Hirsutellide A, a New Antimycobacterial Cyclohexadepsipeptide from the Entomopathogenic Fungus Hirsutella kobayasii

Vongvanich, Namphung; Kittakoop, Prasat; Isaka, Masahiko; Trakulnaleamsai, Srisuda; Vimuttipong, Saovaluk; Tanticharoen, Morakot; Thebtaranonth, Yodhathai

doi:10.1021/np020055+

Cited by 56 publications

(39 citation statements)

References 13 publications

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“…Several small and ultra-small cyclic peptides were reported to exert antimycobacterial activities, including griselmycins [28], depsidomycin [29], hytramycin [30], brunsvicamides [31], pyridomycin [32], hirsutellide A [33] and the wollamides [34]. …”

Section: Introductionmentioning

confidence: 99%

Design, synthesis and structure-activity relationship study of wollamide B; a new potential anti TB agent

et al. 2017

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Wollamide B is a cationic antimycobacterial cyclohexapeptide that exhibits activity against Mycobacterium bovis (M. bovis) (IC50 of 3.1 μM). Aiming to define its structural activity relationship (SAR), optimizing potency and pharmacokinetic properties, libraries of analogues were synthesized following a standard Fmoc-based solid phase peptide synthesis approach. The antimycobacterial activities of wollamide B and all the synthesized analogues were tested against Mycobacterium tuberculosis (Mtb) H37Rv. Parallely, in vitro drug metabolism and pharmacokinetic (ADME) profiling was done for the synthesized compounds to evaluate their drug likeness. Among the 25 synthesized wollamides five of them showed potent activities with MICs ≤ 3.1 μM and found to be nontoxic against human HepG2 cells up to 100 μM. The results of the in vitro ADME profiling revealed the remarkable plasma stability and very good aqueous solubility of the class in general while the metabolic stability was found to be moderate to low. Of particular note, compounds 7c (MIC = 1.1 μM) and 13c (0.6 μM) that exhibited good balance of antimycobacterial activity vs. optimal pharmacokinetic properties could be used as a new lead for further development.

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Section: Introductionmentioning

confidence: 99%

Design, synthesis and structure-activity relationship study of wollamide B; a new potential anti TB agent

et al. 2017

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“…Some entomogenous fungal metabolites exhibited potent antimicrobial activity. For example, epicoccin A isolated from Epicoccum nigrum showed antibacterial activity against Bacilus subtillis (Zhang et al 2007 against Mycobacterium tuberculosis H37Ra with an MIC value of 6 -12 mg/mL (Vongvanich et al 2002). Cordycommunin isolated from Ophiocordyceps communis BCC 16475, showed antimycobacterial activity against M. tuberculosis H37Ra with an MIC value of 15 mM (Haritakun et al 2010).…”

Section: Introductionmentioning

confidence: 99%

A new sesquiterpene from the entomogenous fungusPhomopsis amygdali

Wang

et al. 2015

Natural Product Research

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A new sesquiterpene, (+)-S-1-methyl-abscisic-6-acid (1), together with five known compounds, (+)-S-abscisic acid (2), fusicoccin J (3), 3α-hydroxyfusicoccin J (4), (R)-5-hydroxymethylmellein (5) and 4-hydroxyphenethyl acetate (6) was isolated from the fermentation extract of Phomopsis amygdali, an entomogenous fungus isolated from Call midge. Their structures were determined mainly by analysis of MS and NMR spectroscopic data. Compounds 1-6 were tested for antimicrobial activity against three plant pathogenic fungi: Gibberella zeae, Verticillium albo-atrum, and Fusarium nivale, and two bacteria: Escherichia coli and Pseudomonas aeruginosa 2033E. As a result, compounds 1-4 displayed antibacterial activity against Gram-negative P. aeruginosa 2033E, and the minimum inhibition concentration (MIC value) of 1-4 is 30 μg/mL, 58 μg/mL, 26 μg/mL, and 26 μg/mL, respectively.

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“…As the discovery of the didemnins, cyclic depsi‐peptides continue to stimulate active research in synthetic and medicinal chemistry, as well as clinical oncology and cell biology3. Cyclic depsi‐peptides by definition contain one or more amino acid(s) replaced by a hydroxy acid (seco‐acid) resulting in up to four ester bonds in the core ring structure4–7. These are often secondary metabolites of fungi and plants or originate from the marine environment.…”

Section: Introductionmentioning

confidence: 99%

Total synthesis of a depsidomycin analogue by convergent solid‐phase peptide synthesis and macrolactonization strategy for antitubercular activity

Venugopala

Alberício

Coovadia

et al. 2011

Journal of Peptide Science

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Depsidomycin is a cyclic heptadepsi-peptide isolated from the cultured broth of Streptomyces lavendofoliae MI951-62F2. It exhibits significant antimicrobial and immunosuppressive activity. The total synthesis of a depsidomycin analogue in which 1,2-piperazine-3-carboxylic acid was substituted with proline is described. After several trials using different strategies, the desired depsidomycin analogue was obtained via stepwise synthesis starting by the amino acid 'head' and macrolactonization under Yamaguchi conditions. The cyclic depsipeptide was evaluated to have an minimum inhibitory concentration (MIC) of 4 µg/ml against H37RV and 16 µg/ml against MDR clinical strains of MTB (MDR-MTB), while the linear precursor 8 also had MICs of 4 and 16 µg/ml for the susceptible and resistant strains, respectively.

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Hirsutellide A, a New Antimycobacterial Cyclohexadepsipeptide from the Entomopathogenic Fungus Hirsutella kobayasii

Cited by 56 publications

References 13 publications

Design, synthesis and structure-activity relationship study of wollamide B; a new potential anti TB agent

Design, synthesis and structure-activity relationship study of wollamide B; a new potential anti TB agent

A new sesquiterpene from the entomogenous fungusPhomopsis amygdali

Total synthesis of a depsidomycin analogue by convergent solid‐phase peptide synthesis and macrolactonization strategy for antitubercular activity

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