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Chemical Compound Review:

Bonanzin 2-(3,4-dimethoxyphenyl)-5,7- dihydroxy-3,6...

Synonyms: AC1NTEU1, LMPK12113011, Quercetagetin-3,6,3',4'-tetramethyl ether, Quercetagetin 3,6,3',4'-tetramethyl ether, 5,7-Dihydroxy-3,6,3',4'-tetramethoxyflavone

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Disease relevance of AIDS-097193

The compounds were identified as 5,7,5'-trihydroxy-3,6,2',4'-tetramethoxyflavone (1), scopoletin (2) and centaureidin (3) which inhibited the edema by 67.3 %, 59.8 % and 49.7 %, respectively, at a dose of 1 mg/ear [1].

High impact information on AIDS-097193

In the tumour necrosis factor-alpha (TNF-alpha) assay, only centaureidin and hydroxyachillin significantly inhibited the accumulation of TNF-alpha [2].
Preliminary study of the potential vasodilator effects on rat aorta of centaurein and centaureidin, two flavonoids from Centaurea corcubionensis [3].
Centaureidin (10 microM-0.1 mM) totally relaxed, in a concentration-dependent manner and with almost equal effectiveness, the contractions induced by NA (IC50 = 16.7 +/- 1.9 microM) or by a high K+ concentration (IC50 = 16.1 +/- 3.1 microM) in intact rat aortic rings [3].
A new compound TRANS-3-methoxy-4,5-methylene-dioxycinnamaldehyde ( 1) has been isolated from the aerial parts of CASSIA GRANDIS (Caesalpiniaceae) along with the known compounds aloe emodin, centaureidin, catechin, myristicin, 2,4-dihydroxybenzaldehyde, 3,4,5-trimethoxybenzaldehyde, 2,4,6-trimethoxybenzaldehyde, and beta-sitosterol [4].
Thus, centaureidin appears to inhibit dendrite outgrowth from melanocytes by activating Rho, resulting in the inhibition of melanosome transfer from melanocytes to keratinocytes [5].

Anatomical context of AIDS-097193

During screening for inhibitors of melanosome transfer, we found a novel reagent, centaureidin, that induces significant morphological changes in normal human epidermal melanocytes and inhibits melanocyte dendrite elongation, resulting in a reduction of melanosome transfer in an in vitro melanocyte-keratinocyte co-culture system [5].

Associations of AIDS-097193 with other chemical compounds

In in vitro binding assay, centaureidin activated Rho and furthermore, a Rho inhibitor (C. botulinum C3 exoenzyme), a Rho kinase inhibitor (Y27632) and a small GTPase inhibitor (Toxin B) blocked dendrite retraction induced by centaureidin [5].

Gene context of AIDS-097193

These results suggest centaureidin could act via the Rho signaling pathway, and it may directly or indirectly activate Rho [5].
Antioxidant and free radical scavenging activities of 5,7,3'-trihydroxy-3,6,4'-trimethoxyflavone from Brickellia veronicaefolia [6].
1. The in vitro effects of centaureidin and 5,3'-dihydroxy-4'-methoxy-7-carbomethoxyflavonol (Fig. 1), two anti-inflammatory flavonoids extracted from Tanacetum microphyllum DC., have been examined on both cyclooxygenase and lipoxygenase activity [7].

References

Phenolic compounds with anti-inflammatory activity from Eupatorium buniifolium. Muschietti, L., Gorzalczany, S., Ferraro, G., Acevedo, C., Martino, V. Planta Med. (2001) [Pubmed]
Flavonoids and a sesquiterpene lactone from Tanacetum microphyllum inhibit anti-inflammatory mediators in LPS-stimulated mouse peritoneal macrophages. Abad, M.J., Bermejo, P., Alvarez, M., Guerra, J.A., Silván, A.M., Villar, A.M. Planta Med. (2004) [Pubmed]
Preliminary study of the potential vasodilator effects on rat aorta of centaurein and centaureidin, two flavonoids from Centaurea corcubionensis. Orallo, F., Lamela, M., Camiña, M., Uriarte, E., Calleja, J.M. Planta Med. (1998) [Pubmed]
A New C6-C3 Compound from Cassia grandis. González, A.G., Bermejo, J., Valencia, E. Planta Med. (1996) [Pubmed]
Centaureidin promotes dendrite retraction of melanocytes by activating Rho. Ito, Y., Kanamaru, A., Tada, A. Biochim. Biophys. Acta (2006) [Pubmed]
Antioxidant and free radical scavenging activities of 5,7,3'-trihydroxy-3,6,4'-trimethoxyflavone from Brickellia veronicaefolia. Pérez G, R.M., Vargas S, R., Martinez M, F.J., Cordova R, I. Phytotherapy research : PTR. (2004) [Pubmed]
The activity of flavonoids extracted from Tanacetum microphyllum DC. (Compositae) on soybean lipoxygenase and prostaglandin synthetase. Abad, M.J., Bermejo, P., Villar, A. Gen. Pharmacol. (1995) [Pubmed]

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