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 Four flavonols from the seed of Hibiscus sabdariffa. Linn. growing in Binh Thuan Province

2019 ◽  
Vol 22 (4) ◽  
pp. 348-351
Author(s):  
Pham Nguyen Kim Tuyen ◽  
Truong Van Tien ◽  
Tran The Anh Huy ◽  
Nguyen Thi Hoa ◽  
Huynh Bui Linh Chi ◽  
...  
Keyword(s):  
Ethyl Acetate ◽  
Ethyl Acetate Extract ◽  
2D Nmr ◽  
Hibiscus Sabdariffa ◽  
Asian Countries ◽  
Chromatography Analysis ◽  
Liquid Liquid Extraction ◽  
Nmr Data ◽  
First Time ◽  
Layer Chromatography

Introduction: Hibiscus sabdariffa Linn. (Malvaceae) is a medicinal plant popularly distributed in Asian countries. As of 2019, no chemical investigations from the Vietnamese plant were found. This paper reported the isolation and elucidation of compounds isolated from the seeds of Hibiscus sabdariffa Linn. (Malvaceae) growing in Binh Thuan province. Method: The maceration was applied to the seeds of the plant to afford the crude extract which was then fractionated by liquid-liquid extraction to obtain the ethyl acetate extract. The extract was carried out by using normal phase silica gel column chromatography and thin-layer chromatography. Analysis of spectroscopic data including HR-ESI-MS, 1D and 2D-NMR and a comparison of the NMR data with that in the literature led to the structural elucidation of isolated compounds. Results: Four flavonols comprising quercetin 3-O-α-L-rhamnopyranosyl-(1→6)-β-D-glucopyranoside (1), quercetin 3-O-β-D-glucopyranoside (2), quercetin (3) and kaempferol (4) were isolated from the ethyl acetate extract. Conclusions: This is the first time the isolated compounds were found from the seeds of this plant.

scholarly journals CONTRIBUTE TO STUDY ON CHEMICAL CONSTITUENTS OF URENA LOBATA (L.) OF VIETNAM

2019 ◽  
Vol 57 (2) ◽  
pp. 162
Author(s):  
Quan Minh Pham ◽  
Hoai Van Thi Tran ◽  
Lam Tien Do ◽  
Phuong Lan Doan ◽  
Inh Thi Cam ◽  
...  
Keyword(s):  
Mental Disorders ◽  
Ethyl Acetate ◽  
Ethyl Acetate Extract ◽  
Chemical Constituents ◽  
2D Nmr ◽  
Spectroscopic Methods ◽  
Tree Roots ◽  
Chemical Structures ◽  
Phytochemical Investigation ◽  
First Time

Urena lobata L. is used in Vietnamese traditional medicine for the treatment of several diseases. Tree roots are used to treat rheumatism, dysentery, poor digestion, flu, tonsils, malaria, asthma, goiter. Flowers are used to treat chickenpox, fever, and mental disorders. Branches, leaves or whole trees used to treat injuries bruises, rheumatism, mastitis, bites. Phytochemical investigation of the n-hexan and ethyl acetate extract of Urena lobata L. led to the isolation of β-sitosterol (1), β-sitosterol-3-O-β-D-glucopyranoside (2), a-acetylamino-phenylpropyl a-benzoylamino-phenylpropanoate (3), quercetin (4), and trans-tiliroside (5). Their chemical structures were determined by spectroscopic methods including MS, 1D, 2D NMR and comparing with those reported in previous papers. Two compounds 3, 5 were isolated for the first time from Urena lobata plant.

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 Neuroprotective Metabolites from Vietnamese Marine Derived Fungi of Aspergillus and Penicillium Genera

Marine Drugs ◽  
2020 ◽  
Vol 18 (12) ◽  
pp. 608
Author(s):  
Elena V. Girich ◽  
Anton N. Yurchenko ◽  
Olga F. Smetanina ◽  
Phan Thi Hoai Trinh ◽  
Ngo Thi Duy Ngoc ◽  
...  
Keyword(s):  
Molecular Weight ◽  
Secondary Metabolites ◽  
Cell Viability ◽  
Chemical Structure ◽  
Aspergillus Terreus ◽  
Marine Fungi ◽  
2D Nmr ◽  
Natural Source ◽  
Low Molecular Weight ◽  
First Time

Low molecular weight secondary metabolites of marine fungi Aspergillus flocculosus, Aspergillus terreus and Penicillium sp. from Van Phong and Nha Trang Bays (Vietnam) were studied and a number of polyketides, bis-indole quinones and terpenoids were isolated. The structures of the isolated compounds were determined by 1D and 2D NMR and HR-ESI-MS techniques. Stereochemistry of some compounds was established based on ECD data. A chemical structure of asterriquinone F (6) was thoroughly described for the first time. Anthraquinone (13) was firstly obtained from a natural source. Neuroprotective influences of the isolated compounds against 6-OHDA, paraquat and rotenone toxicity were investigated. 4-Hydroxyscytalone (1), 4-hydroxy-6-dehydroxyscytalone (2) and demethylcitreoviranol (3) have shown significant increasing of paraquat- and rotenone-treated Neuro-2a cell viability and anti-ROS activity.

