Magnolol and Honokiol: Two Natural Compounds with Similar Chemical Structure but Different Physicochemical and Stability Properties

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 acti...

Full description

Saved in:
Bibliographic Details
Published inPharmaceutics Vol. 13; no. 2; p. 224
Main Authors Usach, Iris, Alaimo, Alessandro, Fernández, Juan, Ambrosini, Alessandro, Mocini, Sara, Ochiuz, Lacramioara, Peris, José-Esteban
Format Journal Article
LanguageEnglish
Published Switzerland MDPI AG 06.02.2021
MDPI
Subjects
Bioavailability
honokiol
Hydrochloric acid
liposomes
magnolol
Morphology
Natural products
Potassium
solubility
stability
Spain
solubility
honokiol
magnolol
liposomes
stability
Online AccessGet full text

Cover

Abstract 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 ≈ 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.
AbstractList Magnolia 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 Po/w ≈ 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.
Magnolia 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 o/w ≈ 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.
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 ≈ 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.
Author Ambrosini, Alessandro
Alaimo, Alessandro
Ochiuz, Lacramioara
Mocini, Sara
Peris, José-Esteban
Usach, Iris
Fernández, Juan
AuthorAffiliation 1 Department of Pharmacy and Pharmaceutical Technology and Parasitology, University of Valencia, Burjassot, 46100 Valencia, Spain; iris.usach@uv.es (I.U.); ale_ala.95@hotmail.it (A.A.); juanfernandezge@gmail.com (J.F.); alessandro.ambrosini@student.unife.it (A.A.); sara.mocini@gmail.com (S.M.)
2 Department of Pharmaceutical Technology, “Grigore T. Popa” University of Medicine and Pharmacy, 700115 Iasi, Romania; ochiuzd@yahoo.com
AuthorAffiliation_xml – name: 2 Department of Pharmaceutical Technology, “Grigore T. Popa” University of Medicine and Pharmacy, 700115 Iasi, Romania; ochiuzd@yahoo.com
– name: 1 Department of Pharmacy and Pharmaceutical Technology and Parasitology, University of Valencia, Burjassot, 46100 Valencia, Spain; iris.usach@uv.es (I.U.); ale_ala.95@hotmail.it (A.A.); juanfernandezge@gmail.com (J.F.); alessandro.ambrosini@student.unife.it (A.A.); sara.mocini@gmail.com (S.M.)
Author_xml – sequence: 1
  givenname: Iris
  orcidid: 0000-0002-5786-5668
  surname: Usach
  fullname: Usach, Iris
  organization: Department of Pharmacy and Pharmaceutical Technology and Parasitology, University of Valencia, Burjassot, 46100 Valencia, Spain
– sequence: 2
  givenname: Alessandro
  surname: Alaimo
  fullname: Alaimo, Alessandro
  organization: Department of Pharmacy and Pharmaceutical Technology and Parasitology, University of Valencia, Burjassot, 46100 Valencia, Spain
– sequence: 3
  givenname: Juan
  surname: Fernández
  fullname: Fernández, Juan
  organization: Department of Pharmacy and Pharmaceutical Technology and Parasitology, University of Valencia, Burjassot, 46100 Valencia, Spain
– sequence: 4
  givenname: Alessandro
  surname: Ambrosini
  fullname: Ambrosini, Alessandro
  organization: Department of Pharmacy and Pharmaceutical Technology and Parasitology, University of Valencia, Burjassot, 46100 Valencia, Spain
– sequence: 5
  givenname: Sara
  surname: Mocini
  fullname: Mocini, Sara
  organization: Department of Pharmacy and Pharmaceutical Technology and Parasitology, University of Valencia, Burjassot, 46100 Valencia, Spain
– sequence: 6
  givenname: Lacramioara
  orcidid: 0000-0001-6447-0958
  surname: Ochiuz
  fullname: Ochiuz, Lacramioara
