Unusual C25 steroid isomers with bicyclo[4.4.1]A/B rings from a volcano ash-derived fungus Penicillium citrinum
Unusual C25 steroid isomers with bicyclo[4.4.1]A/B rings from a volcano ash-derived fungus Penicillium citrinum
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DOI：
10.1021/np8000442
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发表时间：
2008-08-01
影响因子：
5.1
通讯作者：
Zhu, Weiming
中科院分区：
文献类型：
--
作者：
Du, Lin;Zhu, Tianjiao;Zhu, Weiming
十一种新的不寻常的具有双环[4.4.1]A/B环的C 25甾族异构体，24-表-环柠檬醇（1），20-O-甲基-24-表-环柠檬醇（3），20-O-甲基环柠檬醇（4），24-氧代环柠檬醇（7），12 R-羟基环柠檬醇（8），新环柠檬醇B（10）和D（12），异丙基-23-O-甲基新环柠檬醇（13），苏式-23-O-甲基新环柠檬醇（14）、异环柠檬醇B（15）和前环柠檬醇B（18），以及五种已知的甾体，环柠檬醇（2）、新环柠檬醇A（9）和C（11）、异环柠檬醇A（16）和22-O-乙酰基异环柠檬醇A（17），从火山灰衍生的真菌桔青霉HGY 1 -5的培养物中表征。通过光谱、化学方法和X-射线衍射分析确定了它们的结构和绝对构型。化合物3，4。和10-14是根据1-4的酸性转化确定的人工产物。通过将C-13标记的乙酸酯进料至桔黄青霉HGY 1-5的生长培养物来研究这些源自麦角固醇的类固醇的生物合成来源。在GPR 12-CHO和WT-CHO细胞上使用cAMP测定测试所有16种类固醇的生物活性。结果表明，化合物1、2、10、11和14可以诱导GPIR 12转染的CHO细胞产生cAMP。
Eleven new unusual C25 steroid isomers with bicyclo[4.4.1]A/B rings, 24-epi-cyclocitrinol (1), 20-O-methyl-24-epi-cyclocitrinol (3), 20-O-methylcyclocitrinol (4), 24-oxocyclocitrinol (7), 12R-hydroxycyclocitrinol (8), neocyclocitrinols B (10) and D (12), erythro-23-O-methylneocyclocitrinol (13), threo-23-O-methylneocyclocitrinol (14), isocyclocitrinol B (15), and precyclocitrinol B (18), and five known steroids, cyclocitrinol (2), neocyclocitrinols A (9) and C (11), isocyclocitrinol A (16), and 22-O-acetylisocyclocitrinol A (17), were characterized from cultures of the volcanic ash-derived fungus Penicillium citrinum HGY1-5. Their structures and absolute configurations were established by spectroscopic and chemical methods together with X-ray diffraction analysis. Compounds 3, 4. and 10-14 were determined to be artifacts on the basis of acidic transformation of 1-4. The biosynthetic origin of these steroids derived from ergosterol was investigated by feeding C-13-labeled acetates to the growing cultures of P. citrinum HGY 1-5. The biological activities of all 16 steroids were tested using the cAMP assay on GPR12-CHO and WT-CHO cells. The results showed that compounds 1, 2, 10, 11, and 14 could induce the production of cAMP in GPIR12-transfected CHO cells.