scholarly journals A Synthetic Butenolide Diterpene is now a Natural Product Isolated from Metaporana sericosepala, a Plant from the Madagascar Dry Forest [1a]

2015 ◽  
Vol 10 (9) ◽  
pp. 1934578X1501000 ◽  
Author(s):  
Christopher C. Presley ◽  
L. Harinantenaina Rakotondraibe ◽  
Peggy J. Brodie ◽  
Martin W. Callmander ◽  
Richard Randrianaivo ◽  
...  
Keyword(s):  
Natural Product ◽  
Ovarian Cancer Cell Line ◽  
Cancer Cell Line ◽  
Ethanolic Extract ◽  
2D Nmr ◽  
Dry Forest ◽  
Synthetic Compound ◽  
Nmr Data ◽  
Bioassay Guided Fractionation ◽  
Product Compound

Antiproliferative bioassay-guided fractionation of the ethanolic extract of the endemic Madagascan plant Metaporana sericosepala led to the first natural product isolation of a butenolide diterpene, which was synthesized during an anti-inflammatory study in 1988. The structure of the compound was elucidated as 3-homofarnesyl-4-hydroxybutenolide (1) by analysis of its spectroscopic data, including 1D- and 2D-NMR data and chemical evidence. The once synthetic compound can now also be considered as a natural product. Compound 1 had modest antiproliferative activity towards the A2780 ovarian cancer cell line with an IC50 value of 8 μM.

scholarly journals Two Antiproliferative Saponins of Tarenna grevei from the Madagascar Dry Forest [1]

2012 ◽  
Vol 7 (6) ◽  
pp. 1934578X1200700 ◽  
Author(s):  
Liva Harinantenaina ◽  
Peggy J. Brodie ◽  
Martin W. Callmander ◽  
L. Jérémie Razafitsalama ◽  
Vincent E. Rasamison ◽  
...  
Keyword(s):  
Ovarian Cancer Cell ◽  
Ovarian Cancer Cell Line ◽  
Cancer Cell Line ◽  
Ethanol Extract ◽  
2D Nmr ◽  
Dry Forest ◽  
Triterpene Saponins ◽  
2D Nmr Spectroscopy ◽  
Bioassay Guided Fractionation ◽  
Chemical Evidence

Antiproliferative bioassay-guided fractionation of the ethanol extract of the endemic Malagasy Rubiaceous plant Tarenna grevei led to the isolation of two new antiproliferative oxygenated oleanane triterpene saponins. The structures of the two active compounds were elucidated as 23-hydroxylongispinogenin 3- O-β-D-glucopyranoside (1) and longispinogenin 3- O-β-D-glucopyranosyl (1→2)-β-D-glucopyranoside (3) by analyses of their spectral data including 1D- and 2D-NMR spectroscopy and chemical evidence. Compounds 1 and 3 displayed moderate antiproliferative activity against the A2780 ovarian cancer cell line with IC50 values of 7.6 and 4 μM, respectively.

scholarly journals Astrotricoumarin, an antiproliferative 4′-hydroxy-2′,3′-dihydroprenylated methylcoumarin from an Astrotrichilia sp. from the Madagascar dry forest[1]

2011 ◽  
Vol 6 (9) ◽  
pp. 1934578X1100600 ◽  
Author(s):  
Liva Harinantenaina ◽  
Peggy J. Brodie ◽  
Martin W. Callmander ◽  
Richard Randrianaivo ◽  
Stephan Rakotonandrasana ◽  
...  
Keyword(s):  
Cell Line ◽  
Endemic Species ◽  
Spectroscopic Data ◽  
Ethanol Extract ◽  
2D Nmr ◽  
Dry Forest ◽  
Nmr Analysis ◽  
A2780 Cell ◽  
Bioassay Guided Fractionation ◽  
A2780 Cell Line

Bioassay guided fractionation of the ethanol extract of a new endemic species of the genus Astrotrichilia led to the isolation of the new antiproliferative 3-(4′-hydroxy-2′,3′-dihydroprenyl)-4,6-dimethoxy-5-methylcoumarin, named astrotricoumarin (8) with an IC50 value of 6.8 μM against the A2780 cell line. The structure of compound 8 was elucidated on the basis of its physical and spectroscopic data, including extensive 1D- and 2D-NMR analysis.

scholarly journals Methylkarranjic acid and Pongamol from Derris indica Seeds and their Antibacterial Activity

