Lanopylins A1, B1, A2 and B2, novel lanosterol synthase inhibitors from Streptomyces sp. K99-5041.

Sakano Y; Shibuya M; Matsumoto A; Takahashi Y; Tomoda H; Omura S; Ebizuka Y

首页> 外文期刊>The Journal of Antibiotics: An International Journal >Lanopylins A1, B1, A2 and B2, novel lanosterol synthase inhibitors from Streptomyces sp. K99-5041.

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Lanopylins A1, B1, A2 and B2, novel lanosterol synthase inhibitors from Streptomyces sp. K99-5041.

机译：Lanopylins A1，B1，A2和B2是来自链霉菌属的新型羊毛甾醇合酶抑制剂。 K99-5041。

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From an actinomycete strain, Streptomyces sp. K99-5041, lanopylins A1, B1, A2 and B2 were isolated as new natural products that inhibited the reaction of recombinant human lanosterol synthase. The crude extract from the whole broth of this strain was fractionated by silica gel column chromatography to afford an active fraction that showed a single spot on TLC. Detailed analyses of this fraction with liquid chromatography-atmospheric pressure chemical ionization mass spectrometry revealed that it contained 20 homologous compounds with differing side chain lengths. The fraction was separated by preparative HPLC to afford four of these homologues, lanopylins A1, B1, A2 and B2. Detailed spectroscopic analyses of these isolated compounds led to the identification of their structures. Lanopylins A1 and B1 were (3E)-isohexadecylmethylidene-2-methyl-1-pyrroline and (3E)-hexadecylmethylidene-2-methyl-1-pyrroline, respectively, and lanopylins A2 and B2 were homologues with the insertion of one cis-ethylenylidenein the side chain of lanopylins A1 and B1, respectively. These compounds inhibited recombinant human lanosterol synthase with IC50 values of 15, 18, 33, and 41 microM, respectively.

机译：从放线菌菌株Streptomyces sp。分离出K99-5041，羊毛脂蛋白A1，B1，A2和B2作为抑制重组人羊毛甾醇合酶反应的新天然产物。通过硅胶柱色谱分离该菌株全培养液的粗提物，得到在TLC上显示单点的活性部分。用液相色谱-大气压化学电离质谱法对该馏分进行的详细分析显示，该馏分包含20种具有不同侧链长度的同源化合物。通过制备型HPLC分离级分，得到这些同源物中的四个，羊毛脂蛋白A1，B1，A2和B2。对这些分离出的化合物进行详细的光谱分析可鉴定其结构。 Lanopylins A1和B1分别是（3E）-异十六烷基亚甲基-2-甲基-1-吡咯啉和（3E）-十六烷基亚甲基-2-甲基-1-吡咯啉，并且Lanopylins A2和B2是同系物，其中插入了一个顺式-亚乙烯基。羊毛脂蛋白A1和B1的侧链。这些化合物抑制的重组人羊毛甾醇合酶的IC50值分别为15、18、33和41 microM。

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来源
《The Journal of Antibiotics: An International Journal》 |2003年第10期|共10页
作者
Sakano Y; Shibuya M; Matsumoto A; Takahashi Y; Tomoda H; Omura S; Ebizuka Y;
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正文语种 eng
中图分类药学;
关键词
A1; B1; A2; Receptors; Complement 3d; lanosterol synthase; 受体; 补体3D;

机译：A1;B1;A2;Receptors;Complement 3d;lanosterol synthase;受体;补体3D;

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机译：Lanopylins A1，B1，A2和B2是来自链霉菌属的新型羊毛甾醇合酶抑制剂。 K99-5041。
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Lanopylins A1, B1, A2 and B2, novel lanosterol synthase inhibitors from Streptomyces sp. K99-5041.

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