Journal of Wood Science

, Volume 59, Issue 5, pp 426–431 | Cite as

Anti-acne activity of tannin-related compounds isolated from Terminalia laxiflora

  • Ali Mahmoud Muddathir
  • Kosei Yamauchi
  • Tohru Mitsunaga
Original article

Abstract

In our investigation to find out new anti-acne agent, we focused on Terminalia laxiflora Engl & Diels (Combretaceae) methanolic wood extract, which has been selected during previous screening experiments for anti-acne agents, which included 29 species of Sudanese medicinal plants. Based on the biologically guided fractionation using an antibacterial assay against Propionibacterium acnes, a lipase inhibitory assay and 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activity assay; five tannin-related compounds were isolated, such as ellagic acid, flavogallonic acid dilactone, terchebulin and gallic acid. Terchebulin showed good antibacterial activity; minimum inhibitory concentration (MIC) = 125 μg/ml and minimum bactericidal concentration (MBC) = 250 μg/ml. Gallic acid exhibited lipase inhibitory activity with IC50 value of 149.3 μM, which showed strong inhibition compared with terchebulin, IC50 260.7 μM. However, all compounds exhibited better or equal DPPH radical scavenging activity to (+)-catechin as positive control. Ellagic acid and terchebulin showed the best DPPH radical scavenging activities, IC50 4.86 and 4.90 μM, respectively. This study demonstrated that terchebulin has potentiality as an anti-acne agent.

Keywords

Terminalia laxiflora Engl & Diels Propionibacterium acnes Lipase inhibitor Terchebulin Flavogallonic acid dilactone 

