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(Reference retrieved automatically from Web of Science through information on FAPESP grant and its corresponding number as mentioned in the publication by the authors.)

Advanced Glycation End Product Inhibition by Alkaloids from Ocotea paranapiacabensis for the Prevention of Skin Aging

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Author(s):
de Freitas, Larissa [1] ; Valli, Marilia [1, 2] ; Dametto, Alessandra C. [1, 3] ; Pennacchi, Paula C. [4] ; Andricopulo, Adriano D. [2] ; Maria-Engler, Silvya S. [4] ; Bolzani, Vanderlan S. [1]
Total Authors: 7
Affiliation:
[1] Sao Paulo State Univ UNESP, Inst Chem, Dept Organ Chem, Nuclei Bioassays Biosynth & Ecophysiol & Nat Prod, Araraquara, SP - Brazil
[2] Univ Sao Paulo, Inst Phys Sao Carlos, Ctr Res & Innovat Biodivers & Drug Discovery CIBF, Lab Med & Computat Chem LQMC, Sao Carlos, SP - Brazil
[3] Fed Inst Educ Sci & Technol Sao Paulo, Matao, SP - Brazil
[4] Univ Sao Paulo, Fac Pharmaceut Sci, Dept Clin & Toxicol Anal, Sao Paulo - Brazil
Total Affiliations: 4
Document type: Journal article
Source: Journal of Natural Products; v. 83, n. 3, SI, p. 649-656, MAR 27 2020.
Web of Science Citations: 1
Abstract

A bioassay-guided study aiming at identifying inhibitors of the glycation process on the leaves of Ocotea paranapiacabensis afforded four benzylisoquinoline alkaloids (1-4), with 1 and 2 identified as new naturals products, while 3 and 4 were previously described in the literature, with 3 being identified as magnocurarine. Purification was performed by column chromatography and high-performance liquid chromatography. The structures of the isolated compounds were elucidated by spectroscopic methods including UV, NMR, and HRMS. The process of skin aging has been recently associated with advanced glycation end products (AGEs), and strategies inhibiting their formation have been addressed by pharmaceutical companies for the development of novel antiaging compounds. Alkaloids 1-4 were evaluated for their potential to inhibit AGE formation and showed inhibition of 62.9%, 83.3%, 26.1%, and 98.2% (150 mu M), respectively. The antiaging potential of compounds 1 and 4 were evaluated with a reconstructed human skin model in vitro, and results showed a decrease in dermis contraction (8.7% and 4.2% respectively for 1 and 4) when compared to the glycated control (57.4%). Additionally, absorption, distribution, metabolism, and excretion (ADME) and toxicity properties were predicted using in silico methods, and the results were considered significantly promising for alkaloids 1 and 4 to continue the development of these alkaloids with skincare properties. (AU)

FAPESP's process: 19/05967-3 - Understanding the biological function of Natural Products' scaffolds from Databases for the design of active compounds for the treatment of infectious diseases
Grantee:Marilia Valli
Support type: Scholarships in Brazil - Post-Doctorate
FAPESP's process: 14/50926-0 - INCT 2014: biodiversity and natural products
Grantee:Vanderlan da Silva Bolzani
Support type: BIOTA-FAPESP Program - Thematic Grants
FAPESP's process: 13/07600-3 - CIBFar - Center for Innovation in Biodiversity and Drug Discovery
Grantee:Glaucius Oliva
Support type: Research Grants - Research, Innovation and Dissemination Centers - RIDC