
Yunuen I. Torres-Blanco ◽  
Carlos M. Cerda-García-Rojas ◽  
...  
Keyword(s):  
Molecular Modeling ◽  
Absolute Configuration ◽  
2D Nmr ◽  
Vibrational Circular Dichroism ◽  
Conformational Preference ◽  
X Ray Diffraction ◽  
X Ray ◽  
The Absolute ◽  
First Time ◽  
Good Agreement

The stems of Bursera multijuga afforded (-)-(1 S,3 E,7 R,8 R,11 E)-7,8-epoxycembra-3,11-dien-1-ol (1) and its acetate 2, together with cembrene A (3), nephthenol (4), and cembrenol (5). The structures of 1 and 2 were elucidated by 1D and 2D NMR, HRESIMS, and X-ray diffraction. The conformational preference of flexible 1 was studied by molecular modeling at the DFT B3LYP/DGDZVP level of theory. Good agreement between calculated and experimental vibrational circular dichroism curves established the absolute configuration of 1. This is the first time that cembrane derivatives have been isolated from the genus Bursera.

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