Tobacco Research Institute, Chinese Academy of Agricultural Sciences, Qingdao, 266101, China; Graduate School of Chinese Academy of Agricultural Sciences, Beijing, 100081, China.
Tobacco Research Institute, Chinese Academy of Agricultural Sciences, Qingdao, 266101, China.
Phytochemistry. 2024 Jul;223:114117. doi: 10.1016/j.phytochem.2024.114117. Epub 2024 May 1.
Cembranoids and labdanes are two important types of diterpenes in tobacco (Nicotiana genus) that are predominantly found in the leaf and flower glandular trichome secretions. This is the first systematic review of the biosynthesis, chemical structures, bioactivities, and utilisation values of cembranoid and labdane diterpenes in tobacco. A total of 131 natural cembranoid diterpenes have been reported in tobacco since 1962; these were summarised and classified according to their chemical structure characteristics as isopropyl cembranoids (1-88), seco-cembranoids (89-103), chain cembranoids (104-123), and polycyclic cembranoids (124-131). Forty natural labdane diterpenes reported since 1961 were also summarised and divided into epoxy side chain labdanes (132-150) and epoxy-free side chain labdanes (151-171). Tobacco cembranoid and labdane diterpenes are both formed via the methylerythritol 4-phosphate pathway and are synthesised from geranylgeranyl diphosphate. Their biosynthetic pathways and the four key enzymes (cembratrienol synthase, cytochrome P450 hydroxylase, copalyl diphosphate synthase, and Z-abienol cyclase) that affect their biosynthesis have been described in detail. A systematic summary of the bioactivity and utilisation values of the cembranoid and labdane diterpenes is also provided. The agricultural bioactivities associated with cembranoid and labdane diterpenes include antimicrobial and insecticidal activities as well as induced resistance, while the medical bioactivities include cytotoxic and neuroprotective activities. Further research into the cembranoid and labdane diterpenes will help to promote their development and utilisation as plant-derived pesticides and medicines.
萜类和贝壳杉烷类是烟草（Nicotiana 属）中两种重要的二萜，主要存在于叶片和花的腺毛分泌中。这是对烟草中贝壳杉烷和贝壳杉烷二萜的生物合成、化学结构、生物活性和利用价值进行的首次系统综述。自 1962 年以来，共报道了 131 种天然贝壳杉烷二萜在烟草中的存在；根据其化学结构特征，将这些化合物进行了总结和分类，包括异丙基贝壳杉烷（1-88）、贝壳杉烷（89-103）、链贝壳杉烷（104-123）和多环贝壳杉烷（124-131）。自 1961 年以来，还报道了 40 种天然贝壳杉烷二萜，也进行了总结，并分为环氧侧链贝壳杉烷（132-150）和无环氧侧链贝壳杉烷（151-171）。烟草贝壳杉烷和贝壳杉烷二萜都是通过甲基赤藓醇 4-磷酸途径形成的，由香叶基香叶基二磷酸合成。详细描述了它们的生物合成途径和影响其生物合成的四个关键酶（贝壳杉烯醇合酶、细胞色素 P450 羟化酶、法呢基二磷酸合酶和 Z-阿比烯醇环化酶）。还对贝壳杉烷和贝壳杉烷二萜的生物活性和利用价值进行了系统总结。贝壳杉烷和贝壳杉烷二萜的农业生物活性包括抗菌和杀虫活性以及诱导抗性，而医学生物活性包括细胞毒性和神经保护活性。进一步研究贝壳杉烷和贝壳杉烷二萜将有助于促进它们作为植物源农药和药物的开发和利用。
