scholarly journals Secondary metabolites of Phlebopus species from Northern Thailand

2020 ◽  
Vol 19 (12) ◽  
pp. 1525-1536
Author(s):  
Boontiya Chuankid ◽  
Hedda Schrey ◽  
Benjarong Thongbai ◽  
Olivier Raspé ◽  
Norbert Arnold ◽  
...  
Keyword(s):  
Secondary Metabolites ◽  
2D Nmr ◽  
Cytotoxic Activities ◽  
Tumor Cell Lines ◽  
Submerged Cultures ◽  
Esi Ms ◽  
Spectroscopic Analyses ◽  
New Compounds ◽  
Comprehensive Characterization

AbstractSubmerged cultures of the edible mushrooms Phlebopus portentosus and Phlebopus spongiosus were screened for their secondary metabolites by HPLC-UV/Vis and HR-LC-ESI-MS. Two new compounds, 9′-hydroxyphenyl pulvinone (1), containing an unusual pulvinone structure, and phlebopyron (2), together with the seven known pigments, atromentic acid (3), xerocomic acid (4), variegatic acid (5), methyl atromentate (6), methyl isoxerocomate (7), methyl variegatate (8), and variegatorubin (9) were isolated from the cultures. Their structures were assigned on the basis of extensive 1D/2D NMR spectroscopic analyses, as well as HR-ESI-MS, and HR-ESI-MS/MS measurements. Furthermore, the isolated compounds were evaluated for their antimicrobial and cytotoxic properties. 9′-hydroxyphenyl pulvinone (1), xerocomic acid (4), and methyl variegatate (8) exhibited weak to moderate cytotoxic activities against several tumor cell lines. The present paper provides a comprehensive characterization of pigments from the class of pulvinic acids that are present in the basidiomes of many edible bolete species.

scholarly journals Synthesis and characterization of new 4-aryl-2-(2-oxopropoxy)-6-(2,5-dichlorothiophene)nicotinonitrile and their furo[2,3-b]pyridine derivatives: Assessment of antioxidant and biological activity

2018 ◽  
Vol 9 (4) ◽  
pp. 375-381 ◽  
Author(s):  
Mahmoud Al‐Refai ◽  
Mohammad Ibrahim ◽  
Abdullah Al‐Fawwaz ◽  
Armin Geyer
Keyword(s):  
Antioxidant Activities ◽  
Radical Scavenging Activity ◽  
Radical Scavenging ◽  
2D Nmr ◽  
Pyridine Derivatives ◽  
Esi Ms ◽  
Scavenging Effect ◽  
Radical Scavenging Effect ◽  
New Compounds

A new series of furo[2,3-b]pyridine derivatives bearing aryl substituents were synthesized in two steps, where, the cyano-(2H)-pyridones (1a-l) were converted to the corresponding nicotinonitriles (2a-l), followed by the Thorpe-Ziegler ring cyclization to the furo[2,3-b]pyridine derivatives (3a-l). All new compounds were characterized by 1D-NMR experiments (1H and 13C) and 2D-NMR experiments (COSY, HMBC and HSQC), as well as ESI-MS and HR-ESI-MS data. The new compounds were screened for their antioxidant activities by 2,2-diphenyl-1-picryl-hydrazylhydrate (DPPH) free radical assay. The highest radical scavenging effect was observed for nicotinonitriles 2d, 2h and 2l and furo[2,3-b]pyridines 3b, 3f and 3j by methanolic solvent at 4.0 mg/mL concentration. Remarkably, all nicotinonitriles and furo[2,3-b]pyridine exhibited a significant radical scavenging activity after 24 and 48 hours compared with 0.5 hour.

Halo-phenolic metabolites and their in vitro antioxidant and cytotoxic activities from the Red Sea alga Avrainvillea amadelpha

2021 ◽  
Vol 76 (5-6) ◽  
pp. 213-218
Author(s):  
Usama W. Hawas ◽  
Lamia T. Abou El-Kassem ◽  
Radwan Al-farawati ◽  
Fekri M. Shaher
Keyword(s):  
2D Nmr ◽  
Cytotoxic Activities ◽  
Dpph Radical ◽  
Srb Assay ◽  
Phenolic Metabolites ◽  
2D Nmr Spectra ◽  
New Compounds ◽  
Benzaldehyde Derivatives ◽  
Mcf 7

