Stimulation of insulin secretion by 5-methylcoumarins and its sulfur analogues isolated from Clutia lanceolata Forssk
Stimulation of insulin secretion by 5-methylcoumarins and its sulfur analogues isolated from Clutia lanceolata Forssk
Clutia lanceolata Forssk. (C. lanceolata) is a medicinal plant native to sub-Saharan Africa and the Arabian Peninsula. Phytochemical investigation of the aerial parts of C. lanceolata yielded twenty-one coumarins including methylthio and methylsulfinyl-coumarins. Thirteen of these compounds are reported here for the first time, named as cluteolin A to M. The remaining eight compounds are known but have not been associated previously with C. lanceolata. The structures of the undescribed compounds were elucidated from their 2D NMR and MS spectra. Single crystal X-ray analyses confirmed the structures of eleven compounds. As, in Saudi Arabian tradition, C. lanceolata has been reported to have anti-diabetic and anti-fungal properties, the coumarins were examined for their biological activity. Seven compounds strongly enhanced the glucose-triggered release of insulin by murine pancreatic islets, with two compounds showing more than two-fold enhancement of insulin secretion, compared with the standard drug glimepiride.
Clutia lanceolata Forssk, Coumarins, Insulin, Methylthiocoumarins, Murine islets, Peraceae, Single X-ray crystallography
Ahmed, Sarfaraz M.
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Nur-e-Alam, Mohammad
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Parveen, Ifat
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Coles, Simon J.
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Hafizur, Rahman M.
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Hameed, Abdul
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Orton, James B.
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Threadgill, Michael D.
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Yousaf, Muhammad
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Alqahtani, Abdulaziz M.
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Al-Rehaily, Adnan J.
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February 2020
Ahmed, Sarfaraz M.
20e27953-71d2-401f-b632-73d42e2e1629
Nur-e-Alam, Mohammad
32b7b448-599c-4918-ab9e-fefdb848293a
Parveen, Ifat
7839b403-8949-4b72-ac84-840c07561b11
Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Hafizur, Rahman M.
01b715fb-41dc-419c-ae93-d842aa17babf
Hameed, Abdul
33899d14-05d1-47fc-b7e3-2fb1d6bc888f
Orton, James B.
4e2a471f-9e11-4cb4-abb6-d0398047939f
Threadgill, Michael D.
46157754-27f0-468a-9714-70803ef609c4
Yousaf, Muhammad
5d73cadf-fe9d-47e3-ad31-85c48f5333b8
Alqahtani, Abdulaziz M.
9302d5e1-379b-4e42-9eb0-6e1dc19a119c
Al-Rehaily, Adnan J.
1e86082e-959c-4412-802b-a8265e475fe1
Ahmed, Sarfaraz M., Nur-e-Alam, Mohammad, Parveen, Ifat, Coles, Simon J., Hafizur, Rahman M., Hameed, Abdul, Orton, James B., Threadgill, Michael D., Yousaf, Muhammad, Alqahtani, Abdulaziz M. and Al-Rehaily, Adnan J.
(2020)
Stimulation of insulin secretion by 5-methylcoumarins and its sulfur analogues isolated from Clutia lanceolata Forssk.
Phytochemistry, 170, [112213].
(doi:10.1016/j.phytochem.2019.112213).
Abstract
Clutia lanceolata Forssk. (C. lanceolata) is a medicinal plant native to sub-Saharan Africa and the Arabian Peninsula. Phytochemical investigation of the aerial parts of C. lanceolata yielded twenty-one coumarins including methylthio and methylsulfinyl-coumarins. Thirteen of these compounds are reported here for the first time, named as cluteolin A to M. The remaining eight compounds are known but have not been associated previously with C. lanceolata. The structures of the undescribed compounds were elucidated from their 2D NMR and MS spectra. Single crystal X-ray analyses confirmed the structures of eleven compounds. As, in Saudi Arabian tradition, C. lanceolata has been reported to have anti-diabetic and anti-fungal properties, the coumarins were examined for their biological activity. Seven compounds strongly enhanced the glucose-triggered release of insulin by murine pancreatic islets, with two compounds showing more than two-fold enhancement of insulin secretion, compared with the standard drug glimepiride.
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More information
Accepted/In Press date: 16 November 2019
e-pub ahead of print date: 28 November 2019
Published date: February 2020
Keywords:
Clutia lanceolata Forssk, Coumarins, Insulin, Methylthiocoumarins, Murine islets, Peraceae, Single X-ray crystallography
Identifiers
Local EPrints ID: 436885
URI: http://eprints.soton.ac.uk/id/eprint/436885
ISSN: 0031-9422
PURE UUID: 7766bfad-b357-4848-96f8-6acf6b70b118
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Date deposited: 13 Jan 2020 17:31
Last modified: 17 Mar 2024 05:10
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Contributors
Author:
Sarfaraz M. Ahmed
Author:
Mohammad Nur-e-Alam
Author:
Ifat Parveen
Author:
Rahman M. Hafizur
Author:
Abdul Hameed
Author:
James B. Orton
Author:
Michael D. Threadgill
Author:
Muhammad Yousaf
Author:
Abdulaziz M. Alqahtani
Author:
Adnan J. Al-Rehaily
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