Bautista Elihú, Fragoso-Serrano Mabel, Pereda-Miranda Rogelio
Departamento de Farmacia, Facultad de Química, Universidad Nacional Autónoma de México , Mexico City, 04510 DF, Mexico.
J Nat Prod. 2015 Jan 23;78(1):168-72. doi: 10.1021/np500762w. Epub 2014 Dec 23.
The first macrocyclic bisdesmoside resin glycoside, jalapinoside (4), was purified by preparative-scale recycling HPLC from the MeOH-soluble extracts of Ipomoea purga roots, the officinal jalap. Purgic acid C (3), a new glycosidic acid of ipurolic acid, was identified as 3-O-β-d-quinovopyranoside, 11-O-β-d-quinovopyranosyl-(1→2)-O-β-d-glucopyranosyl-(1→3)-O-[β-d-fucopyranosyl-(1→4)]-O-α-l-rhamnopyranosyl-(1→2)-O-β-d-glucopyranosyl-(1→2)-O-β-d-quinovopyranoside (3S,11S)-dihydroxytetradecanoic acid. The acylating residues of this core were acetic, (+)-(2S)-methylbutanoic, and dodecanoic acids. The site of lactonization was defined as C-3 of the second saccharide moiety. Reversal of multidrug resistance by this noncytotoxic compound was evaluated in vinblastine-resistant human breast carcinoma cells.
首个大环双去甲氧基树脂糖苷——墨西哥牵牛苷（4），是通过制备规模的循环高效液相色谱法从墨西哥牵牛根的甲醇可溶提取物中纯化得到的。番泻酸C（3），一种新的异普洛酸糖苷酸，被鉴定为3 - O - β - D - 奎诺吡喃糖苷，11 - O - β - D - 奎诺吡喃糖基 -（1→2）- O - β - D - 吡喃葡萄糖基 -（1→3）- O - [β - D - 岩藻吡喃糖基 -（1→4）]- O - α - L - 鼠李吡喃糖基 -（1→2）- O - β - D - 吡喃葡萄糖基 -（1→2）- O - β - D - 奎诺吡喃糖苷（3S，11S）- 二羟基十四烷酸。该核心结构的酰化残基为乙酸、（+）-（2S）- 甲基丁酸和十二烷酸。内酯化位点被确定为第二个糖部分的C - 3位。在长春碱耐药的人乳腺癌细胞中评估了这种非细胞毒性化合物对多药耐药性的逆转作用。
