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Bioactivity-guided identification and isolation of a major antimicrobial compound in Cistus creticus subsp. creticus leaves and resin “ladano”
Industrial Crops and Products ( IF 5.6 ) Pub Date : 2022-05-13 , DOI: 10.1016/j.indcrop.2022.114992
Marijana Skorić , Ana Ćirić , Snežana Budimir , Dušica Janošević , Boban Anđelković , Marina Todosijević , Slađana Todorović , Marina Soković , Jasmina Glamočlija , Vele Tešević , Uroš Gašić , Danijela Mišić , Angelos K. Kanellis

Cistus creticus subsp. creticus is a shrubby Mediterranean plant used since ancient times in folk medicine for the treatment of different diseases. C. creticus extracts and resin contain different types of secondary metabolites, such as terpenoids (predominantly labdane type diterpenoids), and phenylpropanoids. Growth conditions seem to influence the content of labdane-type diterpenes and flavan-3-ols in leaves of C. creticus subsp. creticus. Histochemical staining of leaves’ trichomes and comprehensive phytochemical characterization of resin, leaves and their exudates, indicated that long-stalked capitate trichomes of C. creticus subsp. creticus, grown both in vitro (IV) and in greenhouse (GH), are capable of producing bioactive oleoresin-related terpenoids and phenylpropanoids compounds. Bioactivity-guided approach was implemented in search for the major antibacterial compound in C. creticus resin against two Gram-negative (Escherichia coli and Pseudomonas aeruginosa) and two Gram-positive bacteria (Bacillus cereus and Micrococcus flavus). Bioautographic assay on TLC plates with separated components of Cistus resin extract, revealed a pronounced zone of microbial growth inhibition, corresponded to a highly active compound with Rf values of 0.45, structurally characterized and identified as ent-3β-acetoxy-13-epi-manoyl oxide. This finding opens the route for focusing on isolation and functional characterization of genes involved in the biosynthesis of ent-3β-acetoxy-13-epi-manoyl oxide and its precursor ent-3β-hydroxy-13-epi-manoyl oxide, with the aim to establish sustainable in vitro biotechnological protocols for its large-scale production in homologous and heterologous plant and microbial hosts.



中文翻译:

生物活性指导鉴定和分离 Cistus creticus subsp. 中的主要抗菌化合物。creticus 叶子和树脂“ladano”

岩蔷薇种。creticus是一种地中海灌木植物,自古以来就在民间医学中用于治疗不同的疾病。C. creticus提取物和树脂含有不同类型的次生代谢物,例如萜类化合物(主要是拉丹型二萜类化合物)和苯丙烷类。生长条件似乎会影响C. creticus subsp.叶子中的 labdane 型二萜和 flavan-3-ols 的含量。白垩属。叶片毛状体的组织化学染色和树脂、叶片及其分泌物的综合植物化学表征表明,C. creticus subsp. 的长柄头状毛状体。白垩系, 在体外 (IV) 和温室 (GH) 中生长,能够产生生物活性油树脂相关的萜类化合物和苯丙烷类化合物。实施了生物活性指导的方法,以寻找C. creticus树脂中针对两种革兰氏阴性菌(大肠杆菌铜绿假单胞菌)和两种革兰氏阳性菌(蜡状芽孢杆菌微球菌)的主要抗菌化合物。用岩蔷薇树脂提取物的分离成分在 TLC 板上进行生物自显影分析,揭示了明显的微生物生长抑制区,对应于 Rf 值为 0.45 的高活性化合物,其结构特征和鉴定为ent-3 β -acetoxy -13- epi -manoyl 氧化物。这一发现开辟了关注参与ent -3 β -acetoxy -13- epi -manoyl oxide 及其前体ent -3 β -hydroxy - 13- epi -manoyl oxide 的生物合成的基因的分离和功能表征的途径,具有旨在建立可持续的体外生物技术方案,以在同源和异源植物和微生物宿主中进行大规模生产。

更新日期:2022-05-14
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