ArticlePharmaceutical research2016
Methylation and Esterification of Magnolol for Ameliorating Cutaneous Targeting and Therapeutic Index by Topical Application.
Article in Pharmaceutical research, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 10 papers.
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Who cites it
10 citing papers in PubMed.
- Magnolol Reduces Atopic Dermatitis-like Symptoms in BALB/c Mice.Life (Basel, Switzerland) · 2024Article
- Anti-Aging Potential of a Novel Ingredient Derived from Sugarcane Straw Extract (SSE).International journal of molecular sciences · 2023Article
- Synthesis, anti-aging and mechanism of magnolol derivatives.Frontiers in chemistry · 2023Article
- Natural and natural-like polyphenol compounds:Archives of medical science : AMS · 2023Article
- Coenzyme QFrontiers in pharmacology · 2019Article
- Synthesis of magnolol and honokiol derivatives and their effect against hepatocarcinoma cells.PloS one · 2018Article
- Elucidating the Skin Delivery of Aglycone and Glycoside Flavonoids: How the Structures Affect Cutaneous Absorption.Nutrients · 2017Article
- Synthesis, Characterization, and Biological Evaluations of 1,3,5-Triazine Derivatives of Metformin Cyclization with Berberine and Magnolol in the Presence of Sodium Methylate.Molecules (Basel, Switzerland) · 2017Article
- Magnolol additive as a replacer of antibiotic enhances the growth performance ofAnimal nutrition (Zhongguo xu mu shou yi xue hui) · 2017Article
- Pterostilbene, a Methoxylated Resveratrol Derivative, Efficiently Eradicates Planktonic, Biofilm, and Intracellular MRSA by Topical Application.Frontiers in microbiology · 2017Article
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Authors and funding
6 authors.
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Abstract
purposeAs a continuing effort to elucidate the impact of structure modification upon cutaneous absorption behavior, we attempted to assess the skin permeation of magnolol by methylation and acetylation.
methodsDiacetylmagnolol and 2-O-acetyl-2'-O-methylmagnolol (AMM) were designed and synthesized in this study. The anti-inflammatory activity against stimulated neutrophils and keratinocytes was evaluated to check the bioactivity of the analogues. In vitro skin absorption was investigated using nude mouse and pig skin models at both equimolar and saturated doses.
resultsMagnolol generally showed the strongest anti-inflammatory potential, followed by diacetylmagnolol and AMM. The antibacterial activity was observed for magnolol and diacetylmagnolol but not AMM. Diacetylmagnolol and AMM could be partly hydrolyzed to magnolol and 2-O-methylmagnolol after entering the skin. The hydrolysis rate of diacetylmagnolol was faster than that of AMM. The lipophilicity played a crucial role in cutaneous absorption, with AMM exhibiting the highest skin deposition. AMM accumulation within nude mouse skin was about 2.5-fold greater than that of magnolol and diacetylmagnolol. On the other hand, the transdermal penetration across the skin was lessened by methylation and esterification. This led to a superior skin targeting of AMM. Although the pharmacological activity of AMM was low, the high skin uptake and bioconversion into 2-O-methylmagnolol in the skin contributed to a greater therapeutic index (TI, skin deposition x inflammatory inhibition percentage) compared to the others. The accumulation of AMM in the hair follicles was 77.12 nmol/cm(2), which was significantly greater than that with magnolol (44.84 nmol/cm(2)) and diacetylmagnolol (26.96 nmol/cm(2)). The synthetic analogues were tolerable to the nude mouse skin.
conclusionsBased on the experimental results, we may suggest topically applied AMM as a potent and safe candidate for the treatment of cutaneous inflammation.
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