  organization: Department of Pharmaceutical Technology, "Grigore T. Popa" University of Medicine and Pharmacy, 700115 Iasi, Romania
– sequence: 7
  givenname: José-Esteban
  surname: Peris
  fullname: Peris, José-Esteban
  organization: Department of Pharmacy and Pharmaceutical Technology and Parasitology, University of Valencia, Burjassot, 46100 Valencia, Spain
BackLink https://www.ncbi.nlm.nih.gov/pubmed/33561940$$D View this record in MEDLINE/PubMed
BookMark eNptkstu1DAUhiNUREvpI4AssWEz4EvsxCyQ0HBppQKVpqwtx5eJBydObYdq1rw4nk5btQhvbPl85_c5x__z6mAMo6mqlwi-JYTDd1Mv4yCVmbNTCRGIIcb1k-oIcc4XNcfk4MH5sDpJaQPLIgS1hD-rDgmhDPEaHlV_vsn1GHzwQI4anIYx_HLBvweX1wF8l3mO0oNlGKYwjzqBa5d7sHKD8zKCZW8Gp0p8leOsCmpAN2fwyVlrohkzuOi3yamg7rjdC6ssO-dd3oKLGCYTszPpRfXUSp_Mye1-XP388vlyebo4__H1bPnxfKEopHlBDeKEY84Q0ww2UFutMUSWScsV7GSL6hZ1jeYaW45pzRRSklGmG4SUwpgcV2d7XR3kRkzRDTJuRZBO3FyEuBayFKS8EXXT4aZDRNHa1pQybi02nW2w7JAiqi1aH_Za09wNRqvSbxnVI9HHkdH1Yh1-i4YjSigpAm9uBWK4mk3KYnBJGe_laMKcBK7bFjHO8A59_Q-6CXMcy6huKFr-teaFontKxZBSNPa-GATFzjXiv64pea8ednKfdecR8hcPVsXJ
CitedBy_id crossref_primary_10_3390_foods12061149
crossref_primary_10_1080_10717544_2023_2204207
crossref_primary_10_1016_j_animal_2022_100532
crossref_primary_10_1080_10408398_2022_2157371
crossref_primary_10_3390_pharmaceutics15051461
crossref_primary_10_1016_j_biopha_2024_116866
crossref_primary_10_1016_j_phymed_2021_153692
crossref_primary_10_1016_j_archoralbio_2022_105610
crossref_primary_10_3390_cancers16122257
crossref_primary_10_1016_j_ejmech_2024_116471
crossref_primary_10_1016_j_ejphar_2024_176438
crossref_primary_10_3389_fsufs_2023_1204698
crossref_primary_10_3390_pharmaceutics15020448
crossref_primary_10_1016_j_arr_2024_102398
crossref_primary_10_1002_jssc_202100982
crossref_primary_10_1002_jssc_202300898
crossref_primary_10_1088_2043_6262_ace3b9
crossref_primary_10_3390_antiox11122435
crossref_primary_10_1080_16078454_2024_2337307
crossref_primary_10_1016_j_ejpb_2024_114379
crossref_primary_10_3390_ph16091262
crossref_primary_10_1002_ptr_7786
crossref_primary_10_1016_j_ijpharm_2024_124310
crossref_primary_10_1002_cbdv_202300754
crossref_primary_10_1016_j_indcrop_2023_116553
Cites_doi 10.1002/ptr.2386
10.1080/21691401.2018.1468339
10.1007/s10555-010-9235-2
10.1517/17460441.2012.714363
10.1016/j.pnpbp.2007.11.020
10.1016/j.biochi.2011.06.012
10.1016/j.taap.2014.07.005
10.1016/j.colsurfb.2018.07.021
10.1016/j.pharmthera.2011.01.010
10.3109/03639045.2012.760580
10.1016/S0014-2999(03)02121-6
10.3390/cancers12010048
10.1016/j.ejphar.2004.05.047
10.1007/BF02976465
10.2147/IJN.S178416
10.3390/pharmaceutics11110573
10.1055/a-0642-1966
10.1007/BF02976634
10.1016/j.addr.2007.05.008
10.1002/ptr.3178
10.1007/978-981-10-8022-7_115
10.1016/S0169-409X(00)00129-0
10.1016/j.nut.2018.01.017
10.1016/j.lfs.2018.01.016
10.1016/j.msec.2014.04.049
10.1371/journal.pone.0117695
10.1016/j.colsurfb.2013.12.056
10.1002/pca.1369
10.1016/j.intimp.2015.08.042
10.3390/nano10020286
10.1211/0022357001777432
10.1166/jbn.2017.2342
10.2147/IJN.S68861
10.1016/j.ijpharm.2011.01.056
10.3390/ijms19082362
ContentType Journal Article
Copyright 2021. This work is licensed under http://creativecommons.org/licenses/by/3.0/ (the “License”). Notwithstanding the ProQuest Terms and Conditions, you may use this content in accordance with the terms of the License.
2021 by the authors. 2021
Copyright_xml – notice: 2021. This work is licensed under http://creativecommons.org/licenses/by/3.0/ (the “License”). Notwithstanding the ProQuest Terms and Conditions, you may use this content in accordance with the terms of the License.
– notice: 2021 by the authors. 2021
DBID NPM
AAYXX
CITATION
3V.
