Balticidins A鈥揇, Antifungal Hassallidin-Like Lipopeptides from the Baltic Sea Cyanobacterium Anabaena cylindrica Bio33

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• 作者：Thanh-Huong Bui ; Victor Wray ; Manfred Nimtz ; Torgils Fossen ; Michael Preisitsch ; Gudrun Schr枚der ; Kristian Wende ; Stefan E. Heiden ; Sabine Mundt
• 刊名：Journal of Natural Products
• 出版年：2014
• 出版时间：June 27, 2014
• 年：2014
• 卷：77
• 期：6
• 页码：1287-1296
• 全文大小：429K
• ISSN：1520-6025

文摘

Balticidins A鈥揇 (1鈥?b>4), four new antifungal lipopeptides, were isolated from the laboratory-cultivated cyanobacterium Anabaena cylindrica strain Bio33 isolated from a water sample collected from the Baltic Sea, R眉gen Island, Germany. Fractionation of the 50% aqueous MeOH extract was performed by bioassay-guided silica gel column chromatography followed by SPE and repeated reversed-phase HPLC. The main fraction containing the compounds exhibited a strong and specific antifungal activity with inhibition zones in an agar-diffusion assay from 21 to 32 mm against Candida albicans, Candida krusei, Candida maltosa, Aspergillus fumigatus, Microsporum gypseum, Mucor sp., and Microsporum canis. The structures were elucidated by multidimensional ¹H and ¹³C NMR spectroscopy, HRESIMS, amino acid analysis, and sugar analysis. Spectroscopic data analysis afforded an unambiguous sequence of R.CHO(S1).CHOH.CONH-Thr(1)-Thr(2)-Thr(3)-HOTyr(4)-Dhb(5)-d-Gln(6)-Gly(7)-NMeThr(8)(S2)-l-Gln COOH(9), in which Dhb is dehydroaminobutyric acid, S1 is d(鈭?-arabinose-(3-1)-d-(+)-galacturonic acid, S2 is d-(+)-mannose, and R is the aliphatic residue -C₁₃H₂₆Cl or -C₁₃H₂₇. Besides NMeThr, d-allo-Thr, d-Thr, and l-Thr were identified, but the position of the enantiomers in the sequence is not clear. The four balticidins differ in their cyclic (2, 4)/linear (1, 3) core and the presence (1, 2)/absence (3, 4) of chlorine in the aliphatic unit.