Subscribe to RSS
DOI: 10.1055/s-2007-981596
© Georg Thieme Verlag KG Stuttgart · New York
Flavonoids from Acacia pennata and their Cyclooxygenase (COX-1 and COX-2) Inhibitory Activities
Publication History
Received: December 22, 2006
Revised: July 12, 2007
Accepted: July 16, 2007
Publication Date:
07 September 2007 (online)
Abstract
Two new flavonoids quercetin 4′-O-α-L-rhamnopyranosyl-3-O-ß-D-allopyranoside (1) and apigenin 6-C-[2′′-O-(E)-feruloyl-β-D-glucopyranosyl]-8-C-β-glucopyranoside (2), along with the known isorhamnetin 3-O-α-L-rhamnopyranoside (3), kaempferol 3-O-α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranoside (4), and isovitexin (5) were isolated from the leaves of Acacia pennata Willd. (Mimosaceae) and tested for their anti-inflammatory activity. Their structures were determined by 1D and 2D NMR and mass spectrometry. They were tested for an inhibitory effect on COX-1 and COX-2, showing 60 - 90 % inhibition at 10 - 4 g/mL and 5 - 14 % inhibition at 10 - 4 g/mL, respectively.
Key words
Acacia pennata - Mimosaceae - flavonoids - cyclooxygenase - COX-1 - COX-2
References
- 1 Seigler D S. Phytochemistry of Acacia - sensu lato . Biochem Syst Ecol. 2003; 31 845-73.
- 2 Dhawan B N, Dubey M P, Rastogi R P, Mehrotra B N, Tandon J S. Screening of Indian plants for biological activity: Part IX. Indian J Exp Biol. 1980; 18 594-606.
- 3 Pakrashi A, Roy H, Pal B C, Mahato S B. Sperm immobilizing effect of triterpene saponins from Acacia auriculiformis . Contraception. 1991; 43 475-83.
- 4 Ghosh M, Babu S P, Sukul N C, Mahato S B. Antifilarial effect of two triterpenoid sponins isolated from Acacia auriculiformis . Indian J Exp Biol. 1993; 31 604-6.
- 5 Sengupta P, Chakroborty A K. Terpenoids and related compounds. VIII Acacia pennata bark. J Indian Chem Soc. 1966; 43 1913.
- 6 Dongmo A B, Nguelefack T, Lacaille-Dubois M A. Antinociceptive and anti-inflammatory activities of Acacia pennata Willd. (Mimosaceae). J Ethnopharmacol. 2005; 98 201-6.
- 7 Futaki N, Takahashi S, Yokoyama M, Arai I, Higuchi S, Omoto S. NS-398, a new anti-inflammatory agent, selectively inhibits prostaglandin G/H synthase/cyclooxygenase (COX-2) activity in vitro . Prostaglandins. 1994; 47 55-9.
- 8 Mabry T J, Liu Y L, Pearce J, Dellamonica G, Chopin J, Markham K R. et al . New flavonoids from sugarcane (Saccharum). J Nat Prod. 1984; 47 127-30.
- 9 Ulubelen A, Kerr K M, Mabry T J. New 6-hydroxyflavonoids and their methyl ethers and glycosides from Neurolaena oaxacana . Phytochemistry. 1980; 19 1761-6.
- 10 Agrawal P K. Carbon-13 NMR of flavonoids. Amsterdam; Elsevier 1989.
- 11 Hua L, Peng Z, Chia L S, Goh N K, Tan S N. Separation of kaempferols in Impatiens balsamina flowers by capillary electrophoresis with electrochemical detection. J Chromatogr. 2001; 909 297-303.
- 12 Cheng G, Bai Y, Zhao Y, Tao J, Liu Y, Tu G. et al . Flavonoids from Ziziphus jujuba Mill var. spinosa . Tetrahedron. 2000; 56 8915-20.
- 13 Peng J, Fan G, Hong Z, Chai Y, Wu Y. Preparative separation of isovitexin and isoorientin from Patrinia villosa Juss by high-speed counter-current chromatography. J Chromatogr A. 2005; 1074 111-5.
- 14 Kartal M, Mitaine-Offer A C, Abu-Asaker M, Miyamoto T, Calis I, Wagner H. et al . Two new triterpene saponins from Eryngium campestre . Chem Pharm Bull. 2005; 53 1318-20.
- 15 Mabry T J, Markham K R, Thomas M B. The systematic identification of flavonoids. Berlin; Springer-Verlag 1970.
-
16 Fossen T, Andersen O M. Spectroscopic techniques applied to flavonoids. In: Andersen OM, Markham KR, editors
Flavonoids, chemistry, biochemistry and applications. New York; Taylor & Francis, CRC press book 2006: 37-142. - 17 Marhkam K R, Chari V M. In: Harborne JB, Mabry TJ, editors The flavonoids. Advances in research. London; Chapman and Hall 1982: 19-134.
- 18 Markham K R. Techniques of flavonoid identification. London & New-York; Academic Press 1982
- 19 Liu P, Guo H, Tian Y, Wang Q, Guo D. Benzoic acid allopyranosides from the bark of Pseudolarix kaempferi . Phytochemistry. 2006; 67 1395-8.
- 20 Okuyama T, Hosoyama K, Hiraga Y, Kurono G, Takemoto T. The constituents of Osmunda spp. II A new flavonol glycoside of Osmunda asiatica . Chem Pharm Bull. 1978; 26 3071-5.
-
21 Wagner H, Lacaille-Dubois M A. Recent pharmacological results on bioflavonoids. In: Antus S, Gabor M, Vetschera K, editors
Flavonoids and bioflavonoids. Budapest; Akademiai Kiado 1996: 53-72. - 22 Yoshikawa K, Inoue M, Matsumoto Y, Sakakibara C, Miyataka H. Lanostane triterpenoids and triterpene glycosides from the fruit body of Fomitopsis pinicola and their inhibitory activity against COX-1 and COX-2. J Nat Prod. 2005; 68 69-73.
- 23 El-Seedi H R, Ringbom T, Torssell K, Bohlin L. Constituents of Hypericum laricifolium and their cyclooxygenase (COX) enzyme activities. Chem Pharm Bull. 2003; 51 1439-40.
Prof. Marie-Aleth Lacaille-Dubois
Faculté de Pharmacie
Laboratoire de Pharmacognosie
Unité de Molécules d’Intérêt Biologique UMIB
UPRES-EA 3660
Université de Bourgogne
7 Bd. Jeanne d’Arc
BP 87900
21079 Dijon Cedex
France
Phone: +33-3-8039-3229
Fax: +33-3-8039-3474
Email: m-a.lacaille-dubois@u-bourgogne.fr