Alzatea verticillata (Alzatea verticillata)的植物化学研究

Marcos Marçal Ferreira Queiroz, R. Huber, L. Marcourt, L. Guénée, Pierre-Marie Allard, Adriano Rutz, Louis-Félix Nothias, Concetta Carlotta De Ruvo, J. Kissling, Mahabir P. Gupta, Emerson Ferreira Queiroz, J. Wolfender
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Apolar and polar extracts were purified by semi-preparative HPLC using appropriate stationary phase columns allowing the isolation of 12 compounds: walterolactone B (2) walterolactone A/B β-D-pyranoglucoside (3), gallic acid (4), caffeic acid 4-O-β-D-glucopyranoside (6), walterolactone A/B 6-O-gallate-β-D-glucopyranoside (8), caffeic acid (9), 8-desmethylsideroxylin (11), sideroxylin (12) and 7,7′-bis(3,4-dihydroxyphenyl)-8,8′-cyclobutanedicarboxylic acid (7). Three isolated compounds are natural products described here for the first time: dimethyl-anemonin (1) and two β-truxinic acid derivatives (rel-(7S, 8R, 7′R, 8′S)-7,7′-bis(4-glucosyloxy-3-hydroxyphenyl)-8,8′-cyclobutane dicarboxylic acid (5) and rel-(7S, 8R, 7′R, 8′S)-7,7′-bis(4-glucosyloxy-3-hydroxyphenyl)-8,8′-cyclobutane-9-methyl dicarboxylic acid (10). The structures of the isolated compounds were elucidated by NMR and HRMS. The structure of compound 1 was confirmed by X-ray crystallography. 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引用次数: 0

摘要

Ruiz & Pav。是一种产于中美洲和南美洲的热带树木。它是Alzatea属和Alzateaceae家族中唯一存活的物种,其他所有物种都已灭绝。为了探索发现不同寻常的天然产物的可能性,研究了黄花蒿的二氯甲烷和甲醇提取物(茎和叶)的化学成分。极性和极性提取物采用半制备高效液相色谱法纯化,采用合适的固定相柱,分离出12种化合物:walterolactone B (2) walterolactone A/B β- d -吡喃葡萄糖苷(3),没食子酸(4),咖啡酸4- o -β- d -葡萄糖苷(6),walterolactone A/B 6- o -没食子酸-β- d -葡萄糖苷(8),咖啡酸(9),8-去甲基sideroxylin (11), sideroxylin(12)和7,7 ' -双(3,4-二羟基苯基)-8,8 ' -环丁二羧酸(7)。三个分离的化合物是本文首次报道的天然产物:二甲基银苦苷(1)和两个β-truxinic酸衍生物(rel-(7S, 8R, 7 ' r,8 ' s)-7,7 ' -双(4-葡萄糖氧基-3-羟基苯基)-8,8 ' -环丁烷二羧酸(5)和rel-(7S, 8R, 7 ' r,8 ')-7,7 ' -双(4-葡萄糖氧基-3-羟基苯基)-8,8 ' -环丁烷-9-甲基二羧酸(10))。分离得到的化合物的结构经NMR和HRMS鉴定。化合物1的结构经x射线晶体学证实。基于质谱的黄花蒿提取物代谢物分析显示,在基于特征的分子网络的帮助下,假定注释了额外的truxinic酸衍生物。酚类化合物如曲辛酸衍生物的存在可以解释这种植物的传统用途,因为这些化合物已知具有抗炎和抗伤害性。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
Phytochemical study of Alzatea verticillata, the sole species belonging to the Alzateaceae family
Alzatea verticillata Ruiz & Pav. (Alzateaceae) is a tropical tree from Central and South America. It is the only living species of Alzatea genus and the Alzateaceae family, all others being extinct. With the aim to investigate the possibility to find unusual natural products, the chemical content of the dichloromethane and methanolic extracts (stems and leaves) of A. verticillata have been investigated. Apolar and polar extracts were purified by semi-preparative HPLC using appropriate stationary phase columns allowing the isolation of 12 compounds: walterolactone B (2) walterolactone A/B β-D-pyranoglucoside (3), gallic acid (4), caffeic acid 4-O-β-D-glucopyranoside (6), walterolactone A/B 6-O-gallate-β-D-glucopyranoside (8), caffeic acid (9), 8-desmethylsideroxylin (11), sideroxylin (12) and 7,7′-bis(3,4-dihydroxyphenyl)-8,8′-cyclobutanedicarboxylic acid (7). Three isolated compounds are natural products described here for the first time: dimethyl-anemonin (1) and two β-truxinic acid derivatives (rel-(7S, 8R, 7′R, 8′S)-7,7′-bis(4-glucosyloxy-3-hydroxyphenyl)-8,8′-cyclobutane dicarboxylic acid (5) and rel-(7S, 8R, 7′R, 8′S)-7,7′-bis(4-glucosyloxy-3-hydroxyphenyl)-8,8′-cyclobutane-9-methyl dicarboxylic acid (10). The structures of the isolated compounds were elucidated by NMR and HRMS. The structure of compound 1 was confirmed by X-ray crystallography. A MS-based metabolite analysis of the A. verticillata extracts revealed additional truxinic acid derivatives that were putatively annotated with the help of feature-based molecular network. The presence of phenolic compounds such as truxinic acid derivatives could explain the traditional use of this plant as these compounds are known to possess anti-inflammatory and anti-nociceptive properties.
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