scholarly journals Unusual Polyhydroxylated Steroids from the Starfish Anthenoides laevigatus, Collected off the Coastal Waters of Vietnam

Molecules ◽  
2020 ◽  
Vol 25 (6) ◽  
pp. 1440
Author(s):  
Alla A. Kicha ◽  
Dinh T. Ha ◽  
Timofey V. Malyarenko ◽  
Anatoly I. Kalinovsky ◽  
Roman S. Popov ◽  
...  
Keyword(s):  
Coastal Waters ◽  
2D Nmr ◽  
2D Nmr Spectroscopy ◽  
Cytotoxic Effects ◽  
One Dimensional ◽  
The Common ◽  
Polyhydroxylated Steroids ◽  
New Compounds ◽  
Ht 29 ◽  
Inhibit Cell Proliferation

Four new polyhydroxylated steroids 1–4 were isolated along with two previously known related steroids 5 and 6 from the methanolic extract of the starfish Anthenoides laevigatus collected off the coastal waters of Vietnam. Structures of new compounds were substantially elucidated by one-dimensional (1D) and two-dimensional (2D) NMR spectroscopy and HRESIMS techniques. Heptaol 1 and hexaol 2 contain the common 5α-cholestane skeleton, while hexaol 3 and heptaol 4 have the rare among starfish steroid compounds 5β-cholestane skeleton. Compounds 1, 5, and 6 do not show cytotoxic effects against normal JB6 Cl41 and cancer HT-29 and MDA-MB-231 cells, however they inhibit cell proliferation and colony formation of cancer HT-29 and MDA-MB-231 cells.

scholarly journals 5-((8-Hydroxyquinolin-5-yl)diazenyl)-3-methyl-1H-pyrazole-4-carboxylic Acid

Molbank ◽  
10.3390/m1238 ◽  
2021 ◽  
Vol 2021 (2) ◽  
pp. M1238
Author(s):  
Ion Burcă ◽  
Valentin Badea ◽  
Calin Deleanu ◽  
Vasile-Nicolae Bercean
Keyword(s):  
Chemical Structure ◽  
Functional Group ◽  
Coupling Reaction ◽  
2D Nmr ◽  
Azo Coupling ◽  
2D Nmr Spectroscopy ◽  
Azo Compound ◽  
Ft Ir ◽  
New Compounds ◽  
Carboxylic Functional Group

A new azo compound was prepared via the azo coupling reaction between 4-(ethoxycarbonyl)-3-methyl-1H-pyrazole-5-diazonium chloride and 8-hydroxyquinoline (oxine). The ester functional group of the obtained compound was hydrolyzed and thus a new chemical structure with a carboxylic functional group resulted. The structures of the new compounds were fully characterized by: UV–Vis, FT-IR, 1D and 2D NMR spectroscopy, and HRMS spectrometry.

scholarly journals Isolation and Characterization of Two New Antimicrobial Acids from Quercus incana (Bluejack Oak)

2018 ◽  
Vol 2018 ◽  
pp. 1-5
Author(s):  
Rizwana Sarwar ◽  
Umar Farooq ◽  
Sadia Naz ◽  
Nadia Riaz ◽  
Syed Majid Bukhari ◽  
...  
Keyword(s):  
Ethyl Acetate Fraction ◽  
Structural Formula ◽  
2D Nmr ◽  
Spectroscopic Technique ◽  
Pentanoic Acid ◽  
One Dimensional ◽  
Isolation And Characterization ◽  
Nmr Techniques ◽  
New Compounds

Two new compounds [1-2] were purified from ethyl acetate fraction of Quercus incana. The structure of these compounds is mainly established by using advanced spectroscopic technique such as UV, IR, one-dimensional (ID) and two-dimensional (2D) NMR techniques, and EI mass. The structural formula was deduced to be 4-hydroxydecanoic acid [1] and 4-hydroxy-3-(hydroxymethyl) pentanoic acid [2]. Both isolated compounds were tested for their antimicrobial potential and showed promising antifungal activity against Aspergillus niger and Aspergillus flavus.

