Abouzeid Sara, Beutling Ulrike, Surup Frank, Abdel Bar Fatma M, Amer Mohamed M, Badria Farid A, Yahyazadeh Mahdi, Brönstrup Mark, Selmar Dirk
Institute for Plant Biology, TU Braunschweig , 38106 Braunschweig, Germany.
Pharmacognosy Department, Faculty of Pharmacy, Mansoura University , Mansoura 35516, Egypt.
J Nat Prod. 2017 Nov 22;80(11):2905-2909. doi: 10.1021/acs.jnatprod.7b00424. Epub 2017 Nov 13.
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.
从长春花成熟叶片中提取的生物碱通过制备型高效液相色谱进行分离。借助高分辨质谱（HRMS）和核磁共振（NMR）数据，鉴定出主要生物碱为长春胺、密茱萸碱、10-羟基去甲氧基喜树碱和长春地辛。用茉莉酸甲酯（MeJA）处理后，吲哚生物碱的模式和组成发生了广泛变化。虽然10-羟基去甲氧基喜树碱和密茱萸碱的浓度保持不变，但长春胺和长春地辛的水平显著降低。经MeJA处理后，还检测到另外四种大量的吲哚生物碱。其中三种生物碱已被鉴定为米诺长春宁、米诺长春碱和9-甲氧基长春胺。虽然已知米诺长春宁和米诺长春碱在长春花中微量存在，但9-甲氧基长春胺是一种新型天然产物。基于长春胺和9-甲氧基长春胺的高度相似性及其浓度的反向变化，推测长春胺是9-甲氧基长春胺的前体。同样，长春地辛似乎首先转化为米诺长春宁，最终转化为米诺长春碱。由于MeJA处理极大地改变了长春花的生物碱组成，它可作为在正常条件下不产生的生物碱的潜在诱导剂。
