THE TREMULANES, A NEW GROUP OF SESQUITERPENES FROM THE ASPEN ROTTING FUNGUS PHELLINUS-TREMULAE
THE TREMULANES, A NEW GROUP OF SESQUITERPENES FROM THE ASPEN ROTTING FUNGUS PHELLINUS-TREMULAE
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DOI：
10.1021/jo00078a035
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发表时间：
1993-12-17
影响因子：
3.6
通讯作者：
CRUZ, ER
中科院分区：
文献类型：
--
作者：
AYER, WA;CRUZ, ER
从白杨（Populus tremuloides）腐烂真菌美洲山杨（Populus tremulae）的液体培养物中分离得到一系列新的倍半萜烯类化合物，即美洲山杨烷（Tremulanes），它们具有一个以前未报道的全氢甘菊碳骨架。通过NMR技术（H-1-H-1 COSY、HMQC和HMBC）和其他物理方法（包括对于震颤素A（6），X射线晶体学）确定结构。描述了tremulenedial A（10）与tremulenedial A（6）的化学相关性，以及tremulenedial（8）与tremulenedial B（11）的相关性。化合物的绝对构型是通过应用烯属八分体规则对烯丙醇震颤素A（10）进行指定的。这些新的倍半萜烯不遵守生物异戊二烯规则，有人建议，他们可能不是来自法呢焦磷酸。
A series of new sesquiterpenes, the tremulanes, possessing a previously unreported substituted perhydroazulene carbon skeleton, has been isolated from liquid cultures of the aspen (Populus tremuloides) rotting fungus Phellinus tremulae. The structures were determined by NMR techniques (H-1-H-1 COSY, HMQC, and HMBC) and other physical methods including, in the case of tremulenolide A (6), X-ray crystallography. The chemical correlation of tremulenediol A (10) with tremulenolide A (6) is described as is the correlation of tremulenedial (8) with tremulenediol B (11). The absolute configuration of the compounds is assigned by application of the olefin octant rule to the allylic alcohol tremulenediol A (10). These new sesquiterpenes do not obey the biogenetic isoprene rule and it is suggested that they may not be derived from farnesyl pyrophosphate.