Division of Pharmacognosy and Natural Products Chemistry, Department of Pharmacy, National and Kapodistrian University of Athens, Panepistimiopolis, Zografou, 15771 Athens, Greece.
Section of Botany, Department of Biology, National and Kapodistrian University of Athens, Panepistimiopolis, Zografou, 15781 Athens, Greece.
Fitoterapia. 2023 Oct;170:105648. doi: 10.1016/j.fitote.2023.105648. Epub 2023 Aug 9.
Pistacia lentiscus L. var. Chia belongs to the Anacardiaceae family, and it is cultivated only in the south part of Chios island, in Greece. Even though it is renowned for its unique resin, Chios mastic gum (CMG), the tree leaves have also been used in traditional medicine, while the annual pruning generates a large biomass of unused by-products. Thus, the aim of the present study was the detailed phytochemical investigation of P. lentiscus var. Chia leaves towards the search of antimicrobial agents. UPLC-HRMS & HRMS/MS based dereplication methods led to the detailed characterization of the aqueous leaf extract. In addition, twelve compounds were isolated and purified from the methanol extract and were identified using spectroscopic and spectrometric methods (NMR, HRMS) belonging to phenolic acids, tannins, flavonoids and terpenes, with the most interesting being 2-hydroxy-1,8-cineole β-D-glucopyranoside which was isolated for the first time in the Anacardiaceae family. Remarkably, based on NMR data, methanol and aqueous extracts were found to be particularly rich in shikimic acid, a valuable building block for the pharmaceutical industry, for instance in the synthesis of the active ingredient of Tamiflu®, oseltamivir. Finally, extracts (EtOAc, MeOH, HO) and major compounds i.e., shikimic acid, 2-hydroxy-1,8-cineole β-D-glucopyranoside and myricitrin were evaluated for their antimicrobial properties. MeOH and HO mastic leaf extracts as well as myricitrin and, particularly, 2-hydroxy-1,8-cineole β-D-glucopyranoside showed significant selective activity against pathogenic Mucorales, but not against Aspergilli (Aspergillus nidulans, Aspergillus fumigatus), Candida albicans or bacteria (Escherichia coli, Pseudomonas aeruginosa, Bacillus subtilis).
乳香黄连木（Pistacia lentiscus L. var. Chia）属于漆树科，仅在希腊的希俄斯岛南部种植。尽管它以其独特的树脂——乳香（Chios mastic gum，CMG）而闻名，但树叶也被用于传统医学，而每年的修剪会产生大量未被利用的副产品。因此，本研究的目的是详细研究乳香黄连木（Pistacia lentiscus L. var. Chia）叶的植物化学成分，寻找具有抗菌活性的化合物。基于 UPLC-HRMS 和 HRMS/MS 的鉴定方法，对乳香黄连木（Pistacia lentiscus L. var. Chia）叶的水提物进行了详细的表征。此外，从甲醇提取物中分离并纯化了 12 种化合物，并通过光谱和谱学方法（NMR、HRMS）鉴定了它们的结构，属于酚酸、单宁、类黄酮和萜类化合物，其中最有趣的是首次在漆树科中分离得到的 2-羟基-1,8-桉叶素-β-D-吡喃葡萄糖苷。值得注意的是，根据 NMR 数据，甲醇和水提取物中特别富含莽草酸，这是制药行业的一种有价值的结构单元，例如用于合成达菲（Tamiflu®）的活性成分奥司他韦（oseltamivir）。最后，评估了提取物（EtOAc、MeOH、HO）和主要化合物，即莽草酸、2-羟基-1,8-桉叶素-β-D-吡喃葡萄糖苷和杨梅素，它们的抗菌性能。结果表明，乳香黄连木（Pistacia lentiscus L. var. Chia）的甲醇和水提取物以及杨梅素，特别是 2-羟基-1,8-桉叶素-β-D-吡喃葡萄糖苷，对致病性毛霉科真菌具有显著的选择性活性，但对曲霉菌（构巢曲霉、烟曲霉）、白色念珠菌或细菌（大肠杆菌、铜绿假单胞菌、枯草芽孢杆菌）没有活性。
