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Secondary metabolites from the endophytic Botryosphaeria dothidea of Melia azedarach and their antifungal, antibacterial, antioxidant, and cytotoxic activities.
J Agric Food Chem. 2014 Apr 23; 62(16):3584-90.JA

Abstract

Two new metabolites, an α-pyridone derivative, 3-hydroxy-2-methoxy-5-methylpyridin-2(1H)-one (1), and a ceramide derivative, 3-hydroxy-N-(1-hydroxy-3-methylpentan-2-yl)-5-oxohexanamide (2), and a new natural product, 3-hydroxy-N-(1-hydroxy-4-methylpentan-2-yl)-5-oxohexanamide (3), along with 15 known compounds including chaetoglobosin C (7) and chaetoglobosin F (8) were isolated from the solid culture of the endophytic fungus Botryosphaeria dothidea KJ-1, collected from the stems of white cedar (Melia azedarach L). The structures were elucidated on the basis of spectroscopic analysis (1D and 2D NMR experiments and by mass spectrometric measurements), and the structure of 1 was confirmed by X-ray single-crystal diffraction. These metabolites were evaluated in vitro for antimicrobial, antioxidant, and cytotoxicity activities. Pycnophorin (4) significantly inhibited the growth of Bacillus subtilis and Staphyloccocus aureus with equal minimum inhibitory concentration (MIC) values of 25 μM. Stemphyperylenol (5) displayed a potent antifungal activity against the plant pathogen Alternaria solani with MIC of 1.57 μM comparable to the commonly used fungicide carbendazim. Both altenusin (9) and djalonensone (10) showed markedly DPPH radical scavenging activities. In addition, stemphyperylenol (5) and altenuene (6) exhibited strong cytotoxicity against HCT116 cancer cell line with a median inhibitory concentration (IC50) value of 3.13 μM in comparison with the positive control etoposide (IC50 = 2.13 μM). This is the first report of the isolation of these compounds from the endophytic B. dothidea.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Xiao J
Shaanxi Engineering Center of Bioresource Chemistry and Sustainable Utilization, College of Science, Northwest A&F University , Yangling 712100, Shaanxi China.
Zhang Q
No affiliation info available
Gao YQ
No affiliation info available
Tang JJ
No affiliation info available
Zhang AL
No affiliation info available
Gao JM
No affiliation info available

MeSH

Anti-Bacterial AgentsAntioxidantsAscomycotaBacteriaCell Line, TumorCytotoxinsEndophytesFungiFungicides, IndustrialHumansMelia azedarachMicrobial Sensitivity TestsSecondary Metabolism

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

24689437

Citation

Xiao, Jian, et al. "Secondary Metabolites From the Endophytic Botryosphaeria Dothidea of Melia Azedarach and Their Antifungal, Antibacterial, Antioxidant, and Cytotoxic Activities." Journal of Agricultural and Food Chemistry, vol. 62, no. 16, 2014, pp. 3584-90.
Xiao J, Zhang Q, Gao YQ, et al. Secondary metabolites from the endophytic Botryosphaeria dothidea of Melia azedarach and their antifungal, antibacterial, antioxidant, and cytotoxic activities. J Agric Food Chem. 2014;62(16):3584-90.
Xiao, J., Zhang, Q., Gao, Y. Q., Tang, J. J., Zhang, A. L., & Gao, J. M. (2014). Secondary metabolites from the endophytic Botryosphaeria dothidea of Melia azedarach and their antifungal, antibacterial, antioxidant, and cytotoxic activities. Journal of Agricultural and Food Chemistry, 62(16), 3584-90. https://doi.org/10.1021/jf500054f
Xiao J, et al. Secondary Metabolites From the Endophytic Botryosphaeria Dothidea of Melia Azedarach and Their Antifungal, Antibacterial, Antioxidant, and Cytotoxic Activities. J Agric Food Chem. 2014 Apr 23;62(16):3584-90. PubMed PMID: 24689437.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Secondary metabolites from the endophytic Botryosphaeria dothidea of Melia azedarach and their antifungal, antibacterial, antioxidant, and cytotoxic activities. AU - Xiao,Jian, AU - Zhang,Qiang, AU - Gao,Yu-Qi, AU - Tang,Jiang-Jiang, AU - Zhang,An-Ling, AU - Gao,Jin-Ming, Y1 - 2014/04/09/ PY - 2014/4/3/entrez PY - 2014/4/3/pubmed PY - 2014/10/1/medline SP - 3584 EP - 90 JF - Journal of agricultural and food chemistry JO - J Agric Food Chem VL - 62 IS - 16 N2 - Two new metabolites, an α-pyridone derivative, 3-hydroxy-2-methoxy-5-methylpyridin-2(1H)-one (1), and a ceramide derivative, 3-hydroxy-N-(1-hydroxy-3-methylpentan-2-yl)-5-oxohexanamide (2), and a new natural product, 3-hydroxy-N-(1-hydroxy-4-methylpentan-2-yl)-5-oxohexanamide (3), along with 15 known compounds including chaetoglobosin C (7) and chaetoglobosin F (8) were isolated from the solid culture of the endophytic fungus Botryosphaeria dothidea KJ-1, collected from the stems of white cedar (Melia azedarach L). The structures were elucidated on the basis of spectroscopic analysis (1D and 2D NMR experiments and by mass spectrometric measurements), and the structure of 1 was confirmed by X-ray single-crystal diffraction. These metabolites were evaluated in vitro for antimicrobial, antioxidant, and cytotoxicity activities. Pycnophorin (4) significantly inhibited the growth of Bacillus subtilis and Staphyloccocus aureus with equal minimum inhibitory concentration (MIC) values of 25 μM. Stemphyperylenol (5) displayed a potent antifungal activity against the plant pathogen Alternaria solani with MIC of 1.57 μM comparable to the commonly used fungicide carbendazim. Both altenusin (9) and djalonensone (10) showed markedly DPPH radical scavenging activities. In addition, stemphyperylenol (5) and altenuene (6) exhibited strong cytotoxicity against HCT116 cancer cell line with a median inhibitory concentration (IC50) value of 3.13 μM in comparison with the positive control etoposide (IC50 = 2.13 μM). This is the first report of the isolation of these compounds from the endophytic B. dothidea. SN - 1520-5118 UR - https://www.unboundmedicine.com/medline/citation/24689437/Secondary_metabolites_from_the_endophytic_Botryosphaeria_dothidea_of_Melia_azedarach_and_their_antifungal_antibacterial_antioxidant_and_cytotoxic_activities_ DB - PRIME DP - Unbound Medicine ER -