An Antimycobacterial Cyclodepsipeptide from the Entomopathogenic Fungus Ophiocordyceps communis BCC 16475

Abstract

A novel cyclodepsipeptide, cordycommunin (1), and two dihydroisocoumarins (2 and 3) were isolated from the insect pathogenic fungus Ophiocordyceps communis BCC 16475. The absolute configurations of the amino acid residues of 1 were addressed by application of Marfey's method. Cordycommunin (1) showed growth inhibition of Mycobacterium tuberculosis H37Ra with an MIC value of 15 microM. This compound also exhibited weak cytotoxicity to KB cells with an IC50 of 45 microM, while it was inactive against BC, NCI-H187, and Vero cell lines at a concentration of 88 microM (50 microg/mL).

A new sesquiterpene from the entomogenous fungusPhomopsis amygdali

“…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). Dustanin and 3b-acetoxy-15a, 22-dihydroxyhopane isolated from Aschersonia tubulata showed antimycobacterial activity with an MIC value of 12.5 mg/mL (Boonphong et al 2001).…”

Cyclic lipodepsipeptides verlamelin A and B, isolated from entomopathogenic fungus Lecanicillium sp.

“…The remaining substructure was deduced to be a 5-hydroxytetradecanoic acid moiety by comparison of the dc values of C-2 to C-6 with those on cordycommunin, which has the 5-hydroxytetradecanoic acid substructure. 14 As d H of the oxymethine H-5 was detected relatively downfield (4.79 (1), 4.77 (2)), the C-5 was judged to be involved in ester bonding. The connecting sequence of components was finally determined as 5-hydroxytetradecanoic acid, Thr (1) or Ser (2), Ala, Pro, Gln, Tyr and Val, based on HMBC and ROESY (1) and NOESY (2) correlation.…”

“…The related compounds, W493 A/B, cyclo(3S-hydroxy-4R-methyltetradecanoic acid-D-alloThr-L-Ala-D-Ala-L-Gln-D-Tyr-L-Val/Ile), from Fusarium sp., 18 and cordycommunin, cyclo(5-hydroxytetradecanoic acid-D-alloThr-L-Ala-L-Ala-L-Gln-L-Tyr-L-Val), from Ophiocordyceps communis, 14 have also similar partial structure to fengycin (plilastatin A1, inhibitor of phospholipase A 2 ), which was isolated from Bacillus subtilis as an antifungal lipopeptide compound containing a cyclic peptide moiety composed of L-Tyr-D-alloThr-L-Glu-D-Ala-L-Pro-LGln-D-Tyr-L-Ile. 19,20 Judging from the correlation of the structure …”

“…Stereochemical structure of verlamelin A (1) and B (2), refined in this study. antifungal activity among these cyclic peptide compounds, D-tyrosine after L-glutamine might be critical for antifungal activities because cordycommunin, which possesses L-Tyr instead of D-Tyr, did not show activity against Candida albicans and Magnaporthe grisea 14. …”

A review on anti‐tuberculosis peptides: Impact of peptide structure on anti‐tuberculosis activity

“…Depsipeptides are an interesting class of peptides with important biological properties such as anti‐cancer, antimicrobial, and anti‐inflammatory activity. The cyclo depsipeptides cordycommunin and lydiamycin A have been found active against M tuberculosis with the MIC values of 12.9 and 12.5 μg/mL . A thiopeptide produced by pathogenic Nocardia pseudobrasiliensis , nocardithiocin, has been reported with great anti‐mycobacterial activity with the MIC values 0.78 μg/mL against M tuberculosis H37Rv strain and rifampicin resistance strains .…”