1970 ◽  
Vol 6 (1) ◽  
pp. 9-13 ◽  
Author(s):  
M Abdullahil Baki ◽  
Golam Sadik ◽  
KAM Shahadat Hossain Mondal ◽  
M Ashilk Mosaddik ◽  
M Mukhlesur Rahman
Keyword(s):  
Antibacterial Activity ◽  
Phenolic Compounds ◽  
Soluble Fraction ◽  
Ethanolic Extract ◽  
2D Nmr ◽  
Shigella Dysenteriae ◽  
E Coli ◽  
Nmr Data ◽  
Test Organisms ◽  
Derris Indica

Two phenolic compounds, methylkarranjic (1) acid and pongamol (2), were isolated from the petroleum ether soluble fraction of an ethanolic extract of Derris indica seeds. The structures of these compounds were confirmed by LC-MS and a series of 1D and 2D NMR data. The solvent solvent partionates of the ethanolic extract and compounds (1 and 2) exhibited moderate antibacterial activity against several test organisms. The minimum inhibitory concentrations (MICs) of 1 and 2 were found to be in the range of 32-128 μg/ml against Bacillus megatorium, Streptococcus β-haemolyticus, Shigella dysenteriae and E. coli. Key words: Derris indica; Leguminosae; Methylkarranjic acid; Pongamol; Antibacterial activity Dhaka Univ. J. Pharm. Sci. 6(1): 9-13, 2007 (June) The full text is of this article is available at the Dhaka Univ. J. Pharm. Sci. website

scholarly journals Azaphilones from the Red Sea Fungus Aspergillus falconensis

Marine Drugs ◽  
2020 ◽  
Vol 18 (4) ◽  
pp. 204 ◽  
Author(s):  
Dina H. El-Kashef ◽  
Fadia S. Youssef ◽  
Rudolf Hartmann ◽  
Tim-Oliver Knedel ◽  
Christoph Janiak ◽  
...  
Keyword(s):  
Red Sea ◽  
Cancer Cell Line ◽  
2D Nmr ◽  
X Ray Diffraction ◽  
2D Nmr Spectroscopy ◽  
Nmr Data ◽  
Ic50 Values ◽  
Rice Medium ◽  
Optical Rotations ◽  
New Compounds

The marine-derived fungus Aspergillus falconensis, isolated from sediment collected from the Canyon at Dahab, Red Sea, yielded two new chlorinated azaphilones, falconensins O and P (1 and 2) in addition to four known azaphilone derivatives (3−6) following fermentation of the fungus on solid rice medium containing 3.5% NaCl. Replacing NaCl with 3.5% NaBr induced accumulation of three additional new azaphilones, falconensins Q−S (7−9) including two brominated derivatives (7 and 8) together with three known analogues (10−12). The structures of the new compounds were elucidated by 1D and 2D NMR spectroscopy and HRESIMS data as well as by comparison with the literature. The absolute configuration of the azaphilone derivatives was established based on single-crystal X-ray diffraction analysis of 5, comparison of NMR data and optical rotations as well as on biogenetic considerations. Compounds 1, 3−9, and 11 showed NF-κB inhibitory activity against the triple negative breast cancer cell line MDA-MB-231 with IC50 values ranging from 11.9 to 72.0 µM.

scholarly journals Biologically Active Secondary Metabolites from Asphodelus Microcarpus

2013 ◽  
Vol 8 (8) ◽  
pp. 1934578X1300800 ◽  
Author(s):  
Mohammed M. Ghoneim ◽  
Guoyi Ma ◽  
Atef A. El-Hela ◽  
Abd-Elsalam I. Mohammad ◽  
Saeid Kottob ◽  
...  
Keyword(s):  
Mammalian Cells ◽  
Methicillin Resistant Staphylococcus Aureus ◽  
Ethanolic Extract ◽  
2D Nmr ◽  
Biologically Active ◽  
Naphthoic Acid ◽  
Bioassay Guided Fractionation ◽  
Resistant Strains ◽  
Asphodelus Microcarpus ◽  
First Time

