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天然和合成油菜素内酯在大鼠骨骼肌细胞中依赖 Akt 的合成代谢活性。

Akt-dependent anabolic activity of natural and synthetic brassinosteroids in rat skeletal muscle cells.

机构信息

Biotech Center, SEBS, Rutgers University, 59 Dudley Road, New Brunswick, New Jersey 08901, United States.

出版信息

J Med Chem. 2011 Jun 23;54(12):4057-66. doi: 10.1021/jm200028h. Epub 2011 May 26.

DOI:10.1021/jm200028h
PMID:21491949
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC3128125/
Abstract

Brassinosteroids are plant-derived polyhydroxylated derivatives of 5α-cholestane, structurally similar to cholesterol-derived animal steroid hormones and insect ecdysteroids. In this study, we synthesized a set of brassinosteroid analogues of a natural brassinosteroid (22S,23S)-homobrassinolide (HB, 1), including (22S,23S)-homocastasterone (2), (22S,23S)-3α-fluoro-homobrasinolide (3), (22S,23S)-3α-fluoro-homocastasterone (4), (22S,23S)-7-aza-homobrassinolide (5), and (22S,23S)-6-aza-homobrassinolide (6) and studied their anabolic efficacy in the L6 rat skeletal muscle cells in comparison to other synthetic and naturally occurring brassinosteroids (22R,23R)-homobrassinolide (7), (22S,23S)-epibrassinolide (8), and (22R,23R)-epibrassinolide (9). Presence of the 6-keto group in the B ring and stereochemistry of 22α,23α-vicinal hydroxyl groups in the side chain were critical for the anabolic activity, possibly due to higher cytotoxicity of the 22β,23β-hydroxylated brassinosteroids. All anabolic brassinosteroids tested in this study selectively activated PI3K/Akt signaling pathway as evident by increased Akt phosphorylation in vitro. Plant brassinosteroids and their synthetic derivatives may offer a novel therapeutic strategy for promoting growth, repair, and maintenance of skeletal muscles.

摘要

植物甾醇是 5α-胆甾烷的多羟基衍生物，结构上与胆固醇衍生的动物甾体激素和昆虫蜕皮甾体相似。在这项研究中，我们合成了一组天然油菜素内酯（22S，23S）-同型油菜素内酯（HB，1）的油菜素内酯类似物，包括（22S，23S）-同型表油菜素内酯（2）、（22S，23S）-3α-氟同型油菜素内酯（3）、（22S，23S）-3α-氟同型表油菜素内酯（4）、（22S，23S）-7-氮杂同型油菜素内酯（5）和（22S，23S）-6-氮杂同型油菜素内酯（6），并研究了它们在 L6 大鼠骨骼肌细胞中的合成功效，与其他合成和天然油菜素内酯（22R，23R）-同型油菜素内酯（7）、（22S，23S）-表油菜素内酯（8）和（22R，23R）-表油菜素内酯（9）进行了比较。B 环上的 6-酮基和侧链上 22α、23α-顺式羟基的立体化学是合成活性的关键，可能是由于 22β、23β-羟基化油菜素内酯的细胞毒性更高。本研究中测试的所有具有合成功效的油菜素内酯都选择性地激活了 PI3K/Akt 信号通路，体外试验中 Akt 磷酸化增加。植物油菜素内酯及其合成衍生物可能为促进骨骼肌的生长、修复和维持提供一种新的治疗策略。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3bbf/3128125/79c4ff43314a/nihms299886f5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3bbf/3128125/00255db674f3/nihms299886f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3bbf/3128125/1bd543f50944/nihms299886f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3bbf/3128125/f14271482cba/nihms299886f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3bbf/3128125/180a6d0bb113/nihms299886f4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3bbf/3128125/79c4ff43314a/nihms299886f5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3bbf/3128125/00255db674f3/nihms299886f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3bbf/3128125/1bd543f50944/nihms299886f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3bbf/3128125/f14271482cba/nihms299886f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3bbf/3128125/180a6d0bb113/nihms299886f4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3bbf/3128125/79c4ff43314a/nihms299886f5.jpg

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