Synthesis of Either C2- or C4′-Alkylated Derivatives of Honokiol and Their Biological Evaluation for Anti-inflammatory Activity

Honokiol, a biphenolic neolignan isolated from Magnolia officinalis, was reported to have a promising anti-inflammatory activity for the treatment of various diseases. There are many efforts on the synthesis and structure–activity relationship of honokiol derivatives. However, regioselective O-alkyl...

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Bibliographic Details
Published inChemical & pharmaceutical bulletin Vol. 67; no. 9; pp. 966 - 976
Main Authors Lee, San-ha, Fei, Xiang, Lee, Chaelin, Do, Hien Thi Thu, Rhee, Inmoo, Seo, Seung-Yong
Format Journal Article
LanguageEnglish
Published TOKYO The Pharmaceutical Society of Japan 01.09.2019
Pharmaceutical Soc Japan
Japan Science and Technology Agency
Subjects
Alkylation
anti-inflammatory activity
Anti-inflammatory agents
Benzophenone
Biological activity
Biotin
Chemistry
Chemistry, Medicinal
Chemistry, Multidisciplinary
Cyclooxygenase-2
Derivatives
honokiol
Inflammation
Life Sciences & Biomedicine
Magnolia officinalis
Medical treatment
Mode of action
Nitric oxide
O-alkylation
Organic chemistry
Pharmacology & Pharmacy
photoaffinity probe
Physical Sciences
Regioselectivity
Science & Technology
Synthesis
Target recognition
O-alkylation
NATURAL-PRODUCT
CELLS
ACTIVATION
DESIGN
ANGIOGENESIS
ANALOGS
anti-inflammatory activity
photoaffinity probe
honokiol
IN-VITRO
MAGNOLOL
Magnolia officinalis
INHIBITORS
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Summary:Honokiol, a biphenolic neolignan isolated from Magnolia officinalis, was reported to have a promising anti-inflammatory activity for the treatment of various diseases. There are many efforts on the synthesis and structure–activity relationship of honokiol derivatives. However, regioselective O-alkylation of honokiol remains a challenge and serves as a tool to provide not only some derivatives but also chemical probes for target identification and mode of action. In this study, we examined the reaction condition for regioselective O-alkylation, in which C2 and C4′-alkylated analogs of honokiol were synthesized and evaluated for inhibitory activity on nitric oxide production and cyclooxygenase-2 expression. Furthermore, we successfully synthesized a potential photoaffinity probe consisting of biotin and benzophenone based on a C4′-alkylated derivative.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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content type line 23
ISSN:0009-2363
1347-5223
DOI:10.1248/cpb.c19-00207