A new polyoxygenated cyclohexene and a new megastigmane glycoside from Uvaria grandiflora. Bioorg.

A new polyoxygenated cyclohexene and a new megastigmane glycoside from Uvaria grandiflora. Bioorg.
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一种新的多氧环己烯和一种来自 Uvaria grandiflora 的新的巨豆苷。

DOI:
10.1016/j.bmcl.2015.05.066
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发表时间:
2015
期刊:
Bioorganic Medicinal Chemistry Letters
影响因子:
--
通讯作者:
T. N.
T. N.
中科院分区:
--
文献类型:
--
作者:
Duc;H. V.;Kodama;T.;Hien;L. T. B. P.;Kiem;V.;Thao;D. T.;Tai;B. H.;Anh;L. T.;Win;N. N.;Imagawa;H.;Ito;T.;Morita;H.;Hoai;T. N.

文献摘要

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从越南采集的紫玉盘地上部分中分离得到一个新的多氧环己烯化合物(−)-3-O-脱苯甲酰泽尼酮(1)和一个新的巨豆藤烷糖苷化合物grandonoside A(2),以及10个已知化合物,包括多氧环己烯化合物(3-6)、三萜类化合物(7)、生物碱(8)、长链醇(9)、己烯基吡喃葡萄糖苷(10)、和皂苷(11-12)。它们的化学结构通过结合广泛的NMR光谱与X-射线晶体学分析来阐明1,和化学转化为2。化合物1对LU-1和SK-Mel-2细胞系表现出显著的细胞毒性,IC 50值分别为4.68和3.63 μM。值得注意的是,12对LU-1、KB、Hep-G2、MKN-7和SW-480细胞系的细胞毒性与阳性对照椭圆藤碱相当,IC 50值范围为1.24 - 1.60 μM。
A new polyoxygenated cyclohexene, (−)-3-O-debenzoylzeylenone (1), and a new megastigmane glycoside, grandionoside A (2), were isolated from the aerial parts of Uvariagrandifloracollected in Vietnam, together with ten known compounds including polyoxygenated cyclohexenes (3–6), a triterpenoid (7), an alkaloid (8), a long chain alcohol (9), hexenyl glycopyranoside (10), and saponins (11–12). Their chemical structures were elucidated by a combination of extensive NMR spectroscopy with X-ray crystallographic analysis for1, and chemical conversion for2. Compound1exhibited significant cytotoxicity against the LU-1 and SK-Mel-2 cell lines with IC50values of 4.68 and 3.63 μM, respectively. Remarkably, the cytotoxicity of12against the LU-1, KB, Hep-G2, MKN-7, and SW-480 cell lines was comparable to that of ellipticine, the positive control, with IC50values ranging from 1.24 to 1.60 μM.