Polyketide Derivatives from Mangrove Derived Endophytic Fungus Pseudopestalotiopsis theae

Chemical investigation of secondary metabolites from the endophytic fungus Pseudopestalotiopsis theae led to the isolation of eighteen new polyketide derivatives, pestalotheols I–Q (1–9) and cytosporins O–W (15–23), together with eight known analogs (10–14 and 24–26). The structures of the new compounds were elucidated by HRMS and 1D and 2D NMR data, as well as by comparison with literature data. Modified Mosher’s method was applied to determine the absolute configuration of some compounds. Compound 23 showed significant cytotoxicity against the mouse lymphoma cell line L5178Y with an IC50 value of 3.0 μM. Furthermore, compounds 22 and 23 showed moderate antibacterial activity against drug-resistant Acinetobacter baumannii (ATCC BAA-1605) in combination with sublethal colistin concentrations.

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Pestalotiones A–D: Four New Secondary Metabolites from the Plant Endophytic Fungus Pestalotiopsis Theae

Molecules ◽

10.3390/molecules25030470 ◽

2020 ◽

Vol 25 (3) ◽

pp. 470 ◽

Cited By ~ 2

Author(s):

Longfang Guo ◽

Jie Lin ◽

Shubin Niu ◽

Shuchun Liu ◽

Ling Liu

Keyword(s):

Endophytic Fungus ◽

Diphenyl Ether ◽

2D Nmr ◽

Hela Cell Line ◽

Dpph Radical ◽

Xanthone Derivatives ◽

Ic50 Value ◽

Ic50 Values ◽

New Compounds ◽

Mcf 7

Two new xanthone derivatives, pestalotiones A (1) and B (2), one new diphenyl ketone riboside, pestalotione C (7), and one new diphenyl ether, pestalotione D (8), along with five known compounds isosulochrin dehydrate (3), 3,8-dihydroxy-6-methyl-9-oxo-9H-xanthene-1-carboxylate (4), isosulochrin (5), chloroisosulochrin (6), and pestalotether D (9), were isolated from the crude extract of the plant endophytic fungus Pestalotiopsis theae (N635). The structures of the new compounds were unambiguously deduced by HRESIMS and 1D/2D-NMR spectroscopic data. Compound 6 showed modest cytotoxicity against the HeLa cell line with an IC50 value of 35.2 μM. Compound 9 also showed cytotoxic to the HeLa and MCF-7 cell lines, with IC50 values of 60.8 and 22.6 μM, respectively. Additionally, compounds 1 and 2 exhibited antioxidant activity in scavenging DPPH radical with IC50 values of 54.2 and 59.2 μg/mL, respectively.

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Rhinoclactones A-E, Resorcylic Acid Analogs from Desert Plant Endophytic Fungus Rhinocladiella similis

Molecules ◽

10.3390/molecules24071405 ◽

2019 ◽

Vol 24 (7) ◽

pp. 1405 ◽

Cited By ~ 2

Author(s):

Luying Li ◽

Xiaoyan Zhang ◽

Xiangmei Tan ◽

Bingda Sun ◽

Bin Wu ◽

...

Keyword(s):

Endophytic Fungus ◽

Cytotoxic Activities ◽

Desert Plant ◽

Ionization Mass ◽

X Ray Diffraction ◽

Nmr Data ◽

The Common ◽

Resorcylic Acid Lactones ◽

New Compounds ◽

Modified Mosher’S Method

Seven resorcylic acid lactones (RALs) including five new analog rhinoclactones, A–E (1, 2, 4–6), were isolated from an endophytic fungus Rhinocladiella similis in the plant Agriophyllum squarrosum collected from the Tengger Desert of the Ningxia Province, China. The structures of these new compounds were determined by HR-ESI-MS (High Resolution Electrospray Ionization Mass Spectrometry), NMR data, modified Mosher’s method, and X-ray diffraction experiments. All compounds isolated from this fungus possessed the 16-OMe/14-OH, not the common 16-OH/14-OH or 16-OH/14-OMe groups on the aromatic ring, which are rarely found in nature. Compound 7 displayed cytotoxic activities against HCT116 and HeLa cancer cell lines. The possible biosynthesis of 1–7 is suggested, and the potential ecological roles of these fungal secondary metabolites is discussed.