Peptaibol metabolites of Tolypocladium geodes

1996 ◽  
Vol 74 (2) ◽  
pp. 165-172 ◽  
Author(s):  
Youla S. Tsantrizos ◽  
Sotiria Pischos ◽  
Françoise Sauriol ◽  
Paul Widden
Keyword(s):  
Amino Acid ◽  
2D Nmr ◽  
Chemical Shift Assignments ◽  
Pentanoic Acid ◽  
2D Nmr Spectroscopy ◽  
New Members ◽  
The Common ◽  
Unusual Amino Acid ◽  
Acid Unit ◽  
C Nmr

Three antibiotic peptides, LP237-F8 (1), F5 (2), and F7 (3), were isolated from the liquid culture of the fungus Tolypocladium geodes. Chemical shift assignments of the 1H and 13C NMR resonances and sequencing of these metabolites were achieved by extensive high-field 2D NMR spectroscopy. The N-terminal of peptides 1 and 2 is protected with an octanoyl (Oc) fatty acid unit, whereas that of peptide 3 is protected with a decanoyl (Dec) unit. The C-terminal of all three peptides is protected with the amino alcohol leucinol (Lol). All three metabolites contain the common amino acids Ala, Phe or Tyr, Pro, and Gln, as well as the unusual amino acid α-aminoisobutyric acid (Aib). In addition, peptides 1 and 2 contain the amino acid α-amino-α-ethyl-n-pentanoic acid (α-ethylnorvaline, EtNor), which has not been previously reported as a constituent of a natural product. Metabolites 1, 2, and 3 are new members of the class of natural products known as peptaibols. Key words: Tolypocladium geodes, peptaibols, leucinol, α-amino-α-ethyl-n-pentanoic acid.

scholarly journals New 3-Hydroxyquinaldic Acid Derivatives from Cultures of the Marine Derived Actinomycete Streptomyces cyaneofuscatus M-157

Marine Drugs ◽  
2018 ◽  
Vol 16 (10) ◽  
pp. 371 ◽  
Author(s):  
Francisco Ortiz-López ◽  
Elsa Alcalde ◽  
Aida Sarmiento-Vizcaíno ◽  
Caridad Díaz ◽  
Bastien Cautain ◽  
...  
Keyword(s):  
Nmr Spectra ◽  
2D Nmr ◽  
Two Dimensional ◽  
Amino Acid Residues ◽  
Trace Level ◽  
One Dimensional ◽  
2D Nmr Spectra ◽  
Ic50 Values ◽  
New Compounds ◽  
Tof Ms

Fractionation of the bioactive extract of a culture of the marine derived actinomycete Streptomyces cyaneofuscatus M-157 led to the isolation of the known 3-hydroxyquinaldic acid (4), its amide (5) and three new derivatives (1–3) containing different amino acid residues. The structures of the new molecules (1–3), including their absolute configuration, were determined by the analysis of their ESI-TOF MS and one-dimensional (1D) and two-dimensional (2D) NMR spectra and advanced Marfey’s analysis of their hydrolyzation products. Compound 3 spontaneously dimerized in solution to give the disulfide derivative 6. Unfortunately, none of the new compounds isolated confirmed the antimicrobial activity found in the bacterial extract, perhaps indicating that such antibacterial activity might be due to presence in the extract at the trace level of larger bioactive 3-hydroxyquinaldic acid derivatives from which compounds 1–3 are biosynthetic precursors. Cytotoxicity tests confirmed the moderate and weak IC50 values of 15.6 and 51.5 µM for compounds 5 and 1, respectively.

scholarly journals Anti-allergic and Cytotoxic Effects of Sesquiterpenoids and Phenylpropanoids Isolated from Magnolia biondii

2017 ◽  
Vol 12 (10) ◽  
pp. 1934578X1701201 ◽  
Author(s):  
Thi Tuyet Mai Nguyen ◽  
Thi Thu Nguyen ◽  
Hyun-Su Lee ◽  
Bomi Lee ◽  
Byung Sun Min ◽  
...  
Keyword(s):  
T Cells ◽  
Optical Rotation ◽  
Interleukin 2 ◽  
2D Nmr ◽  
Inhibitory Effect ◽  
2D Nmr Spectroscopy ◽  
Jurkat T Cells ◽  
Cytotoxic Effects ◽  
D 12 ◽  
Mcf 7

