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Flavonoid Constituents of Acacia catechu

Acacia catechu의 플라보노이드 성분

  • Received : 2014.03.23
  • Accepted : 2014.04.13
  • Published : 2015.06.30

Abstract

Ten compounds were isolated from the ethanolic extract of the leaves of Acacia catechu (Fabaceae), and their structures were identified as nine flavonoids [(+)-catechin (1), (-)-epicatechin (2), (+)-afzelechin (3), (-)-epiafzelechin (4), (+)-mesquitol (5), kaempferol (6), quercetin (7), quercetin 3-methyl ether (8), and caryatin (9)] and an ellagic acid (10). The chemical structures of these compounds were identified on the basis of spectroscopic methods (mass spectrometry, 1D and 2D nuclear magnetic resonance) and comparison with literature values. This is the first time that the isolation of caryatin (9) has been reported from Acacia genus.

전통생약으로서 다양한 효능과 염색제로서 사용되어온 A. catechu의 식물화학적 성분연구를 위해 열수추출물 중 ethyl acetate 분획으로부터 9종의 flavonoid와 1종의 tannin을 단리하였으며, 이들의 물리화학적 성상과 spectral data로부터 구조를 확인한 결과 (+)-catechin (1), (-)-epicatechin (2), (+)-afzelechin (3), (-)-epiafzelechin (4), (+)-mesquitol (5), kaempferol (6), quercetin (7), quercetin 3-methyl ether (8) caryatin (9) 및 ellagic acid (10)로 각각 확인 동정하였다. 이들 화합물 중 caryatin (9)은 Acacia 속으로부터 처음으로 분리되었다.

