Cimmino Alessio, Masi Marco, Evidente Marco, Superchi Stefano, Evidente Antonio
Dipartimento di Scienze Chimiche, Università di Napoli Federico II, Complesso Universitario Monte S. Angelo, Napoli, Italy.
Dipartimento di Scienze, Università degli Studi della Basilicata, Potenza, Italy.
Chirality. 2017 Sep;29(9):486-499. doi: 10.1002/chir.22719. Epub 2017 Jun 26.
Plants belonging to the Amaryllidaceae family are well known for their ornamental and medicinal use. Plant members of this group are distributed through both tropical and subtropical regions of the world and are dominant in Andean South America, the Mediterranean basin, and southern Africa. Amaryllidaceae plants have been demonstrated to be a good source of alkaloids with a large spectrum of biological activities, the latter being strictly related to the absolute stereochemistry of the alkaloid scaffold. Among them, great importance for practical applications in medicine has galanthamine, which has already spawned an Alzheimer's prescription drug as a potent and selective inhibitor of the enzyme acetylcholinesterase. Furthermore, lycorine as well as its related isocarbostyryl analogs narciclasine and pancratistatine have shown a strong anticancer activity in vitro against different solid tumors with malignant prognosis. This review addresses the assignment of the absolute configuration of several Amaryllidaceae alkaloids and its relationship with their biological activities.
石蒜科植物以其观赏和药用价值而闻名。该科植物分布于世界热带和亚热带地区,在南美洲安第斯地区、地中海盆地和非洲南部占主导地位。已证明石蒜科植物是生物碱的良好来源,这些生物碱具有广泛的生物活性,而生物活性与生物碱骨架的绝对立体化学密切相关。其中,加兰他敏在医学实际应用中具有重要意义,它已催生出一种治疗阿尔茨海默病的处方药,作为一种强效且选择性的乙酰胆碱酯酶抑制剂。此外,石蒜碱及其相关的异卡波酰基类似物水仙环素和 pancratistatine 在体外对不同预后不良的实体瘤显示出强大的抗癌活性。本综述探讨了几种石蒜科生物碱绝对构型的确定及其与生物活性的关系。