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Treatment of Vinca minor Leaves with Methyl Jasmonate Extensively Alters the Pattern and Composition of Indole Alkaloids
Journal of Natural Products ( IF 5.1 ) Pub Date : 2017-11-13 00:00:00 , DOI: 10.1021/acs.jnatprod.7b00424
Sara Abouzeid 1, 2 , Ulrike Beutling , Frank Surup , Fatma M. Abdel Bar 2 , Mohamed M. Amer 2 , Farid A. Badria 2 , Mahdi Yahyazadeh 1 , Mark Brönstrup , Dirk Selmar 1
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Alkaloids extracted from mature Vinca minor leaves were fractionated by preparative HPLC. By means of HRMS and NMR data, the main alkaloids were identified as vincamine, strictamine, 10-hydroxycathofoline, and vincadifformine. Upon treatment with methyl jasmonate (MeJA), the pattern and composition of the indole alkaloids changed extensively. While 10-hydroxycathofoline and strictamine concentrations remained unaltered, vincamine and vincadifformine levels showed a dramatic reduction. Upon MeJA treatment, four other indole alkaloids were detected in high quantities. Three of these alkaloids have been identified as minovincinine, minovincine, and 9-methoxyvincamine. Whereas minovincinine and minovincine are known to occur in trace amounts in V. minor, 9-methoxyvincamine represents a novel natural product. Based on the high similarities of vincamine and 9-methoxyvincamine and their inverse changes in concentrations, it is postulated that vincamine is a precursor of 9-methoxyvincamine. Similarly, vincadifformine seems to be converted first to minovincinine and finally to minovincine. Because MeJA treatment greatly altered the alkaloidal composition of V. minor, it could be used as a potential elicitor of alkaloids that are not produced under normal conditions.

中文翻译:

用茉莉酸甲酯处理长春蔓小叶可广泛改变吲哚生物碱的模式和组成

从成熟长春蔓小叶中提取的生物碱通过制备型HPLC进行分级分离。通过HRMS和NMR数据,鉴定出主要生物碱为长春胺,严格胺,10-羟基cathofoline和长春花草碱。茉莉酸甲酯(MeJA)处理后,吲哚生物碱的模式和组成发生了很大变化。尽管10-羟基cathofoline和strictamine的浓度保持不变,但vinincamine和vincadifformine的含量却显着降低。经MeJA处理后,还大量检测到其他四种吲哚生物碱。这些生物碱中的三种已被鉴定为米诺西汀,米诺西汀和9-甲氧基长春胺。已知米诺菌素和米诺菌素在小肠弧菌中以痕量存在,9-甲氧基长春胺代表一种新型的天然产物。基于长春胺和9-甲氧基长春胺的高度相似性及其浓度的逆变化,推测长春胺是9-甲氧基长春胺的前体。同样,长春花青碱似乎先被转化为氨基长春新碱,最后被转化为氨基长春新碱。由于MeJA处理极大地改变了V. minor的生物碱组成,因此可以用作正常条件下不产生的生物碱的潜在诱因。
更新日期:2017-11-13
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