7XB
8FK
8G5
ABUWG
AFKRA
AZQEC
BENPR
CCPQU
DWQXO
GNUQQ
GUQSH
M2O
MBDVC
PIMPY
PQEST
PQQKQ
PQUKI
PRINS
Q9U
7X8
5PM
DOA
DOI 10.3390/pharmaceutics13020224
DatabaseName PubMed
CrossRef
ProQuest Central (Corporate)
ProQuest Central (purchase pre-March 2016)
ProQuest Central (Alumni) (purchase pre-March 2016)
Research Library (Alumni Edition)
ProQuest Central (Alumni)
ProQuest Central
ProQuest Central Essentials
ProQuest Central
ProQuest One Community College
ProQuest Central
ProQuest Central Student
Research Library Prep
Research Library (ProQuest Database)
Research Library (Corporate)
Publicly Available Content Database
ProQuest One Academic Eastern Edition (DO NOT USE)
ProQuest One Academic
ProQuest One Academic UKI Edition
ProQuest Central China
ProQuest Central Basic
MEDLINE - Academic
PubMed Central (Full Participant titles)
Directory of Open Access Journals
DatabaseTitle PubMed
CrossRef
Publicly Available Content Database
Research Library Prep
ProQuest Central Student
ProQuest Central Basic
ProQuest Central Essentials
ProQuest One Academic Eastern Edition
ProQuest Central (Alumni Edition)
ProQuest One Community College
Research Library (Alumni Edition)
ProQuest Central China
ProQuest Central
ProQuest One Academic UKI Edition
ProQuest Central Korea
ProQuest Research Library
ProQuest One Academic
ProQuest Central (Alumni)
MEDLINE - Academic
DatabaseTitleList CrossRef

Publicly Available Content Database
PubMed
Database_xml – sequence: 1
  dbid: DOA
  name: Directory of Open Access Journals
  url: https://www.doaj.org/
  sourceTypes: Open Website
– sequence: 2
  dbid: NPM
  name: PubMed
  url: https://proxy.k.utb.cz/login?url=http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed
  sourceTypes: Index Database
– sequence: 3
  dbid: BENPR
  name: ProQuest Central
  url: https://www.proquest.com/central
  sourceTypes: Aggregation Database
DeliveryMethod fulltext_linktorsrc
Discipline Pharmacy, Therapeutics, & Pharmacology
EISSN 1999-4923
ExternalDocumentID oai_doaj_org_article_47b27b13c54f45569ff2ebf72ab1c3c8
10_3390_pharmaceutics13020224
33561940
Genre Journal Article
GeographicLocations Spain
GeographicLocations_xml – name: Spain
GroupedDBID ---
3V.
53G
5VS
8G5
AADQD
ABDBF
ABUWG
ACGFO
ACIHN
AEAQA
AFKRA
AFZYC
ALMA_UNASSIGNED_HOLDINGS
AZQEC
BENPR
BPHCQ
CCPQU
DIK
DWQXO
EBD
ESX
F5P
FD6
GNUQQ
GROUPED_DOAJ
GUQSH
GX1
HH5
HYE
IAO
IHR
KQ8
M2O
M48
MK0
MODMG
M~E
NPM
OK1
P6G
PGMZT
PIMPY
PQQKQ
PROAC
RIG
RNS
RPM
TR2
TUS
AAYXX
CITATION
7XB
8FK
MBDVC
PQEST
PQUKI
PRINS
Q9U
7X8
5PM
ID FETCH-LOGICAL-c505t-5e193929616d6070dfdd201f6af9c0ba81481b7d9d2f92546c1ca656d711cc223
IEDL.DBID RPM
ISSN 1999-4923
IngestDate Tue Oct 22 15:12:53 EDT 2024
Tue Sep 17 21:00:04 EDT 2024
Fri Oct 25 05:24:23 EDT 2024
Thu Oct 10 19:48:38 EDT 2024
Mon Nov 04 10:01:30 EST 2024
Wed Oct 16 00:44:14 EDT 2024
IsDoiOpenAccess true
IsOpenAccess true
IsPeerReviewed true
IsScholarly true
Issue 2
Keywords solubility
honokiol
magnolol
liposomes
stability
Language English
License Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
LinkModel DirectLink
MergedId FETCHMERGED-LOGICAL-c505t-5e193929616d6070dfdd201f6af9c0ba81481b7d9d2f92546c1ca656d711cc223
Notes ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ORCID 0000-0001-6447-0958
0000-0002-5786-5668
OpenAccessLink https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7915353/
PMID 33561940
PQID 2488503349
PQPubID 2032349
ParticipantIDs doaj_primary_oai_doaj_org_article_47b27b13c54f45569ff2ebf72ab1c3c8
pubmedcentral_primary_oai_pubmedcentral_nih_gov_7915353
proquest_miscellaneous_2488169623
proquest_journals_2488503349
crossref_primary_10_3390_pharmaceutics13020224
pubmed_primary_33561940
PublicationCentury 2000
PublicationDate 20210206
PublicationDateYYYYMMDD 2021-02-06
PublicationDate_xml – month: 2
  year: 2021
  text: 20210206
  day: 6
PublicationDecade 2020
PublicationPlace Switzerland
PublicationPlace_xml – name: Switzerland
– name: Basel
PublicationTitle Pharmaceutics
PublicationTitleAlternate Pharmaceutics
PublicationYear 2021
Publisher MDPI AG
MDPI
Publisher_xml – name: MDPI AG
– name: MDPI
References Lin (ref_25) 2014; 40
Xu (ref_15) 2008; 32
Wu (ref_24) 2018; 13
Liou (ref_5) 2003; 475
Shen (ref_4) 2018; 196
Lu (ref_6) 2015; 29
Manconi (ref_32) 2018; 171
ref_34
Immordino (ref_30) 2006; 1
ref_33
ref_31
Chen (ref_10) 2014; 279
Kuribara (ref_14) 2000; 52
Jiang (ref_19) 2012; 23
Avdeef (ref_36) 2007; 59
Ding (ref_22) 2018; 46
Kang (ref_3) 2008; 22
Han (ref_23) 2014; 116
ref_38
Lee (ref_2) 2011; 130
Coimbra (ref_27) 2011; 416
Pyo (ref_13) 2002; 25
Parray (ref_11) 2018; 50
Zhao (ref_9) 2011; 93
Wang (ref_39) 2019; 9
Bozzuto (ref_29) 2015; 10
Lee (ref_37) 2017; 13
Lipinski (ref_41) 2001; 46
Zhijuan (ref_35) 2004; 26
ref_21
ref_20
Hoi (ref_12) 2010; 24
Arnott (ref_40) 2012; 7
Gupta (ref_1) 2010; 29
Park (ref_8) 2004; 496
Zhang (ref_17) 2019; 2019
Felice (ref_28) 2014; 41
ref_26
Bang (ref_18) 2000; 23
Sarrica (ref_16) 2018; 84
ref_7
References_xml – volume: 22
  start-page: 883
  year: 2008
  ident: ref_3
  article-title: Antiinflammatory activity of methanol extract isolated from stem bark ofMagnolia kobus
  publication-title: Phytother. Res.
