PLANT ANTITUMOR AGENTS .6. ISOLATION AND STRUCTURE OF TAXOL, A NOVEL ANTILEUKEMIC AND ANTITUMOR AGENT FROM TAXUS-BREVIFOLIA
PLANT ANTITUMOR AGENTS .6. ISOLATION AND STRUCTURE OF TAXOL, A NOVEL ANTILEUKEMIC AND ANTITUMOR AGENT FROM TAXUS-BREVIFOLIA
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DOI：
10.1021/ja00738a045
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发表时间：
1971-01-01
影响因子：
15
通讯作者：
MCPHAIL, AT
中科院分区：
文献类型：
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作者：
WANI, MC;TAYLOR, HL;MCPHAIL, AT
OC-Br具有抗白血病和肿瘤抑制特性，是第一个具有紫杉烷环的化合物，已被证明具有这种活性。将茎皮的醇提取物浓缩并在水和氯仿之间分配。以9 KB和各种白血病系统的测定为指导，将氯仿提取物的残留物在Florisil、Sephadex LH-20和硅胶上连续三次层析，然后从甲醇水溶液中结晶，得到紫杉醇（1）：7产率0.02%; M+ m/e 853，计算为C_（47）H_（51）NO_（14），853;[a] 20 o-49（MeOH）; Xmax（MeOH）227 nm（e 29，800），273（1700）; vZH'3300-3500（OH，NH），1730（酯），1710（酮），1650（酰胺）cm-1。1的特征化学位移8示于表I中。由于紫杉醇的量极其有限，而且其证据十分复杂，人们试图制备适合于X射线分析的衍生物。阿尔-
OC——Br antileukemic and tumor inhibitory properties6 and is the first compound possessing the taxane6 ring which has been demonstrated to have such activity. The alcohol extract of the stem bark was concentrated and partitioned between water and chloroform. Guided by assay in 9KB and various leukemia systems, three successive chromatographies of the residue from the chloroform extract on Florisil, Sephadex LH-20, and silica gel followed by crystallization from aqueous methanol gave taxol (1) as needles: 7 yield 0.02%; M+ at m/e 853, caled for C47H51NO14, 853; mp 213—216 dec;[a] 20o-49 (MeOH); Xmax (MeOH) 227 nm (e 29,800), 273 (1700); vZH'3300-3500 (OH, NH), 1730 (ester), 1710 (ketone), 1650 (amide) cm-1. The characteristic chemical shifts8 of 1 are shown in Table I. Because of the extremely limited quantity of taxol and its evidentcomplexity, attempts were made to prepare derivatives suitable for X-ray analysis. Al-