Triterpenoids from the resin of Styrax tonkinensis and their antiproliferative and differentiation effects in human leukemia HL-60 cells
Triterpenoids from the resin of Styrax tonkinensis and their antiproliferative and differentiation effects in human leukemia HL-60 cells
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DOI：
10.1021/np050371z
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发表时间：
2006-05-26
影响因子：
5.1
通讯作者：
Jing, Yongkui
中科院分区：
文献类型：
--
作者：
Wang, Feng;Hua, Huiming;Jing, Yongkui
四种新的三萜类化合物，6 β-羟基-3-氧代-11 R，12 R-环氧甾烷-28，13 β-甾烷（1），3 β，6 β-二羟基-11 α，12 α-环氧甾烷-28，13 β-甾烷（2），3 β，6 β-二羟基-11-氧代-甾烷-12-烯-28-酸（3）和3 β-羟基-12-氧代-13 H α-甾烷-28，从越南安息香树脂中分离得到19 β-藜芦（4）和5种已知的三萜类化合物：19 α-羟基-3-氧代-藜芦-12-烯-28-酸（5）、6 β-羟基-3-氧代-藜芦-12-烯-28-酸（6）、苏玛树脂酸（7）、siaresinolic acid（8）和油酸（9）。通过物理化学和光谱方法确定了这些三萜类化合物的结构。化合物4的构型通过X-射线晶体学分析确认。所有这些三萜类化合物均抑制HL-60细胞生长，IG（50）值范围为8.9 - 99.4 μ M。油酸（9）是最有效的抗增殖剂，IG（50）值为8.9 μ M。虽然3 β，6 β-二羟基-11-氧代-藜芦-12-烯-28-酸（3）在这些三萜类化合物中表现出最小有效的生长抑制，但它诱导HL-60细胞经历分化，如通过NBT还原测定所测量的。
Four new triterpenoids, 6 beta-hydroxy-3-oxo-11R, 12R-epoxyolean-28,13 beta-olide ( 1), 3 beta, 6 beta-dihydroxy-11 alpha, 12 alpha-epoxyolean-28, 13 beta-olide ( 2), 3 beta, 6 beta-dihydroxy-11-oxo-olean-12-en-28-oic acid ( 3), and 3 beta-hydroxy-12-oxo-13H alpha-olean-28, 19 beta-olide ( 4), and five known triterpenes, 19 alpha-hydroxy-3-oxo-olean-12-en-28-oic acid ( 5), 6 beta-hydroxy-3-oxo-olean-12-en-28-oic acid ( 6), sumaresinolic acid ( 7), siaresinolic acid ( 8), and oleanolic acid ( 9), were isolated from the resin of Styrax tonkinensis. The structures of these triterpenoids were determined by physicochemical and spectroscopic methods. The configuration of compound 4 was confirmed by X-ray crystallographic analysis. All these triterpenoids inhibited HL-60 cell growth with IG(50) values ranging from 8.9 to 99.4 mu M. Oleanolic acid ( 9) was the most effective antiproliferative agent, with an IG(50) value of 8.9 mu M. While 3 beta, 6 beta-dihydroxy-11-oxo-olean-12-en-28-oic acid ( 3) exhibited the least effective growth inhibition among these triterpenoids, it induced HL-60 cells to undergo differentiation as measured by an NBT reduction assay.