Jaceosidin

Names

[ Name ]:
Jaceosidin

[Synonym ]:
5,7,4'-trihydroxy-3',6-dimethoxyflavone
4H-1-Benzopyran-4-one, 5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-6-methoxy-
5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-6-methoxychromen-4-one
5,7-Dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-6-methoxy-4H-chromen-4-one
5,7,4'-trihydroxy-6,3'-dimethoxyflavone
JACEOSIDINE
4',5,7-Trihydroxy-3',6-dimethoxyflavone
6-methoxyluteolin-3'-methyl ether
Jaceosidin

Biological Activity

[Description]:

Jaceosidin is a flavonoid isolated from Artemisia vestita, induces apoptosis in cancer cells, activates Bax and down-regulates Mcl-1 and c-FLIP expression[1]. Jaceosidin exhibits anti-cancer[2], anti-inflammatory activities, decreases leves of inflammatory markers, and suppresses COX-2 expression and NF-κB activation[3].

[Related Catalog]:

Signaling Pathways >> Apoptosis >> Bcl-2 Family

Research Areas >> Cancer

Research Areas >> Inflammation/Immunology

Signaling Pathways >> Immunology/Inflammation >> COX

[Target]

Bax

COX-2

[In Vitro]

Jaceosidin (30, 50, 75 μM) induces apoptosis in human renal carcinoma Caki cells after treatment for 24 h, shows no obvious effect on normal cells[1]. Jaceosidin (75 μM) reduces MMP levels and causes cytochrome c release into the cytoplasm through Bax activation[1]. Jaceosidin-mediated apoptosis is involved in downregulation of Mcl-1, c-FLIP expression, which is via inhibition of NF-κB and/or Sp1 transcriptional activity[1]. Jaceosidin shows cytostatic activity to HES and HESC cells with IC50s of 52.68 and 55.10 μM, and is less cytotocxic on Hec1 A and KLE (IC50, 70.54, 147.14 μM, respectively), after treatment for 48 h[2]. Cell Viability Assay[2] Cell Line: Hec1A, KLE, HES and HESC cells Concentration: 3.125, 6.25, 12.5, 25, 50, and 100 μM Incubation Time: 48 hour Result: Showed cytostatic activity to HES and HESC cells with IC50s of 52.68 and 55.10 μM, less cytotocxic on Hec1 A and KLE (IC50, 70.54, 147.14 μM).

[In Vivo]

Jaceosidin (10 and 20 mg/kg, p.o., once a day for 3 days) blocks carrageenan-induced increase in leukocyte number and protein levels in air pouch exudates in mice[3]. Jaceosidin (10, 20 mg/kg, p.o.) suppresses COX-2 expression and NF-κB activation in mice[3]. Jaceosidin (20 mg/kg, p.o. for 2 hours) reduces hind paw edema volume in rats[3]. Animal Model: 5-week-old male BALB/c mice (23-26 g)[3] Dosage: 10 and 20 mg/kg Administration: P.O. once a day for 3 days Result: Decreased the volumes of exudates (inflammatory markers), cell number and protein levels. Inhibited TNF-α by 46.7% and 50.8%, IL-1β by 46.0% and 44.7%, and PGE2 by 21.7% and 16.9%, respectively, at 20 mg/kg. Blocked COX-2 expression and NF-κB activation. Animal Model: Male Sprague-Dawley rats (180-200 g)[3] Dosage: 20 mg/kg Administration: P.O., for 2 hour Result: Reduced hind paw edema volume by 27.1% at 1 h, and 24.0% at 2 h, respectively.

[References]

[1]. Woo SM, et al. Jaceosidin induces apoptosis through Bax activation and down-regulation of Mcl-1 and c-FLIP expression in human renal carcinoma Caki cells. Chem Biol Interact. 2016 Dec 25;260:168-175.

[2]. Lee JG, et al. Jaceosidin, isolated from dietary mugwort (Artemisia princeps), induces G2/M cell cycle arrest by inactivating cdc25C-cdc2 via ATM-Chk1/2 activation. Food Chem Toxicol. 2013 May;55:214-21.

[3]. Min SW, et al. Inhibitory effect of eupatilin and jaceosidin isolated from Artemisia princeps on carrageenan-induced inflammation in mice. J Ethnopharmacol. 2009 Sep 25;125(3):497-500.

Chemical & Physical Properties

[ Density]:
1.5±0.1 g/cm3

[ Boiling Point ]:
619.0±55.0 °C at 760 mmHg

[ Molecular Formula ]:
C₁₇H₁₄O₇

[ Molecular Weight ]:
330.29

[ Flash Point ]:
232.0±25.0 °C

[ Exact Mass ]:
330.073944

[ PSA ]:
109.36000

[ LogP ]:
1.30

[ Vapour Pressure ]:
0.0±1.9 mmHg at 25°C

[ Index of Refraction ]:
1.671

[ Storage condition ]:
2-8℃

Safety Information

[ HS Code ]:
2914509090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2914509090

[ Summary ]:
HS:2914509090 other ketones with other oxygen function VAT:17.0% Tax rebate rate:9.0% Supervision conditions:none MFN tariff:5.5% General tariff:30.0%