References

  1. 1.
    Park J, Lee J, Jung E, Park Y, Kim K, Park B, Jung K, Park E, Kim J, Park D (2004) In vitro antibacterial and anti-inflammatory effect of honokiol and mangolol against Propionibacterium sp. Eur J Pharmacol 496:189–195PubMedCrossRefGoogle Scholar
  2. 2.
    Toyoda M, Morohashi M (2001) Pathogenesis of acne. Med Electron Microsc 34:29–40PubMedCrossRefGoogle Scholar
  3. 3.
    Kanlayavattanakul M, Lourith N (2011) Therapeutic agents and herbs in tropical application for acne treatment. Int J Cosmet Sci 33:289–297PubMedCrossRefGoogle Scholar
  4. 4.
    Muddathir AM, Mitsunaga T (2013) Evaluation of anti-acne activity of selected Sudanese medicinal plants. J Wood Sci 59:73–79CrossRefGoogle Scholar
  5. 5.
    Wickens GE (1973) Flora of tropical east Africa: Combretaceae. East African community Royal botanic gardens, Kew, p 99Google Scholar
  6. 6.
    Srivastav PK (1993) Pollination mechanisms in genus Terminalia Linn. Indian For 119:147–150Google Scholar
  7. 7.
    Rogers CB, Verotta L (1996) Chemistry, biological and pharmacological properties of African medicinal plants. University of Zimbabwe Publications, Harare, pp 121–141Google Scholar
  8. 8.
    Kuete V, Tabopda TK, Ngameni B, Nana F, Tshikalange TE, Ngadijui BT (2010) Antimycobacterial, antibacterial and antifungal activities of Terminalia superba (Combretaceae). S Afr J Bot 76:125–131CrossRefGoogle Scholar
  9. 9.
    Kandil FE, Nassar MI (1998) A tannin anti-cancer promotor from Terminalia arjuna. Phytochemistry 47:1567–1568PubMedCrossRefGoogle Scholar
  10. 10.
    Eldeen IM, Elgorashi EE, Mulholland DA, Van Staden J (2006) Anolignan B: a bioactive compound from the roots of Terminalia sericea. J Ethnopharmacol 103:135–138PubMedCrossRefGoogle Scholar
  11. 11.
    Kameswara Rao B, Renuka Sudarshan P, Rajasekhar MD, Nagaraju N, Appa Rao Ch (2003) Antidiabetic activity of Terminalia pallida fruit in alloxan induced diabetic rats. J Ethnopharmacol 85:169–172PubMedCrossRefGoogle Scholar
  12. 12.
    Rathore HS, Soni S, Bhatnagar D (2004) Hypocholesterolemic effect of Terminalia chebula fruit (Myrobalan) in mice. Anc Sci Life 23:11–15PubMedGoogle Scholar
  13. 13.
    Gupta M, Mazumder UK, Manikandan L, Bhattacharya S, Senthilkumar GP, Suresh R (2005) Anti-ulcer activity of ethanol extract of Terminalia pallida Brandis. in Swiss albino rats. J Ethnopharmacol 97:405–408PubMedCrossRefGoogle Scholar
  14. 14.
    Jagtap AG, Karkera SG (1999) Potential of the aqueous extract of Terminalia chebula as an anticaries agent. J Ethnopharmacol 68:299–306PubMedCrossRefGoogle Scholar
  15. 15.
    Valsaraj R, Pushpangadan P, Smitt UW, Adsersen A, Christensen SB, Sittie A, Nyman U, Nielsen C, Olsen CE (1997) New anti-HIV-1, antimalarial, and antifungal compounds from Terminalia bellerica. J Nat Prod 60:739–742PubMedCrossRefGoogle Scholar
  16. 16.
    Manosroi A, Jantrawut P, Akazawa H, Akihisa T, Manosroi J (2010) Biological activities of phenolic compounds isolated from galls of Terminalia chebula Retz. (Combretaceae). Nat Prod Res 24:1915–1926PubMedCrossRefGoogle Scholar
  17. 17.
    Musa S, Abdelrasool F, Elsheikh El, Ahmed L, Mahmoud A, Yagi S (2011) Ethnobotanical study of medicinal plants in the Blue Nile State, South-eastern Sudan. J Med Plants Res 5:4287–4297Google Scholar
  18. 18.
    Ogbazghi W, Bein E (2006) Assessment of non-wood forest products and their role in the livelihoods of rural communities in the Gash-Barka region, Eritrea. Drylands Coordination Group Report No 40, pp 26–27Google Scholar
  19. 19.
    Ekong DEU, Idemudia OG (1967) Constituents of some West African members of the genus Terminalia. J Chem Soc C 863–864Google Scholar
  20. 20.
    Hirano Y, Kondo R, Sakai K (2003) 5α-Reductase inhibitory tannin-related compounds isolated from Shorea laeviforia. J Wood Sci 49:339–343CrossRefGoogle Scholar
  21. 21.
    Lin TC, Nonaka GI, Nishioka I, Ho FC (1990) Tannins and related compounds, CII. Structures of terchebulin, an ellagitannin having a novel tetraphenylcarboxylic acid (terchebulic acid) moiety, and biogenetically related tannins from Terminalia chebula Retz. L. Chem Pharm Bull 38:3004–3008CrossRefGoogle Scholar
  22. 22.
    Batubara I, Mitsunaga T, Ohashi H (2009) Screening antiacne potency of Indonesian medicinal plants: antibacterial, lipase inhibition, and antioxidant activities. J Wood Sci 55:230–235CrossRefGoogle Scholar
