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Rubicordifolin is a natural product that is produced by ''Rubia cordifolia'', a plant that is a member of the ''Rubiaceae'' family.〔Lumb, J.P., Trauner, D. (2005) Biomimetic Synthesis and Structure Elucidation of Rubicordifolin, a Cytotoxic Natural Product from Rubia cordifolia. J. Am. Chem. Soc. 127, 2870-2871.〕 The molecule is isolated from the roots of ''Rubia cordifolia'' and was first characterized in 1993.〔Itokawa, H., Ibrahein, Z.Z., Qiao, Y.F., Takeya, K. (1993) Anthraquinones, Naphthohydroquinones, and Naphthohydroquinone Dimers from Rubia cordifolia and Their Cytoxic Activity. Chem. Pharm. Bull. 41, 1869-1872.〕 In 2004, the first synthesis of rubicordifolin was accomplished.〔 The molecule has been shown to have both cytotoxic and antitumor properties.〔 ==Biosynthesis== A biosynthetic pathway for rubicordifolin has yet been elucidated. However, it has been hypothesized that the dimerization of the two napthoquinone units yields rubicordifolin. Napthoquinones can be traced back to the shikamate pathway in plants. Shikamate is converted into chorismic acid, which is further converted into 2-succinylbenzoic acid through a TPP dependent reaction.〔Schultz, G., Soll, J., Diedler, E., Schulze-Siebert, D., (1985) Synthesis of prenylquinones in chloroplasts. Physiol. Plant. 65, 123-129.〕〔Herrmann, K.M., Weaver, L.M. (1999) The Shikamate Pathway. Annu. Plant Physiol. Plant Mol. Bio. 50, 473-503.〕 After 2-succinylbenzoic acid has been produced, a cyclization, a prenylation, a methylation, and an oxidation occur which yields a napthoquinone.〔Heide, L., Leistner, E. (1981) 2-Methoxycarbonyl-3-prenyl-1,4-napthoquinone, a Metabolite related to the Biosynthesis of Mollugin and Anthraquinones in Galium mollugo L. J.C.S. Chem. Comm. 334-336.〕 center Once this napthoquinone has been made, a series of oxidations and cyclizations lead to two substrates that can undergo a () cycloaddition that leads to the product.〔 center 抄文引用元・出典: フリー百科事典『 ウィキペディア（Wikipedia）』 ■ウィキペディアで「Rubicordifolin」の詳細全文を読む スポンサード リンク
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