Isolation and identification of secondary metabolites of Umbilicaria crustulosa (Ach.) Frey

Herein, we have studied secondary metabolites of Umbilicaria crustulosa (Ach.) Frey. By using preparative HPLC, four compounds were isolated from the U. crustulosa methanol extract. The structure of isolated lichen substances was determined on the basis of their 1H, 13C and 2D NMR spectra as follows: methyl orsellinate, lecanoric acid, methyl lecanorate and gyrophoric acid. In addition to methanol, the composition of acetone and ethanol extracts were also studied (analytical HPLC). Relative distributions (%) of the detected constituents were as follows (in methanol/acetone/ethanol extracts): methyl orsellinate (5.7/1.5/0.9), lecanoric acid (17.9/5.7/6.7), crustinic acid (8.0/2.8/2.5), methyl lecanorate (4.8/0/0) and gyrophoric acid (59.2/78.0/85.7). A significant difference in the chemical profiles of the studied extracts was in the presence/absence of methyl esters of lichen acids. Nonetheless, the chemical composition of the ethanol extracts (no ethyl esters were detected) and the fact that treatment of acetone and ethanol extracts with methanol does not lead to changes in their composition suggests that methyl esters were not artifacts of the isolation procedure. The lower content of methyl orsellinate and the absence of methyl lecanorate from acetone and ethanol extracts may be the result of different solubilities of these compounds in methanol, ethanol and acetone.

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

Molecules ◽

10.3390/molecules23112772 ◽

2018 ◽

Vol 23 (11) ◽

pp. 2772 ◽

Cited By ~ 5

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.

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Antimicrobial Secondary Metabolites from the Seawater-Derived Fungus Aspergillus sydowii SW9

Molecules ◽

10.3390/molecules24244596 ◽

2019 ◽

Vol 24 (24) ◽

pp. 4596 ◽

Cited By ~ 5

Author(s):

Yu-Jing Liu ◽

Jian-Long Zhang ◽

Chen Li ◽

Xue-Gen Mu ◽

Xiao-Li Liu ◽

...

Keyword(s):

Secondary Metabolites ◽

Pathogenic Bacteria ◽

2D Nmr ◽

Aspergillus Sydowii ◽

Isolation And Identification ◽

Spectrometric Data ◽

Lead Compounds ◽

Acid Analogue ◽

Chorismic Acid ◽

Quantum Chemical Computations

Marine-derived fungi are considered to be valuable producers of bioactive secondary metabolites used as lead compounds with medicinal importance. In this study, chemical investigation of the seawater-derived fungus Aspergillus sydowii SW9 led to the isolation and identification of one new quinazolinone alkaloid, 2-(4-hydroxybenzyl)-4-(3-acetyl)quinazolin-one (1), one new aromatic bisabolene-type sesquiterpenoid, (2) and one new chorismic acid analogue (3), as well as two known alkaloids (compounds 4 and 5). Their structures were determined by extensive 1D/2D NMR and mass spectrometric data, and the absolute configurations of 2 and 3 were assigned by the analysis of ECD spectra aided by quantum chemical computations. Compounds 1, 2, and 4 exhibited selective inhibitory activities against the human pathogenic bacteria Escherichia coli, Staphylococcus aureus, S. epidermidis, and Streptococcus pneumoniae, with MIC values ranging from 2.0 to 16 μg/mL.

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A New Colchicinoid from Colchicum tauri, an Unexplored Meadow Saffron Native to Jordan

Natural Product Communications ◽

10.1177/1934578x0600100203 ◽

2006 ◽

Vol 1 (2) ◽

pp. 1934578X0600100 ◽

Cited By ~ 3

Author(s):

Feras Q. Alali ◽

Amani S. Ma'aya'h ◽

Ahmad Alkofahi ◽

Amjad Qandil ◽

Chen Li ◽

...

