Synthesis and Biological Evaluation of New Natural Phenolic (2E,4E,6E)‐Octa‐2,4,6‐trienoic Esters

Abstract

In the present study the esterification of the OH groups of resveratrol, caffeic acid, ferulic acid, and β-sitosterol with an antioxidant polyconjugated fatty acid, (2E,4E,6E)-octa-2,4,6-trienoic acid, was achieved. As the selective esterification of OH groups of natural compounds can affect their biological activity, a selective esterification of resveratrol and caffeic acid was performed by an enzymatic approach. The new resulting compounds were characterized spectroscopically (FT-IR, NMR mono, and bidimensional techniques); when necessary the experimental data were integrated by quantum chemical calculations. The antioxidant, anti-inflammatory and proliferative activity was evaluated. The good results encourage the use of these molecules as antioxidant and/or anti-inflammatory agents in dermocosmetic application.

Positive Promoting Effects of Smilax China Flower Absolute on the Wound Healing/Skin Barrier Repair‐Related Responses of HaCaT Human Skin Keratinocytes

“…In particular, of the compounds identified, n‐hexadecanoic acid (palmitic acid) and β‐sitosterol have been reported to promote the migratory and/or proliferative activities in monocytes, neural stem cells, fibroblasts, and endothelial cells [27–30] . In addition, n‐hexadecanoic acid and β‐sitosterol have been reported to promote keratinocyte proliferation, [31,32] which suggests these two compounds contributed to SCF absolute‐induced HaCaT cell proliferation. To the best of our knowledge, the present study provides first evidence that SCF absolute promotes the migration and proliferation of keratinocytes.…”

Novel ferrocene‐containing triacyl derivative of resveratrol improves viability parameters in ovary cells

“…Exposure to the new resveratrol derivative resulted in a significant increase in keratinocyte proliferation after 72 h of incubation, and the authors concluded that esterification also leads to an improvement in cell proliferation. The results obtained by Gandolfi et al (2017) encourage the use of this molecule as an antioxidant and/or anti‐inflammatory agent in dermocosmetic applications. Our results reflect the similar protective effects in ovarian cells.…”

“…FEHH4‐1 showed enhanced antiproliferative and pro‐apoptotic activities against Jurkat leukemia CD4 + T‐cells compared to RSV, with no results in normal cells. Gandolfi et al (2017) investigated the proliferative activity of newly synthetized resveratrol triester (esterification of ‐OH groups with an antioxidant polyconjugated fatty acid, [2 E ,4 E ,6 E ]‐octa‐2,4,6‐trienoic acid) on normal human keratinocyte NCTC 2544 cells. Exposure to the new resveratrol derivative resulted in a significant increase in keratinocyte proliferation after 72 h of incubation, and the authors concluded that esterification also leads to an improvement in cell proliferation.…”

Lespedeza maximowiczii flower absolute promotes skin epithelization, barrier properties, and moisturization-related beneficial responses in human keratinocytes

“…In addition, GC/MS analysis identified 12 compounds in LMFAb. In particular, β-sitosterol has been reported to promote keratinocyte proliferation [ 36 ], implying a potential contribution of β-sitosterol to LMFAb-promoted HaCaT cell proliferation. Therefore, LMFAb may facilitate re-epithelization of the skin by promoting keratinocyte migration and proliferation.…”