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BIOSYNTHESIS OF DIELS-ALDER TYPE ADDUCTS IN MORUS ALBA L. CELL CULTURES

桑树细胞培养物中狄尔斯-桤木型加合物的生物合成

基本信息

批准号：
62570955
负责人：
NOMURA Taro
金额：
$ 1.54万
依托单位：
TOHO UNIVERSITY
依托单位国家：
日本
项目类别：
Grant-in-Aid for General Scientific Research (C)
财政年份：
1987
资助国家：
日本
起止时间：
1987 至 1988
项目状态：
已结题

项目摘要

Callus and cell suspension cultures of high Diels-Alder type adducts productivity have been obtained through the selection of callus tissues induced from the seedlings or the leaves of Morus alba L. Experiments with [1-^<13>C]-, [2-^<13>]-, and [1,2-^<13>C_2]-acetates administered to the cell suspension induced from the leaves revealed that both optically active Diels-Alder type adducts chalcomoracin and kuwanon J, main components in the cell cultures, are formed through the condensation of two molecules of cinnamoy1-polkkeide-derived skeletons. In the ^<13>C-acetate labeled chalcomoracins, which is regarded as adduct of a dehydropreny1-2-arylbenzofuran derivative and a prenylchalcone derivative, the 2-arylbenzofuran skeleton is formed by a aldol type cyclization of the cinnamoylpolyketide, followed by decarboxylation, and the chalcone moiety is formed by a Claisen type cyclization of the precursor. The ^<13>C-labeling pattern in kuwanon J, which is regarded as a adduct of a dehydroprenylchalcone and a prenylchalcone, indicating the incorporation of three successive acetate units into the aromatic rings corroborates that kuwanon J is composed of two cinnamoylpolketide-derived chalcone skeletons, and that the possibility as a member of retrochalcone has been ruled out. On the other hand, in the ^<13>C-aceate labeled chalcomoracins, the [2-^<13> C]acetate was barely incorporated into the starter acetate carbons in the biosynthesis of the preny1 moieties, while the [1-^<13> C] acetate was not incorporated into the preny1 moieties. This may be due to the participation of the tricarboxylic acid (TCA) cycle. These labeling patterns clearly demonstrated that mixed biosynthesis of mulberry prenylchalcones from different origins. From the above results, the Diels-Alder type adducts, chalcomoracin and kuwanon J in the Morus alba cell cultures could be cycloaddition products of the , -double bond of the chalcone and the preny1 portion.

通过对桑树幼苗或叶片愈伤组织的筛选，获得了高产Diels-Alder型加合物的愈伤组织和细胞悬浮培养物。用[1-^<13>C]-、[2-^<13>]-和[1，2-^<13>C_2]-乙酸酯处理由叶片诱导的细胞悬浮液，发现细胞培养物中的主要成分查氏菌素和kuwanon J是由两个肉桂酰-polkkeide衍生的骨架分子缩合而成的。在<13>被认为是脱氢异戊二烯基-2-芳基苯并呋喃衍生物和异戊二烯基查耳酮衍生物的加合物的13 C-乙酸酯标记的查耳科黑菌素中，2-芳基苯并呋喃骨架通过肉桂酰基聚酮化合物的羟醛型环化，随后脱羧形成，查耳酮部分通过前体的克莱森型环化形成。kuwanon <13>J被认为是一个脱氢异戊二烯基查耳酮和一个异戊二烯基查耳酮的加合物，它的^C-标记模式表明在芳香环中有三个连续的乙酸酯单元，这证实了kuwanon J是由两个肉桂酰聚氧乙烯醚衍生的查耳酮骨架组成的，并且作为逆查耳酮成员的可能性已经被排除。另一方面，在14 <13>C-乙酸酯标记的查科黑菌素中，[2- 14 <13>C]乙酸酯在异戊二烯1部分的生物合成中几乎不掺入起始乙酸酯碳中，而[1- 14 <13>C]乙酸酯不掺入异戊二烯1部分中。这可能是由于三羧酸（TCA）循环的参与。这些标记模式清楚地表明，混合生物合成的桑葚异戊二烯基查耳酮从不同的来源。从以上结果可以看出，桑树细胞培养物中的Diels-Alder型加合物查科莫拉辛和kuwanon J可能是查耳酮的，-双键与异戊二烯基1部分的环加成产物。