Keyword(s):

Brine Shrimp ◽

2D Nmr ◽

Biological Evaluation ◽

Preparative Hplc ◽

Low Resolution ◽

Isolation And Identification ◽

Brine Shrimp Lethality ◽

Chromatographic Techniques ◽

General Toxicity ◽

First Time

This study reports the isolation, characterization, and biological evaluation of constituents of Colchicum tauri Siehe ex Stef. (Colchicaceae), an unexplored Colchicum species native to Jordan. Methanolic extraction, crude alkaloid fractionation, and separation using several different chromatographic techniques (open columns, preparative TLC, and semi-preparative HPLC), as directed by the brine shrimp lethality test (BST), resulted in the isolation and identification of nine compounds: (-)-colchicine (1), (-)-2-demethylcolchicine (2), (-)-3-demethylcolchicine (3), (-)-demecolcine (4), (-)- N-methyldemecolcine (5), (-)-3-demethyl- N-methyldemecolcine (6), β-lumicolchicine (7), 3-demethyl-β-lumicolchicine (8), and apigenin (9). Compounds 1–5 and 7–8 were isolated for the first time from this species, while compound (6) represents a new colchicinoid. The structure elucidations were achieved using a series of spectroscopic and spectrometric techniques, principally 1D-NMR (1H, and 13C), 2D-NMR (COSY, ROESY, HMBC, and HSQC), and low resolution EI-MS. All compounds were tested for general toxicity using the BST, and compounds 1 and 4 were found to be the most potent, with LC50 values of 2.5 and 8.1 μg/mL, respectively.

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CPC driven isolation and identification of Pistacia vera pericarp secondary metabolites: New source of rare and biologically active triterpenic acids

10.1055/s-0037-1608275 ◽

2017 ◽

Author(s):

J Popp ◽

E Petrakis ◽

A Angelis ◽

I Pisimisi ◽

M Halabalaki ◽

...

Keyword(s):

Secondary Metabolites ◽

Biologically Active ◽

Pistacia Vera ◽

Isolation And Identification ◽

Triterpenic Acids

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Effects of Saccharomyces Cerevisiae Strains on Chemical Profiles of Cabernet Sauvignon Wines: Based on the Combined Results of 1H NMR, HS-SPME/GC-MS and HPLC-DAD-ESI-MS/MS

Current Topics in Nutraceutical Research ◽

10.37290/ctnr2641-452x.18:115-131 ◽

2018 ◽

Vol 18 (2) ◽

pp. 115-131

Author(s):

Liang Heng-Yu ◽

Su Ning ◽

Guo Kun ◽

Wang Yuan ◽

Yang De-Yu

Keyword(s):

Saccharomyces Cerevisiae ◽

Principal Component ◽

Grape Juice ◽

Pilot Scale ◽

Ethyl Esters ◽

Cabernet Sauvignon ◽

Esi Ms ◽

H Nmr ◽

Chemical Profiles ◽

Indigenous Yeasts

Five Saccharomyces cerevisiae strains (Chinese indigenous yeasts SC5, WC5, SC8, CC17 and commercial starter F15) were inoculated into Cabernet sauvignon grape must and fermented at pilot scale. For the first time, combination of 1H NMR, HS-SPME/GC-MS and HPLC-DAD-ESI-MS/MS metabonomic profiling techniques was performed to analyze the global chemical fingerprints of sampled wines at the end of alcoholic and malolactic fermentation respectively, then 13 non-volatile flavor compounds, 52 volatile organic aromas and 43 polyphenolic molecules were identified and determined correspondently. All principal component analysis (PCA) of two fermentation stages based on the analytical results of 1H NMR, HS-SPME/GC-MS and HPLC-DAD-ESI-MS/MS divided these strains into three clusters: (1) SC5 and SC8, (2) WC5 and F15 and (3) CC17. The wine fermented by indigenous yeast, CC17, showed a very unique chemical profile, such as low pH and high color intensity, reduced amino acids (including proline) and the lowest total higher alcohols levels, most of the fixed acids, glycerol, ethyl esters and anthocyanins concentrations. The statistical results indicate that CC17 strain possesses very special anabolism and catabolism abilities on such substances in grape juice and has potentiality to produce characteristic wines with high qualities.

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A Cytotoxic Natural Product from Patrinia villosa Juss

Anti-Cancer Agents in Medicinal Chemistry ◽

10.2174/1871520619666190416101014 ◽

2019 ◽

Vol 19 (11) ◽

pp. 1399-1404 ◽

Cited By ~ 1

Author(s):

Yangcheng Liu ◽

Wei Liu ◽

Changlan Chen ◽

Zheng Xiang ◽

Hongwei Liu

Keyword(s):

