One new cyclopeptide, cyclo(L-Phe-L-Ala-L-Phe-Gly), named as vinaceuline (1) and three known cyclodipeptides, cyclo (Phe-Gly), cyclo (Phe-4-hydroxyl-Pro) and cyclo (Phe-Ile) were isolated from broth culture of endophytic Streptomyces YIM 64018 associated with Paraboea sinensis. The planar structure of the new compound was assigned on the basis of 1D and 2D NMR spectroscopic techniques, while the absolute configurations of the amino acid residues were determined by application of the advanced Marfey method. Cyclotetrapeptides are rarely found as Streptomycete metabolites.
GenilloudO., GonzálezI., SalazarO., MartínJ., TormoJ.R., VicenteF. (2011) Current approaches to exploit actinomycetes as a source of novel natural products. Journal of Industrial Microbiology & Biotechnology, 38, 375–389.
2.
ZhangY., HanT., MingQ., WuL., RahmanK., QinL. (2012) Alkaloids produced by endophytic fungi: a review. Natural Product Communications, 7, 963–968.
3.
RomanoA., VitulloD., Di PietroA., LimaG., LanzottiV. (2011) Antifungal lipopeptides from Bacillus amyloliquefaciens strain BO7. Journal of Natural Products, 74, 145–151.
4.
KanohK., MatsuoY., AdachiK., ImagawaH., NishizawaM., ShizuriY. (2005) Mechercharmycins A and B, cytotoxic substances from marine-derived Thermoactinomyces sp. YM3–251. The Journal of Antibiotics, 58, 289–292.
5.
LiD.H., GuQ.Q., ZhuW.M., LiuH.B., FangY.C., ZhuT.J. (2005) Antitumor components from marine actinomycete 11014 I. cyclic dipeptides. Chinese Journal of Antibiotics, 30, 449–452.
6.
WangY.C., ZhouJ., TanN.H., DingZ.T., JiangX. (1999) Cyclic dipeptides from Schizandra chinensis and their syntheses. Acta Pharmaceutica Sinica, 34, 19–22.
7.
FujiiK., IkaiY., OkaH., SuzukiM., HaradaK. (1997) A nonempirical method using LC/MS for determination of the absolute configuration of constituent amino acids in a peptide: combination of Marfey's method with mass spectrometry and its practical application. Analytical Chemistry, 69, 5146–5151.