  doi: 10.1002/ptr.2386
  contributor:
    fullname: Kang
– volume: 46
  start-page: 668
  year: 2018
  ident: ref_22
  article-title: Improved oral bioavailability of magnolol by using a binary mixed micelle system
  publication-title: Artif. Cells Nanomed. Biotechnol.
  doi: 10.1080/21691401.2018.1468339
  contributor:
    fullname: Ding
– volume: 29
  start-page: 405
  year: 2010
  ident: ref_1
  article-title: Regulation of survival, proliferation, invasion, angiogenesis, and metastasis of tumor cells through modulation of inflammatory pathways by nutraceuticals
  publication-title: Cancer Metastasis Rev.
  doi: 10.1007/s10555-010-9235-2
  contributor:
    fullname: Gupta
– ident: ref_34
– volume: 7
  start-page: 863
  year: 2012
  ident: ref_40
  article-title: The influence of lipophilicity in drug discovery and design
  publication-title: Expert Opin. Drug Discov.
  doi: 10.1517/17460441.2012.714363
  contributor:
    fullname: Arnott
– volume: 32
  start-page: 715
  year: 2008
  ident: ref_15
  article-title: Antidepressant-like effects of the mixture of honokiol and magnolol from the barks of Magnolia officinalis in stressed rodents
  publication-title: Prog. Neuro Psychopharmacol. Biol. Psychiatry
  doi: 10.1016/j.pnpbp.2007.11.020
  contributor:
    fullname: Xu
– volume: 93
  start-page: 1755
  year: 2011
  ident: ref_9
  article-title: Comparison of antioxidant abilities of magnolol and honokiol to scavenge radicals and to protect DNA
  publication-title: Biochimie
  doi: 10.1016/j.biochi.2011.06.012
  contributor:
    fullname: Zhao
– volume: 279
  start-page: 294
  year: 2014
  ident: ref_10
  article-title: Magnolol protects neurons against ischemia injury via the downregulation of p38/MAPK, CHOP and nitrotyrosine
  publication-title: Toxicol. Appl. Pharmacol.
  doi: 10.1016/j.taap.2014.07.005
  contributor:
    fullname: Chen
– volume: 171
  start-page: 115
  year: 2018
  ident: ref_32
  article-title: Thymus essential oil extraction, characterization and incorporation in phospholipid vesicles for the antioxidant/antibacterial treatment of oral cavity diseases
  publication-title: Colloids Surf. B Biointerfaces
  doi: 10.1016/j.colsurfb.2018.07.021
  contributor:
    fullname: Manconi
– volume: 130
  start-page: 157
  year: 2011
  ident: ref_2
  article-title: Therapeutic applications of compounds in the Magnolia family
  publication-title: Pharmacol. Ther.
  doi: 10.1016/j.pharmthera.2011.01.010
  contributor:
    fullname: Lee
– volume: 40
  start-page: 330
  year: 2014
  ident: ref_25
  article-title: Enhancing the bioavailability of magnolol in rabbits using melting solid dispersion with polyvinylpyrrolidone
  publication-title: Drug Dev. Ind. Pharm.
  doi: 10.3109/03639045.2012.760580
  contributor:
    fullname: Lin
– volume: 475
  start-page: 19
  year: 2003
  ident: ref_5
  article-title: The anti-inflammatory effect of honokiol on neutrophils: Mechanisms in the inhibition of reactive oxygen species production
  publication-title: Eur. J. Pharmacol.
  doi: 10.1016/S0014-2999(03)02121-6
  contributor:
    fullname: Liou
– ident: ref_20
  doi: 10.3390/cancers12010048
– volume: 496
  start-page: 189
  year: 2004
  ident: ref_8
  article-title: In vitro antibacterial and anti-inflammatory effects of honokiol and magnolol against Propionibacterium sp
  publication-title: Eur. J. Pharmacol.
  doi: 10.1016/j.ejphar.2004.05.047
  contributor:
    fullname: Park
– volume: 23
  start-page: 46
  year: 2000
  ident: ref_18
  article-title: Antifungal activity of magnolol and honokiol
  publication-title: Arch. Pharm. Res.