Bioassay guided fractionation of the ethanolic extract of Asphodelus microcarpus Salzm.et Vivi (Asphodelaceae) resulted in the isolation of one new metabolite, 1,6-dimethoxy-3-methyl-2-naphthoic acid (1) as well as nine known compounds: asphodelin (2), chrysophanol (3), 8-methoxychrysophanol (4), emodin (5), 2-acetyl-1,8-dimethoxy-3-methylnaphthalene (6), 10-(chrysophanol-7’-yl)-10-hydroxychrysophanol-9-anthrone (7), aloesaponol-III-8-methyl ether (8), ramosin (9) and aestivin (10). The compounds were identified by 1D and 2D NMR and HRESIMS. Compounds 3, 6 and 10 were isolated for the first time from this species. Compounds 3 and 4 showed moderate to weak antileishmanial activity with IC50 values of 14.3 and 35.1 μg/mL, respectively. Compound 4 exhibited moderate antifungal activity against Cryptococcus neoformans with an IC50 value of 15.0 μg/mL, while compounds 5, 7 and 10 showed good to potent activity against methicillin resistant Staphylococcus aureus (MRSA) with IC50 values of 6.6, 9.4 μg/mL and 1.4 μg/mL respectively. Compounds 5, 8 and 9 displayed good activity against S. aureus with IC50 values of 3.2, 7.3 and 8.5 μg/mL, respectively. Compounds 7 and 9 exhibited a potent cytotoxic activity against leukemia LH60 and K562 cell lines. Compound 10 showed potent antimalarial activities against both chloroquine-sensitive and chloroquine-resistant strains of Plasmodium falciparum with IC50 values in the range of 0.8-0.7 μg/mL without showing any cytotoxicity to mammalian cells.

A New Clerodane Diterpene and Other Constituents from Ajuga chamaepitys ssp. laevigata

2004 ◽  
Vol 59 (5) ◽  
pp. 584-588 ◽  
Author(s):  
Gülaçtı Topçu ◽  
Gamze Kökdil ◽  
Zeynep Türkmen ◽  
Wolfgang Voelter ◽  
Eba Adou ◽  
...  
Keyword(s):  
Ovarian Cancer ◽  
Cell Line ◽  
Cell Lines ◽  
Ovarian Cancer Cell ◽  
Ovarian Cancer Cell Line ◽  
Cancer Cell Line ◽  
2D Nmr ◽  
Human Ovarian Cancer ◽  
Human Ovarian Cancer Cell ◽  
Spectroscopic Analyses

Abstract From Ajuga chamepitys ssp. laevigata, a new clerodane diterpene, ajugalaevigatic acid, has been isolated besides five known compounds, a diterpene, (13S)-15-hydroxylabd-8(17)-en-19-oic acid, a steroidal glucoside, 3-O-β -D-glucopyranosyl-stigmasta-5,25-diene, and triterpenes,α- and β -amyrin and ursolic acid. Their structural elucidation is based on NMR and MS spectroscopic analyses. For the new compound 2D NMR experiments were carried out. Ajugalaevigatic acid was tested against a panel of cytotoxic cell lines, and only found to be active against the A2780 human ovarian cancer cell line.

Isolation, Structure Elucidation and Activity of Anthracycline Acetates from a Terrestrial Streptomyces sp.

2003 ◽  
Vol 58 (12) ◽  
pp. 1242-1246 ◽  
Author(s):  
Serge Fotso ◽  
Rajendra P. Maskey ◽  
Iris Grün-Wollny ◽  
Hartmut Laatsch
Keyword(s):  
Molecular Weight ◽  
Natural Product ◽  
Structure Elucidation ◽  
Ethyl Acetate Extract ◽  
2D Nmr ◽  
Streptomyces Sp ◽  
Naturally Occurring ◽  
Nmr Data ◽  
New Antibiotics ◽  
First Time

The red coloured ethyl acetate extract of the Streptomyces sp. isolate GW37/3236 delivered the two new antibiotics 13-O-acetyl-bisanhydro-13-dihydrodaunomycinone (3c) and 4,13-O-diacetylbisanhydro- 4-O-demethyl-13-dihydrodaunomycinone (3d) and additionally several known compounds. The quinones 3c and 3d are the first naturally occurring quinone acetates. Their structures were derived by comparison of the NMR data with those of bisanhydro-13-dihydrodaunomycinone (3b) and by interpretation of the 2D NMR data accompanied by the molecular weight and formula. 2-Acetamido-3-hydroxybenzamide (5) was also isolated from the extract and was identified by comparison of the NMR data with those of 2-acetamidobenzamide and by 2D NMR correlations. 6,9,11- Trihydroxy-4-methoxy-5,12-naphthacenedione (4) is isolated for the first time as a natural product.

scholarly journals An antiproliferative xanthone of Symphonia pauciflora from the Madagascar rainforest