Ten sesquiterpenoids (1-10) and six phenylpropanoid derivatives (11-16) were isolated from the flower buds of Magnolia biondii Pamp. Their structures were determined by 1D- and 2D-NMR spectroscopy, mass spectrometry, and optical rotation. To evaluate their anti-allergic properties, the inhibitory effect of each isolate (1-16) on interleukin-2 (IL-2) gene expression was examined in Jurkat T cells. Among the isolated compounds, three sesquiterpenoids (2, 5, and 7) and two monoterpenoids (12 and 13) strongly inhibited IL-2 production in Jurkat T cells. Four compounds, (-)-parthenolide (2), eudesm-4(15)-eno-1β,6α-diol (5), biondinin D (12), and tiliroside (16), showed cytotoxicity against Jurkat T cells. In addition, (-)-parthenolide (2) exhibited cytotoxicity against the human cervical cancer HeLa cell line, the human breast cancer MCF-7, and human promyelocytic leukemia HL-60 cell lines.

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 Isolation of Sesquiterpenoids and Steroids from the Soft Coral Sinularia brassica and Determination of Their Absolute Configuration

Marine Drugs ◽  
2021 ◽  
Vol 19 (9) ◽  
pp. 523
Author(s):  
Giang Nam Pham ◽  
Da Yeun Kang ◽  
Min Ju Kim ◽  
Se Jong Han ◽  
Jun Hyuck Lee ◽  
...  
Keyword(s):  
Escherichia Coli ◽  
Leishmania Donovani ◽  
Spectroscopic Analysis ◽  
Soft Coral ◽  
Antimicrobial Effect ◽  
2D Nmr ◽  
2D Nmr Spectroscopy ◽  
Polyhydroxylated Steroids

Two undescribed rearranged cadinane-type sesquiterpenoids (1–2), named sinulaketol A-B, together with one new chlorinated steroid (3), one new gorgosterol (4), one known sesquiterpene (5), one known dibromoditerpene (6) and two known polyhydroxylated steroids (7–8) were isolated from the soft coral Sinularia brassica. The structures of these compounds were established by extensive spectroscopic analysis, including HRESIMS, 1D, and 2D NMR spectroscopy. Their absolute configurations were also determined by the ECD calculations and DP4+ probability analysis. Antileishmanial activity of compounds 1–8 was evaluated in vitro against the amastigote forms of Leishmania donovani, in which compounds 3, 6, and 7 inhibited the growth of L. donovani by 58.7, 74.3, 54.7%, respectively, at a concentration of 50 μM. Antimicrobial effect of the isolated compounds were also evaluated against Candida albicans, Staphylococcus aureus, and Escherichia coli. Compound 6, a brominated diterpene, exhibited antimicrobial effect against S. aureus.

scholarly journals Apoptotic Activity of New Oxisterigmatocystin Derivatives from the Marine-Derived Fungus Aspergillus nomius NC06

Marine Drugs ◽  
2021 ◽  
Vol 19 (11) ◽  
pp. 631
Author(s):  
Muh. Ade Artasasta ◽  
Yanwirasti Yanwirasti ◽  
Muhammad Taher ◽  
Akmal Djamaan ◽  
Ni Putu Ariantari ◽  
...  
Keyword(s):  
High Resolution Mass Spectrometry ◽  
2D Nmr ◽  
2D Nmr Spectroscopy ◽  
Cytotoxic Compounds ◽  
Ic50 Values ◽  
Rice Medium ◽  
Double Staining Method ◽  
Aspergillus Nomius ◽  
Apoptotic Activity ◽  
Ht 29

Sponge-derived fungi have recently attracted attention as an important source of interesting bioactive compounds. Aspergillus nomius NC06 was isolated from the marine sponge Neopetrosia chaliniformis. This fungus was cultured on rice medium and yielded four compounds including three new oxisterigmatocystins, namely, J, K, and L (1, 2, and 3), and one known compound, aspergillicin A (4). Structures of the compounds were elucidated by 1D and 2D NMR spectroscopy and by high-resolution mass spectrometry. The isolated compounds were tested for cytotoxic activity against HT 29 colon cancer cells, where compounds 1, 2, and 4 exhibited IC50 values of 1.21, 2.23, and 5.62 µg/mL, respectively. Under the fluorescence microscope by using a double staining method, HT 29 cells were observed to be viable, apoptotic, and necrotic after treatment with the cytotoxic compounds 1, 2, and 4. The result shows that compounds 1 and 2 were able to induce apoptosis and cell death in HT 29 cells.

