Fujimoto H, Nakamura E, Okuyama E, Ishibashi M
Faculty of Pharmaceutical Sciences, Chiba University, Japan.
Chem Pharm Bull (Tokyo). 2000 Oct;48(10):1436-41. doi: 10.1248/cpb.48.1436.
Fractionation monitored by the immunomodulatory activity of the AcOEt extract of an Ascomycete, Emericella aurantio-brunnea, afforded two known fungal sesterterpenes, variecolin (1) and variecolactone (2), two new variecolin congeners named variecoacetals A (3) and B (4), and a new sesquiterpenetriol diester named emeremophiline (5), as the immunosuppressive constituents of this fungus. The absolute configuration of 1, which was previously not determined, was determined to be (2S,3S,6R,10S,11R,14S,15R,16S) from the NMR spectral data of the (6R,7R)-dimethyl-1,3,5-trioxacycloheptyl derivative of 1 (7). The absolute configurations of the other variecolin congeners, 2-4, and variecolol (6) are also proposed from biosynthetic considerations.
通过对一种子囊菌——金褐曲霉（Emericella aurantio-brunnea）乙酸乙酯提取物的免疫调节活性进行分级分离，得到了两种已知的真菌倍半萜烯，变色菌素（1）和变色菌素内酯（2），两种名为变色缩醛A（3）和B（4）的新型变色菌素类似物，以及一种名为橙黄曲霉醇（5）的新型倍半萜三醇二酯，它们是该真菌的免疫抑制成分。1的绝对构型此前未确定，根据1的(6R,7R)-二甲基-1,3,5-三氧杂环庚基衍生物（7）的核磁共振光谱数据，确定其绝对构型为(2S,3S,6R,10S,11R,14S,15R,16S)。还从生物合成的角度推测了其他变色菌素类似物2-4以及变色醇（6）的绝对构型。
