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ECKOL

Names

[ CAS No. ]:
88798-74-7

[ Name ]:
ECKOL

[Synonym ]:
Eckol
1-(3,5-Dihydroxyphenoxy)-2,4,7,9-tetrahydroxydibenzo-1,4-dioxin
4-(3,5-dihydroxyphenoxy)dibenzo-p-dioxin-1,3,6,8-tetrol
4-(3,5-dihydroxyphenoxy)oxanthrene-1,3,6,8-tetrol

Biological Activity

[Description]:

Eckol is a potent hMAO-A (Mixed) and hMAO-B (non-competitive) inhibitor with IC50s of 7.20 and 83.44 μM, respectively. Eckol shows stimulatory effects in maize and can be used as a plant biostimulant. Eckol also shows antiallergic and antiviral effects[1][2][3][4].

[Related Catalog]:

Signaling Pathways >> Anti-infection >> Influenza Virus
Research Areas >> Infection
Signaling Pathways >> Neuronal Signaling >> Monoamine Oxidase
Research Areas >> Inflammation/Immunology
Research Areas >> Neurological Disease

[Target]

hMAO-A:7.20 μM (IC50)

hMAO-B:83.44 μM (IC50)

H1N1:89.5 μM (IC50)


[In Vitro]

Eckol (25-100 μg/mL; 2 h) 预处理以剂量依赖的方式显著降低 IgE/BSA 刺激的 BMCMC 中 β-hexosaminidase 的释放[3]。 Eckol (25-100 μg/mL; 1 h) 抑制 Th2 型细胞因子的产生,如 IL-4、IL-5、 IL-13 以及促炎细胞因子,如 IL-6[3]。 Eckol (25-100 μg/mL) 减弱 IgE/BSA 刺激的 BMCMC 细胞中细胞因子 mRNA 水平,如IL-1β、IL-4、IL-5、IL-6、IL-13、IFN-γ 和 TNF-α[3]。 Eckol (25-100 μg/mL; 1 h) 在 IgE/BSA 刺激的 BMCMC 中抑制 NF-κB 的激活[3]。 Eckol 抑制 influenza A/Bervig-Mission/1/18 (H1N1) 病毒,IC50 为 89.5 µM[4]。 Western Blot Analysis[3] Cell Line: Bone marrow-derived cultured mast cells (BMCMC) Concentration: 25, 50 and 100 μg/mL Incubation Time: 1 h Result: Inhibited the degradation of IκB-α within the cytosol and the translocation of the NF-κB/p65 subunit into the nucleus that were induced by IgE/BSA.

[In Vivo]

叶面喷施 Eckol (1 μM) 显著提高了茎长和根长、茎干鲜重、叶面积和叶数[2]。 Eckol (50 or 100 μg/mouse; intradermal; once) 降低被动皮肤过敏反应 (PCA) 诱导小鼠的过敏性炎症反应[3]。 Animal Model: BALB/c mice (8 weeks old), IgE/BSA-induced passive cutaneous anaphylaxis (PCA) model[3] Dosage: 50 or 100 μg/mouse Administration: Intradermal injection, applied on mice ear 2 h prior to anaphylaxis induction Result: Reduced allergic inflammatory responses.

[References]

[1]. Jung HA, et al. Evaluation of the inhibitory effects of eckol and dieckol isolated from edible brown alga Eisenia bicyclis on human monoamine oxidases A and B. Arch Pharm Res. 2017 Apr;40(4):480-491.  

[2]. Rengasamy KR, et al. Enhancing growth, phytochemical constituents and aphid resistance capacity in cabbage with foliar application of eckol--a biologically active phenolic molecule from brown seaweed. N Biotechnol. 2016 Mar 25;33(2):273-9.  

[3]. Han EJ, et al. Eckol from Ecklonia cava Suppresses Immunoglobulin E-mediated Mast Cell Activation and Passive Cutaneous Anaphylaxis in Mice. Nutrients. 2020 May 9;12(5):1361.  

[4]. Besednova NN, et al. Antiviral Effects of Polyphenols from Marine Algae. Biomedicines. 2021 Feb 17;9(2):200.  

Chemical & Physical Properties

[ Density]:
1.778g/cm3

[ Boiling Point ]:
685.5ºC at 760 mmHg

[ Molecular Formula ]:
C18H12O9

[ Molecular Weight ]:
372.28200

[ Flash Point ]:
368.4ºC

[ Exact Mass ]:
372.04800

[ PSA ]:
149.07000

[ LogP ]:
3.61050

[ Index of Refraction ]:
1.807

Safety Information

[ HS Code ]:
2932999099

Customs

[ HS Code ]: 2932999099

[ Summary ]:
2932999099. other heterocyclic compounds with oxygen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%