scholarly journals Secondary Metabolites with Antimycobacterial Activities from One Actinobacteria: Herbidospora yilanensis

Molecules ◽  
2021 ◽  
Vol 26 (20) ◽  
pp. 6236
Author(s):  
Ming-Jen Cheng ◽  
Ming-Der Wu ◽  
Jih-Jung Chen ◽  
Yung-Shun Su ◽  
Yueh-Hsiung Kuo
Keyword(s):  
Mass Spectrometry ◽  
Secondary Metabolites ◽  
2D Nmr ◽  
Sediment Samples ◽  
Spectroscopic Analyses ◽  
First Time

The cultivation of one actinobacteria strain, Herbidospora yilanensis, was isolated from sediment samples collected from Yilan County City in Taiwan, resulting in the isolation of five previously undescribed compounds: herbidosporayilanensins A–E (1–5), and four compounds isolated from nature for the first time: herbidosporayilanensins F–I (6–9). Their structures were elucidated by spectroscopic analyses, including 1D- and 2D-NMR experiments with those of known analogues, and on the basis of HR-EI-MS mass spectrometry, their antimycobacterial activities were also evaluated.

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 Studies on the Chemical Diversities of Secondary Metabolites Produced by Neosartorya fischeri via the OSMAC Method

Molecules ◽  
2018 ◽  
Vol 23 (11) ◽  
pp. 2772 ◽  
Author(s):  
You-Min Ying ◽  
Lu Huang ◽  
Ting Tian ◽  
Cui-Yu Li ◽  
Shi-Lei Wang ◽  
...  
Keyword(s):  
Secondary Metabolites ◽  
Cancer Cell Line ◽  
2D Nmr ◽  
Natural Occurrence ◽  
Fungal Metabolites ◽  
Isolation And Identification ◽  
Late Step ◽  
Neosartorya Fischeri ◽  
The One ◽  
First Time

The One Strain Many Compounds (OSMAC) method was applied to explore the chemical diversities of secondary metabolites produced by Neosartorya fischeri NRRL 181. Four pyripyropenes 1–4, eight steroids 5–11, and four prenylated indole alkaloids 12–15, were obtained from the fungus cultured in petri dishes containing potato dextrose agar (PDA). 1,7,11-trideacetylpyripyropene A (1) and 1,11-dideacetyl pyripyropene A (2) were obtained and spectroscopically characterized (1D, 2D NMR, and HR-ESI-MS) from a natural source for the first time. It offered a sustainable source of these two compounds, which were usually used as starting materials in preparing pyripyropene derivatives. In addition, as compared with all the other naturally occurring pyripyropenes, 1 and 2 possessed unique acetylation patterns that did not follow the established late-step biosynthetic rules of pyripyropenes. The natural occurrence of 1 and 2 in the fungus implied that the timing and order of hydroxylation and acetylation in the late-step biosynthetic pathway of pyripyropenes remained to be revealed. The isolation and identification of 1–15 indicated that the OSMAC method could remarkably alter the metabolic profile and enrich the chemical diversities of fungal metabolites. Compounds 1–4 exhibited no obvious cytotoxicity against the triple-negative breast cancer cell line MDA-MB-231 as compared with taxol.

scholarly journals tert-Butylphenolic Derivatives from Paenibacillus odorifer—A Case of Bioconversion

Molecules ◽  
2018 ◽  
Vol 23 (8) ◽  
pp. 1951 ◽  
Author(s):  
Thi-Bach-Le Nguyen ◽  
Olivier Delalande ◽  
Isabelle Rouaud ◽  
Solenn Ferron ◽  
Laura Chaillot ◽  
...  
Keyword(s):  
Bacterial Strain ◽  
2D Nmr ◽  
One Dimensional ◽  
Spectroscopic Analyses ◽  
Human Keratinocyte ◽  
Rhizocarpon Geographicum ◽  
Ionisation Mass Spectrometry ◽  
Keratinocyte Cell ◽  
Ic50 Values ◽  
First Time

