Design and synthesis of ten biphenyl-neolignan derivatives and their in vitro inhibitory potency against cyclooxygenase-1/2 activity and 5-lipoxygenase-mediated LTB4-formation

Schühly, Wolfgang; Hüfner, Antje; Pferschy‐Wenzig, Eva‐Maria; Prettner, Elke; Adams, Michael; Bodensieck, Antje; Kunert, Olaf; Oluwemimo, Asije; Haslinger, Ernst; Bauer, Rudolf

doi:10.1016/j.bmc.2009.05.018

Cited by 36 publications

(37 citation statements)

References 26 publications

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“…MH inhibits COX-2 activity with an IC 50 of 4.3 lM in RAW264.7 cells (Schuhly et al 2009b). Another paper shows different inhibitory potency on COX-2, in that MH inhibits COX-2 with an IC 50 of 0.06 lM and COX-1 with an IC 50 of 0.1 lM (Schuhly et al 2009a).…”

Section: Introductionmentioning

confidence: 96%

Validation of cyclooxygenase-2 as a direct anti-inflammatory target of 4-O-methylhonokiol in zymosan-induced animal models

et al. 2014

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4-O-methylhonokiol (MH) is known to inhibit inflammation by partially understood mechanisms. Here, the anti-inflammatory mechanisms of MH were examined using enzymatic, cellular, and animal assays. In enzymatic assays, MH inhibited COX-2 activity with an IC50 of 0.062 μM, and also COX-1 with an IC50 of 2.4 μM. In cellular assays, MH was immunotoxic above 10 μM. At non-toxic concentrations (below 3 μM), MH strongly inhibited COX-2-mediated prostaglandin production with an IC50 of 0.1 μM, whereas did not or slightly affect other functions of B cells, T cells, dendritic cells, and macrophages. In an animal model, MH inhibited the increase in footpad thickness and popliteal lymph node weight in zymosan-injected mice. When analyzed the draining pLNs of zymosan-injected mice on day 5, MH inhibited the overall inflammatory responses. However, MH inhibited cyclooxygenase (COX)-2-mediated prostaglandin production without affecting tumor necrosis factor-α production in inflamed tissues within 6 h after zymosan injection. In summary, our data suggest that COX-2 may be a direct anti-inflammatory target of MH in vitro and in vivo.

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Section: Introductionmentioning

confidence: 96%

Validation of cyclooxygenase-2 as a direct anti-inflammatory target of 4-O-methylhonokiol in zymosan-induced animal models

et al. 2014

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“…18 Biphenyl-neolignans such as magnolol and honokiol and derivatives thereof have been shown to act as potent inhibitors of COXisoenzymes and 5-LOX. [19][20][21][22] In these compounds the biphenyl axis is more or less flexible, whereas in S. chinensis lignans this torsion angle is fixed by the presence of a cyclooctadiene ring. Apart from some reports indicating minor activities, no detailed studies revealing significant activity of Schisandra lignans and related structures on COX/LOX were carried out to date to the best of our knowledge.…”

Section: Introductionmentioning

confidence: 99%

Derivatives of schisandrin with increased inhibitory potential on prostaglandin E2 and leukotriene B4 formation in vitro

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Pferschy‐Wenzig

Fabian

et al. 2010

Bioorganic & Medicinal Chemistry

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“…(5) Lignan derivatives represent a group of constituents in the roots of K. lappacea , and previous studies have shown that members of this compound class may have the potential to act as anti-inflammatory agents. 10,11 Thus, the aim of the present investigation was to examine whether lignans from K. lappacea may block inflammation. From the dichloromethane extract of K. lappacea roots, 11 lignan derivatives were isolated and identified.…”

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confidence: 99%

Lignan Derivatives from Krameria lappacea Roots Inhibit Acute Inflammation in Vivo and Pro-inflammatory Mediators in Vitro

et al. 2011

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The roots of Krameria lappacea are used traditionally against oropharyngeal inflammation. So far, the astringent and antimicrobial properties of its proanthocyanidin constituents are considered to account for the anti-inflammatory effect. The aim of the present study was to characterize pharmacologically a lipophilic extract of K. lappacea roots and several isolated lignan derivatives (1–11) in terms of their putative anti-inflammatory activity. The dichloromethane extract (ID50 77 μg/cm2) as well compounds 1–11 (ID50 0.31–0.60 μmol/cm2) exhibited topical antiedematous properties comparable to those of indomethacin (ID50 0.29 μmol/cm2) in a mouse ear in vivo model. Two of the most potent compounds, 2-(2-hydroxy-4-methoxyphenyl)-5-(3-hydroxypropyl)benzofuran (5) and (+)-conocarpan (7), were studied regarding their time-dependent edema development and leukocyte infiltration up to 48 h after croton oil-induced dermatitis induction, and they showed activity profiles similar to that of hydrocortisone. In vitro studies of the isolated lignan derivatives demonstrated the inhibition of NF-κB, cyclooxygenase-1 and -2, 5-lipoxygenase, and microsomal prostaglandin E2 synthase-1 as well as antioxidant properties, as mechanisms possibly contributing to the observed in vivo effects. The present findings not only support the ethnopharmacological use of K. lappacea roots but also reveal that the isolated lignan derivatives contribute strongly to the anti-inflammatory activity of this herbal drug.

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Design and synthesis of ten biphenyl-neolignan derivatives and their in vitro inhibitory potency against cyclooxygenase-1/2 activity and 5-lipoxygenase-mediated LTB4-formation

Cited by 36 publications

References 26 publications

Validation of cyclooxygenase-2 as a direct anti-inflammatory target of 4-O-methylhonokiol in zymosan-induced animal models

Validation of cyclooxygenase-2 as a direct anti-inflammatory target of 4-O-methylhonokiol in zymosan-induced animal models

Derivatives of schisandrin with increased inhibitory potential on prostaglandin E2 and leukotriene B4 formation in vitro

Lignan Derivatives from Krameria lappacea Roots Inhibit Acute Inflammation in Vivo and Pro-inflammatory Mediators in Vitro

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