对Pseudotsugagaussenii(中国特有的一种脆弱的植物)的枝条和针叶的MeOH提取物进行了初步的植物化学研究,结果分离并表征了25种结构多样的单萜和二聚体三萜类化合物。其中19个以前没有描述过,包括八种葫芦烷型三萜类化合物(高森醇A-H,1-8,分别。),一种serratene型三萜(gaussenolI,9),和10个三萜二聚体(高斯诺尔J-S,10-19,分别。).通过光谱数据阐明了它们的化学结构,一些化学转化,修改后的Mosher\的方法,和单晶X射线衍射分析。化合物9是来自自然界的第一个13R非对映体丝兰酸型三萜类化合物衍生物。前所未有的二聚体三萜类化合物是通过酯键(10-18)或通过醚键(19)在相同或不同类型的三萜类骨架的侧链之间构建的(例如,葫芦烷型,lanostane型,和/或环artane型)。化合物9、15、21和25对人蛋白酪氨酸磷酸酶1B(PTP1B,治疗II型糖尿病和肥胖症的潜在药物靶标),IC50值为3.1、8.6、9.0和5.6μM,分别。生物活性化合物与PTP1B的相互作用此后通过采用分子对接研究进行,结合亲和力范围为-6.9至-7.3千卡/摩尔。上述发现可以揭示保护植物物种多样性在支持化学多样性和新疗法的潜在来源方面的重要作用。
A preliminary phytochemical investigation on the MeOH extract of the twigs and needles of
Pseudotsuga gaussenii (a \'vulnerable\' plant endemic to
China) led to the isolation and characterization of 25 structurally diverse mono- and dimeric triterpenoids. 19 of them are previously undescribed, including eight cucurbitane-type triterpenoids (gaussenols A-H, 1-8, resp.), one serratene-type triterpene (gaussenol I, 9), and 10 triterpenic dimers (gaussenols J-S, 10-19, resp.). Their chemical structures were elucidated by means of spectroscopic data, some chemical transformations, the modified Mosher\'s method, and single crystal X-ray diffraction analyses. Compound 9 is the first 13R diastereoisomeric serratene-type triterpenoid derivative from nature. The unprecedented dimeric triterpenoids are constructed either through ester linkage (10-18) or via ether bond (19) among the side chains of same or different types of triterpenoid skeletons (e.g., cucurbitane-type, lanostane-type, and/or cycloartane-type). Compounds 9, 15, 21, and 25 exhibited inhibitory effects against the human protein tyrosine phosphatase 1B (PTP1B, a potential drug target for the treatment of type-II diabetes and obesity), with IC50 values of 3.1, 8.6, 9.0, and 5.6 μM, respectively. The interactions of the bioactive compounds with PTP1B were thereafter performed by employing molecular docking studies, with binding affinities ranging from - 6.9 to - 7.3 kcal/mol. The above findings could reveal the important role of protecting plant species diversity in support of chemical diversity and potential sources of new therapeutics.