Magnolol and Honokiol: Two Natural Compounds with Similar Chemical Structure but Different Physicochemical and Stability Properties
<i>Magnolia</i> spp. extracts are known for their use in traditional Korean, Chinese, and Japanese medicine in the treatment of gastrointestinal disorders, anxiety, and allergies. Among their main components with pharmacological activity, the most relevant are magnolol and honokiol, whic...
| Main Authors: | , , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2021-02-01
|
| Series: | Pharmaceutics |
| Subjects: | |
| Online Access: | https://www.mdpi.com/1999-4923/13/2/224 |
| _version_ | 1827602693287313408 |
|---|---|
| author | Iris Usach Alessandro Alaimo Juan Fernández Alessandro Ambrosini Sara Mocini Lacramioara Ochiuz José-Esteban Peris |
| author_facet | Iris Usach Alessandro Alaimo Juan Fernández Alessandro Ambrosini Sara Mocini Lacramioara Ochiuz José-Esteban Peris |
| author_sort | Iris Usach |
| collection | DOAJ |
| description | <i>Magnolia</i> spp. extracts are known for their use in traditional Korean, Chinese, and Japanese medicine in the treatment of gastrointestinal disorders, anxiety, and allergies. Among their main components with pharmacological activity, the most relevant are magnolol and honokiol, which also show antitumoral activity. The objectives of this work were to study some physicochemical properties of both substances and their stability under different conditions of temperature, pH, and oxidation. Additionally, liposomes of honokiol (the least stable compound) were formulated and characterized. Both compounds showed pH-dependent solubility, with different solubility–pH profiles. Magnolol showed a lower solubility than honokiol at acidic pH values, but a higher solubility at alkaline pH values. The partition coefficients were similar and relatively high for both compounds (log P<sub>o/w</sub> ≈ 4.5), indicating their lipophilic nature. Honokiol was less stable than magnolol, mainly at neutral and basic pH values. To improve the poor stability of honokiol, it was suitably loaded in liposomes. The obtained liposomes were small in size (175 nm), homogeneous (polydispersity index = 0.17), highly negatively charged (−11 mV), and able to incorporate high amounts of honokiol (entrapment efficiency = 93.4%). The encapsulation of honokiol in liposomes increased its stability only at alkaline pH values. |
| first_indexed | 2024-03-09T05:25:10Z |
| format | Article |
| id | doaj.art-47b27b13c54f45569ff2ebf72ab1c3c8 |
| institution | Directory Open Access Journal |
| issn | 1999-4923 |
| language | English |
| last_indexed | 2024-03-09T05:25:10Z |
| publishDate | 2021-02-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Pharmaceutics |
| spelling | doaj.art-47b27b13c54f45569ff2ebf72ab1c3c82023-12-03T12:37:33ZengMDPI AGPharmaceutics1999-49232021-02-0113222410.3390/pharmaceutics13020224Magnolol and Honokiol: Two Natural Compounds with Similar Chemical Structure but Different Physicochemical and Stability PropertiesIris Usach0Alessandro Alaimo1Juan Fernández2Alessandro Ambrosini3Sara Mocini4Lacramioara Ochiuz5José-Esteban Peris6Department of Pharmacy and Pharmaceutical Technology and Parasitology, University of Valencia, Burjassot, 46100 Valencia, SpainDepartment of Pharmacy and Pharmaceutical Technology and Parasitology, University of Valencia, Burjassot, 46100 Valencia, SpainDepartment of Pharmacy and Pharmaceutical Technology and Parasitology, University of Valencia, Burjassot, 46100 Valencia, SpainDepartment of Pharmacy and Pharmaceutical Technology and Parasitology, University of Valencia, Burjassot, 46100 Valencia, SpainDepartment of Pharmacy and Pharmaceutical Technology and Parasitology, University of Valencia, Burjassot, 46100 Valencia, SpainDepartment of Pharmaceutical Technology, “Grigore T. Popa” University of Medicine and Pharmacy, 700115 Iasi, RomaniaDepartment of Pharmacy