Diterpenoids with inhibitory activity of nitrite production from Croton floribundus

Author(s)

Queiroz, Suzana Aparecida S. ^[1] ; Pinto, Meri Emili F. ^[1] ; Bobey, Antonio F. ^[1] ; Russo, Helena M. ^[1] ; Batista, Andrea N. L. ^[2] ; Batista, Jr., Joao M. ^[3] ; Codo, Ana C. ^[4] ; Medeiros, Alexandra I. ^[4] ; Bolzani, Vanderlan S. ^[1]

Affiliation

^[1] Sao Paulo State Univ, Inst Chem, BR-14800060 Araraquara, SP - Brazil

^[2] Fluminense Fed Univ, Inst Chem, BR-24020141 Niteroi, RJ - Brazil

^[3] Univ Fed Sao Paulo, Inst Sci & Technol, BR-12231280 Sao Jose Dos Campos, SP - Brazil

^[4] Sao Paulo State Univ, Sch Pharmaceut Sci, BR-01049010 Araraquara, SP - Brazil

• Document type: Journal article
• Source: Journal of Ethnopharmacology; v. 249, MAR 1 2020.
• Web of Science Citations: 0

Abstract

Ethnopharmacological relevance: Croton floribundus Spreng. (Euphorbiaceae), popularly known as Capixingui, stands out due to its widespread use in traditional medicine to treat wounds, syphilis, hemorrhoids, eye diseases and as a purgative. Aim of the study: To characterize clerodanes diterpenes from C. floribundus and to evaluate the effects of the fraction and diterpenes (1-5) on inhibition of nitrite production. Materials and methods: The hydroethanolic root extract of C. floribundus was fractionated on a solid phase extraction column to obtain the fraction named Fr80%. From this, five compounds were obtained and characterized. The absolute configuration of compound 1 was determined by a combination of electronic and vibrational circular dichroism spectroscopies. Additionally, compounds 1-5 were evaluated for their inhibitory effects on nitrite production induced by lipopolysaccharide (LPS) in RAW 264 macrophage cell. Results: Five clerodane diterpenoids were characterized, and the absolute stereochemistry of 1 was established as 3R,4R,5R,8R,9R,10S,12S. The IC50 values obtained through inhibition of nitrite production were 28.52 +/- 2.21 mu M (1), 40.26 +/- 2.79 mu M (2), 25.47 +/- 2.16 mu M (3), 35.78 +/- 2.93 mu M (4) and 40.58 +/- 4.78 mu M (5). In the tested concentrations, the samples presented low toxicity in macrophages. Conclusions: Four new diterpenes were characterized from C. floribundus, these being croflorins A-D (1-4) and a known halimane (5). These compounds exhibited inhibitory effect on nitrite production. (AU)

• FAPESP's process: 19/04381-5 - The Last Advances on Solid-Phase Peptide Synthesis and NMR New Methodologies Applied to Cyclotides from Brazilian Plant Species
• Grantee: Meri Emili Pinto Nascimento
• Support Opportunities: Scholarships abroad - Research Internship - Post-doctor
• FAPESP's process: 13/07600-3 - CIBFar - Center for Innovation in Biodiversity and Drug Discovery
• Grantee: Glaucius Oliva
• Support Opportunities: Research Grants - Research, Innovation and Dissemination Centers - RIDC
• FAPESP's process: 14/25222-9 - Vibrational chiroptical spectroscopy for stereochemical characterization of small molecules and macromolecules
• Grantee: João Marcos Batista Junior
• Support Opportunities: Research Grants - Young Investigators Grants
• FAPESP's process: 17/19870-6 - Effect of phagocytosis of infected apoptotic cells during activation of M1/M2 Macrophages
• Grantee: Alexandra Ivo de Medeiros
• Support Opportunities: Regular Research Grants
• FAPESP's process: 17/18807-9 - Efferocytosis of Streptococcus pneumoniae infected apoptotic cells impact on m2 macrophages and Th2 lymphocytes reprogramming
• Grantee: Ana Campos Codo
• Support Opportunities: Scholarships in Brazil - Scientific Initiation
• FAPESP's process: 14/50926-0 - INCT 2014: biodiversity and natural products
• Grantee: Vanderlan da Silva Bolzani
• Support Opportunities: BIOTA-FAPESP Program - Thematic Grants
• FAPESP's process: 17/17098-4 - Application of MALDI Imaging (MSI) on non-nodulated and nodulated leaves of Psychotria and Hybanthus: Localization, analysis of cyclotides and its relationship with endosymbionts bacteria
• Grantee: Meri Emili Pinto Nascimento
• Support Opportunities: Scholarships in Brazil - Post-Doctoral