A neoclerodane orthoester and other new neoclerodane diterpenoids from Teucrium yemense chemistry and effect on secretion of insulin
Abstract Teucrium yemense, a medicinal plant commonly grown in Saudi Arabia and Yemen, is traditionally used to treat infections, kidney diseases, rheumatism, and diabetes. Extraction of the dried aerial parts of the plant with methanol, followed by further extraction with butanol and chromatography...
Guardado en:
| Autores principales: | , , , , , , , , |
|---|---|
| Formato: | article |
| Lenguaje: | EN |
| Publicado: |
Nature Portfolio
2021
|
| Materias: | |
| Acceso en línea: | https://doaj.org/article/82fc41ffecd743cc935b70e07d5596b3 |
| Etiquetas: |
Agregar Etiqueta
Sin Etiquetas, Sea el primero en etiquetar este registro!
|
| id |
oai:doaj.org-article:82fc41ffecd743cc935b70e07d5596b3 |
|---|---|
| record_format |
dspace |
| spelling |
oai:doaj.org-article:82fc41ffecd743cc935b70e07d5596b32021-12-02T14:27:59ZA neoclerodane orthoester and other new neoclerodane diterpenoids from Teucrium yemense chemistry and effect on secretion of insulin10.1038/s41598-021-87513-32045-2322https://doaj.org/article/82fc41ffecd743cc935b70e07d5596b32021-04-01T00:00:00Zhttps://doi.org/10.1038/s41598-021-87513-3https://doaj.org/toc/2045-2322Abstract Teucrium yemense, a medicinal plant commonly grown in Saudi Arabia and Yemen, is traditionally used to treat infections, kidney diseases, rheumatism, and diabetes. Extraction of the dried aerial parts of the plant with methanol, followed by further extraction with butanol and chromatography, gave twenty novel neoclerodanes. Their structures, relative configurations and some conformations were determined by MS and 1-D and 2-D NMR techniques. Most were fairly conventional but one contained an unusual stable orthoester, one had its (C-16)–(C-13)–(C-14)–(C-15) (tetrahydro)furan unit present as a succinic anhydride and one had a rearranged carbon skeleton resulting from ring-contraction to give a central octahydroindene bicyclic core, rather than the usual decalin. Mechanisms are proposed for the biosynthetic formation of the orthoester and for the ring-contraction. Four novel neoclerodanes increased the glucose-triggered release of insulin from isolated murine pancreatic islets by more than the standard drug tolbutamide, showing that they are potential leads for the development of new anti-diabetic drugs.Mohammad Nur-e-AlamIfat ParveenBarrie WilkinsonSarfaraz AhmedRahman M. HafizurAhmed BariTimothy J. WoodmanMichael D. ThreadgillAdnan J. Al-RehailyNature PortfolioarticleMedicineRScienceQENScientific Reports, Vol 11, Iss 1, Pp 1-17 (2021) |
| institution |
DOAJ |
| collection |
DOAJ |
| language |
EN |
| topic |
Medicine R Science Q |
| spellingShingle |
Medicine R Science Q Mohammad Nur-e-Alam Ifat Parveen Barrie Wilkinson Sarfaraz Ahmed Rahman M. Hafizur Ahmed Bari Timothy J. Woodman Michael D. Threadgill Adnan J. Al-Rehaily A neoclerodane orthoester and other new neoclerodane diterpenoids from Teucrium yemense chemistry and effect on secretion of insulin |
| description |
Abstract Teucrium yemense, a medicinal plant commonly grown in Saudi Arabia and Yemen, is traditionally used to treat infections, kidney diseases, rheumatism, and diabetes. Extraction of the dried aerial parts of the plant with methanol, followed by further extraction with butanol and chromatography, gave twenty novel neoclerodanes. Their structures, relative configurations and some conformations were determined by MS and 1-D and 2-D NMR techniques. Most were fairly conventional but one contained an unusual stable orthoester, one had its (C-16)–(C-13)–(C-14)–(C-15) (tetrahydro)furan unit present as a succinic anhydride and one had a rearranged carbon skeleton resulting from ring-contraction to give a central octahydroindene bicyclic core, rather than the usual decalin. Mechanisms are proposed for the biosynthetic formation of the orthoester and for the ring-contraction. Four novel neoclerodanes increased the glucose-triggered release of insulin from isolated murine pancreatic islets by more than the standard drug tolbutamide, showing that they are potential leads for the development of new anti-diabetic drugs. |
