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Licarin A


  • Brand : BIOFRON

  • Catalogue Number : BD-P0884

  • Specification : 98.0%(HPLC&TLC)

  • CAS number : 51020-86-1

  • Formula : C20H22O4

  • Molecular Weight : C20H22O4

  • Volume : 25mg

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Antioxidant,CCR-3,Anticancer,Caspase,p38 MAPK,COX,Antiparasitic / Antioxidant,Asthma,Allergic rhinitis,Cancer,Cardiovascular disorder,Cystic fibrosis,Pancreatic cancer

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Licarin A is a candidate compound for the treatment of immediate hypersensitivity via inhibition of rat mast cell line RBL-2H3 cells. PUMID/DOI:DOI: 10.1111/jphp.12475 J Pharm Pharmacol. 2015 Dec;67(12):1723-32. OBJECTIVES:We previously demonstrated that some phenylpropanoids are capable of inhibiting activated mast cells. This study evaluated the anti-allergic effects of licarin A, a neolignan isolated from various plants, on antigen-stimulated rat mast cell line.METHODS:The inhibitory effects of licarin A on histamine release, tumour necrosis factor-α (TNF-α) and prostaglandin D2 (PGD2) production, and cyclooxygenase-2 (COX-2) expression in dinitrophenyl-human serum albumin (DNP-HSA) rat basophilic leukemia cells (DNP-HSA-stimulated RBL-2H3 cells), were investigated by spectrofluorometry, ELISA and immunoblotting.KEY FINDINGS:Licarin A significantly and dose-dependently reduced TNF-α production (IC50 12.6?±?0.3?μm) in DNP-HSA-stimulated RBL-2H3 cells. Furthermore, the levels of PGD2 secretion in DNP-HSA-stimulated cells pretreated with licarin A were lower than those stimulated with DNP-HSA alone (positive control). Treatment with licarin A at 20?μm produced slight suppression of DNP-HSA-induced increases in COX-2 mRNA and protein levels. We identified several signalling pathways that mediated these pharmacological effects. Licarin A treatment tended to reduce phosphorylated protein kinase C alpha/beta II (PKCα/βII) and p38 mitogen-activated protein kinase (MAPK) protein levels.CONCLUSIONS:Our results demonstrate that licarin A reduces TNF-α and PGD2 secretion via the inhibition of PKCα/βII and p38 MAPK pathways; this compound may be useful for attenuating immediate hypersensitivity. Neolignan Licarin A presents effect against Leishmania (Leishmania) major associated with immunomodulation in vitro. PUMID/DOI:DOI: 10.1016/j.exppara.2013.07.007 Exp Parasitol. 2013 Oct;135(2):307-13. Leishmaniasis′ treatment is based mostly on pentavalent antimonials or amphotericin B long-term administration, expensive drugs associated with severe side effects. Considering these aforementioned, the search for alternative effective and safe leishmaniasis treatments is a necessity. This work evaluated a neolignan, licarin A anti-leishmanial activity chemically synthesized by our study group. It was observed that licarin A effectively inhibited Leishmania (Leishmania) major promastigotes (IC?? of 9.59 ± 0.94 μg/mL) growth, by inducing in these parasites genomic DNA fragmentation in a typical death pattern by apoptosis. Additionally, the neolignan proved to be even more active against intracellular amastigotes of the parasite (EC?? of 4.71 ± 0.29 μg/mL), and significantly more effective than meglumine antimoniate (EC?? of 216.2 ± 76.7 μg/mL) used as reference drug. The antiamastigote activity is associated with an immunomodulatory activity, since treatment with licarin A of the infected macrophages induced a decrease in the interleukin (IL)-6 and IL-10 production. This study demonstrates for the first time the antileishmanial activity of licarin A and suggests that the compound may be a promising in the development of a new leishmanicidal agent. Schistosomicidal and trypanocidal structure-activity relationships for (±)-licarin A and its (-)- and (+)-enantiomers. PUMID/DOI:DOI: 10.1016/j.phytochem.2011.04.007 Phytochemistry. 