tectoridin

Names

[ CAS No. ]:
611-40-5

[ Name ]:
tectoridin

[Synonym ]:
4H-1-Benzopyran-4-one, 7-(β-D-glucopyranosyloxy)-5-hydroxy-3-(4-hydroxyphenyl)-6-methoxy-
Tectorigenin 7-glucoside
4',5-Dihydro-6-methoxy-7-(o-glucoside)isoflavone
5-Hydroxy-3-(4-hydroxyphenyl)-6-methoxy-4-oxo-4H-chromen-7-yl β-D-glucopyranoside
Shekanin
tectoridin
Tectoridin (7CI,8CI)
5-hydroxy-3-(4-hydroxyphenyl)-6-methoxy-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one

Biological Activity

[Description]:

Tectoridin is a isoflavone isolated from Maackia amurensis. Tectoridin is a phytoestrogen and activates estrogen and thyroid hormone receptors. Tectoridin exerts the estrogenic effects via ER-dependent genomic pathway and GPR30-dependent nongenomic pathway[1][2].

[Related Catalog]:

Signaling Pathways >> Others >> Estrogen Receptor/ERR

Research Areas >> Cancer

[In Vitro]

Tectoridin scarcely binds to ER alpha as compared to 17beta-estradiol and genistein[2]. Tectoridin induceds potent estrogenic effects, namely recovery of the population of cells in the S-phase after serum starvation, transactivation of the estrogen response element, and induction of MCF-7 cell proliferation[2]. Tectoridin induces estrogenic effect, and this effect is severely abrogated by treatment with U0126 ( MEK1/2 inhibitor). Tectoridin promotes phosphorylation of ERK1/2, but does not affect phosphorylation of ER alpha at Ser (118). It also increases cellular accumulation of cAMP[2].

[References]

[1]. Shim M, et al. Tectoridin from Maackia amurensis modulates both estrogen and thyroid receptors.Phytomedicine. 2014 Apr 15;21(5):602-6.

[2]. Kang K, et al. Tectoridin, a poor ligand of estrogen receptor alpha, exerts its estrogenic effects via an ERK-dependent pathway.Mol Cells. 2009 Mar 31;27(3):351-7.

Chemical & Physical Properties

[ Density]:
1.6±0.1 g/cm3

[ Boiling Point ]:
798.1±60.0 °C at 760 mmHg

[ Melting Point ]:
261.8-263.2ºC

[ Molecular Formula ]:
C₂₂H₂₂O₁₁

[ Molecular Weight ]:
462.404

[ Flash Point ]:
279.7±26.4 °C

[ Exact Mass ]:
462.116211

[ PSA ]:
179.28000

[ LogP ]:
0.29

[ Vapour Pressure ]:
0.0±3.0 mmHg at 25°C

[ Index of Refraction ]:
1.695

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: DJ3090000

CHEMICAL NAME :: 4H-1-Benzopyran-4-one, 7-(beta-D-glucopyranosyloxy)-5-hydroxy-3-(4-hydroxyph enyl)-6-methoxy-

CAS REGISTRY NUMBER :: 611-40-5

BEILSTEIN REFERENCE NO. :: 0068384

LAST UPDATED :: 199709

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C22-H22-O11

MOLECULAR WEIGHT :: 462.44

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 4200 mg/kg

TOXIC EFFECTS :: Behavioral - altered sleep time (including change in righting reflex) Behavioral - somnolence (general depressed activity) Lungs, Thorax, or Respiration - dyspnea

REFERENCE :: NYKZAU Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. (Nippon Yakuri Gakkai, c/o Kyoto Daigaku Igakubu Yakurigaku Kyoshitsu, Konoe-cho, Yoshida, Sakyo-ku, Kyoto 606, Japan) V.40- 1944- Volume(issue)/page/year: 64,186,1968

Safety Information

[ Hazard Codes ]:
C

[ RIDADR ]:
NONH for all modes of transport

[ RTECS ]:
DJ3090000

[ HS Code ]:
29389090

Precursor & DownStream

Precursor

DownStream

Articles

Tectorigenin inhibits IFN-gamma/LPS-induced inflammatory responses in murine macrophage RAW 264.7 cells.

Arch. Pharm. Res. 31(11) , 1447-56, (2008)

Tectorigenin (Tg) and tectoridin (Td) are the major compounds isolated from the rhizomes of iridaceous plant Belamcanda chinensis which is well known as a chinese traditional medicine for the treatmen...

Tectoridin, a poor ligand of estrogen receptor alpha, exerts its estrogenic effects via an ERK-dependent pathway.

Mol. Cells 27(3) , 351-7, (2009)

Phytoestrogens are the natural compounds isolated from plants, which are structurally similar to animal estrogen, 17beta-estradiol. Tectoridin, a major isoflavone isolated from the rhizome of Belamcan...

Microbial transformation and bioactivation of isoflavones from Pueraria flowers by human intestinal bacterial strains.

J. Nat. Med. 63(3) , 254-60, (2009)

The flowers from Pueraria, which are called Puerariae Flos, have been used since ancient times for recovery from alcohol intoxication. We elucidated the microbial transformation of the main isoflavone...