First total synthesis and biological screening of hymenamide E.

Department of Pharmaceutical Chemistry, Rajiv Academy for Pharmacy, Mathura-281 001, India.
Acta Pharmaceutica (Impact Factor: 1.03). 12/2006; 56(4):399-415.
Source: PubMed

ABSTRACT A new potent bioactive, proline-rich cyclic heptapeptide hymenamide E (13) was synthesized using the solution phase technique by cyclization of the linear peptide Boc-Phe-Pro-Thr-Thr-Pro-Tyr-Phe-OMe (12) after proper deprotection at carboxyl and amino terminals. Linear peptide segment was prepared by coupling the tripeptide unit Boc-Phe-Pro-Thr-OH (10a) with the tetrapeptide unit Thr-Pro-Tyr-Phe-OMe (11a) using dicyclohexylcarbodiimide as the coupling agent and N-methylmorpholine as the base. Structures of all new compounds were characterized by IR, 1H NMR spectral data as well as elemental analyses. In addition, the structure of compound 13 was verified by 13C NMR, fast atom bombardment mass spectroscopy and differential scanning calorimetry. The newly synthesized cyclopeptide was screened for its antibacterial, antifungal and anthelmintic activities against eight pathogenic microbes and two earthworm species. Compound 13 showed potent antifungal activity against Candida albicans and Ganoderma species comparable to that of griseofulvin as a reference drug and potent anthelmintic activity against earthworms Megascoplex konkanensis and Eudrilus species in comparison to piperazine citrate.

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    ABSTRACT: Cited By (since 1996): 1, Export Date: 22 January 2013, Source: Scopus, Language of Original Document: English, Correspondence Address: A Ab Kadir, M.Z.; Department of Electrical and Electronics Engineering, Faculty of Engineering, Universiti Putra Malaysia, 43400 Serdang, Selangor, Malaysia; email:, References: Dugan, R.C., McGranaghan, M.F., Beaty, H.W., (1996) Electrical Power System Quality, , McGraw Hill, New York. ISBN-10: 0070180318;
    European Journal of Scientific Research 01/2008; 21(2):288-295. · 0.74 Impact Factor
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    ABSTRACT: Plant-originated cyclopolypeptide (XIII) was synthesized by coupling of dipeptide Boc-l-asn(bzh)-l-phe-OH and tetrapeptide gly-l-leu-l-ala-l-tyr-OMe followed by cyclization of a linear hexapeptide segment. Structure elucidation of XIII was done on basis of detailed spectral analysis including FTIR, 1H NMR, 13C NMR, FAB MS and elemental analysis. From the results of pharmacological screening, it was concluded that XIII possesses high cytotoxic activity against DLA and EAC cell lines with CTC50 values of 15.1 μM and 18.6 μM, and potent antimicrobial activity against pathogenic fungi C. albicans with MIC of 6 μg mL−1. Moreover, XIII possesses moderate anthelmintic activity against earthworms M. konkanensis, P. corethruses, and Eudrilus sp. at 2 mg mL−1 dose level.
    Chemical Papers- Slovak Academy of Sciences 10/2008; 62(5):527-535. DOI:10.2478/s11696-008-0052-9 · 1.19 Impact Factor
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    ABSTRACT: Present study deals with synthesis of a novel proline-rich cyclopeptide - gypsin B 7 via coupling of tripeptide units Boc-L-Tyr-L-Phe-L-Pro-OH and Gly-L-Leu-L-Pro-OMe utilizing two different carbodiimides, followed by cyclization of linear polypeptide fragment. Structure elucidation of newly synthesized peptide was done on basis of FT-IR, 1H-NMR, 13C-NMR, ESI-MS/MS data. From biological evaluation, it was concluded that cyclic hexapeptide 7 exhibited potent antidermatophyte activity against pathogenic Microsporum audouinii and Trichophyton mentagrophytes. Also, good bioactivity against pathogenic Candida albicans and Gram-negative bacteria, and moderate antihelmintic activity against three species of earthworms was observed for newly synthesized cyclohexapeptide.

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