• Title/Summary/Keyword: Cyclodepsipeptide

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Structure and Bioactivity of Boholamide A from a Tidal Mudflat Actinomycete (갯벌 방선균 유래 Boholamide A의 구조 및 생리활성에 대한 연구)

  • Seo, Jeongwon;Moon, Kyuho
    • Korean Journal of Pharmacognosy
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    • v.52 no.4
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    • pp.203-207
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    • 2021
  • LC/MS approach targeting secondary metabolites of bacterial strain resulted in the discovery of boholamide A (1), from the culture of marine actinomycete strain which was isolated from a tidal mudflat in Muan, Republic of Korea. Boholamide A (1), a cyclodepsipeptide with HDMN, APD, glycine, and valine was structurally determined by using 1D/2D NMR spectroscopy, mass spectrometry and UV spectroscopy. Boholamide A (1) showed the inhibitory activity against Bacillus subtilis, with IC50 value of 0.08 mM.

Antifungal Activity of Valinomycin, a Cyclodepsipeptide from Streptomyces padanus TH-04

  • Lim, Tae-Heon;Oh, Hyun-Cheol;Kwon, Soon-Youl;Kim, Jin-Ho;Seo, Hyo-Won;Lee, Jeong-Hun;Kim, Jin-Cheol;Lim, Chi-Hwan;Cha, Byeong-Jin;Min, Byung-Sun
    • Natural Product Sciences
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    • v.13 no.2
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    • pp.144-147
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    • 2007
  • Using antifungal activity-guided fractionation, an actinomycete, Streptomyces padanus strain TH-04, which was isolated from mummified peaches infected with Monilinia fructicola, was found to produce the valinomycin (1). The structure of 1 was established using spectroscopic data, which including one- and two-dimensional NMR experimental and mass spectroscopy. Valinomycin (1) showed antifungal activity against Phytophthora capsici, with an IC$_{50}$ value of 15.9 ${\mu}$g/mL.

Statistical Optimization of Growth Medium for the Production of the Entomopathogenic and Phytotoxic Cyclic Depsipeptide Beauvericin from Fusarium oxysporum KFCC 11363P

  • Lee, Hee-Seok;Song, Hyuk-Hwan;Ahn, Joong-Hoon;Shin, Cha-Gyun;Lee, Gung-Pyo;Lee, Chan
    • Journal of Microbiology and Biotechnology
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    • v.18 no.1
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    • pp.138-144
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    • 2008
  • The production of the entomopathogenic and phytotoxic cyclic depsipeptide beauvericin (BEA) was studied in submerged cultures of Fusarium oxysporum KFCC 11363P isolated in Korea. The influences of various factors on mycelia growth and BEA production were examined in both complete and chemically defined culture media. The mycelia growth and BEA production were highest in Fusarium defined medium. The optimal carbon and nitrogen sources for maximizing BEA production were glucose and $NaNO_3$, respectively. The carbon/nitrogen ratio for maximal production of BEA was investigated using response surface methodology (RSM). Equations derived by differentiation of the RSM model revealed that the production of BEA was maximal when using 108 mM glucose and 25 mM $NaNO_3$.

Analysis of Beauvericin and Unusual Enniatins Co-Produced by Fusarium oxysporum FB1501 (KFCC 11363P)

  • Song Hyuk-Hwan;Ahn Joong-Hoon;Lim Yoong-Ho;Lee Chan
    • Journal of Microbiology and Biotechnology
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    • v.16 no.7
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    • pp.1111-1119
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    • 2006
  • Beauvericins and enniatins are cyclohexadepsipeptides exhibiting various biological activities on animal systems, including humans. Fusarium oxysporum FB1501 (KFCC 11363P) that produces four different cyclohexadepsipeptides was isolated from soil in Korea and the structures of the four cyclohexadepsipeptides elucidated by HPLC, MS, IR, and NMR analyses. The molecular weights for compounds 1,2,3, and 4 were determined to be 654.5, 784.5, 668.6, and 682.5, respectively, on the basis of ESI-MS measurements. The IR spectra for all the compounds exhibited absorptions for ester $(1,733-1,743\;cm^{-1})$ and amide $(1,649-1,655\;cm^{-1})$ bonds that were very similar to those for beauvericin and enniatins with ester and amide absorptions. The results of the NMR analysis $(^{1}H,\;^{13}C,\;135-DEPT,\;COSY,\;HMQC,\;and\;HMBC;\;in\;COCl_{3})$ revealed that compounds 1,3, and 4 consisted of $_{L}-N-methyl\;valine$ (N-MeVal), $_{D}-{\alpha}-hydroxyisovaleic\;acid$ (Hiv), and 2-hydroxy-3-methylpentanoic acid (Hmp) residues (compound 1: three N-MeVal residues, two Hiv residues, and one Hmp residue; compound 3: three N-MeVal residues, one Hiv, and two Hmp residues; compound 4: three N-MeVal residues and three Hmp residues). Therefore, the compounds were identified as enniatin H (compound 1), enniatin I (compound 3), and enniatin MK1688 (compound 4). Compound 2 was analyzed as beauvericin according to 1D and 2D NMR analyses. This study is the first report related to the co-production of beauvericin with other unusual enniatins, such as enniatin H, enniatin I, and enniatin MK1688, by Fusarium oxysporum.