来自壶花花瓣豆的4,5-二羟基哌啶酸单甲醚：一种神秘豆科植物的神秘化学

Monomethyl ethers of 4,5-dihydroxypipecolic acid from Petaladenium urceoliferum: Enigmatic chemistry of an enigmatic legume.

作者信息

Kite Geoffrey C, Cardoso Domingos, Lewis Gwilym P, Zartman Charles E, de Queiroz Luciano Paganucci, Veitch Nigel C

机构信息

Royal Botanic Gardens, Kew, Richmond, Surrey TW9 3AB, UK.

Departamento de Botânica, Instituto de Biologia, Universidade Federal da Bahia, Rua Barão de Geremoabo, s/n, Campus Universitário de Ondina, 40170-115 Salvador, Bahia, Brazil; Programa de Pós-Graduação em Botânica (PPGBot), Universidade Estadual de Feira de Santana, Av. Transnordestina, s/n, Novo Horizonte, 44036-900 Feira de Santana, Bahia, Brazil.

出版信息

Phytochemistry. 2015 Aug;116:198-202. doi: 10.1016/j.phytochem.2015.02.026. Epub 2015 Mar 24.

DOI:10.1016/j.phytochem.2015.02.026

PMID:25817832

Abstract

Leaves of Petaladenium (Leguminosae), an Amazonian monospecific genus recently revealed as a member of the Amburaneae clade among the earliest-diverging papilionoid legumes, were found to accumulate three monomethyl ethers of 4,5-dihydroxypipecolic acids. These were characterised by spectroscopic means as the (2S,4S,5R) and (2S,4R,5S) epimers of 5-hydroxy-4-methoxypipecolic acid and (2S,4R,5R)-4-hydroxy-5-methoxypipecolic acid. These compounds were not detected in any other genera in the Amburaneae clade or the wider Angylocalyceae-Dipterygeae-Amburaneae (ADA) clade of papilionoid legumes. Hydroxypipecolic acids, however, were detected in leaves of Myrocarpus and Myroxylon (sister genera in the Amburaneae clade), Angylocalyx and Xanthocercis (sister genera in the Angylocalyceae clade) and Monopteryx (Dipterygeae clade), and were also present in Petaladenium. Iminosugars, known to be accumulated by all four genera in the Angylocalyceae clade (Alexa, Angylocalyx, Castanospermum and Xanthocercis), were found to be characteristic of this group within the ADA clade.

摘要

花瓣豆属（豆科）是一种亚马逊单种属植物，最近被发现是最早分化的蝶形花亚科豆科植物中安布拉内族分支的成员，其叶子中积累了三种4,5 - 二羟基哌啶酸的单甲醚。通过光谱手段将这些化合物鉴定为5 - 羟基 - 4 - 甲氧基哌啶酸的(2S,4S,5R)和(2S,4R,5S)差向异构体以及(2S,4R,5R) - 4 - 羟基 - 5 - 甲氧基哌啶酸。在安布拉内族分支的任何其他属或蝶形花亚科豆科植物更广泛的安吉利ocalyceae - Dipterygeae - Amburaneae（ADA）分支中均未检测到这些化合物。然而，在Myrocarpus和Myroxylon（安布拉内族分支中的姐妹属）、Angylocalyx和Xanthocercis（安吉利ocalyceae族分支中的姐妹属）以及Monopteryx（Dipterygeae族分支）的叶子中检测到了羟基哌啶酸，并且在花瓣豆属中也存在。已知安吉利ocalyceae族分支中的所有四个属（Alexa、Angylocalyx、Castanospermum和Xanthocercis）都会积累亚氨基糖，结果发现亚氨基糖是ADA分支中该类群的特征。