Petit Bastien, Mitaine-Offer Anne-Claire, Fischer Jochen, Schüffler Anja, Delaude Clément, Miyamoto Tomofumi, Tanaka Chiaki, Thines Eckhard, Lacaille-Dubois Marie-Aleth
PEPITE EA 4267, Laboratoire de Pharmacognosie, UFR des Sciences de Santé, Université de Bourgogne Franche-Comté, BP 87900, 21079, Dijon, Cedex, France.
PEPITE EA 4267, Laboratoire de Pharmacognosie, UFR des Sciences de Santé, Université de Bourgogne Franche-Comté, BP 87900, 21079, Dijon, Cedex, France.
Phytochemistry. 2021 Aug;188:112797. doi: 10.1016/j.phytochem.2021.112797. Epub 2021 May 20.
Chytranthus macrobotrys and Radlkofera calodendron are two Sapindaceae characterized by a lack of phytochemical data. Both root barks from the two Sapindaceae species were processed by ethanol extraction followed by the isolation of their primary constituents by liquid chromatography. This process yielded four previously undescribed terpenoid glycosides together with eight known analogues. Extracts and isolated compounds from C. macrobotrys and R. calodendron were then screened for antimicrobial activity against fifteen phytopathogens. The biological screening also involved extracts and pure compounds from Blighia unijugata and Blighia welwitschii, two Sapindaceae previously studied by our group. Phytopathogens were chosen based on their economic impact on agriculture worldwide. The selection was composed primarily of fungal species including; Pyricularia oryzae, Gaeumannomyces graminis var. tritici, Zymoseptoria tritici, Fusarium oxysporum, Botrytis cinerea, Pythium spp., Trichoderma spp. and Rhizoctonia solani. Furthermore, pure terpenoid glycosides were tested for the first time against wood-inhabiting phytopathogens such as; Phaeomoniella chlamydospora, Phaeoacremonium minimum, Fomitiporia mediterranea, Eutype lata and Xylella fastidiosa. Raw extracts exhibited different levels of activity dependent on the organism. Some pure compounds, including 3-O-α-L-arabinopyranosyl-(1 → 4)-β-D-xylopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosylhederagenin, 3-O-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosylhederagenin (α-hederin), 3-O-β-D-glucopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosylhederagenin (macranthoside A) and 3-O-α-L-arabinopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosylhederagenin (clemontanoside C), exhibited significant growth inhibitions on Pyricularia oryzae, Gaeumannomyces graminis var. tritici, Fomitiporia mediterranea and Zymoseptoria tritici. Monodesmoside triterpene saponins, in particular, exhibited MIC (IC) values as low as 25 μg/ml and IC values as low as 10 μg/ml against these phytopathogens. Structure-activity relationships, as well as plant-microbe interactions, were discussed.
大花黄钟木（Chytranthus macrobotrys）和卡氏红椤（Radlkofera calodendron）是无患子科的两个物种，其特点是缺乏植物化学数据。对这两种无患子科植物的根皮进行乙醇提取，然后通过液相色谱法分离其主要成分。该过程产生了四种以前未描述的萜类糖苷以及八种已知类似物。然后对大花黄钟木和卡氏红椤的提取物和分离出的化合物进行了针对15种植物病原体的抗菌活性筛选。生物筛选还涉及单珠无患子（Blighia unijugata）和韦氏无患子（Blighia welwitschii）的提取物和纯化合物，这两种无患子科植物是我们团队之前研究过的。根据植物病原体对全球农业的经济影响来选择它们。所选植物病原体主要包括真菌物种，如稻瘟病菌（Pyricularia oryzae）、小麦全蚀病菌（Gaeumannomyces graminis var. tritici）、小麦黄斑叶枯病菌（Zymoseptoria tritici）、尖孢镰刀菌（Fusarium oxysporum）、灰葡萄孢（Botrytis cinerea）、腐霉属（Pythium spp.）、木霉属（Trichoderma spp.）和立枯丝核菌（Rhizoctonia solani）。此外，首次对纯萜类糖苷针对诸如拟茎点霉（Phaeomoniella chlamydospora）、极小拟茎点霉（Phaeoacremonium minimum）、地中海拟层孔菌（Fomitiporia mediterranea）、宽孢盘菌（Eutype lata）和木质部难养菌（Xylella fastidiosa）等木材栖居植物病原体进行了测试。粗提物根据生物体表现出不同程度的活性。一些纯化合物，包括3 - O-α-L-阿拉伯吡喃糖基-(1→4)-β-D-木吡喃糖基-(1→3)-α-L-鼠李吡喃糖基-(1→2)-α-L-阿拉伯吡喃糖基常春藤皂苷元、3 - O-α-L-鼠李吡喃糖基-(1→2)-α-L-阿拉伯吡喃糖基常春藤皂苷元（α-常春藤皂苷）、3 - O-β-D-葡萄糖吡喃糖基-(1→3)-α-L-鼠李吡喃糖基-(1→2)-α-L-阿拉伯吡喃糖基常春藤皂苷元（大花苷A）和3 - O-α-L-阿拉伯吡喃糖基-(1→3)-α-L-鼠李吡喃糖基-(1→2)-α-L-阿拉伯吡喃糖基常春藤皂苷元（楔叶常春藤皂苷C），对稻瘟病菌、小麦全蚀病菌、地中海拟层孔菌和小麦黄斑叶枯病菌表现出显著的生长抑制作用。单糖链三萜皂苷尤其对这些植物病原体表现出低至25μg/ml的最低抑菌浓度（MIC）值和低至10μg/ml的半数抑制浓度（IC）值。讨论了构效关系以及植物与微生物的相互作用。