Abstract From the green alga Avrainvillea amadelpha, two new naturally halo-benzaldehyde derivatives were isolated by various chromatographic methods along with 10 known metabolites of bromophenols, sulfonoglycolipid, and steroids. Based on the 1D and 2D NMR spectra as well as on MS data, the structures of the new compounds were identified as 5-bromo-2-(3-bromo-4-hydroxybenzyl)-3,4-dihydroxybenzaldehyde named avrainvilleal (1), and 3-iodo-4-hydroxy-benzaldehyde (2). Using SRB assay, both compounds showed mild and weak cytotoxic activity against HeLa and MCF-7 cancer cell lines, compared to the good activity of their extract (IC50 values 3.1 and 4.3 μg/mL, respectively). However, avrainvilleal (1) displayed an effective scavenged DPPH radical activity with IC50 value 3.5 μM, compared to the antioxidant quercetin with IC50 value 1.5 μM.

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 Six New 3,5-Dimethylcoumarins from Chelonopsis praecox, Chelonopsis odontochila and Chelonopsis pseudobracteata

2021 ◽  
Author(s):  
Chang-An Geng ◽  
Zhen-Tao Deng ◽  
Qian Huang ◽  
Chun-Lei Xiang ◽  
Ji-Jun Chen
Keyword(s):  
Protein Tyrosine Phosphatase ◽  
Tyrosine Phosphatase ◽  
2D Nmr ◽  
Cell Protein ◽  
Protein Tyrosine Phosphatase 1B ◽  
Protein Tyrosine ◽  
Aerial Parts ◽  
Spectroscopic Analyses ◽  
New Compounds

AbstractTen 3,5-dimethylcoumarins (1–6 and 8‒11) involving six new ones (1–6), together with a known 3-methylcoumarin (7), were isolated from the aerial parts of three Chelonopsis plants, C. praecox, C. odontochila, and C. pseudobracteata. The structures of the new compounds were determined by extensive HRESIMS, 1D and 2D NMR spectroscopic analyses. According to the substitution at C-5, these coumarins were classified into 5-methyl, 5-hydroxymethyl, 5-formyl, and 5-nor types. All the isolates were assayed for their inhibition on α-glucosidase, protein tyrosine phosphatase 1B, and T-cell protein tyrosine phosphatase in vitro. Graphic Abstract

scholarly journals Four New Pterosins from Pteris cretica and Their Cytotoxic Activities

Molecules ◽  
2019 ◽  
Vol 24 (15) ◽  
pp. 2767
Author(s):  
Jian Lu ◽  
Caiying Peng ◽  
Shuang Cheng ◽  
Jianqun Liu ◽  
Qinge Ma ◽  
...  
Keyword(s):  
Human Tumor ◽  
2D Nmr ◽  
Cytotoxic Activities ◽  
Aerial Parts ◽  
Pteris Cretica ◽  
Phytochemical Investigation ◽  
Hct 116 ◽  
Hct 116 Cells ◽  
New Compounds

Phytochemical investigation of the aerial parts of Pteris cretica led to the isolation and elucidation of nine pterosins, including four new pterosins, creticolacton A (1), 13-hydroxy-2(R),3(R)-pterosin L (2), creticoside A (3), and spelosin 3-O-β-d-glucopyranoside (4), together with five known pterosins 5–9. Their structures were identified mainly on the basis of 1D and 2D NMR spectral data, ESI-MS and literature comparisons. Compounds 1 and 3 were new type of petrosins with a six membered ring between C-14 and C-15. The new compounds were tested in vitro for their cytotoxic activities against four human tumor cell lines (SH-SY5Y, SGC-7901, HCT-116, Lovo). Results showed that compounds 1 and 2 exhibited cytotoxic activity against HCT-116 cells with IC50 value of 22.4 μM and 15.8 μM, respectively.

scholarly journals Cytotoxic Stilbenes and Canthinone Alkaloids from Brucea antidysenterica (Simaroubaceae)

Molecules ◽  
2019 ◽  
Vol 24 (23) ◽  
pp. 4412 ◽  
Author(s):  
Yves Salomon Makong ◽  
Gervais Mouthé Happi ◽  
Judith Liliane Djouaka Bavoua ◽  
Jean Duplex Wansi ◽  
Lutfun Nahar ◽  
...  
Keyword(s):  
Secondary Metabolites ◽  
Ethyl Acetate ◽  
Propionic Acid ◽  
2D Nmr ◽  
Spectroscopic Methods ◽  
Phytochemical Study ◽  
Methanolic Extracts ◽  
New Compounds ◽  
Soluble Fractions ◽  
Mcf 7

