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New Prenylated Aeruginosin Microphycin Anabaenopeptin and Micropeptin Analogues from a Microcystis Bloom Material Collected in Kibbutz Kfar Blum Israel

机译:从以色列基布兹·卡法尔·布卢姆收集的微囊藻开花物质中获得的新的异戊酰化的铜绿素酶微藻素阿那巴肽素和微肽素类似物

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摘要

Thirteen new and eighteen known natural products were isolated from a bloom material of an assembly of various Microcystis spp. collected in November, 2008, from a commercial fishpond near Kibbutz Kfar Blum, the Jordan Valley, Israel. The new natural products included the prenylated aeruginosin KB676 (>1), microphycin KB921 (>2), anabaenopeptins KB906 (>3) and KB899 (>4) and micropeptins KB928 (>5), KB956 (>6), KB970A (>7), KB970B (>8), KB984 (>9), KB970C (>10), KB1048 (>11), KB992 (>12) and KB1046 (>13). Their structures were elucidated primarily by interpretation of their 1D and 2D nuclear magnetic resonance spectra and high-resolution mass spectrometry. Marfey’s and chiral-phase high performance liquid chromatography methods were used to determine the absolute configurations of their chiral centers. Aeruginosin KB676 (>1) contains the rare (2S,3aS,6S,7aS)-Choi and is the first prenylated aeruginosin derivative described in the literature. Compounds >1 and >5–>11 inhibited trypsin with sub-μM IC50s, while Compounds >11–>13 inhibited chymotrypsin with sub-μM IC50s. The structures and biological activities of the new natural products and our procedures of dereplication are described.
机译:从各种微囊藻属物种的花序材料中分离出十三种新的和十八种已知的天然产物。于2008年11月从以色列约旦河谷的基布兹·卡法尔·布卢姆附近的商业鱼塘收集而来。新的天然产物包括异戊烯化的铜绿素酶KB676(> 1 ),微藻素KB921(> 2 ),Anabaenopeptins KB906(> 3 )和KB899(> > 4 )和微肽KB928(> 5 ),KB956(> 6 ),KB970A(> 7 ),KB970B(> 8 ),KB984(> 9 ),KB970C(> 10 ),KB1048(> 11 ),KB992(> 12 < / strong>)和KB1046(> 13 )。主要通过解释其一维和二维核磁共振谱以及高分辨率质谱来阐明其结构。 Marfey和手性高效液相色谱方法用于确定其手性中心的绝对构型。 Aeruginosin KB676(> 1 )包含稀有(2S,3aS,6S,7aS)-Choi,是文献中描述的首个异戊烯醛化铜绿素衍生物。化合物> 1 和> 5 – > 11 具有低于μMIC50的胰蛋白酶抑制作用,而化合物> 11 – > 13 通过亚μMIC50抑制胰凝乳蛋白酶。描述了新天然产物的结构和生物学活性以及我们的重复复制程序。

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