Cell Cycle ◽

Cell Lines ◽

Silica Gel ◽

Column Chromatography ◽

Bioactive Compound ◽

Antitumor Agent ◽

2D Nmr ◽

Preparative Hplc ◽

Dependent Manner ◽

2D Nmr Spectra

Background and Purpose:: Patrinia villosa Juss is an important Chinese herbal medicine widely used for thousands of years, but few reports on the ingredients of the herb have been presented. In this study, we aim to isolate the bioactive compound from the plant. Material and Methods:: The air-dried leaves of P. villosa (15kg) were extracted three times with 70% EtOH under reflux. The condensed extract was suspended in H2O and partitioned with light petroleum, dichloromethane and n-BuOH. The dichloromethane portion was then subjected to normal-phase silica gel column chromatography, ODS silica gel column chromatography and semi-preparative HPLC to yield compound 1. Cytotoxicities of 1 were assayed on HepG2, A549 and A2780 cell lines. The mechanism of apoptosis and cell cycle on A549 was confirmed subsequently. Results: A new impecylone (Impecylone A) was isolated from the leaves of Patrinia villosa Juss, and its structures were established using 1D, 2D-NMR spectra and HR-ESI-MS. Impecylone A could selectivity inhibit HepG2 and A549 cell lines. The compound could induce apoptosis of A549 and arrest the cell cycle at G2/M phase in a dose-dependent manner. Conclusion: Impecylone A is a novel compound from Patrinia villosa Juss and could be a potential antitumor agent especially in the cell lines of A549.

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Phytochemical Fingerprinting and In Vitro Antimicrobial and Antioxidant Activity of the Aerial Parts of Thymus marschallianus Willd. and Thymus seravschanicus Klokov Growing Widely in Southern Kazakhstan

Molecules ◽

10.3390/molecules26113193 ◽

2021 ◽

Vol 26 (11) ◽

pp. 3193

Author(s):

Bagda Sagynaikyzy Zhumakanova ◽

Izabela Korona-Głowniak ◽

Krystyna Skalicka-Woźniak ◽

Agnieszka Ludwiczuk ◽

Tomasz Baj ◽

...

Keyword(s):

Antioxidant Activity ◽

Protocatechuic Acid ◽

Antioxidant Activities ◽

Methyl Esters ◽

Bactericidal Effect ◽

Ethyl Esters ◽

Volatile Fraction ◽

Aerial Parts ◽

Antimicrobial And Antioxidant Activity

The chemical composition of the hydroethanolic extracts (60% v/v) from the aerial parts of Thymus marschallianus Willd (TM) and Thymus seravschanicus Klokov (TS) from Southern Kazakhstan flora was analyzed together with their hexane fractions. Determination of antibacterial, antifungal and antioxidant activities of both extracts was also performed. RP-HPLC/PDA and HPLC/ESI-QTOF-MS showed that there were some differences between the composition of both extracts. The most characteristic components of TM were rosmarinic acid, protocatechuic acid, luteolin 7-O-glucoside, and apigenin 7-O-glucuronide, while protocatechuic acid, luteolin 7-O-glucoside, luteolin 7-O-glucuronide, and eriodictyol predominated in TS. The content of polyplenols was higher in TS than in TM. The GC-MS analysis of the volatile fraction of both examined extracts revealed the presence of thymol and carvacrol. Additionally, sesquiterpenoids, fatty acids, and their ethyl esters were found in TM, and fatty acid methyl esters in TS. The antioxidant activity of both extracts was similar. The antibacterial activity of TS extract was somewhat higher than TM, while antifungal activity was the same. TS extract was the most active against Helicobacter pylori ATCC 43504 with MIC (minimal inhibitory concentration) = 0.625 mg/mL, exerting a bactericidal effect. The obtained data provide novel information about the phytochemistry of both thyme species and suggest new potential application of TS as a source of bioactive compounds, especially with anti-H. pylori activity.

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Metabolomic analysis reveals the interaction of primary and secondary metabolism in white, pale green, and green pak choi (Brassica rapa subsp. chinensis)

Applied Biological Chemistry ◽

10.1186/s13765-020-00574-2 ◽

2021 ◽

Vol 64 (1) ◽

Author(s):

Hyeon Ji Yeo ◽

Seung-A Baek ◽

Ramaraj Sathasivam ◽

Jae Kwang Kim ◽

Sang Un Park

Keyword(s):

