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Neoverataline A and B, two antifungal alkaloids with a novel carbon skeleton from Veratrum taliense
Tetrahedron ( IF 2.1 ) Pub Date : 21 July 2003 , DOI: 10.1016/s0040-4020(03)00882-2
Chang-Xin Zhou , Jun-Yan Liu , Wen-Cai Ye , Chang-Hong Liu , Ren-Xiang Tan

Bioassay-guided fractionation of the ethanol extract of the roots and rhizomes of Veratrum taliense yielded two new and thirteen known steroidal alkaloids. The structures of the two new compounds, neoverataline A and B, were established by extensive spectroscopic analyses to be 3,4-secocevane-4,9-olid-14,15,16,20-tetra-ol-3-oic acid and 3,4-secocevane-4,9-olid-7,14,15,16,20-penta-ol-3-oic acid, respectively, and are a novel carbon skelton. All of the fifteen alkaloids were subjected to in vitro antifungal assays, which showed that the verazine- (veramitaline, stenophylline B, stenophylline B-3-O-β-d-glucopyranoside, veramiline-3-O-β-d-glucopyranoside) and jerveratrum-type (jervine, jervine-3-O-β-d-glucopyranoside) alkaloids exhibited strong antifungal activities against the phytopathogenic fungus Phytophthora capisis with MICs of 160, 120, 160, 80, 80 and 120 μg·L−1, respectively. Furthermore, the verazine-type alkaloids stenophylline B, stenophylline B 3-O-β-d-glucopyranoside and veramiline 3-O-β-d-glucopyranoside were shown to also inhibit the growth of another fungal phytopathogen Rhizoctonia cerealis with MICs of 160, 120 and 120 μg mL−1. The MICs of triadimefon (an antifungal agrochemical used herein as a positive control) against P. capisis and R. cerealis were 120 and 80 μg mL−1, respectively. A preliminary structure–activity relationship regarding these alkaloids has been formulated.

中文翻译:

Neoverataline A和B,两种具有新型碳骨架的抗真菌生物碱,均来自塔拉木(Veratrum taliense)

生物测定指导的塔拉木(Veratrum taliense)根和根茎乙醇提取物的分级分离产生了两种新的和十三种已知的甾体生物碱。通过广泛的光谱分析,确定了两种新化合物neoverataline A和B的结构为3,4-secocevane-4,9-olid-14,15,16,20-tetra-ol-3-oic acid和3,4-secocevane-4,9-olid-7,14,15,16,20-penta-ol-3-oic acid,是一种新型的碳骨架。对这15种生物碱进行了体外抗真菌试验,结果显示了维拉嗪-(维拉米林,甜菊碱B,甜茶碱B-3- O -β-d-吡喃葡萄糖苷,veramiline-3- O - β -d-吡喃葡萄糖苷)和j皮型(rum皮,j皮3- O-β-d-吡喃葡萄糖苷)生物碱对植物病原真菌疫霉具有很强的抗真菌活性,其MIC分别为160、120、160、80、80和120μg·L -1。此外,verazine型生物碱stenophylline B,stenophylline乙3- ö -β-d-D-吡喃葡萄糖苷和veramiline 3- ö -β-d-D-吡喃葡萄糖苷显示出也抑制另一植物病原真菌的生长纹枯病与160的MIC, 120和120μgmL -1。三唑酮(抗真菌农用化学品本文所使用的,作为阳性对照)的MIC抗P. capisisR.禾谷分别为120和80微克毫升-1, 分别。已经建立了有关这些生物碱的初步构效关系。
更新日期:2017-01-31
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