2010 ◽  
Vol 5 (5) ◽  
pp. 1934578X1000500 ◽  
Author(s):  
Ende Pan ◽  
Shugeng Cao ◽  
Peggy J. Brodie ◽  
James S. Miller ◽  
Rolland Rakotodrajaona ◽  
...  
Keyword(s):  
Ovarian Cancer ◽  
Cell Line ◽  
Cancer Cell ◽  
Ovarian Cancer Cell ◽  
Ovarian Cancer Cell Line ◽  
Cancer Cell Line ◽  
2D Nmr ◽  
Mass Spectral Data ◽  
Endemic Plant ◽  
Mass Spectral

Investigation of a Malagasy endemic plant identified as Symphonia pauciflora Baker (Clusiaceae) for antiproliferative activities against the A2780 ovarian cancer cell line led to the isolation of a new compound identified as 2-(3,3-dimethylallyl)-7-methoxy-1,5,6-trihydroxy-2″″,2″″-dimethylpyrano(6″″,5″″:3,4) xanthone (1) and the two known guttiferones A (2) and I (3). The structure elucidation of 1 was based on the analysis of its 1D and 2D NMR and mass spectral data. Compound 1 showed good antiproliferative activity with an IC50 value of 3.8 μM against the A2780 human ovarian cancer cell line, while the known guttiferone analogues (2 and 3) exhibited moderate activities with IC50 values of 8.3 μM and 7.8 μM, respectively.

scholarly journals Antiproliferative Diterpenes from a Malleastrum sp. from the Madagascar dry forest [1]

2015 ◽  
Vol 10 (9) ◽  
pp. 1934578X1501000 ◽  
Author(s):  
Yixi Liu ◽  
C. Houston Wiedle ◽  
Peggy J. Brodie ◽  
Martin W. Callmander ◽  
R. Rakotondrajaona ◽  
...  
Keyword(s):  
Ovarian Cancer Cell ◽  
Ovarian Cancer Cell Line ◽  
Cancer Cell Line ◽  
Ethanol Extract ◽  
Dry Forest ◽  
Nmr Spectrum ◽  
Relative Stereochemistry ◽  
Clerodane Diterpenes ◽  
Labdane Diterpene ◽  
Acid Lactone

An ethanol extract of leaves of the plant species Malleastrum sp. collected in northern Madagascar afforded the new clerodane diterpene 18-oxo-cleroda-3,13-dien-16,15-olide (1), together with the three known clerodane diterpenes 16,18-dihydroxykolavenic acid lactone (2), solidagolactone (3) and (-)-kolavenol (4), and the known labdane diterpene 3-oxo-ent-Iabda-8(17),13-dien-15,16-olide (5). Compounds 1, 3, and 4 showed moderate antiproliferative activities against the A2780 ovarian cancer cell line, with the IC50 values of 3.01 ± 0.8, 7.84 ± 0.2, and 17.9 ± 3 μM, respectively. The structure elucidations of all compounds were carried out based on analysis of NMR and mass spectroscopic data. The relative stereochemistry of compound 1 was determined by NOESY NMR spectrum.

scholarly journals A New Bioactive Diterpene Glycoside from Molinaea Retusa from the Madagascar Dry Forest

2013 ◽  
Vol 8 (9) ◽  
pp. 1934578X1300800 ◽  
Author(s):  
Alexander L. Eaton ◽  
Liva Harinantenaina ◽  
Peggy J. Brodie ◽  
Maria B. Cassera ◽  
Jessica D. Bowman ◽  
...  
Keyword(s):  
Ovarian Cancer ◽  
Plasmodium Falciparum ◽  
Ovarian Cancer Cell ◽  
Ovarian Cancer Cell Line ◽  
Cancer Cell Line ◽  
Ethanol Extract ◽  
Dry Forest ◽  
Human Ovarian Cancer ◽  
Spectroscopic Methods ◽  
Human Ovarian Cancer Cell

In a continuing collaboration in a search for new antiproliferative compounds in Madagascar as part of an International Cooperative Biodiversity Group (ICBG), an ethanol extract of Molinaea retusa Radlk. (Sapindaceae) was investigated on the basis of its moderate antiproliferative activity against the A2780 human ovarian cancer cell line (IC50 16 μg/mL). One new compound, 2″,3″,4″,6′-de- O-acetylcupacinoside (1, IC50 15.4 μM) and two known compounds, cupacinoside (2, IC50 9.5 μM) and 6-de- O-acetylcupacinoside (3, IC50 10.9 μM), were isolated by bioassay-directed fractionation using liquid-liquid partitioning, column chromatography, and HPLC. Compounds 2 and 3 also had moderate antiplasmodial activities, with IC50 values of 4.0 and 6.4 μM, respectively, against Plasmodium falciparum, Dd2 strain. The structures were determined using spectroscopic methods.

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