Two compounds (1) and (2) containing tert-butylphenol groups were, for the first time, produced during the culture of Paenibacillus odorifer, a bacterial strain associated with the crustose lichen, Rhizocarpon geographicum. Their entire structures were identified by one-dimensional (1D) and two-dimensional (2D) NMR and high-resolution electrospray ionisation mass spectrometry (HRESIMS) spectroscopic analyses. Among them, Compound 1 exhibited significant cytotoxicity against B16 murine melanoma and HaCaT human keratinocyte cell lines with micromolar half maximal inhibitory concentration (IC50) values. Furthermore, after supplementation studies, a putative biosynthesis pathway was proposed for Compound 1 throughout a bioconversion by this bacterial strain of butylated hydroxyanisole (BHA), an antioxidant polymer additive.

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 Lanostane-Type Saponins from Vitaliana primuliflora

Molecules ◽  
2019 ◽  
Vol 24 (8) ◽  
pp. 1606 ◽  
Author(s):  
Włodarczyk ◽  
Szumny ◽  
Gleńsk
Keyword(s):  
Mass Spectrometry ◽  
High Resolution Mass Spectrometry ◽  
2D Nmr ◽  
Resonance Spectroscopy ◽  
Tandem Mass ◽  
Triterpenoid Saponins ◽  
The Family ◽  
Chemotaxonomic Markers ◽  
First Time

The phytochemistry of the genera Androsace, Cortusa, Soldanella, and Vitaliana, belonging to the Primulaceae family is not well studied so far. Hence, in this paper, we present the results of UHPLC-MS/MS analysis of several primrose family members as well as isolation and structure determination of two new saponins from Vitaliana primuliflora subsp. praetutiana. These two nor-triterpenoid saponins were characterized as (23S)-17α,23-epoxy-29-hydroxy-3β-[(O-β-d-glucopyranosyl-(1→2)-O-α-l-rhamnopyranosyl-(1→2)-O-β-d-glucopyranosyl-(1→2)-O-α-l-arabinopyranosyl-(1→6)-β-d-glucopyranosyl)oxy]-27-nor-lanost-8-en-25-one and (23S)-17α,23-epoxy-29-hydroxy-3β-[(O-α-l-rhamnopyranosyl-(1→2)-O-β-d-glucopyranosyl-(1→2)-O-α-l-arabinopyranosyl-(1→6)-β-d-glucopyranosyl)oxy]-27-nor-lanost-8-en-25-one, respectively. Their structures were determined by high resolution mass spectrometry (HRMS), tandem mass spectrometry (MS/MS), one- and two-dimensional nuclear magnetic resonance spectroscopy (1D-, and 2D-NMR) analyses. So far, the 27-nor-lanostane monodesmosides were rarely found in dicotyledon plants. Therefore their presence in Vitaliana and also in Androsace species belonging to the Aretia section is unique and reported here for the first time. Additionally, eleven other saponins were determined by HRMS and MS/MS spectra. The isolated lanostane saponins can be considered as chemotaxonomic markers of the family Primulaceae.

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 Spirostane-type Saponins from Dracaena fragrans « Yellow Coast »

2015 ◽  
Vol 10 (1) ◽  
pp. 1934578X1501000
Author(s):  
Abdelmalek Rezgui ◽  
Anne-Claire Mitaine-Offer ◽  
Tomofumi Miyamoto ◽  
Chiaki Tanaka ◽  
Marie-Aleth Lacaille-Dubois
Keyword(s):  
Mass Spectrometry ◽  
2D Nmr ◽  
Steroidal Glycosides ◽  
Nmr Data ◽  
First Time

Three steroidal glycosides were isolated from the bark of Dracaena fragrans (L.) Ker Gawl. « Yellow Coast », and a fourth from the roots and the leaves. Their structures were characterized on the basis of extensive 1D and 2D NMR experiments and mass spectrometry, and by comparison with NMR data of the literature. These saponins have the spirostane-type skeleton and are reported in this species for the first time.

