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

doi:10.1021/acs.jnatprod.2c00761

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

Department of Life Sciences

Research output: Contribution to journal › Article › peer-review

Abstract

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.

Original language	English
Pages (from-to)	1129-1149
Number of pages	21
Journal	Journal of Natural Products
Volume	86
Issue number	5
Early online date	2 May 2023
DOIs	https://doi.org/10.1021/acs.jnatprod.2c00761
Publication status	Published - 26 May 2023

Bibliographical note

Funding Information:
The authors extend their appreciation to Researchers Supporting Project number (RSP2023R380), King Saud University, Riyadh, Saudi Arabia, for funding this work. We are thankful for support from BEACON Plus (grant EDRF 80851) from the European Regional Development Fund through the Welsh European Funding Office, part of the Welsh Assembly, and to Aberystwyth University. We also thank Helen C. Phillips (Aberystwyth University) for providing many of the mass spectra.

ASJC Scopus subject areas

Analytical Chemistry
Molecular Medicine
Pharmacology
Pharmaceutical Science
Drug Discovery
Complementary and alternative medicine
Organic Chemistry

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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https://research.aber.ac.uk/cy/publications/compounds-related-to-saudin-and-three-new-series-of-diterpenoids-Licence: CC BY-NC

Cite this

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abstract = "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.",

author = "Sarfaraz Ahmed and Mohammad Nur-E-Alam and Ifat Parveen and Threadgill, {Michael D.} and Orton, {James B.} and Hafizur, {Rahman M.} and Israr Khan and Mai Al-Oqail and Al-Rehaily, {Adnan J.}",

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

Abstract

Bibliographical note

ASJC Scopus subject areas

UN SDGs

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