2011 Aug;72(11-12):1424-30. (±)-Licarin A (1) was obtained by oxidative coupling, and its enantiomers, (-)-licarin A (2) and (+)-licarin A (3), were resolved by chiral HPLC. Schistosomicidal and trypanocidal activities of these compounds were evaluated in vitro against Schistosoma mansoni adult worms and trypomastigote forms of Trypanosoma cruzi. The racemic mixture (1) displayed significant schistosomicidal activity with an LC?? value of 53.57 μM and moderate trypanocidal activity with an IC?? value of 127.17 μM. On the other hand, the (-)-enantiomer (2), displaying a LC?? value of 91.71 μM, was more active against S. mansoni than the (+)-enantiomer (3), which did not show activity. For the trypanocidal assay, enantiomer 2 showed more significant activity (IC?? of 23.46 μM) than enantiomer 3, which showed an IC?? value of 87.73 μM. Therefore, these results suggest that (±)-licarin A (1) and (-)-licarin A (2) are promising compounds that could be used for the development of schistosomicidal and trypanocidal agents. Meso-dihydroguaiaretic acid and licarin A of Machilus thunbergii protect against glutamate-induced toxicity in primary cultures of a rat cortical cells. PUMID/DOI:DOI: 10.1038/sj.bjp.0706380 Br J Pharmacol. 2005 Nov;146(5):752-9. 1We previously reported that four lignans isolated from the bark of Machilus thunbergii Sieb. et Zucc. (Lauraceae) protected primary cultures of rat cortical neurons from neurotoxicity induced by glutamate. 2 Among the lignans, meso-dihydroguaiarectic acid (MDGA) and licarin A significantly attenuated glutamate-induced neurotoxicity when added prior to or right after the excitotoxic glutamate challenge. 3 The neuroprotective activities of two lignans appeared to be more effective in protecting neurons against neurotoxicity induced by NMDA than that induced by kainic acid. 4 MDGA and licarin A diminished the calcium influx that routinely accompanies with the glutamate-induced neurotoxicity, and inhibited the subsequent overproduction of cellular nitric oxide and peroxide to the level of control cells. They also preserved cellular activities of antioxidative enzymes such as superoxide dismutase, glutathione peroxidase and glutathione reductase reduced in the glutamate-injured neuronal cells. 5 Thus, our results suggest that MDGA and licarin A significantly protect primary cultured neuronal cells against glutamate-induced oxidative stress, via antioxidative activities. Biological evaluation of secondary metabolites from the root of Machilus obovatifolia. PUMID/DOI:DOI:10.1002 / cbdv.201400196 Chem Biodivers. 2015 Jul;12(7):1057-67 Bioassay-guided fractionation of the root of Machilus obovatifolia led to the isolation of four new lignans, epihenricine B (1), threo-(7′R,8′R) and threo-(7′S,8′S)-methylmachilusol D (2 and 3), and isofragransol A (4), along with 23 known compounds. The compounds were obtained as isomeric mixtures (i.e., 2/3 and 4/20, resp.). The structures were elucidated by spectral analyses. Among the isolates, 1, licarin A (12), guaiacin (14), (±)-syringaresinol (21), and (-)-epicatechin (23) showed ABTS (=2,2′-azinobis(3-ethylbenzothiazoline-6-sulfonic acid) cation radical-scavenging activity, with SC50 values of 11.7±0.5, 12.3±1.1, 11.0±0.1, 10.6±0.3, and 9.5±0.2?μM in 20?min, respectively. In addition, kachirachirol B (17) showed cytotoxicity against the NCI-H460 cell line with an IC50 value of 3.1?