Laboratório de Biologia Celular e Tecidual, Centro de Biociências e Biotecnologia, Universidade Estadual do Norte Fluminense Darcy Ribeiro, 28013-602, Campos dos Goytacazes, Brazil.
Departamento de Botânica, Instituto de Ciências Biológicas e da Saúde, Universidade Federal Rural do Rio de Janeiro, 23890-000, Seropédica, Brazil.
Phytochemistry. 2021 Mar;183:112616. doi: 10.1016/j.phytochem.2020.112616. Epub 2020 Dec 17.
The Papilionoideae, which comprises 503 genera and approximately 14,000 species, is the largest and most diverse subfamily of the Fabaceae family. In this subfamily, the Crotalarieae, Genisteae, Podalyrieae, Thermopsideae, Sophoreae and Euchresteae tribes are closely related by micro and macromolecular features, thus forming the genistoid clade. This group combines well-known genera, whereas other genera lack phytochemical and chemotaxonomic studies. Thus, this work aimed to characterize the special metabolites in these genera in order to define the chemical profile, the micromolecular markers and the chemical diversity, as well as to evaluate the group evolutionary trends. Flavonoids and alkaloids were identified as chemosystematic markers for the studied tribes due to high occurrence number and structural diversity. Among flavonoids, the flavones and isoflavones predominated. Low protection indexes of flavonoid hydroxyls by O-glycosylation or O-methylation were observed, whereas C-prenylation and C-glycosylation were frequent, mainly at C-6 and C-8 positions. The flavone/flavonol ratio shows the predominance of the flavones. Quinolizidine and piperidine alkaloids were present in most genera. Pyrrolizidine alkaloids were found in a few genera from Thermopsideae, Genisteae and Crotalarieae, which suggests a mechanism of adaptive convergence. Cluster analysis allowed separation of genera for each tribe by chemical similarities. The micromolecular trends of protection of flavonoid hydroxyls and alkaloid oxidation indicate the genistoid clade is through evolutionary transition, which is consistent with its phylogenetic position in the Papilionoideae subfamily.
被膜豆亚科包含 503 属和大约 14000 种，是豆科植物家族中最大和最多样化的亚科。在这个亚科中，紫云英族、槐蓝族、百脉根族、古豆族、木蓝族和猪屎豆族通过微观和宏观分子特征密切相关，从而形成了豆族系统发育枝。该组结合了广为人知的属，而其他属缺乏植物化学和化学分类学研究。因此，这项工作旨在表征这些属中的特殊代谢物，以定义化学特征、微观分子标记和化学多样性，并评估该组的进化趋势。由于出现数量高和结构多样性，黄酮类化合物和生物碱被确定为研究族的化学分类学标记。在黄酮类化合物中，黄酮类和异黄酮类化合物占主导地位。观察到黄酮类化合物的羟基通过 O-糖苷化或 O-甲基化的低保护指数，而 C-异戊烯基化和 C-糖基化则很常见，主要在 C-6 和 C-8 位。黄酮/黄酮醇比值表明黄酮类化合物占优势。喹啉啶和哌啶生物碱存在于大多数属中。在 Thermopsideae、Genisteae 和 Crotalarieae 族的少数属中发现了吡咯里西啶生物碱，这表明存在适应趋同的机制。聚类分析允许通过化学相似性对每个族进行分类。黄酮类化合物羟基保护和生物碱氧化的微观分子趋势表明，豆族系统发育枝是通过进化过渡而来的，这与其在豆科被膜豆亚科中的系统发育位置一致。