scholarly journals Mersaquinone, A New Tetracene Derivative from the Marine-Derived Streptomyces sp. EG1 Exhibiting Activity against Methicillin-Resistant Staphylococcus aureus (MRSA)

Antibiotics ◽  
2020 ◽  
Vol 9 (5) ◽  
pp. 252 ◽  
Author(s):  
Min Cheol Kim ◽  
Reiko Cullum ◽  
Ali M. S. Hebishy ◽  
Hala A. Mohamed ◽  
Ahmed H. I. Faraag ◽  
...  
Keyword(s):  
Staphylococcus Aureus ◽  
Methicillin Resistant Staphylococcus Aureus ◽  
2D Nmr ◽  
North Coast ◽  
Spectroscopic Techniques ◽  
Methicillin Resistant ◽  
Streptomyces Sp ◽  
The North ◽  
Societal Challenges ◽  
New Antibiotics

New antibiotics are desperately needed to overcome the societal challenges being encountered with methicillin-resistant Staphylococcus aureus (MRSA). In this study, a new tetracene derivative, named Mersaquinone (1), and the known Tetracenomycin D (2), Resistoflavin (3) and Resistomycin (4) have been isolated from the organic extract of the marine Streptomyces sp. EG1. The strain was isolated from a sediment sample collected from the North Coast of the Mediterranean Sea of Egypt. The chemical structure of Mersaquinone (1) was assigned based upon data from a diversity of spectroscopic techniques including HRESIMS, IR, 1D and 2D NMR measurements. Mersaquinone (1) showed antibacterial activity against methicillin-resistant Staphylococcus aureus with a minimum inhibitory concentration of 3.36 μg/mL.

Juglomycins G-J: Isolation from Streptomycetes and Structure Elucidation

2005 ◽  
Vol 60 (2) ◽  
pp. 183-188 ◽  
Author(s):  
R. P. Maskey ◽  
H. Lessmann ◽  
S. Fotso ◽  
I. Grün-Wollny ◽  
H. Lackner ◽  
...  
Keyword(s):  
Antibacterial Activity ◽  
Absolute Configuration ◽  
Structure Elucidation ◽  
Mass Spectra ◽  
2D Nmr ◽  
Cd Spectra ◽  
Streptomyces Spp ◽  
Nmr Data ◽  
Related Compounds ◽  
Weak Antibacterial Activity

From the Streptomyces spp. 815 and GW4184, four new 4-juglon-2-ylbutyric acid derivatives, the juglomycins G - J (3a, 4a, 4c, 5c), have been isolated and characterised. The structures were derived from the 1D and 2D NMR data and mass spectra and confirmed by comparison with structurally related compounds. The absolute configuration was deduced from the CD spectra. The new natural products exhibited weak antibacterial activity similar to juglomycin A (5a).

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.

Isolation of Bioactive Compounds from Aspergillus terreus

2004 ◽  
Vol 59 (3) ◽  
pp. 324-328 ◽  
Author(s):  
Muhammad I. Choudhary ◽  
Syed G. Musharraf ◽  
Talat Mukhmoor ◽  
Farzana Shaheen ◽  
Shamsher Ali ◽  
...  
Keyword(s):  
Antioxidant Activity ◽  
13C Nmr ◽  
Culture Medium ◽  
Aspergillus Terreus ◽  
Ethyl Acetate Extract ◽  
Microsporum Canis ◽  
Spectroscopic Techniques ◽  
Significant Activity ◽  
Nmr Data ◽  
First Time

A new metabolite, 6-(4’-hydroxy-2’-methyl phenoxy)-(-)-(3R)-mellein (1) was isolated from the ethyl acetate extract of Aspergillus terreus culture medium along with three known isocoumarin derivatives, (-)-(3R)-6-methoxymellein (2), (-)-(3R)-6,7-dimethoxymellein (Kigelin) (3) and (3R, 4R)-6,7-dimethoxy-4-hydroxymellein (4). Metabolites 1 and 4 showed significant activity against human pathogenic dermatophytes, Microsporum canis and Trichophyton longifusus. Metabolite 1 also exhibited potent antioxidant activity. The structures of metabolites were characterized on the basis of spectroscopic techniques. 13C NMR data of metabolites 2 - 4 are also being reported for the first time

Isolierung von Venturicidin X, dem Aglycon der Venturicidine A und B aus Streptomyceten / Isolation of Venturicidin X, the Aglycon of Venturicidines A and B from Streptopyces sp

1994 ◽  
Vol 49 (7) ◽  
pp. 977-980 ◽  
Author(s):  
Hartmut Laatsch ◽  
Michael Kellner ◽  
Yong-Se Lee ◽  
Gerhard Wolf
Keyword(s):  
Natural Product ◽  
Broad Spectrum ◽  
Pathogenic Fungi ◽  
Plant Pathogenic Fungi ◽  
Streptomyces Sp ◽  
Highly Active ◽  
First Time

Abstract Venturicidin X (la ), the aglycon of the venturicidins A (1b) and B (1c) was isolated for the first time as a natural product from an unidentified Streptomyces sp. Venturicidin X (1a) is highly active against a broad spectrum of plant pathogenic fungi.

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