<br>Alstoboonine，一种来自 Alstonia boonei 叶的 Ulean 型吲哚生物碱,Journal of Natural Products

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Alstoboonine，一种来自 Alstonia boonei 叶的 Ulean 型吲哚生物碱
Journal of Natural Products ( IF 3.3 ) Pub Date : 2023-11-09 , DOI: 10.1021/acs.jnatprod.3c00832
Manuel Grimm ₁ , Ramona Börner ₁ , John N Addotey ₂ , Thomas J Schmidt ₁ , Verena Spiegler ₁

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Alstonia boonei De Wild 是西非的一种常见植物，用于传统医学中的多种适应症。虽然茎皮经常被研究，但人们对叶子的植物化学和生物活性知之甚少。在当前的研究中，通过 MS、NMR 和 ECD 分离并表征了氢乙醇叶提取物的主要生物碱。这导致了 alstoboonine 1的鉴定，这是一种新的乌兰型生物碱，以及之前报道的八种吲哚生物碱：15-羟基安古替洛宾 A ( 2 )、6,7-seco-angustilobine B ( 3 )、6,7-seco- 19,20-α-环氧安古替洛宾 B ( 4 )、阿曲斯汀 E ( 5 )、阿曲斯汀 C ( 6 )、阿曲斯汀 D ( 7 )、12-甲氧基乙酰脒 ( 8 ) 和 19-氧代-12-甲氧基乙酰脒 ( 9 )。 1在体外对恶性疟原虫NF54 有中等活性 (IC ₅₀ 6.9 μM)，但对其他原生动物寄生虫（布氏锥虫、克氏锥虫、杜氏利什曼原虫）无活性。在 L6 大鼠骨骼肌细胞和 MCF-7 乳腺癌细胞中未观察到明显的细胞毒性作用。类似地，化合物3至9在MCF-7细胞中未表现出细胞毒性。由于据报道该植物传统上用作驱虫剂，因此针对线虫秀丽隐杆线虫测试了主要生物碱2、5、6和8 。观察到6 号(LC ₅₀ 400 μM) 具有杀线虫作用，而2 号、 5 号和8 号则无活性。

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Alstoboonine, an Ulean-Type Indole Alkaloid from Alstonia boonei Leaves

Alstonia boonei De Wild is a common plant in West Africa used in traditional medicine for various indications. While the stem bark has frequently been investigated, not much is known about the phytochemistry and bioactivity of the leaves. Within the current study, the major alkaloids of a hydroethanolic leaf extract were therefore isolated and characterized by MS, NMR, and ECD. This led to the identification of alstoboonine 1, a new ulean-type alkaloid, along with eight previously reported indole alkaloids, 15-hydroxyangustilobine A (2), 6,7-seco-angustilobine B (3), 6,7-seco-19,20-α-epoxyangustilobine B (4), alstrostine E (5), alstrostine C (6), alstrostine D (7), 12-methoxyechitamidine (8), and 19-oxo-12-methoxyechitamidine (9). 1 was moderately active in vitro against Plasmodium falciparum NF54 (IC₅₀ 6.9 μM), but inactive against other protozoan parasites (Trypanosoma brucei, Trypanosoma cruzi, Leishmania donovani). No significant cytotoxic effects were observed in L6 rat skeletal myoblast cells and MCF-7 breast cancer cells. Similarly, compounds 3 to 9 did not show cytotoxicity in MCF-7 cells. Due to the reported traditional use of the plant as an anthelmintic, the major alkaloids 2, 5, 6, and 8 were tested against the nematode Caenorhabditis elegans. Nematicidal effects were observed for 6 (LC₅₀ 400 μM), whereas 2, 5, and 8 were inactive.

更新日期：2023-11-09

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