  23. 23.
    Poulin Y (2004) Practical approach to the hormonal treatment of acne. J Cutan Med Surg 4:16–21Google Scholar
  24. 24.
    Tan AW, Tan HH (2005) Acne vulgaris: a review of antibiotic therapy. Expert Opin Pharmacother 6:409–418PubMedCrossRefGoogle Scholar
  25. 25.
    Leyden JJ (2004) Antibiotic resistance in the topical treatment of acne vulgaris. Cutis 73:6–10PubMedGoogle Scholar
  26. 26.
    Yemisci A, Gorgulu A, Piskin S (2005) Effects and side-effects of spironolactone therapy in women with acne. J Eur Acad Dermatol Venereol 19:163–166PubMedCrossRefGoogle Scholar
  27. 27.
    Silva O, Viegas S, de Mello-Sampayo C, Costa MJ, Serrano R, Cabrita J, Gomes ET (2012) Anti-Helicobacter pylori activity of Terminalia macroptera root. Fitoterapia 83:872–876PubMedCrossRefGoogle Scholar
  28. 28.
    Patil V, Bandivadekar A, Debjani D (2012) Inhibition of Propionibacterium acnes lipase by extracts of Indian medicinal plants. Int J Cosmet Sci 34:234–239PubMedCrossRefGoogle Scholar
  29. 29.
    Panichayupakaranant P (2010) Antibacterial activity of ellagic acid-rich pomegranate rind extracts. Planta Med. doi: 10.1055/s-0030-1264706
  30. 30.
    Lee WL, Shalita AR, Suntharalingam K, Fikrig SM (1982) Neutrophil chemotaxis by Propionibacterium acnes lipase and its inhibition. Infect Immun 35:71–78PubMedGoogle Scholar
  31. 31.
    Strauss JS, Pochi PE (1965) Intracutaneous injection of sebum and comedones, histological observations. Arch Dermatol 92:443–456PubMedCrossRefGoogle Scholar
  32. 32.
    Falcocchio S, Ruiz C, Pastor FIJ, Saso L, Diaz P (2006) Propionibacterium acnes GehA lipase, an enzyme involved in acne development, can be successfully inhibited by defined natural substances. J Mol Catal B-Enzym 40:132–137CrossRefGoogle Scholar
  33. 33.
    Wawruch M, Bozekova L, Krcmery S, Kriska M (2002) Risks of antibiotic treatment. Bratisl Lek L 103:270–275Google Scholar
  34. 34.
    Oi Y, Hou IC, Fujita H, Yazawa K (2012) Antiobesity effects of Chinese black tea (Pu-erh tea) extract and gallic acid. Phytother Res 26:475–481PubMedCrossRefGoogle Scholar
  35. 35.
    Makihara H, Shimada T, Machida E, Oota M, Nagamine R, Tsubata M, Kinoshita K, Takahashi K, Aburada M (2012) Preventive effect of Terminalia bellirica on obesity and metabolic disorders in spontaneously obese type 2 diabetic model mice. J Nat Med 66:459–467PubMedCrossRefGoogle Scholar
  36. 36.
    Trefzer U, Brockhaus M, Loetscher H, Parlow F, Budnik A, Grewe M, Christoph H, Kapp A, Schöpf E, Luger TA (1993) The 55-kDa tumor necrosis factor receptor on human keratinocytes is regulated by tumor necrosis factor-alpha and by ultraviolet B radiation. J Clin Invest 92:462–470PubMedCrossRefGoogle Scholar
  37. 37.
    Leyden JJ (2001) The evolving role of Propionibacterium acnes in acne. Semin Cutan Med Surg 20:139–143PubMedCrossRefGoogle Scholar
  38. 38.
    Vowels BR, Yang S, Leyden JJ (1995) Induction of proinflammatory cytokines by a soluble factor of Propionibacterium acnes: implications for chronic inflammatory acne. Infect Immun 63:3158–3165PubMedGoogle Scholar
  39. 39.
    Grange PA, Chéreau C, Raingeaud J, Nicco C, Weill B, Dupin N, Batteux F (2009) Production of superoxide anions by keratinocytes initiates P. acnes-induced inflammation of the skin. Plos Pathog. doi: 10.1371/journal.ppat.1000527
  40. 40.
    Yokozawa T, Chen CP, Dong E, Tanaka T, Nonaka GI, Nishioka I (1998) Study on the inhibitory effect of tannins and flavonoids against the 1,1-Diphenyl-2-picrylhydrazyl radical. Biochem Pharmacol 56:213–222PubMedCrossRefGoogle Scholar
  41. 41.
    Pfundstein B, El Desouky SK, Hull WE, Haubner R, Erben G, Owen RW (2010) Polyphenolic compounds in the fruits of Egyptian medicinal plants (Terminalia bellerica, Terminalia chebula and Terminalia horrida): characterization, quantitation and determination of antioxidant capacities. Phytochemistry 71:1132–1148PubMedCrossRefGoogle Scholar

Copyright information

© The Japan Wood Research Society 2013

Authors and Affiliations

  • Ali Mahmoud Muddathir
    • 1
  • Kosei Yamauchi
    • 1
  • Tohru Mitsunaga
    • 2
  1. 1.United Graduate School of Agricultural Science, Gifu UniversityGifuJapan
  2. 2.Department of Applied Biological Science, Faculty of Applied Biological ScienceGifu UniversityGifuJapan

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