PHENOL AND GUAIACOL - BIOSYNTHESIS, DETOXICATION, AND FUNCTION IN A POLYDESMID MILLIPEDE, OXIDUS-GRACILIS
PHENOL AND GUAIACOL - BIOSYNTHESIS, DETOXICATION, AND FUNCTION IN A POLYDESMID MILLIPEDE, OXIDUS-GRACILIS
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DOI：
10.1016/0020-1790(77)90057-9
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发表时间：
1977-01-01
期刊：
影响因子：
--
通讯作者：
BLUM, MS
中科院分区：
文献类型：
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作者：
DUFFEY, SS;BLUM, MS
多脉千足虫O.纤毛虫，Euryurus maculatus，和Pseudopolydesmus eruginosa分泌酚和愈创木酚在氰发生过程中，这些化合物存在于氰腺的反应室。细菌学和酶学研究表明，这两种酚类物质都是节肢动物自身代谢的结果，而不是共生细菌的作用。在活体条件下，O. gracilis和所有3种属的体外研究。利用14 C-前体的研究表明，苯酚和愈创木酚衍生自酪氨酸。酪氨酸酚裂解酶（EC 4.1.99.2）是从O. gracilis，并显示可逆地催化酪氨酸转化为苯酚或反之亦然。解毒研究O. gracilis的研究表明，H14 CN主要被罗丹酸盐转化为硫氰酸盐，少量转化为β-还存在氰基丙氨酸和天冬酰胺。苯酚在体内转化为苯酚-β- D-糖苷、酪氨酸和可能的氢醌-β- D-糖苷（熊果苷）。平行的生化途径在植物和千足虫的独立进化进行了讨论。本文讨论了愈创木酚和苯酚在千足虫生氰防御分泌物中的作用。
The polydesmid millipedes O. gracilis, Euryurus maculatus, and Pseudopolydesmus erasus secrete phenol and guaiacol during cyanogenesis; these compounds are present in the reaction chamber of the cyanogenic gland. Bacteriological and enzymic studies showed that both these phenolics arise as the result of the arthropods''s own metabolism, and not from the action of symbiotic bacteria. In vivo with O. gracilis and in vitro studies with all 3 spp. utilizing 14C-precursors showed that phenol and guaiacol are derived from tyrosine. The enzyme tyrosine phenol lyase (EC 4.1.99.2) was isolated from the phlanges of O. gracilis and shown to reversibly catalyze the conversion of tyrosine to phenol or vice versa. Detoxication studies with O. gracilis showed that H14CN was converted primarily to thiocyanate by rhodanese with minor conversion to .beta.-cyanoalanine and asparagine also occurring. Phenol was converted in vivo to phenol-.beta.-D-glycoside, tyrosine and possibly hydroquinone-.beta.-D-glycoside (arbutin). The independent evolution of parallel biochemical pathways in plants and millipedes is discussed. The functions of guaiacol and phenol in the cyanogenic defensive secretions of millipede are discussed.