and Pharmaceutical Technology and Parasitology, University of Valencia, Burjassot, 46100 Valencia, Spain<i>Magnolia</i> spp. extracts are known for their use in traditional Korean, Chinese, and Japanese medicine in the treatment of gastrointestinal disorders, anxiety, and allergies. Among their main components with pharmacological activity, the most relevant are magnolol and honokiol, which also show antitumoral activity. The objectives of this work were to study some physicochemical properties of both substances and their stability under different conditions of temperature, pH, and oxidation. Additionally, liposomes of honokiol (the least stable compound) were formulated and characterized. Both compounds showed pH-dependent solubility, with different solubility–pH profiles. Magnolol showed a lower solubility than honokiol at acidic pH values, but a higher solubility at alkaline pH values. The partition coefficients were similar and relatively high for both compounds (log P<sub>o/w</sub> ≈ 4.5), indicating their lipophilic nature. Honokiol was less stable than magnolol, mainly at neutral and basic pH values. To improve the poor stability of honokiol, it was suitably loaded in liposomes. The obtained liposomes were small in size (175 nm), homogeneous (polydispersity index = 0.17), highly negatively charged (−11 mV), and able to incorporate high amounts of honokiol (entrapment efficiency = 93.4%). The encapsulation of honokiol in liposomes increased its stability only at alkaline pH values.https://www.mdpi.com/1999-4923/13/2/224magnololhonokiolsolubilitystabilityliposomes |
| spellingShingle | Iris Usach Alessandro Alaimo Juan Fernández Alessandro Ambrosini Sara Mocini Lacramioara Ochiuz José-Esteban Peris Magnolol and Honokiol: Two Natural Compounds with Similar Chemical Structure but Different Physicochemical and Stability Properties Pharmaceutics magnolol honokiol solubility stability liposomes |
| title | Magnolol and Honokiol: Two Natural Compounds with Similar Chemical Structure but Different Physicochemical and Stability Properties |
| title_full | Magnolol and Honokiol: Two Natural Compounds with Similar Chemical Structure but Different Physicochemical and Stability Properties |
| title_fullStr | Magnolol and Honokiol: Two Natural Compounds with Similar Chemical Structure but Different Physicochemical and Stability Properties |
| title_full_unstemmed | Magnolol and Honokiol: Two Natural Compounds with Similar Chemical Structure but Different Physicochemical and Stability Properties |
| title_short | Magnolol and Honokiol: Two Natural Compounds with Similar Chemical Structure but Different Physicochemical and Stability Properties |
| title_sort | magnolol and honokiol two natural compounds with similar chemical structure but different physicochemical and stability properties |
| topic | magnolol honokiol solubility stability liposomes |
| url | https://www.mdpi.com/1999-4923/13/2/224 |
| work_keys_str_mv | AT irisusach magnololandhonokioltwonaturalcompoundswithsimilarchemicalstructurebutdifferentphysicochemicalandstabilityproperties AT alessandroalaimo magnololandhonokioltwonaturalcompoundswithsimilarchemicalstructurebutdifferentphysicochemicalandstabilityproperties AT juanfernandez magnololandhonokioltwonaturalcompoundswithsimilarchemicalstructurebutdifferentphysicochemicalandstabilityproperties AT alessandroambrosini magnololandhonokioltwonaturalcompoundswithsimilarchemicalstructurebutdifferentphysicochemicalandstabilityproperties AT saramocini magnololandhonokioltwonaturalcompoundswithsimilarchemicalstructurebutdifferentphysicochemicalandstabilityproperties AT lacramioaraochiuz magnololandhonokioltwonaturalcompoundswithsimilarchemicalstructurebutdifferentphysicochemicalandstabilityproperties AT joseestebanperis magnololandhonokioltwonaturalcompoundswithsimilarchemicalstructurebutdifferentphysicochemicalandstabilityproperties |