  doi: 10.1007/BF02976465
  contributor:
    fullname: Bang
– volume: 9
  start-page: 1
  year: 2019
  ident: ref_39
  article-title: Toxicity and possible mechanisms of action of honokiol from Magnolia denudata seeds against four mosquito species
  publication-title: Sci. Rep.
  contributor:
    fullname: Wang
– volume: 13
  start-page: 5469
  year: 2018
  ident: ref_24
  article-title: Preparation of honokiol nanoparticles by liquid antisolvent precipitation technique, characterization, pharmacokinetics, and evaluation of inhibitory effect on HepG2 cells
  publication-title: Int. J. Nanomed.
  doi: 10.2147/IJN.S178416
  contributor:
    fullname: Wu
– ident: ref_38
  doi: 10.3390/pharmaceutics11110573
– volume: 84
  start-page: 1151
  year: 2018
  ident: ref_16
  article-title: Safety and Toxicology of Magnolol and Honokiol
  publication-title: Planta Med.
  doi: 10.1055/a-0642-1966
  contributor:
    fullname: Sarrica
– volume: 25
  start-page: 325
  year: 2002
  ident: ref_13
  article-title: Anti-platelet effect of the constituents isolated from the barks and fruits of Magnolia obovata
  publication-title: Arch. Pharm. Res.
  doi: 10.1007/BF02976634
  contributor:
    fullname: Pyo
– volume: 59
  start-page: 568
  year: 2007
  ident: ref_36
  article-title: Solubility of sparingly-soluble ionizable drugs
  publication-title: Adv. Drug Deliv. Rev.
  doi: 10.1016/j.addr.2007.05.008
  contributor:
    fullname: Avdeef
– ident: ref_33
– volume: 24
  start-page: 1538
  year: 2010
  ident: ref_12
  article-title: Neuroprotective effect of honokiol and magnolol, compounds from Magnolia officinalis, on beta-amyloid-induced toxicity in PC12 cells
  publication-title: Phytother. Res.
  doi: 10.1002/ptr.3178
  contributor:
    fullname: Hoi
– ident: ref_26
  doi: 10.1007/978-981-10-8022-7_115
– volume: 46
  start-page: 3
  year: 2001
  ident: ref_41
  article-title: Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings
  publication-title: Adv. Drug Deliv. Rev.
  doi: 10.1016/S0169-409X(00)00129-0
  contributor:
    fullname: Lipinski
– volume: 50
  start-page: 82
  year: 2018
  ident: ref_11
  article-title: Magnolol promotes thermogenesis and attenuates oxidative stress in 3T3-L1 adipocytes
  publication-title: Nutrition
  doi: 10.1016/j.nut.2018.01.017
  contributor:
    fullname: Parray
– volume: 196
  start-page: 69
  year: 2018
  ident: ref_4
  article-title: Magnolol treatment attenuates dextran sulphate sodium-induced murine experimental colitis by regulating inflammation and mucosal damage
  publication-title: Life Sci.
  doi: 10.1016/j.lfs.2018.01.016
  contributor:
    fullname: Shen
– volume: 26
  start-page: 66
  year: 2004
  ident: ref_35
  article-title: Determination of the Dissociation Constants of Magnolol and Honokiol by UV Spectrophotometry
  publication-title: J. Yunnan Univ. Nat. Sci. Ed.
  contributor:
    fullname: Zhijuan
– volume: 41
  start-page: 178
  year: 2014
  ident: ref_28
  article-title: Drug delivery vehicles on a nano-engineering perspective
  publication-title: Mater. Sci. Eng. C Mater. Biol. Appl.
  doi: 10.1016/j.msec.2014.04.049
  contributor:
    fullname: Felice
– ident: ref_7
  doi: 10.1371/journal.pone.0117695
– volume: 116
  start-page: 114
  year: 2014
  ident: ref_23
  article-title: Honokiol nanosuspensions: Preparation, increased oral bioavailability and dramatically enhanced biodistribution in the cardio-cerebro-vascular system
  publication-title: Colloids Surf. B Biointerfaces
  doi: 10.1016/j.colsurfb.2013.12.056
  contributor:
    fullname: Han
– volume: 23
  start-page: 387
  year: 2012
  ident: ref_19
  article-title: Quality Assessment of Commercial Magnoliae Officinalis Cortex by 1H-NMR-based Metabolomics and HPLC Methods
  publication-title: Phytochem. Anal.
  doi: 10.1002/pca.1369
  contributor:
    fullname: Jiang
– volume: 2019
  start-page: 1847130
  year: 2019
  ident: ref_17
  article-title: Insights on the Multifunctional Activities of Magnolol
  publication-title: BioMed. Res. Int.
  contributor:
    fullname: Zhang
– volume: 29
  start-page: 770
  year: 2015
  ident: ref_6
  article-title: Activation of Nrf2/HO-1signaling pathway involves the anti-inflammatory activity of magnolol in Porphyromonas gingivalis lipopolysaccharide-stimulated mouse RAW 264.7 macrophages
  publication-title: Int. Immunopharmacol.
