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Structure–Activity Relationship Study of Acyclic Terpenes in Blood Glucose Levels: Potential α-Glucosidase and Sodium Glucose Cotransporter (SGLT-1) Inhibitors

Authors
  • Valdes, Miguel1, 2
  • Calzada, Fernando2
  • Mendieta-Wejebe, Jessica1
  • 1 Instituto Politécnico Nacional, Sección de Estudios de Posgrado e Investigación, Escuela Superior de Medicina, Plan de San Luis y Salvador Díaz Mirón S/N, Col. Casco de Santo Tomás, Ciudad de México CP 11340, CDMX, Mexico
  • 2 UMAE Hospital de Especialidades 2º Piso CORSE Centro Médico Nacional Siglo XXI, Instituto Mexicano del Seguro Social, Av. Cuauhtemoc 330, Col. Doctores, Ciudad de México CP 06720, CDMX, Mexico
Type
Published Article
Journal
Molecules
Publisher
MDPI AG
Publication Date
Nov 06, 2019
Volume
24
Issue
22
Identifiers
DOI: 10.3390/molecules24224020
PMID: 31698833
PMCID: PMC6891574
Source
PubMed Central
Keywords
License
Green

Abstract

Twelve terpenoids were evaluated in the treatment of type 2 diabetes mellitus: seven monoterpenes (geranyl acetate ( 1 ), geranic acid ( 2 ), citral ( 3) , geraniol ( 4 ), methyl geranate ( 5 ), nerol ( 6 ), and citronellic acid ( 7 )), three sesquiterpenes (farnesal ( 8 ), farnesol ( 9 ), and farnesyl acetate ( 10 )), one diterpene (geranylgeraniol ( 11 )), and one triterpene (squalene ( 12 )) were selected to carry out a study on normoglycemic and streptozotocin-induced diabetic mice. Among these, 2 , 3 , 7 , 8 , 9 , and 10 showed antihyperglycemic activity in streptozotocin-induced diabetic mice. They were then selected for evaluation in oral sucrose and lactose tolerance tests (OSTT and OLTT) as well as in an oral glucose tolerance test (OGTT). In the OSTT and OLTT, compounds 3 , 7 , 8 , 9 , and 10 showed a reduction in postprandial glucose peaks 2 h after a sucrose or lactose load (comparable to acarbose). In the case of the OGTT, 2 , 7 , 8 , 9 , and 10 showed a reduction in postprandial glucose peaks 2 h after a glucose load (comparable to canagliflozin). Our results suggest that the control of postprandial hyperglycemia may be mediated by the inhibition of disaccharide digestion, such as sucrose and lactose, and the regulation of the absorption of glucose. The first case could be associated with an ∝ -glucosidase inhibitory effect and the second with an inhibition of the sodium–glucose type 1 (SGLT-1) cotransporter. Finally, five acyclic terpenes may be candidates for the development and search for new α-glucosidase and SGLT-1 cotransporter inhibitors.

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