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Chemical constituents of Chaenomeles sinensis twigs and their biological activity

Beilstein Journal of Organic Chemistry ◽

10.3762/bjoc.16.257 ◽

2020 ◽

Vol 16 ◽

pp. 3078-3085

Author(s):

Joon Min Cha ◽

Dong Hyun Kim ◽

Lalita Subedi ◽

Zahra Khan ◽

Sang Un Choi ◽

...

Keyword(s):

Biological Activity ◽

Data Analysis ◽

Cell Lines ◽

Chemical Structure ◽

Biological Effects ◽

Chemical Constituents ◽

2D Nmr ◽

Nmr Data ◽

Chaenomeles Sinensis ◽

Modified Mosher’S Method

A new megastigmane-type norsesquiterpenoid glycoside, chaemeloside (1), was isolated from the twigs of Chaenomeles sinensis together with 11 known phytochemicals through chromatographic methods. The chemical structure of the new isolate 1 was determined by conventional 1D and 2D NMR data analysis, ECD experiment, hydrolysis followed by a modified Mosher’s method, and LC–MS analysis. The characterized compounds’ biological effects including cytotoxicity against cancer cell lines, antineuroinflammatory activity, and potential neurotrophic effect were evaluated.

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α-Amylase and α-Glucosidase Inhibitory Activities of Chemical Constituents from Wedelia chinensis (Osbeck.) Merr. Leaves

Journal of Analytical Methods in Chemistry ◽

10.1155/2018/2794904 ◽

2018 ◽

Vol 2018 ◽

pp. 1-8 ◽

Cited By ~ 1

Author(s):

Nguyen Phuong Thao ◽

Pham Thanh Binh ◽

Nguyen Thi Luyen ◽

Ta Manh Hung ◽

Nguyen Hai Dang ◽

...

Keyword(s):

Spectroscopic Data ◽

Chemical Constituents ◽

2D Nmr ◽

Inhibitory Effects ◽

Meoh Extract ◽

Inhibitory Activities ◽

Isolated Compound ◽

New Compounds ◽

Modified Mosher’S Method

As part of an ongoing search for new natural products from medicinal plants to treat type 2 diabetes, two new compounds, a megastigmane sesquiterpenoid sulfonic acid (1) and a new cyclohexylethanoid derivative (2), and seven related known compounds (3–9) were isolated from the leaves of Wedelia chinensis (Osbeck.) Merr. The structures of the compounds were conducted via interpretation of their spectroscopic data (1D and 2D NMR, IR, and MS), and the absolute configurations of compound 1 were determined by the modified Mosher’s method. The MeOH extract of W. chinensis was found to inhibit α-amylase and α-glucosidase inhibitory activities as well as by the compounds isolated from this extract. Furthermore, compound 7 showed the strongest effect with IC50 values of 112.8 ± 15.1 μg/mL (against α-amylase) and 785.9 ± 12.7 μg/mL (against α-glucosidase). Compounds 1, 8, and 9 showed moderate α-amylase and α-glucosidase inhibitory effects. Other compounds showed weak or did not show any effect on both enzymes. The results suggested that the antidiabetic properties from the leaves of W. chinensis are not simply a result of each isolated compound but are due to other components such as the accessibility of polyphenolic groups to α-amylase and α-glucosidase activities.

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Juglomycins G-J: Isolation from Streptomycetes and Structure Elucidation

Zeitschrift für Naturforschung B ◽

10.1515/znb-2005-0210 ◽

2005 ◽

Vol 60 (2) ◽

pp. 183-188 ◽

Cited By ~ 8

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).