Keywords

References

  1. Abdallaha HM, Salama MM, Abd-elrahman EH, and El-Maraghy SA (2011) Antidiabetic activity of phenolic compounds from Pecan bark in streptozotocin-induced diabetic rats. Phytochem Lett 4, 337-41. https://doi.org/10.1016/j.phytol.2011.07.004
  2. Ahmadu AA, Onanuga A, and Ebeshi BU (2011) Isolation of antibacterial flavonoids from the aerial parts of Indigofera secundiflora. Phcog J 3, 25-8.
  3. Alam G, Singh MP, and Singh A (2011) Wound healing potential of some medicinal plants. Inter J Pharm Sci Rev Res 9, 136-49.
  4. Anitha Roy, Geetha RV, and Lakshmi T (2011) In vitro evaluation of anti mycotic activity of heartwood extract of Acacia catechu Willd. J Pharm Res 4, 2010-1.
  5. Azad AK, Ogiyama K, and Sassa T (2001) Isolation of (+)-catechin and a new polyphenolic compound in Bengal catechu. J Wood Sci 47, 406-9. https://doi.org/10.1007/BF00766794
  6. Chang YC, Chang FR, and Wu YC (2000) The constituents of Lindera Glauca. J Chin Chem Soc 47, 373-80. https://doi.org/10.1002/jccs.200000050
  7. Dhingra D and Jangra A (2014) Antiepileptic activity of ellagic acid, a naturally occurring polyphenolic compound, in mice. J Funct Foods 10, 364-9. https://doi.org/10.1016/j.jff.2014.07.011
  8. Dok-Go H, Lee KH, Kim HJ, Lee EH, Lee J, Song YS et al. (2003) Neuroprotective effects of antioxidative flavonoids, quercetin, (+)- dihydroquercetin and quercetin 3-methyl ether, isolated from Opuntia ficus-indica var. saboten. Brain Res 965, 130-6. https://doi.org/10.1016/S0006-8993(02)04150-1
  9. Gao H, Kuroyanagi M, Wu L, Kawahara N, Yasuno T, and Nakamura Y (2002) Antitumor-promoting constituents from Dioscorea bulbifera L. in JB6 mouse epidermal cells. Biol Pharm Bull 25, 1241-3. https://doi.org/10.1248/bpb.25.1241
  10. Guleria S, Tiku A, Singh G, Vyas D, and Bhardwaj A (2011) Antioxidant activity and protective effect against plasmid DNA strand scission of leaf, bark, and heartwood extracts from Acacia catechu. J Food Sci 76, C959-64. https://doi.org/10.1111/j.1750-3841.2011.02284.x
  11. Hashmat MA and Hussain, R (2013) A review on Acacia catechu Willd, Interdiscip J Contemp Res Bus 5, 593-600.
  12. Jagadeeshwar Roa R, Tiwari AK, Kumar US, Reddy SV, Ali AZ, and Rao JM (2003) Novel 3-O-acyl mesquitol analogues as free-Radical scavengers and enzyme inhibitors: synthesis, biological evaluation and structureactivity relationship. Bioorg Med Chem Lett 13, 2777-80. https://doi.org/10.1016/S0960-894X(03)00494-3
  13. Jain R, Patni V, and Arora DK (2007) Isolation and identification of flavonoid "quercetin" from Acacia catechu (L.f.) Willd- A Katha yielding plant. J Phytol Res 20, 43-5.
  14. Jayasekhar P, Mohanan PV, and Rathinam K (1997) Hepatoprotective activity of ethyl acetate extract of Acacia catechu. Indian J Pharmacol 29, 426-8.
  15. Kim JK, Kwon DJ, Lim SS, and Bae YS (2010) Chemical constituents of domestic Quercus spp. Barks. J Korean Wood Sci Technol 38, 359-74. https://doi.org/10.5658/WOOD.2010.38.4.359
  16. Kpegba K, Agbonon A, Petrovic AG, Amouzou E, Gbeassor M, Proni G et al. (2011) Epiafzelechin from the root bark of Cassia sieberiana: Detection by DART mass spectrometry, spectroscopic characterization, and antioxidant properties. J Nat Prod 74, 455-9. https://doi.org/10.1021/np100090e
  17. Kwon DJ, Kim JK, and Bae YS (2011) DPPH radical scavenging activity of phenolic compounds isolated from the stem wood of Acer tegmentosum. J Korean Wood Sci Technol 39, 104-12. https://doi.org/10.5658/WOOD.2011.39.1.104
  18. Lakshmi T, Anitha Roy, and Geetha RV (2011) Acacia catechu willd -A gift from ayurveda to mankind - A Review. T Ph Res 5, 273-93.
  19. Lakshmi T, Rajendran R, and Madhusudhanan N (2012) Chromatographic fingerprint analysis of Acacia catechu ethanolic leaf extract by HPTLC technique. Int J Drug Dev Res 4, 180-5.
  20. Lee EH, Kim HJ, Song YS, Jin C, Lee KT, Cho J et al. (2003) Constituents of the stems and fruits of Opuntia ficus-indica var. saboten. Arch Pharm Res 26, 1018-23. https://doi.org/10.1007/BF02994752
  21. Li X, Wang H, Liu C, and Chen R (2010) Chemical constituents of Acacia catechu. China J Chin Mat Med 35, 1425-7.
  22. Li XC, Liu C, Yang LX, and Chen RY (2011) Phenolic compounds from the aqueous extract of Acacia catechu. J Asian Nat Prod Res 13, 826-30. https://doi.org/10.1080/10286020.2011.597384
  23. Liu X, Li W, Hua H, Li W, Chen F, and Wu L (2006) An NMR study of a phenyl propanoid-substituted catechin from Polygonum bistorta. Asian J Tradit Med 1, 73-5.
  24. Monga J, Chauhan CS, and Sharma M (2011) Human epithelial carcinoma cytotoxicity and inhibition of DMBA/TPA induced squamous cell carcinoma in Balb/c mice by Acacia catechu heartwood. J Pharm Pharmacol 63, 1470-82. https://doi.org/10.1111/j.2042-7158.2011.01354.x
  25. Monu, Parle M, Kadian R, and Sharma K (2014) Phytopharmacology of Acacia catechu Willd: A review. World J Pharm Pharm Sci 3, 1380-9.
  26. Nadumane KV and Nair S (2011) Evaluation of the anticancer and cytotoxic potentials of Acacia catechu extracts in vitro. J Nat Pharma 2, 190-5. https://doi.org/10.4103/2229-5119.92857
  27. Nagaraja TG, Sarang SV, and Jambhale DC (2008) Evaluation of anti-mycotic activity of Acacia catechu Willd. (Mimosaceae) J Biopest 1, 197-8.
  28. Nam KY and Lee JS (2010) Dyeability and functionality of Catechu (Part I) - Characteristics of Catechu and dyeing properties of cotton-. Korean J Human Ecol 19, 699-707. https://doi.org/10.5934/KJHE.2010.19.4.699
  29. Ray D, Sharatchandra KH, and Thokchom IS (2006) Antipyretic, antidiarrhoeal, hypoglycaemic and hepatoprotective activities of ethyl acetate extract of Acacia catechu Wild. In albino rats. Indian J Pharmcol 38, 408-13. https://doi.org/10.4103/0253-7613.28207
  30. Saijyo J, Suzuki Y, Okuno Y, Yamaki H, Suzuki T, and Miyazawa M (2008) $\alpha$-Glucosidase Inhibitor from Bergenia ligulata. J Oleo Sci 57, 431-5. https://doi.org/10.5650/jos.57.431
  31. Saraswathy A and Vidhya B (2012) (+)-Afzelechin from the rhizome of Calamus rotang Linn. Indian drugs 49, 49-50.
  32. Selvaraj K, Chowdhury R, and Bhattacharjee C (2013) Isolation and structural elucidation of flavonoids from aquatic fern Azolla microphylla and evaluation of free radical scavenging activity. Int J Pharm Sci 5, 743-9.
  33. Ulubelen A, Tan N, and Tuzlaci E (1990) Constituents of Daphne mucronata. Fitoterapia 61, 281.
  34. Velazquez C, Correa-Basurto J, Garcia-Hernandez N, Barbosa E, Tesoro-Cruz E, Calzada S et al. (2012) Anti-diarrheal activity of (-)-epicatechin from Chiranthodendron pentadactylon Larreat: Experimental and computational studies. J Ethnopharmacol 143, 716-9. https://doi.org/10.1016/j.jep.2012.07.039
  35. Wang L, Waltenberger B, Pferschy-Wenzig EM, Blunder M, Liu X, Malainer C et al. (2014) Natural product agonists of peroxisome proliferatoractivated receptor gamma ($PPAR{\gamma}$): a review. Biochem Pharmacol 92, 73-89. https://doi.org/10.1016/j.bcp.2014.07.018
  36. Wong KC, Law MC, Wong MS, and Chan TH (2014) Development of a UPLC-MS/MS bioanalytical method for the pharmacokinetic study of (−)-epiafzelechin, a flavan-3-ol with osteoprotective activity, in C57BL/6J mice. J Chromatogr B 967, 162-7. https://doi.org/10.1016/j.jchromb.2014.07.028
  37. Yadava RN and Sodhi S (2002) A new flavone glycoside: 5,7,3',4'-tetrahydroxy-3-methoxy flavone-7-O-$\beta$-D-galactopyranosyl-($1{\rightarrow}4$)-O-$\beta$-D-glucopyranoside from the stem of Acacia catechu Willd. J Asian Nat Prod Res 4, 11-5. https://doi.org/10.1080/10286020290019640

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