Compounds Related to Saudin and Three New Series of Diterpenoids from Clutia lanceolata

Sarfaraz Ahmed, Mohammad Nur-e-Alam, Ifat Parveen, Michael D. Threadgill, James B. Orton, Rahman M. Hafizur, Israr Khan, Mai Al-Oqail, Adnan J. Al-Rehaily

Allbwn ymchwil: Cyfraniad at gyfnodolynErthygladolygiad gan gymheiriaid

16 Wedi eu Llwytho i Lawr (Pure)

Crynodeb

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.
Iaith wreiddiolSaesneg
Tudalennau (o-i)1129-1149
Nifer y tudalennau21
CyfnodolynJournal of Natural Products
Cyfrol86
Rhif cyhoeddi5
Dyddiad ar-lein cynnar02 Mai 2023
Dynodwyr Gwrthrych Digidol (DOIs)
StatwsCyhoeddwyd - 26 Mai 2023

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