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Antimicrobial Constituents from Leaves of Dolichandrone spathacea and Their Relevance to Traditional Use

Planta Medica International Open ◽

10.1055/s-0043-125339 ◽

2018 ◽

Vol 5 (01) ◽

pp. e14-e23 ◽

Cited By ~ 1

Author(s):

Phuc-Dam Nguyen ◽

Amin Abedini ◽

Sophie Gangloff ◽

Catherine Lavaud

Keyword(s):

Antibacterial Activity ◽

Methanolic Extract ◽

Iridoid Glycosides ◽

Folk Medicine ◽

2D Nmr ◽

Antimicrobial Activities ◽

Traditional Use ◽

Triterpenoid Saponins ◽

Methoxycinnamic Acid ◽

New Compounds

AbstractFive new compounds, three iridoid glycosides (1-3) and two triterpenoid saponins (4, 5), along with thirty-two known compounds were isolated from the methanolic extract of the leaves of Dolichandrone spathacea. This traditional medicinal plant is widely used in Asia and India as antiseptic, for bronchitis and thrush treatment, and the methanolic extract has been shown to possess antibacterial activity against methicillin-resistant Staphylococcus aureus. The new iridoids were esterified derivatives of 6-ajugol and 6-catalpol, and the new saponins were glucosides of two polyhydroxy triterpenes with ursan skeleton. Their structures were elucidated by spectroscopic methods, including 1D and 2D NMR experiments and HR-ESI-MS analysis, and from comparison with the literature. This study aimed at investigating extracts and isolated compounds for their antimicrobial activities against bacterial and yeast strains, in order to validate the uses of the plant in folk medicine. The 6-O-esterified iridoids had weaker antibacterial activity; verbascoside and p-methoxycinnamic acid, the major compounds of the methanol extract, possessed strong antibacterial activity, which could account for the traditional antiseptic and anti-infectious uses of the leaves of D. spathacea.

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Methylkarranjic acid and Pongamol from Derris indica Seeds and their Antibacterial Activity

Dhaka University Journal of Pharmaceutical Sciences ◽

10.3329/dujps.v6i1.337 ◽

1970 ◽

Vol 6 (1) ◽

pp. 9-13 ◽

Cited By ~ 1

Author(s):

M Abdullahil Baki ◽

Golam Sadik ◽

KAM Shahadat Hossain Mondal ◽

M Ashilk Mosaddik ◽

M Mukhlesur Rahman

Keyword(s):

Antibacterial Activity ◽

Phenolic Compounds ◽

Soluble Fraction ◽

Ethanolic Extract ◽

2D Nmr ◽

Shigella Dysenteriae ◽

E Coli ◽

Nmr Data ◽

Test Organisms ◽

Derris Indica

Two phenolic compounds, methylkarranjic (1) acid and pongamol (2), were isolated from the petroleum ether soluble fraction of an ethanolic extract of Derris indica seeds. The structures of these compounds were confirmed by LC-MS and a series of 1D and 2D NMR data. The solvent solvent partionates of the ethanolic extract and compounds (1 and 2) exhibited moderate antibacterial activity against several test organisms. The minimum inhibitory concentrations (MICs) of 1 and 2 were found to be in the range of 32-128 μg/ml against Bacillus megatorium, Streptococcus β-haemolyticus, Shigella dysenteriae and E. coli. Key words: Derris indica; Leguminosae; Methylkarranjic acid; Pongamol; Antibacterial activity Dhaka Univ. J. Pharm. Sci. 6(1): 9-13, 2007 (June) The full text is of this article is available at the Dhaka Univ. J. Pharm. Sci. website

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Terpenes from Zingiber montanum and Their Screening against Multi-Drug Resistant and Methicillin Resistant Staphylococcus aureus

Molecules ◽

10.3390/molecules24030385 ◽

2019 ◽

Vol 24 (3) ◽

pp. 385 ◽

Cited By ~ 1

Author(s):

Holly Siddique ◽

Barbara Pendry ◽

M. Mukhlesur Rahman

Keyword(s):

