Planta Med 2007; 73(11): 1202-1207
DOI: 10.1055/s-2007-981596
Natural Product Chemistry
Original Paper
© Georg Thieme Verlag KG Stuttgart · New York

Flavonoids from Acacia pennata and their Cyclooxygenase (COX-1 and COX-2) Inhibitory Activities

Alain B. Dongmo1 , Tomofumi Miyamoto2 , Kazuko Yoshikawa3 , Shigenobu Arihara3 , Marie-Aleth Lacaille-Dubois1
  • 1Faculté de Pharmacie, Laboratoire de Pharmacognosie, Unité de Molécules d’Intérêt Biologique, UMIB, UPRES-EA 3660, Université de Bourgogne, Dijon, France
  • 2Graduate School of Pharmaceutical Sciences, Kyushu University, Fukuoka, Japan
  • 3Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Yamashiro-Cho, Tokushima, Japan
Further Information

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.

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