| format |
article |
| author |
Mohammad Nur-e-Alam Ifat Parveen Barrie Wilkinson Sarfaraz Ahmed Rahman M. Hafizur Ahmed Bari Timothy J. Woodman Michael D. Threadgill Adnan J. Al-Rehaily |
| author_facet |
Mohammad Nur-e-Alam Ifat Parveen Barrie Wilkinson Sarfaraz Ahmed Rahman M. Hafizur Ahmed Bari Timothy J. Woodman Michael D. Threadgill Adnan J. Al-Rehaily |
| author_sort |
Mohammad Nur-e-Alam |
| title |
A neoclerodane orthoester and other new neoclerodane diterpenoids from Teucrium yemense chemistry and effect on secretion of insulin |
| title_short |
A neoclerodane orthoester and other new neoclerodane diterpenoids from Teucrium yemense chemistry and effect on secretion of insulin |
| title_full |
A neoclerodane orthoester and other new neoclerodane diterpenoids from Teucrium yemense chemistry and effect on secretion of insulin |
| title_fullStr |
A neoclerodane orthoester and other new neoclerodane diterpenoids from Teucrium yemense chemistry and effect on secretion of insulin |
| title_full_unstemmed |
A neoclerodane orthoester and other new neoclerodane diterpenoids from Teucrium yemense chemistry and effect on secretion of insulin |
| title_sort |
neoclerodane orthoester and other new neoclerodane diterpenoids from teucrium yemense chemistry and effect on secretion of insulin |
| publisher |
Nature Portfolio |
| publishDate |
2021 |
| url |
https://doaj.org/article/82fc41ffecd743cc935b70e07d5596b3 |
| work_keys_str_mv |
AT mohammadnurealam aneoclerodaneorthoesterandothernewneoclerodanediterpenoidsfromteucriumyemensechemistryandeffectonsecretionofinsulin AT ifatparveen aneoclerodaneorthoesterandothernewneoclerodanediterpenoidsfromteucriumyemensechemistryandeffectonsecretionofinsulin AT barriewilkinson aneoclerodaneorthoesterandothernewneoclerodanediterpenoidsfromteucriumyemensechemistryandeffectonsecretionofinsulin AT sarfarazahmed aneoclerodaneorthoesterandothernewneoclerodanediterpenoidsfromteucriumyemensechemistryandeffectonsecretionofinsulin AT rahmanmhafizur aneoclerodaneorthoesterandothernewneoclerodanediterpenoidsfromteucriumyemensechemistryandeffectonsecretionofinsulin AT ahmedbari aneoclerodaneorthoesterandothernewneoclerodanediterpenoidsfromteucriumyemensechemistryandeffectonsecretionofinsulin AT timothyjwoodman aneoclerodaneorthoesterandothernewneoclerodanediterpenoidsfromteucriumyemensechemistryandeffectonsecretionofinsulin AT michaeldthreadgill aneoclerodaneorthoesterandothernewneoclerodanediterpenoidsfromteucriumyemensechemistryandeffectonsecretionofinsulin AT adnanjalrehaily aneoclerodaneorthoesterandothernewneoclerodanediterpenoidsfromteucriumyemensechemistryandeffectonsecretionofinsulin AT mohammadnurealam neoclerodaneorthoesterandothernewneoclerodanediterpenoidsfromteucriumyemensechemistryandeffectonsecretionofinsulin AT ifatparveen neoclerodaneorthoesterandothernewneoclerodanediterpenoidsfromteucriumyemensechemistryandeffectonsecretionofinsulin AT barriewilkinson neoclerodaneorthoesterandothernewneoclerodanediterpenoidsfromteucriumyemensechemistryandeffectonsecretionofinsulin AT sarfarazahmed neoclerodaneorthoesterandothernewneoclerodanediterpenoidsfromteucriumyemensechemistryandeffectonsecretionofinsulin AT rahmanmhafizur neoclerodaneorthoesterandothernewneoclerodanediterpenoidsfromteucriumyemensechemistryandeffectonsecretionofinsulin AT ahmedbari neoclerodaneorthoesterandothernewneoclerodanediterpenoidsfromteucriumyemensechemistryandeffectonsecretionofinsulin AT timothyjwoodman neoclerodaneorthoesterandothernewneoclerodanediterpenoidsfromteucriumyemensechemistryandeffectonsecretionofinsulin AT michaeldthreadgill neoclerodaneorthoesterandothernewneoclerodanediterpenoidsfromteucriumyemensechemistryandeffectonsecretionofinsulin AT adnanjalrehaily neoclerodaneorthoesterandothernewneoclerodanediterpenoidsfromteucriumyemensechemistryandeffectonsecretionofinsulin |
| _version_ |
1718391262113955840 |