4.7 Article

Phytochemical Screening and Isolation of New Ent-Clerodane Diterpenoids from Croton guatemalensis Lotsy

Journal

PLANTS-BASEL
Volume 11, Issue 22, Pages -

Publisher

MDPI
DOI: 10.3390/plants11223159

Keywords

Croton guatemalensis; ent-clerodane diterpenoid; circular dichroism; HPLC quantification; alpha-glucosidase inhibitor; docking

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Funding

  1. Universidad Nacional Autonoma de Mexico of the Programa de Apoyo a Proyectos de Investigacion e Innovacion Tecnologica (UNAM-PAPIIT) [IN213222, IN215823]

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This study isolated and identified compounds from the bark of Croton guatemalensis. The structures and configurations were determined and a HPLC method for quantifying rutin was developed. Affinity-directed fractionation and in silico analysis revealed that ent-clerodane diterpenoids were active compounds inhibiting alpha-glucosidases from Saccharomyces cerevisiae.
Phytochemical screening of an ethanol-water extract (EWE) from the bark of Croton guatemalensis led to the isolation and identification of eight compounds, among them: five entclerodane diterpenoids [junceic acid (1), 6(s)-acetoxy-15,16-diepoxy-ent-cleroda-3,13(16),14-trien-20oic acid (crotoguatenoic acid A) (2), 6(s)-hydroxyoxy-15,16-diepoxy-ent-cleroda-3,13(16),14-trien-20-oic acid (crotoguatenoic acid B) (3), formosin F (4), bartsiifolic acid (5)], and three flavonoids [rutin (6), epicatechin (7), and quercetin (8)]. Of these, 2 and 3 are reported here for the first time. Structures were established through conventional spectroscopy methods and their absolute configurations were determined by optical rotation and comparison of experimental electronic circular dichroism (ECD) and theoretical calculated ECD spectra. A suitable high performance liquid chromatography (HPLC) method for quantifying rutin (6) was developed and validated according to standard protocols. Affinity-directed fractionation was used to identify possible in vitro active compounds on a-glucosidases from Saccharomyces cerevisiae. HPLC-ESI-MS was used to identify the inhibitors as free ligands after being released from the enzymatic complex by denaturing acidic conditions. The affinity studies led to the identification of ent-clerodane diterpenoids as active compounds. In silico analysis allowed us to determine the best conformational rearrangement for the alpha-glucosidase inhibitors.

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