  doi: 10.1016/j.intimp.2015.08.042
  contributor:
    fullname: Lu
– ident: ref_31
  doi: 10.3390/nano10020286
– volume: 52
  start-page: 1425
  year: 2000
  ident: ref_14
  article-title: The Anxiolytic Effect of Two Oriental Herbal Drugs in Japan Attributed to Honokiol from Magnolia Bark
  publication-title: J. Pharm. Pharmacol.
  doi: 10.1211/0022357001777432
  contributor:
    fullname: Kuribara
– volume: 13
  start-page: 255
  year: 2017
  ident: ref_37
  article-title: Magnolol Nanoparticles Exhibit Improved Water Solubility and Suppress TNF-α-Induced VCAM-1 Expression in Endothelial Cells
  publication-title: J. Biomed. Nanotechnol.
  doi: 10.1166/jbn.2017.2342
  contributor:
    fullname: Lee
– volume: 10
  start-page: 975
  year: 2015
  ident: ref_29
  article-title: Liposomes as nanomedical devices
  publication-title: Int. J. Nanomed.
  doi: 10.2147/IJN.S68861
  contributor:
    fullname: Bozzuto
– volume: 416
  start-page: 433
  year: 2011
  ident: ref_27
  article-title: Improving solubility and chemical stability of natural compounds for medicinal use by incorporation into liposomes
  publication-title: Int. J. Pharm.
  doi: 10.1016/j.ijpharm.2011.01.056
  contributor:
    fullname: Coimbra
– volume: 1
  start-page: 297
  year: 2006
  ident: ref_30
  article-title: Stealth liposomes: Review of the basic science, rationale, and clinical applications, existing and potential
  publication-title: Int. J. Nanomed.
  contributor:
    fullname: Immordino
– ident: ref_21
  doi: 10.3390/ijms19082362
SSID ssj0000331839
Score 2.4032767
Snippet spp. extracts are known for their use in traditional Korean, Chinese, and Japanese medicine in the treatment of gastrointestinal disorders, anxiety, and...
Magnolia spp. extracts are known for their use in traditional Korean, Chinese, and Japanese medicine in the treatment of gastrointestinal disorders, anxiety,...
Magnolia spp. extracts are known for their use in traditional Korean, Chinese, and Japanese medicine in the treatment of gastrointestinal disorders, anxiety,...
SourceID doaj
pubmedcentral
proquest
crossref
pubmed
SourceType Open Website
Open Access Repository
Aggregation Database
Index Database
StartPage 224
SubjectTerms Bioavailability
honokiol
Hydrochloric acid
liposomes
magnolol
Morphology
Natural products
Potassium
solubility
stability
SummonAdditionalLinks – databaseName: Directory of Open Access Journals
  dbid: DOA
  link: http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwrV1La9wwEBYhp15CX2ndJkWFkFPcrCxZXvXWV1gCCQvZQG5GT7J0a4fsLmXP-eOdkbyvEsglV0tYsmc0-mY0-oaQI8PB4HGvcisUOCguiLwvtM4DwFemQuGli9kWl3JwLc5vypuNUl-YE5bogdOPOxWVKSrDuC1FEGUpVYAXmFAV2jDLbbrm21MbzlS0wRx1VaUrOxz8-tO723WIeIqndbh5bW1GkbP_MaD5f77kxgZ09pLsdciRfkszfkV2fPOaHA_TgIsTOlrfpJqe0GM6XJNSL96QhwtMqZu0E6obRwdt0_4et5OvdPS3pZc6km9QtA1YZWlKMTpLr8Z_xuD30iWnAL2KXLPze0_NfEZ_dqVVZjRmkVosvZX64QgAYmPa7YIOMdx_j7ytb8n12a_Rj0HeFWDILQCjWV56gHeAnySTToJtcME5AAxB6qBsz-g--FLMVE65Iigk1rfMagCIrmLMWgAe-2S3aRv_nlBmCq2CKX3wTFQB3Ly-dAVz_Z4IHMbJyJelJOq7xLNRg3-CoqsfFV1GvqO8Vp2RJjs-AOWpO-Wpn1KejBwspV13a3daF2DT8HBXqIx8XjXDqsOjFN34dp76MKkAO2bkXVKO1Uw4LzE01MtItaU2W1PdbmnGt5HZu1KwAZX8w3N820fyosD8G8wwlwdkF1TEHwKAmplPca38A72dHwU
