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Compounds Related to Saudin and Three New Series of Diterpenoids from Clutia lanceolata
Journal of Natural Products ( IF 3.3 ) Pub Date : 2023-05-02 , DOI: 10.1021/acs.jnatprod.2c00761 Sarfaraz Ahmed 1 , Mohammad Nur-E-Alam 1 , Ifat Parveen 2 , Michael D Threadgill 2, 3 , James B Orton 4 , Rahman M Hafizur 5 , Israr Khan 5 , Mai Al-Oqail 1 , Adnan J Al-Rehaily 1
Journal of Natural Products ( IF 3.3 ) Pub Date : 2023-05-02 , DOI: 10.1021/acs.jnatprod.2c00761 Sarfaraz Ahmed 1 , Mohammad Nur-E-Alam 1 , Ifat Parveen 2 , Michael D Threadgill 2, 3 , James B Orton 4 , Rahman M Hafizur 5 , Israr Khan 5 , Mai Al-Oqail 1 , Adnan J Al-Rehaily 1
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Clutia lanceolata is a medicinal plant native to Ethiopia and sub-Saharan Africa and to the Arabian Peninsula. It is used traditionally in Saudi Arabia for the treatment of diabetes. Previous phytochemical analysis of this species has been limited to the identification of methylthiocoumarins. Further work has led to isolation of 19 new diterpenoids in three structural classes. Their structures were established by HRMS and by a range of NMR techniques (1H, 13C, COSY, NOESY, HSQC, HMBC), with confirmation for some examples by X-ray crystallography. NOESY and 1H–1H NMR coupling constants gave the relative stereochemical configurations and conformational information, with absolute configurations being established through X-ray crystallography. One example closely related to the known hypoglycemic compound saudin (found in C. richardiana and also in C. lanceolata) and one with a different core tetracycle were found to enhance strongly the glucose-triggered release of insulin from murine pancreatic islets. Biosynthetic proposals for the three groups of new diterpenoids by alternative cyclization of a common precursor are put forward. Lanceolide P (16) is proposed as a lead compound for further development for the treatment of diabetes.
中文翻译：
与Saudin相关的化合物及披针花三类新二萜类化合物
Clutia lanceolata是一种药用植物，原产于埃塞俄比亚和撒哈拉以南非洲以及阿拉伯半岛。它在沙特阿拉伯传统上用于治疗糖尿病。先前对该物种的植物化学分析仅限于甲硫香豆素的鉴定。进一步的工作已分离出 3 个结构类别的 19 种新二萜类化合物。它们的结构通过 HRMS 和一系列 NMR 技术（1 H、13 C、COSY、NOESY、HSQC、HMBC）确定，并通过 X 射线晶体学确认了一些例子。NOESY 和1 H- 1 H NMR 耦合常数给出了相对立体化学构型和构象信息，并通过 X 射线晶体学建立了绝对构型。一个与已知的降血糖化合物 saudin（在C. richardiana和C. lanceolata中都有发现）密切相关的例子和一个具有不同核心四环的例子被发现可以强烈增强葡萄糖触发的小鼠胰岛胰岛素的释放。提出了通过共同前体的选择性环化来生物合成三组新二萜类化合物的建议。Lanceolid P ( 16 ) 被提议作为进一步开发治疗糖尿病的先导化合物。
更新日期：2023-05-02
中文翻译：
与Saudin相关的化合物及披针花三类新二萜类化合物
Clutia lanceolata是一种药用植物，原产于埃塞俄比亚和撒哈拉以南非洲以及阿拉伯半岛。它在沙特阿拉伯传统上用于治疗糖尿病。先前对该物种的植物化学分析仅限于甲硫香豆素的鉴定。进一步的工作已分离出 3 个结构类别的 19 种新二萜类化合物。它们的结构通过 HRMS 和一系列 NMR 技术（1 H、13 C、COSY、NOESY、HSQC、HMBC）确定，并通过 X 射线晶体学确认了一些例子。NOESY 和1 H- 1 H NMR 耦合常数给出了相对立体化学构型和构象信息，并通过 X 射线晶体学建立了绝对构型。一个与已知的降血糖化合物 saudin（在C. richardiana和C. lanceolata中都有发现）密切相关的例子和一个具有不同核心四环的例子被发现可以强烈增强葡萄糖触发的小鼠胰岛胰岛素的释放。提出了通过共同前体的选择性环化来生物合成三组新二萜类化合物的建议。Lanceolid P ( 16 ) 被提议作为进一步开发治疗糖尿病的先导化合物。
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