A phytochemical study of the root and bark of Brucea antidysenterica J. F. Mill. (Simaroubaceae) afforded three new compounds, including a stilbene glycoside bruceanoside A (1), and two canthinone alkaloids bruceacanthinones A (3) and B (4), along with ten known secondary metabolites, rhaponticin (2), 1,11-dimethoxycanthin-6-one (5), canthin-6-one (6), 1-methoxycanthin-6-one (7), 2-methoxycanthin-6-one (8), 2-hydroxy-1,11-dimethoxycanthin-6-one (9), β-carboline-1-propionic acid (10), cleomiscosin C (11), cleomiscosin A (12), and hydnocarpin (13). The structures of all the compounds were determined using spectrometric and spectroscopic methods including 1D and 2D NMR, and HRSEIMS. The identities of the known compounds were further confirmed by comparison of their data with those reported in the literature. The root and bark methanolic extracts, the dichloromethane and ethyl acetate soluble fractions, and the isolated compounds (3–13), were assessed for their cytotoxicity against the cancer cell lines A-549, MCF-7, and PC-3. The results suggested that compounds in the extracts might possess a synergic action in their cytotoxicity.

scholarly journals Two New Compounds from Artemisia sacrorum

2016 ◽  
Vol 11 (4) ◽  
pp. 1934578X1601100
Author(s):  
Qinghu Wang ◽  
Rongjun Wu ◽  
Narenchaoketu Han ◽  
Nayintai Dai ◽  
Jiesi Wu
Keyword(s):  
Structure Elucidation ◽  
2D Nmr ◽  
Etoac Extract ◽  
First Report ◽  
Esi Ms ◽  
New Compounds

Two new compounds, named as sacric acid A (1) and sacric acid B (2), were isolated from the EtOAc extract of Artemisia sacrorum Ledeb. This is the first report on the structure elucidation of these compounds based on UV, IR, and extensive 1D and 2D NMR spectroscopic, and ESI-MS techniques.

scholarly journals New Triterpene Glycosides from Camptosorus Sibiricus

2010 ◽  
Vol 5 (10) ◽  
pp. 1934578X1000501
Author(s):  
Ning Li ◽  
Wan Xiao ◽  
Bailing Hou ◽  
Xian Li
Keyword(s):  
Human Tumor ◽  
2D Nmr ◽  
Spectroscopic Methods ◽  
Tumor Cell Lines ◽  
Human Tumor Cell ◽  
Human Tumor Cell Lines ◽  
Mtt Method ◽  
Cycloartane Glycosides ◽  
New Compounds

Two new cycloartane glycosides were isolated from the whole herbs of Camptosorus sibiricus Rupr. By means of chemical and spectroscopic methods (1D and 2D NMR, HRMS, ESIMS), the structures were established as (24 R)-3β,7β,24,25,30-pentahydroxycycloartane-30- O-coumaroyl-3- O-β-D-glucopyranosyl-24- O-β-D-glucopyranosyl-(1→6)-β-D-glucopyranoside (1) and (24 R)-3β,7β,24,25,30-pentahydroxy-1-ene-cycloartane 24- O-β-D-glucopyranoside (2). The two new compounds were inactive in vitro against A375-S2 and Hela human tumor cell lines using the MTT method.

scholarly journals Three New Cytotoxic Withanolides from the Chinese Folk Medicine Physalis angulata

2015 ◽  
Vol 10 (12) ◽  
pp. 1934578X1501001 ◽  
Author(s):  
Cai-Yun Gao ◽  
Ting Ma ◽  
Jun Luo ◽  
Ling-Yi Kong
Keyword(s):  
Cell Line ◽  
Folk Medicine ◽  
2D Nmr ◽  
Cytotoxic Activities ◽  
Spectroscopic Techniques ◽  
Aerial Parts ◽  
Physalis Angulata ◽  
The Absolute ◽  
New Compounds

Physagulides M-O, three new withanolides (1–3), were isolated from the aerial parts of Physalis angulata L. Their structures were elucidated through extensive spectroscopic techniques, including 1D and 2D NMR, and HRESIMS. The absolute configurations (22- R) of these new compounds were determined by CD analysis. Compounds 1 and 3 showed significant selective cytotoxic activities on the MG-63 cell line, with IC50 values of 4.28 and 5.44 μM, respectively.

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.

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