scholarly journals Synthesis of N-Heterocyclic Analogues of 28-O-Methyl Betulinate, and Their Antibacterial and Antifungal Properties

Molbank ◽  
10.3390/m1100 ◽  
2019 ◽  
Vol 2020 (1) ◽  
pp. M1100
Author(s):  
Elvira R. Shakurova ◽  
Lyudmila V. Parfenova
Keyword(s):  
Nmr Spectroscopy ◽  
Minimum Inhibitory Concentration ◽  
Methyl Ester ◽  
Inhibitory Concentration ◽  
2D Nmr ◽  
2D Nmr Spectroscopy ◽  
One Pot ◽  
The One ◽  
Antibacterial And Antifungal ◽  
New Compounds

The paper presents the results on the one-pot pyridine quaternization using betulinic 28-O-methyl ester (1) and Tempo+Br3− cation followed by reduction of the resulting salt (2) to 1,2,5,6-tetrahydropyridine derivative (3). The structures of new compounds are confirmed by means of 1D and 2D-NMR spectroscopy, as well as MALDI TOF/TOF spectrometry. The derivatives 2 and 3 are active against S. aureus at the minimum inhibitory concentration (MIC) of 4 μg/mL and 16 μg/mL, correspondingly.

scholarly journals Antiparasitic and Anticancer Carvotacetone Derivatives of Sphaeranthus bullatus

2012 ◽  
Vol 7 (9) ◽  
pp. 1934578X1200700
Author(s):  
Francis Machumi ◽  
Abiy Yenesew ◽  
Jacob O. Midiwo ◽  
Matthias Heydenreich ◽  
Erich Kleinpeter ◽  
...  
Keyword(s):  
2D Nmr ◽  
Specific Rotation ◽  
Anticancer Activities ◽  
2D Nmr Spectroscopy ◽  
Cytotoxic Effects ◽  
H Nmr ◽  
Aerial Parts ◽  
Annual Herb ◽  
Derivatives Of

The CH2Cl2-MeOH (1:1) extract of the aerial parts of Sphaeranthus bullatus, an annual herb native to tropical East Africa, showed activity against chloroquine sensitive D6 (IC50 9.7 μg/mL) and chloroquine resistant W2 (IC50 15.0 μg/mL) strains of Plasmodium falciparum. Seventeen secondary metabolites were isolated from the extract through conventional chromatographic techniques and identified using various spectroscopic methods. The compounds were evaluated for their in vitro antiplasmodial, antileishmanial and anticancer activities revealing activity of four carvotacetone derivatives, namely 3-acetoxy-7-hydroxy-5-tigloyloxycarvotacetone (1), 3,7-dihydroxy-5-tigloyloxycarvotacetone (2), 3-acetoxy-5,7-dihydroxycarvotacetone (3) and 3,5,7-trihydroxy-carvotacetone (4); with antiplasmodial IC50 values of 1.40, 0.79, 0.60 and 3.40 μg/mL, respectively, against chloroquine sensitive D6 strains of P. falciparum; antiplasmodial activity of IC50 2.00, 0.90, 0.68 and 2.80 μg/mL, respectively, against chloroquine resistant W2 strains of P. falciparum; antileishmanial IC50 values of 0.70, 3.00, 0.70 and 17.00 μg/mL, respectively, against the parasite L. donovanii promastigotes, and anticancer activity against human SK-MEL, KB, BT-549 and SK-OV-3 tumor cells, with IC50 values between <1.1 - 5.3 μg/mL for 1-3. In addition, cytotoxic effects of the active compounds were evaluated against monkey kidney fibroblasts (VERO) and pig kidney epithelial cells (LLC-PK11). The structures of carvotacetone derivatives were determined by 1D and 2D NMR spectroscopy; the absolute stereochemical configuration of 3-acetoxy-7-hydroxy-5-tigloyloxycarvotacetone (1) was determined as 3 R, 4 R, 5 S by circular dichroism, specific rotation, 1H NMR and 2D NMR ROESY and NOESY experiments.

Sign in / Sign up

Export Citation Format

Share Document