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Journal of Natural Medicines
Published in: Journal of Natural Medicines 3-4/2011

01-07-2011 | Note

Compounds isolated from Curcuma aromatica Salisb. inhibit human P450 enzymes

Authors: Yoshinori Bamba, Young Sook Yun, Akira Kunugi, Hideshi Inoue

Published in: Journal of Natural Medicines | Issue 3-4/2011

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Abstract

Curcuma species (Zingiberaceae) are used as both food and medicine in Asia. Ten sesquiterpenes (1–10) and two curcuminoids (11 and 12) were isolated from the rhizomes of Curcuma aromatica Salisb. and identified. The compounds were evaluated for their ability to inhibit cytochrome P450 (CYP). Among them, the sesquiterpene (4S,5S)-(+)-germacrone-4,5-epoxide (7) inhibited certain subtypes of CYP more potently than or at levels comparable to the curcuminoids curcumin (11) and demethoxycurcumin (12); 7 (IC50 = 1.0 ± 0.2 μM) > 12 (IC50 = 7.0 ± 1.7 μM) > 11 (IC50 = 14.9 ± 1.4 μM) for CYP3A4 inhibition; 12 (IC50 = 1.4 ± 0.2 μM) > 11 (IC50 = 6.0 ± 1.4 μM) > 7 (IC50 = 7.6 ± 2.5 μM) for CYP2C9 inhibition; and 7 (IC50 = 33.2 ± 3.6 μM) = 12 (IC50 = 34.0 ± 14.2 μM) > 11 (IC50 > 100 μM) for CYP1A2 inhibition. These results suggest the possibility that Curcuma aromatica Salisb. may cause food–drug interactions via cytochrome P450 inhibition by sesquiterpene 7 and curcuminoids 11 and 12.
Literature
1.
Jangde CR, Phadnaik BS, Bisen VV (1998) Anti-inflammatory activity of extracts of Curcuma aromatica Salisb. Indian Vet J 75:76–77
2.
Lee YL, Weng CC, Mau JL (2007) Antioxidant properties of ethanolic and hot water extracts from the rhizome of Curcuma aromatica. J Food Biochem 31:757–771CrossRef
3.
Kim JH, Shim JS, Lee SK, Kim KW, Rha SY, Chung HC, Kwon HJ (2002) Microarray-based analysis of anti-angiogenic activity of demethoxycurcumin on human umbilical vein endothelial cells; crucial involvement of the down-regulation of matrix metalloproteinase. Jpn J Cancer Res 93(12):1378–1385PubMed
4.
Li Y, Wo JM, Liu Q, Li X, Martin RC (2009) Chemoprotective effects of Curcuma aromatica on esophageal carcinogenesis. Ann Surg Oncol 16:515–523PubMedCrossRef
5.
Itokawa H, Shi Q, Akiyama T, Morris-Natschke SL, Lee KH (2008) Recent advances in the investigation of curcuminoids. Chin Med 3:11–23PubMedCrossRef
6.
Hou XL, Takahashi K, Kinoshita N, Qiu F, Tanaka K, Komatsu K, Takahashi K, Azuma J (2007) Possible inhibitory mechanism of Curcuma drugs on CYP3A4 in 1α,25 dihydroxyvitamin D3 treated Caco-2 cells. Int J Pharm 337:169–177PubMedCrossRef
7.
Volak LP, Ghirmai S, Cashman JR, Court MH (2008) Curcuminoids inhibit multiple human cytochrome P450, UDP-glucuronosyltransferase, and sulfotransferase enzymes, whereas piperine is a relatively selective CYP3A4 inhibitor. Drug Metab Disp 36:1594–1605CrossRef
8.
Zhou SF (2008) Potential strategies for minimizing mechanism-based inhibition of cytochrome P450 3A4. Curr Pharm Des 14:990–1000PubMedCrossRef
9.
Kuroyanagi M, Ueno A, Ujiie K, Sato S (1987) Structures of sesquiterpenes from Curcuma aromatica SALISB. Chem Pharm Bull 35:53–59
10.
Ohshiro M, Kuroyanagi M, Ueno A (1990) Structures of sesquiterpenes from Curcuma longa. Phytochemistry 29:2201–2205CrossRef
11.
Masuda T, Jitoe A, Nakatani N (1991) Structure of Aerugidiol, a new bridge-head oxygenated guaiane sesquiterpene. Chem Lett 9:1625–1628CrossRef
12.
Péret-Almeida L, Cherubino APF, Alves RJ, Dufossé L, Glória MBA (2005) Separation and determination of the physico-chemical characteristics of curcumin, demethoxycurcumin and bisdemethoxycurcumin. Food Res Int 38:1039–1044CrossRef
13.
Asakawa Y, Takahashi H, Toyota M (1991) Biotransformation of germacrane-type sesquiterpenoids by Aspergillus niger. Phytochemistry 30:3993–3997CrossRef
14.
Horiike T, Ohshiro M, Kuroyanagi M (1997) Biotransformation of the germacrane type sesquiterpene curdione by suspension cultured cells of Lonicera japonica, 44:627–632
15.
Kourounakis AP, Rekka EA, Kourounakis PN (1997) Effect of guaiazulene on some cytochrome P450 activities: Implication in the metabolic activation and hepatotoxicity of paracetamol. Arch Pharm (Weinheim) 330:7–11CrossRef
Metadata
Title
Compounds isolated from Curcuma aromatica Salisb. inhibit human P450 enzymes
Authors
Yoshinori Bamba
Young Sook Yun
Akira Kunugi
Hideshi Inoue
Publication date
01-07-2011
Publisher
Springer Japan
Published in
Journal of Natural Medicines / Issue 3-4/2011
Print ISSN: 1340-3443
Electronic ISSN: 1861-0293
DOI
https://doi.org/10.1007/s11418-011-0507-0

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