The crystal structure and cytotoxicity of goniodiol-7-monoacetate from Goniothalamus amuyon.
The crystal structure and cytotoxicity of goniodiol-7-monoacetate from Goniothalamus amuyon.
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Goniothalamus amuyon 的 goniodiol-7-monoacetate 的晶体结构和细胞毒性。
DOI：
10.1021/np50076a024
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发表时间：
1991
影响因子：
5.1
通讯作者：
Lee,KH
中科院分区：
文献类型：
--
作者：
Wu,YC;Duh,CY;Chang,FR;Chang,GY;Wang,SK;Chang,JJ;McPhail,DR;McPhail,AT;Lee,KH
从Goniothalamus amuyon中分离到一种名为goniodiol-7-monoacetate的苯丙酮[6R-QR， 8r -二氢-7-乙酰氧基-8-羟基苯乙烯基)- 5,6 -二氢-2-pyrone]，并通过x射线晶体分析确定了其详细的分子结构。对KB、P-388、RPMI和TE671肿瘤细胞具有强效（ED； 0值< 0.1µg/ml）的细胞毒性。性腺丘脑（Blanco）；是一种小乔木或灌木，原产于台湾南部沿海地区附近(1)。木香种子的提取物已被用于治疗水肿和风湿病(2)。在之前的一项植物化学研究中，发现这种植物的茎中含有五种异喹啉碱(3)。进一步的研究表明，该化合物具有细胞毒性，并被鉴定为Goniothalamus sesquipedalis的叶子和树枝以及Goniothalamus grifithii的树皮。(4)Talapatra等人首次从Goniothalamus sesquipedalis和Goniothalamus grifithii的树皮中分离到化合物1，阐明了其结构，并提出了6S， 7S，从h -nmr光谱数据得出的8S绝对立体化学和基于分配给goniothalamin的6S构型的立体参数结合生物遗传学考虑(5)。然而，Gesson等人(6)随后提出，由于(+)-goniothalamin的几次全合成表明它具有6R构型，因此1的整体立体化学应该修改为6R， 7R, 8R。x射线晶体学分析已经毫无疑问地确定了后者的相对立体化学，并提供了分子几何结构的细节。首次证实了1的细胞毒性。
The styrylpyrone, goniodiol-7-monoacetate [1][6R-QR, 8R-dihydro-7-acetoxy-8-hydroxystyryl)-5, 6-dihydro-2-pyrone], has been isolated from Goniothalamus amuyon, and its detailed molecular structure has been determined by X-ray crystallographic anaylsis. Goniodiol-7-monoacetate showed potent (ED; o values< 0.1 µg/ml) cytotoxicities against KB, P-388, RPMI, and TE671 tumor cells.Goniothalamus amuyon (Blanco) Merr.(Annonaceae) is a small tree or shrub indige-nous to southern Taiwan near the coastal regions (1). Extracts of the seeds of G. amuyon have been used for the treatment of edema and rheumatism (2). In a previous phytochemical study, the stems of this plant were found to contain five isoquinoline al-kaloids (3). Further investigations on structurally novel bioactive compounds from the leaves of G. amuyon have now resulted in the isolation of a cytotoxic styrylpyrone which from spectral data has been identified as the known goniodiol-7-monoacetate [1], Com-pound 1 was first isolated from the leaves and twigs of Goniothalamus sesquipedalis and the bark of Goniothalamus grifithii by Talapatra et al.(4), who elucidated itsconstitution and proposed a 6S, 7S, 8S absolute stereochemistry from’H-nmr spectral data and steric arguments in conjunction with biogenetic considerations based on the 6S configuration assigned to goniothalamin (5). Gesson et al.(6), however, have subsequently suggested that, since several total syntheses of (+)-goniothalamin have shown it to possess a 6R configuration, the overall stereochemistry of 1 should be revised to 6R, 7R, 8R. An X-ray crystallographic analysis has now established the latter relative stereochemistry beyond doubt and provided details of the molecular geometry. The cytotoxicityof 1 is demonstrated for the first time.