  priority: 102
  providerName: Directory of Open Access Journals
– databaseName: ProQuest Central
  dbid: BENPR
  link: http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwfV1Lb9NAEB5BeuGCeGMoaJFQTzXN2uu1lwui0CpCIopoKvVm7bONCHbIQyhn_jgztpMQVHH1rrUrzWO_mZ39BuCtSdHhpV7FVigMUFwQcSG0jgPCV65C4qVrqi2GcnApvlxlV13CbdGVVW58YuOoXW0pR36SoKbRlZtQH2Y_Y-oaRberXQuNu3CQYKTQ78HB6dlw9G2bZcEfCAK0T3dSjO9PZje7VPGCbu3oENs7lBru_tsA5791k38dROcP4H6HINnHVuQP4Y6vHsHRqF1wfczGuxdVi2N2xEY7cur1Y_j9lUrrpvWU6cqxQV3V3yf19D0b_6rZUDckHIx8BHVbWjDK0rKLyY8Jxr9swy3ALhrO2dXcM7Nass9di5Ula6pJLbXgaufRCghmm_LbNRtR2n9O_K1P4PL8bPxpEHeNGGKLAGkZZx5hHuIoyaWT6CNccA6BQ5A6KNs3usCYipvcKZcERQT7lluNQNHlnFuLAOQp9Kq68s-BcZNoFUzmg-ciDxjuFdIl3BV9EVJcJ4J3G0mUs5Zvo8Q4hURX3iq6CE5JXtvJRJfdfKjn12VnfaXITZIbntpMBJFlUgXUQhPyRBtuU1tEcLiRdtnZ8KLcaVwEb7bDaH10paIrX6_aOVwqxJARPGuVY7uTNM0oRdSPIN9Tm72t7o9Uk5uG4TtXeBBl6Yv_b-sl3EuowoZqyOUh9FD4_hVCpKV53dnBH-gqF2k
  priority: 102
  providerName: ProQuest
– databaseName: Scholars Portal Open Access Journals
  dbid: M48
  link: http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwlV1LbxMxELZKuXBB5b2lICOhnrolfqw3RkKIVxUhUUVqIvW28mPdRoTdkocgZ_44M97dhKBw4Lq21pZnPP7GM_6GkJdWgMETpU6d1OCg-CDTvjQmDQBfmQ68VD5mW5yrwVh-vswu90hHqNAu4Hyna4f1pMaz6enP76u3sOHfoMcJLvurm-vN7e8cA3F4Lt0it7kEZx2z-VrEH42zQCXWMdassb4aF827nn__aevEisT-u9Do30mVf5xSZwfkbgsv6btGH-6RvbK6T46HzYCrEzraPLean9BjOtwwV68ekF9fMO9uWk-pqTwd1FX9dVJPX9PRj5qem8jQQdGAYCmmOcUrXHox-TaBFaQd8QC9iIS0y1lJ7XJBP7b1VxY0ppo6rM_V9MMRAOnG3NwVHWJMYIbkrg_J-OzT6MMgbas0pA7Q0yLNSsCAALIUU16BAfHBe0AVQZmgXc-aPjhczOZeex40su875gygSJ8z5hygk0dkv6qr8gmhzHKjg83KUDKZB_AF-8pz5vs9GQSMk5DTThLFTUPGUYATg6IrdoouIe9RXuvOyKUdP9Szq6LdmoXMLc8tEy6TQWaZ0gFU1IacG8uccP2EHHXSLjr9LDgYPowAS52QF-tm2JoYbzFVWS-bPkxpAJgJedwox3omQmR4f9RLSL6lNltT3W6pJteR_jvXcEpl4vB_F-MpucMxIQdTztUR2Qd1KJ8BolrY53GP_AbhLCSz
  priority: 102
  providerName: Scholars Portal
Title Magnolol and Honokiol: Two Natural Compounds with Similar Chemical Structure but Different Physicochemical and Stability Properties
URI https://www.ncbi.nlm.nih.gov/pubmed/33561940
https://www.proquest.com/docview/2488503349
https://search.proquest.com/docview/2488169623
https://pubmed.ncbi.nlm.nih.gov/PMC7915353
https://doaj.org/article/47b27b13c54f45569ff2ebf72ab1c3c8
Volume 13
hasFullText 1
inHoldings 1
isFullTextHit
isPrint
link http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwnV1ba9swGP1oOxh9GbvPXRc0GH2qk8iWL9rb2rWEQUJYU-ib0cVazRI75ELJ8_74Psl20ow-7cUPtowE35F0PunoCOCLDHHAC3PuK8YxQdGG-SkTwjdIXyk3QR5rp7YYxYNb9uMuujuAqD0L40T7ShbdcjrrlsW901bOZ6rX6sR64-FlwrGfRmHvEA4RoI9SdDf8hhamvD6tE2JK35vf71aHl3ajzs5bx_A8DCObw_f3piTn3P8U3fxXNfloGrp-CS8a_ki-1e18BQd5-RrOxnXdm3My2Z2nWp6TMzLeWVNv3sCfoRXWTaspEaUmg6qsfhfV9CuZPFRkJJwFB7EjhL1raUnsGi25KWYFZr-kdRYgN85xdr3IiVyvyPfmgpUVcVpSZS_gqsvZGpDKOvHthoztov_Cure-hdvrq8nlwG-uYfAV0qOVH-VI8pBFxTTWMY4Q2miNtMHEwnDVlyLFjIrKRHMdGG7t9RVVAmmiTihVCunHOzgqqzL_AITKQHAjo9zklCUGk7001gHVaZ-ZEOvxoNtGIpvXbhsZZik2itmTUfTgwsZrW9iaZbsX1eJX1kAmY4kMEklDFTHDoijmBjEoTRIISVWoUg9O22hnTQ9eZgGObHaLl3EPPm8_Y9-zGyqizKt1XYbGHBmkB-9rcGxb0oLLg2QPNntN3f-CcHf-3g28T_77z49wHFjpjRWXx6dwhLjIPyF3WskOPLu4Go1_dtzaAz6HLO24_vMX_noiZA