μg/ml. Inhibition of phospholipase Cgamma1 and cancer cell proliferation by lignans and flavans from Machilus thunbergii. PUMID/DOI:15554262 Arch Pharm Res. 2004 Oct;27(10):1043-7. Thirteen compounds were isolated from the CH2Cl2 fraction of Machilus thunbergii as phospholipase Cgamma1 (PLCgamma1) inhibitors. These compounds were identified as nine lignans, two neolignans, and two flavans by spectroscopic analysis. Of these, 5,7-di-O-methyl-3′,4′-methylenated (-)-epicatechin (12) and 5,7,3′-tri-O-methyl (-)-epicatechin (13) have not been reported previously in this plant. In addition, seven compounds, machilin A (1), (-)-sesamin (3), machilin G (5), (+)-galbacin (9), licarin A (10), (-)-acuminatin (11) and compound 12 showed dose-dependent potent inhibitory activities against PLCgamma1 in vitro with IC50 values ranging from 8.8 to 26.0 microM. These lignans, neolignans, and flavans are presented as a new class of PLCgamma1 inhibitors. The brief study of the structure activity relationship of these compounds suggested that the benzene ring with the methylene dioxy group is responsible for the expression of inhibitory activities against PLCgamma1. Moreover, it is suggested that inhibition of PLCgamma1 may be an important mechanism for an antiproliferative effect on the human cancer cells. Therefore, these inhibitors may be utilized as cancer chemotherapeutic and chemopreventive agents. Increase of caspase-3 activity by lignans from Machilus thunbergii in HL-60 cells. PUMID/DOI:15305043 Biol Pharm Bull. 2004 Aug;27(8):1305-7. Nine lignans and two butanolides were isolated from the stem bark of Machilus thunbergii and their structures were identified as machilin A (1), licarin B (2), zuonin B (3), macelignan (4), secoisolancifolide (5), isolancifolide (6), oleiferin C (7), meso-dihydroguaiaretic acid (8), licarin A (9), machilin F (10), and nectandrin B (11) by spectroscopic means. These compounds were assessed for their abilities to activate a caspase-3 activity in human promyeloid leukemic HL-60 cells. The intracellular caspase-3 activity of macelignan (4), oleiferin C (7), meso-dihydroguaiaretic acid (8), and licarin A (9) increased approximately 3.04, 6.16, 2.10, and 3.10-fold at 100 microM over that of untreated control. In addition, compounds 4, 7, 8, and 9 induced internucleosomal DNA fragmentation in HL-60 cells. Neolignans from the Arils of Myristica fragrans as Potent Antagonists of CC Chemokine Receptor 3. PUMID/DOI:DOI: 10.1021/acs.jnatprod.6b00262 J Nat Prod. 2016 Aug 26;79(8):2005-13. CC chemokine receptor 3 (CCR3) is expressed selectively in eosinophils, basophils, and some Th2 cells and plays a major role in allergic diseases. A methanol extract from the arils of Myristica fragrans inhibited CC chemokine ligand 11-induced chemotaxis in CCR3-expressing L1.2 cells at 100 μg/mL. From this extract, eight new neolignans, maceneolignans A-H (1-8), were isolated, and their stereostructures were elucidated from their spectroscopic values and chemical properties. Of those constituents, compounds 1, 4, 6, and 8 and (+)-erythro-(7S,8R)-Δ(8′)-7-hydroxy-3,4-methylenedioxy-3′,5′-dimethoxy-8-O-4′-neolignan (11), (-)-(8R)-Δ(8′)-3,4-methylenedioxy-3′,5′-dimethoxy-8-O-4′-neolignan (17), (+)-licarin A (20), nectandrin B (25), verrucosin (26), and myristicin (27) inhibited CCR3-mediated chemotaxis at a concentration of 1 μM. Among them, 1 (EC50 1.6 μM), 6 (1.5 μM), and 8 (1.4 μM) showed relatively strong activities, which were comparable to that of a synthetic CCR3 selective antagonist, SB328437 (0.78 μM).



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For Reference Standard and R&D, Not for Human Use Directly.

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