Chemical constituents of the stem bark of Acacia AuriculiformisA.Cunn ex. Benth. (fabaceae)

2020 ◽  
Vol 23 ◽  
pp. 88-91
Author(s):  
A.A. Ahmadu ◽  
B.A. Lawal ◽  
B. Olanipekun ◽  
A. Udobre ◽  
N. Tsafantakis ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Secondary Metabolites ◽  
Acid Ester ◽  
Spectroscopic Analysis ◽  
Chemical Constituents ◽  
Stem Bark ◽  
Acacia Auriculiformis ◽  
Compound I ◽  
Literature Report ◽  
First Time

The genus Acacia has been known to be a rich source of many secondary metabolites. This study was carried to isolate chemical constituents present in the stem bark of Acacia auriculiformis. The dichloromethane extract of the stem bark of Acacia auriculiformis was obtained by maceration. The extract obtained was subjected to silica gel column chromatography and preparative TLC. The isolated compounds were identified by spectroscopic analysis. This led to the isolation of ferulic acid ester (I), along with a steroid (II) and a triterpenoid (III). The structure of compound I was established using spectroscopic analysis (UV, IR, NMR and mass spectrometry) and identified to be dodecyl-4-hydroxy-3-methoxy-trans-cinnamate (I), compounds II and III were found to be á-spinasterol and lupenol respectively, based on the comparison of their spectral data NMR and MS with literature report. Compound I is being reported for the first time in the genus Acacia.

Structural Studies of Chelirubine and Chelilutine Free Bases

1998 ◽  
Vol 63 (7) ◽  
pp. 1045-1055 ◽  
Author(s):  
Jiří Dostál ◽  
Jiří Slavík ◽  
Milan Potáček ◽  
Radek Marek ◽  
Otakar Humpa ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Nmr Spectroscopy ◽  
Quantum Chemical ◽  
2D Nmr ◽  
Molecular Symmetry ◽  
Structural Studies ◽  
Free Base ◽  
2D Nmr Spectroscopy ◽  
Sanguinaria Canadensis ◽  
First Time

The structures of chelirubine and chelilutine free bases have been examined by 2D NMR spectroscopy and mass spectrometry. Chelirubine chloride (1a) upon treatment with Na2CO3 yielded free base which possessed the constitution of bis(5,6-dihydrochelirubin-6-yl) ether (2a). The free base of chelilutine (1b) was determined to be bis(5,6-dihydrochelilutin-6-yl) ether (2b). The aqueous NH3 treatment of chelilutine (1b) produced bis(5,6-dihydrochelilutin-6-yl)amine (3b). 6-Hydroxy-5,6-dihydrochelirubine (4a) and 6-hydroxy-5,6-dihydrochelilutine (4b) were detected only in CDCl3 solution by NMR spectroscopy. In CDCl3, the compound 2b underwent hydrolysis to 4b that was immediately followed by the reverse condensation to a diastereomer of 2b. Pseudokinetics of this reaction was followed by NMR spectroscopy and quantum chemical calculations were carried out to support the suggested type of molecular symmetry alteration. The known alkaloid dihydrochelirubine (5) was isolated for the first time from Sanguinaria canadensis.

scholarly journals Two New Cyclopeptides and One New Nonenolide from Xylaria sp. 101

2011 ◽  
Vol 6 (12) ◽  
pp. 1934578X1100601
Author(s):  
Yao-Yao Li ◽  
Zhi-Yu Hu ◽  
Yue-Mao Shen
Keyword(s):  
Mass Spectrometry ◽  
Fruiting Body ◽  
Yunnan Province ◽  
2D Nmr ◽  
Fungal Strain ◽  
Chemical Structures ◽  
Spectroscopic Analyses

Two novel cyclopeptides, xylarotides A (1), and B (2), and one novel nonenolide, xylarolide (3), along with two known compounds, coriloxin (4), and 2-hydroxy-3-methoxy-5-methyl- p-benzoquinone (5) were isolated from the fungal strain Xylaria sp. 101. This strain was isolated from the fruiting body of Xylaria sp. collected in Gaoligong Mountain, Yunnan Province. The chemical structures were elucidated by spectroscopic analyses, including 1D- and 2D-NMR spectroscopic experiments, and on the basis of HR-Q-TOF mass spectrometry. Antibacterial assays of 1 - 3 were carried out; no effects on the growth of the tested bacteria and yeast were observed.

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