link.rule.ids 230,315,730,783,787,867,888,2109,2228,21400,24330,27936,27937,33756,33757,43817,53804,53806,74636
linkProvider National Library of Medicine
linkToHtml http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwfV3Nb9MwFLdgO8AF8U1ggJHQTgurE8eJuSAGmwpsVcU6abfIn6yiJKVphXrmH-c9J20pmrjGjmzpffj3np9_j5DXOgWHlzoZGy4hQLGexwVXKvYAX5n0iRM2VFsMRP-Cf77MLruEW9OVVa58YnDUtjaYIz9MQNPwyo3Ld9OfMXaNwtvVroXGTbKLVFUQfO0eHQ-GX9dZFvgBIUD7dCeF-P5werVJFTd4a4eH2NahFLj7rwOc_9ZN_nUQndwldzoESd-3Ir9HbrjqPtkftgsuD-ho86KqOaD7dLghp14-IL_PsLRuUk-oqizt11X9fVxP3tLRr5oOVCDhoOgjsNtSQzFLS8_HP8YQ_9IVtwA9D5yzi5mjejGnH7sWK3MaqkkNtuBq5-EKAGZD-e2SDjHtP0P-1ofk4uR49KEfd40YYgMAaR5nDmAe4CjBhBXgI6y3FoCDF8pL09OqgJiK6dxKm3iJBPuGGQVA0eaMGQMA5BHZqerKPSGU6URJrzPnHeO5h3CvEDZhtuhxn8I6EXmzkkQ5bfk2SohTUHTltaKLyBHKaz0Z6bLDh3r2reysr-S5TnLNUpNxz7NMSA9aqH2eKM1MaoqI7K2kXXY23JQbjYvIq_UwWB9eqajK1Yt2DhMSMGREHrfKsd5JmmaYIupFJN9Sm62tbo9U46vA8J1LOIiy9On_t_WS3OqPzk7L00-DL8_I7QSrbbCeXOyRHVAE9xzg0ly_6GziD1KJGmM
linkToPdf http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwfV1bb9MwFLagkxAviPsyBhgJ7WmhdeI4MS-IsVXlVlWsk_YW-RKzipJ0TSvUZ_445yRuS9HEa-LIls7F37nkO4S81jE4vLiQoeESAhTreJhxpUIH8JVJFxXCNt0WQzG44J8uk0vf_1T7tsq1T2wcta0M5si7EWgalty47DrfFjE67b-bXYc4QQorrX6cxm2ylyILVofsnZwNR982GRf4GOFA-xtPDLF-d3a1TRvXWMHDC23ngmp4_G8Cn__2UP51KfXvk3seTdL3rfgfkFtF-ZAcjdoNV8d0vP27qj6mR3S0JapePSK_v2Kb3bSaUlVaOqjK6sekmr6l418VHaqGkIOiv8DJSzXFjC09n_ycQCxM1zwD9Lzhn13OC6qXC3rqx60saNNZanAcV7sOdwBg27TirugISwBz5HJ9TC76Z-MPg9APZQgNgKVFmBQA-QBTCSasAH9hnbUAIpxQTpqeVhnEV0ynVtrISSTbN8woAI02ZcwYACNPSKesymKfUKYjJZ1OClcwnjoI_TJhI2azHncx7BOQN2tJ5LOWeyOHmAVFl98ouoCcoLw2i5E6u3lQzb_n3hJznuoo1Sw2CXc8SYR0oJHapZHSzMQmC8jhWtq5t-c632pfQF5tXoMlYnlFlUW1bNcwIQFPBuRpqxybk8RxgumiXkDSHbXZOerum3Jy1bB9pxIupSQ--P-xXpI7YA75l4_Dz8_I3Qgbb7C1XBySDuhB8RyQ00K_8CbxB0C4Hpc
openUrl ctx_ver=Z39.88-2004&ctx_enc=info%3Aofi%2Fenc%3AUTF-8&rfr_id=info%3Asid%2Fsummon.serialssolutions.com&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.atitle=Magnolol+and+Honokiol%3A+Two+Natural+Compounds+with+Similar+Chemical+Structure+but+Different+Physicochemical+and+Stability+Properties&rft.jtitle=Pharmaceutics&rft.au=Usach%2C+Iris&rft.au=Alaimo%2C+Alessandro&rft.au=Fern%C3%A1ndez%2C+Juan&rft.au=Ambrosini%2C+Alessandro&rft.date=2021-02-06&rft.issn=1999-4923&rft.eissn=1999-4923&rft.volume=13&rft.issue=2&rft.spage=224&rft_id=info:doi/10.3390%2Fpharmaceutics13020224&rft.externalDBID=n%2Fa&rft.externalDocID=10_3390_pharmaceutics13020224
thumbnail_l http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/lc.gif&issn=1999-4923&client=summon
thumbnail_m http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/mc.gif&issn=1999-4923&client=summon
thumbnail_s http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/sc.gif&issn=1999-4923&client=summon