(2S)-2-メチル酪酸[(1S)-1,2,3,7,8,8aα-ヘキサヒドロ-7α-メチル-8α-[2-[(2R,4R)-テトラヒドロ-4-ヒドロキシ-6-オキソ-2H-ピラン-2-イル]エチル]ナフタレン-1β-イル] 化学特性,用途語,生産方法
外観
白色～ほとんど白色, 結晶性粉末～粉末
溶解性
エタノール及びアセトンに溶け、水にほとんど溶けない。
解説
コンパクチン，C23H34O5(390.52)．Panicillium citrinumの培養液中よりコレステロール生合成阻害剤として発見された化合物．融点152 ℃．[α]D22"＋283°(アセトン)．コレステロールの生合成に関与する重要な調節酵素の一つである，3-ヒドロキシ-3-メチルグルタリルCoA還元酵素を特異的に阻害する．抗真菌作用をもつ．シンバスタチンは半合成誘導体である
用途
病理研究用、昆虫神経ペプチド類の作用機構の研究用。
化学的特性
Off-White Solid
使用
Mevastatin (compactin) is a diterpene produced by several species of the genera Penicillium and Monascus, first reported in 1976. Mevastatin, the prtotype of the statin class, is a potent competitive inhibitor of HMG-CoA reductase, a regulatory enzyme for cholesterol biosynthesis. Mevastatin has also been shown to induce apoptosis by inhibiting post-translational prenylation of proteins such as Ras, increasing eNOS mRNA and protein levels by blocking the geranylgeranylation of Rho, and inhibiting myoblast fusion. It induces cell cycle arrest in late G1 phase and may induce bone morphogenic protein-2 (BMP-2).
定義
ChEBI: A carboxylic ester that is pravastatin that is lacking the allylic hydroxy group and in which the lactone moiety has been hydrolysed to the corresponding delta-hydroxy-carboxylic acid. A hydroxymethylglutaryl-CoA reductase inhibitor (stati
) isolated from Penicillium citrinum and from Penicillium brevicompactum, its clinical use as a lipid-regulating drug ceased following reports of toxicity in animals.
一般的な説明
Chemical structure: statin
生物活性
Inhibitor of HMG-CoA reductase; decreases cholesterol biosynthesis, in vitro and in vivo . Induces apoptosis, arrests cancer cells in G1 phase and downregulates cdk 2, 4, and 6, cyclin D1 and E1, p21 and p27.
純化方法
Purify compactin by recrystallisation from aqueous EtOH. UV (EtOH): max 230, 237 and 246nm (log 4.28, 4.30 and 4.11); IR (KBr): 3520, 1750 (lactone CO) and 1710 (CO ester) cm-1. [Clive et al. J Am Chem Soc 110 6914 1988, Review: Rosen & Heathcock Tetrahedron 42 4909 1986, IR, NMR, MS: Brown et al. J Chem Soc Perkin Trans 1 1165 1976.] It is a potent inhibitor of 3-hydroxy-3-methylglutaryl-CoA reductase (HMG-CoA reductase), an enzyme in cholesterol biosynthesis, and lowers cholesterol levels [Brown et al. J Biol Chem 253 1121 1978, Nakamura & Ableles Biochemistry 24 1364 1985, Beilstein 18/3 V 145].
(2S)-2-メチル酪酸[(1S)-1,2,3,7,8,8aα-ヘキサヒドロ-7α-メチル-8α-[2-[(2R,4R)-テトラヒドロ-4-ヒドロキシ-6-オキソ-2H-ピラン-2-イル]エチル]ナフタレン-1β-イル] 上流と下流の製品情報
原材料
準備製品