2017
DOI: 10.1080/14786419.2017.1350666
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Acetyl- and O-alkyl- derivatives of β-mangostin from Garcinia mangostana and their anti-inflammatory activities

Abstract: Pure β-mangostin (1) was isolated from the stem bark of Garcinia mangostana L. One monoacetate (2) and five O-alkylated β-mangostin derivatives (3-7) were synthesised from β-mangostin. The structures of these compounds were elucidated and determined using spectroscopic techniques such as 1D NMR and MS. The cytotoxicities and anti-inflammatory activities of these five compounds against RAW cell 264.7 were tested. The structural-activity relationship studies indicated that β-mangostin showed a significant activi… Show more

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Cited by 21 publications
(8 citation statements)
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“…Using a LPS-induced RAW264.7 macrophage model, 3,4,5,6-tetrahydroxyxanthone (4) and mangiferin (7) were found to suppress the generation of TNF-α and intercellular adhesion molecule-1 (ICAM-1) [28]. Six xanthones, including 1,3,6,7-tetrahydroxy-8-prenylxanthone (19) [29], β-mangostin (22) [30], nagostenone F (30) [31], inophinnin (33) [32], garcinoxanghone B (40) [33], and garcinoxanthone C (41) [33], were reported to reduce NO production in LPS-stimulated RAW264.7 macrophage. 6'-O-acetyl mangiferin (OAM) (8), an acetylated xanthone C-glucoside, was reported to suppress iNOS and COX-2 expression, thereby inhibiting the levels of TNF-α, IL-1β, and IL-6 in LPS-stimulated RAW264.7 cells.…”
Section: Xanthones With Anti-inflammatory Propertiesmentioning
confidence: 99%
“…Using a LPS-induced RAW264.7 macrophage model, 3,4,5,6-tetrahydroxyxanthone (4) and mangiferin (7) were found to suppress the generation of TNF-α and intercellular adhesion molecule-1 (ICAM-1) [28]. Six xanthones, including 1,3,6,7-tetrahydroxy-8-prenylxanthone (19) [29], β-mangostin (22) [30], nagostenone F (30) [31], inophinnin (33) [32], garcinoxanghone B (40) [33], and garcinoxanthone C (41) [33], were reported to reduce NO production in LPS-stimulated RAW264.7 macrophage. 6'-O-acetyl mangiferin (OAM) (8), an acetylated xanthone C-glucoside, was reported to suppress iNOS and COX-2 expression, thereby inhibiting the levels of TNF-α, IL-1β, and IL-6 in LPS-stimulated RAW264.7 cells.…”
Section: Xanthones With Anti-inflammatory Propertiesmentioning
confidence: 99%
“…Buravlev et al (2018) modified α-and γ-mangostin through Mannich reactions (aminomethylated at the C-4/C-5 positions) which consequently led to higher anti-oxidant activities than their original compounds. Furthermore, Karunakaran et al (2018) showed that β-mangostin could inhibit the inflammatory response in lipopolysaccharide-induced RAW 264.7 macrophages, but this activity was not retained when the hydroxyl (OH) group at its position C-6 was replaced with acetyl or alkyl. These lines of evidence highlight the importance of certain functional groups in xanthones to confer their bioactivities including anti-oxidant and anti-inflammation.…”
Section: Introductionmentioning
confidence: 99%
“…Buravlev et al (2018) modified α-and γmangostin through Mannich reactions (aminomethylated at the C-4/C-5 positions) which consequently led to higher anti-oxidant activities than their original compounds. Furthermore, Karunakaran et al (2018) showed that β-mangostin could inhibit the inflammatory response in lipopolysaccharide (LPS)-induced RAW 264.7 macrophages, but this activity was not retained when the hydroxyl (OH) group at its position C-6 was replaced with acetyl or alkyl. These lines PeerJ reviewing PDF | (2018:09:30985:1:1:NEW 30 Nov 2018)…”
Section: Metabolite Composition Of Mangosteenmentioning
confidence: 99%