Staphylococcus Aureus ◽

Antibacterial Activity ◽

Secondary Metabolites ◽

Mass Spectra ◽

Methicillin Resistant Staphylococcus Aureus ◽

Drug Resistant ◽

Two Dimensional ◽

Methicillin Resistant ◽

One Dimensional ◽

Nmr Data

Bioassay directed isolation of secondary metabolites from the rhizomes of Zingiber montanum (Fam. ‎Zingiberaceae) led to the isolation of mono-, sesqui-, and di-terpenes. The compounds were characterized as (E)-8(17),12-labdadiene-15,16-dial (1), zerumbol (2), zerumbone (3), buddledone A (4), furanodienone (5), germacrone (6), borneol (7), and camphor (8) by analysing one-dimensional (1D) (1H and 13C) and two-dimensional (2D) (COSY, HSQC, HMBC, and NOESY) NMR data and mass spectra. Among these terpenes, compounds 1 and 2 revealed potential antibacterial activity (minimum inhibitory concentrations (MIC) values 32–128 µg/mL; 0.145–0.291 mM)) against a series of clinical isolates of multi-drug resistant (MDR) and Methicillin resistant Staphylococcus aureus (MRSA).

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New Alkaloids and Polyketides from the Marine Sponge-Derived Fungus Penicillium sp. SCSIO41015

Marine Drugs ◽

10.3390/md17070398 ◽

2019 ◽

Vol 17 (7) ◽

pp. 398 ◽

Cited By ~ 1

Author(s):

Xiaoyan Pang ◽

Guodi Cai ◽

Xiuping Lin ◽

Limbadri Salendra ◽

Xuefeng Zhou ◽

...

Keyword(s):

Antibacterial Activity ◽

2D Nmr ◽

Specific Rotation ◽

Human Gastric Cancer ◽

X Ray Diffraction ◽

Gastric Cancer Cells ◽

Penicillium Sp ◽

Ic50 Value ◽

Rice Medium ◽

Weak Antibacterial Activity

The sponge-derived fungus Penicillium sp. SCSIO41015 cultured on solid rice medium yielded twenty-one compounds (1–21), including two new alkaloids (1 and 2) and one new pyrone derivative (3). Their structures were elucidated by analysis of 1D/2D NMR data and HR–ESI–MS. Their absolute configurations were established by single-crystal X-ray diffraction analysis and comparison of the experimental with reported specific rotation values. Compound 16 exhibited selective cytotoxic activity against the human gastric cancer cells MGC803, with IC50 value of 5.19 μM. Compounds 9 and 18 showed weak antibacterial activity against Staphylococcus aureus and Acinetobacter baumannii, respectively, both with MIC values of 57 μg/mL. Furthermore, compound 16 displayed potent antibacterial activity against S. aureus with an MIC value of 3.75 μg/mL.

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Phytochemical Investigation of Tradescantia Albiflora and Anti-Inflammatory Butenolide Derivatives

Molecules ◽

10.3390/molecules24183336 ◽

2019 ◽

Vol 24 (18) ◽

pp. 3336 ◽

Cited By ~ 2

Author(s):

Ping-Chen Tu ◽

Han-Chun Tseng ◽

Yu-Chia Liang ◽

Guan-Jhong Huang ◽

Te-Ling Lu ◽

...

Keyword(s):

2D Nmr ◽

Raw 264.7 Cells ◽

No Production ◽

Isolation And Characterization ◽

Whole Plant ◽

Phytochemical Investigation ◽

Ic50 Value ◽

Anti Inflammatory ◽

New Compounds ◽

First Time

Phytochemical investigation of the whole plant of Tradescantia albiflora Kunth led to the isolation and characterization of a butanolide, rosmarinosin B (1), that was isolated from natural sources for the first time, a new butenolide, 5-O-acetyl bracteanolide A (2), and a new apocarotenoid, 2β-hydroxyisololiolide (11), together with 25 known compounds (compounds 3–10 and 12–28). The structures of the new compounds were elucidated by analysis of their spectroscopic data, including MS, 1D, and 2D NMR experiments, and comparison with literature data of known compounds. Furthermore, four butenolides 4a–4d were synthesized as novel derivatives of bracteanolide A. The isolates and the synthesized derivatives were evaluated for their preliminary anti-inflammatory activity against lipopolysaccharide (LPS)-stimulated nitric oxide (NO) production in RAW 264.7 cells. Among them, the synthesized butenolide derivative n-butyl bracteanolide A (4d) showed enhanced NO inhibitory activity compared to the original compound, with an IC50 value of 4.32 ± 0.09 μg/mL.

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