Secondary Metabolites ◽

Brassica Rapa ◽

High Performance ◽

Reducing Power ◽

Total Phenolic ◽

Pak Choi ◽

Primary And Secondary Metabolites ◽

Chlorophyll Contents ◽

Significant Difference ◽

Pale Green

AbstractThis study aimed to comprehensively analyze primary and secondary metabolites of three different-colored (white, pale green, and green) pak choi cultivars (Brassica rapa subsp. chinensis) using gas chromatography attached with time-of-flight mass spectrometry (GC-TOFMS) and high-performance liquid chromatography (HPLC). In total, 53 primary metabolites were identified and subjected to partial least-squares discriminant analysis. The result revealed a significant difference in the primary and secondary metabolites between the three pak choi cultivars. In addition, 49 hydrophilic metabolites were detected in different cultivars. Total phenolic and glucosinolate contents were highest in the pale green and green cultivars, respectively, whereas total carotenoid and chlorophyll contents were highest in the white cultivar. Superoxide dismutase activity, 2,2-diphenyl-1-picrylhydraz scavenging, and reducing power were slightly increased in the white, pale green, and green cultivars, respectively. In addition, a negative correlation between pigments and phenylpropanoids was discovered by metabolite correlation analysis. This approach will provide useful information for the development of strategies to enhance the biosynthesis of phenolics, glucosinolates, carotenoids, and chlorophyll, and to improve antioxidant activity in pak choi cultivars. In addition, this study supports the use of HPLC and GC-TOFMS-based metabolite profiling to explore differences in pak choi cultivars.

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Secondary Metabolites with Nitric Oxide Inhibition from Marine-Derived Fungus Alternaria sp. 5102

Marine Drugs ◽

10.3390/md18080426 ◽

2020 ◽

Vol 18 (8) ◽

pp. 426 ◽

Cited By ~ 1

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.

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NEW FLAVONOIDS FROM THE AERIAL PARTS OF POLYGONUM EQUISETIFORME SM (POLYGONACEAE)

International Journal of Pharmacy and Pharmaceutical Sciences ◽

10.22159/ijpps.2017v9i2.15593 ◽

2017 ◽

Vol 9 (2) ◽

pp. 166 ◽

Cited By ~ 2

Author(s):

Sayed A. El-toumy ◽

Joslin Y. Salib ◽

Nabila H. Shafik ◽

Asmaa S. Abd Elkarim ◽

Gihan A. Mick

Keyword(s):

Antioxidant Activity ◽

Methyl Ester ◽

Secondary Metabolites ◽

Gallic Acid ◽

Total Phenolic ◽

Flavonoid Content ◽

Isolation And Identification ◽

Aerial Parts ◽

Dpph Method ◽

Phenolic And Flavonoid

Objective: The current study was to deal the isolation and identification of secondary metabolites from Polygonum equisetiforme and evaluation of antioxidant activity of its extract.Methods: The methanol-water extract (7:3) of the air-dried aerial parts of Polygonum equisetiforme was fractionated and separated to obtain the isolated compounds by different chromatographic techniques. Structures of these compounds were elucidated by UV and 1D⁄2D H⁄ C NMR spectroscopy and compared with the literature data. The crude extract was evaluated for in vitro antioxidant activity using the 2,2 diphenyl dipicryl hydrazine (DPPH) method.Results: Ten secondary metabolites were isolated from Polygonum equisetiforme in this study. Of which three new flavonoids named as 3,5,7,2’,5’ pentahydroxyflavone 3-O-b-D-glucopyranoside (1), 3,5,7,2’,5’ pentahydroxyflavone 3-O-b-D-glucopyranoside 8 C-sulphated (2) and quercetin 3-O-β-D-glucucorinde 6''-methyl ester 8-sulphated (3) as well as quercetin 3-O-β-D-glucucorinde methyl ester (4), quercetin 3-O-β-D-glucopyranoside (5), quercetin 7-O-β-D-glucopyranoside (6), quercetin(7), myricetin (8), P-methoxy gallic acid methyl ester (9) and gallic acid (10). The antioxidant potential of P. equisetiforme extract was evaluated by investigating it's total phenolic and flavonoid content and DPPH radical scavenging activity whereby the extract showed significant antioxidant activity (IC50 = 37.45 μg/ml). The total phenolic and flavonoid content was found to be 130.79±5.502 and 45.8±1.63 μg/ml, respectively.Conclusion: Polygonum equisetiforme is a promising medicinal plant, and our study tends to support the therapeutic value of this plant as an antioxidant drug.

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