Journal of Wood Science

, Volume 55, Issue 4, pp 308–313 | Cite as

Antimicrobial activity against Streptococcus sobrinus and glucosyltransferase inhibitory activity of taxifolin and some flavanonol rhamnosides from kempas (Koompassia malaccensis) extracts

  • Harlinda Kuspradini
  • Tohru MitsunagaEmail author
  • Hideo Ohashi


Twenty plant materials collected from the islands of Java and Kalimantan in Indonesia were extracted with 50% aqueous ethanol (crude extract). The crude extracts were assayed for antimicrobial activities against Streptococcus sobrinus and for glucosyltransferase (GTase) inhibition. Fourteen extracts inhibited the growth of S. sobrinus by more than 50% and six extracts inhibited GTase activity by more than 50% at a concentration of 100 μg/ml. Koompassia malaccensis (kempas) extracts showed 90% depression of S. sobrinus growth and 80% inhibition of GTase activity at a concentration of 100 μg/ml. Kempas crude extracts were subjected to column chromatography using Sephadex LH-20 and then preparative high-performance liquid chromatography to isolate four compounds A, B, C, and D. These compounds were identified as taxifolin and the flavanonol rhamnoside isomers neoastilbin, astilbin, and isoastilbin, respectively, from 1H and 13C nuclear magnetic resonance (NMR) spectra and other two-dimensional NMR techniques (COSY, HMBC, and HMQC). Each compound depressed the growth of S. sobrinus over a concentration range of 9.3242.7 μg/ml and showed GTase inhibitory activity with IC50 values in the range 27.4–57.3 μg/ml. Taxifolin and flavanonol rhamnoside isomers isolated for the first time from kempas could be potent compounds for preventing dental caries.

Key words

Kempas Streptococcus sobrinus Taxifolin Neoastilbin Astilbin 


  1. 1.
    Tanzer JM (1995) Dental caries is a transmissible infectious disease: the Keyes and Fitzgerald revolution. J Dent Res 74:1536–1542CrossRefPubMedGoogle Scholar
  2. 2.
    Hamada S, Slade HD (1980) Biology, immunology, and cariogenicity of Streptococcus mutans. Microbiol Rev 44:331–384PubMedPubMedCentralGoogle Scholar
  3. 3.
    Fujiwara T, Sasada EE, Mima N, Ooshima T (1991) Caries prevalence and salivary mutans streptococci in 0–2 year old children of Japan. Comm Dent Oral Epidemiol 19:151–154CrossRefGoogle Scholar
  4. 4.
    Newman DJ, Cragg GM, Snader KM (2003) Natural product as sources of new drugs over period. J Nat Prod 66:1022–1037CrossRefPubMedGoogle Scholar
  5. 5.
    Ooshima T, Minami T, Matsumoto M, Fujiwara T, Sobue S, Hamada S (1998) Comparison of the cariostatic effects between regimens to administer oolong tea polyphenols in SPF rats. Caries Res 32:75–80CrossRefPubMedGoogle Scholar
  6. 6.
    Hamilton-Miller JMT (2001) Anti-cariogenic properities of tea (Camellia sinensis). J Med Microbiol 50:299–302CrossRefPubMedGoogle Scholar
  7. 7.
    Mitsunaga T, Abe I (1997) Inhibitory effects of bark proanthocyanidins on the activities of glucosyltransferases of Streptococcus sobrinus. J Wood Chem Technol 17:327–340CrossRefGoogle Scholar
  8. 8.
    Ooshima T, Osaka Y, Sasaki H, Osawa K, Yasuda H, Matsumura M (2000) Caries inhibitory activity of cocao bean husk extract in in-vitro and animal experiments. Arch Oral Biol 45:639–645CrossRefPubMedGoogle Scholar
  9. 9.
    Koo H, Gomes BPFA, Rosalen PL, Ambrosano GMB, Park YK, Cury JA (2000) In vitro antimicrobial activity of propolis and Arnica montana against oral pathogens. Arch Oral Biol 45:141–148CrossRefPubMedGoogle Scholar
  10. 10.
    Yanagida A, Kanda T, Tanabe M, Matsudaira F, Oliveria CJG (2000) Inhibitory effects of apple polyphenols and related compounds on cariogenic factors of mutans streptococci. J Agr Food Chem 48:5666–5671CrossRefGoogle Scholar
  11. 11.
    Ito K, Nakamura Y, Tokunaga T, Iijima D, Fukushima K (2003) Anti-cariogenic properties of a water-soluble extract from cacao. Biosci Biotechnol Biochem 67:2567–2573CrossRefPubMedGoogle Scholar
  12. 12.
    Steinberg D, Feldman M, Ofek I, Weiss EI (2004) Effect of high molecular weight component of cranberry on constituent of dental biofilm. J Antimicrob Chemother 54:86–89CrossRefPubMedGoogle Scholar
  13. 13.
    Kuspradini H, Rie M, Mitsunaga T, Ohashi H (2007) Investigating glucosyltransferase inhibitory activities of polyphenols from kapur (Dryobalanops sp.) heartwood extracts. J Nat Med 61:462–467CrossRefGoogle Scholar
  14. 14.
    Kobayashi M, Mahmud T, Yoshioka N, Shibuya H, Kitagawa I (1996) Kompasinol A, a new stilbeno-phenylpropanoid from the bark of Koompassia malaccensis. Chem Pharm Bull 44:2249–2253CrossRefGoogle Scholar
  15. 15.
    Szynol A, de Soet JJ, Sieben-van Tuyl E, Bos JW, Frenken LG (2004) Bactericidal effects of a fusion protein of Llama heavychain antibodies coupled to glucose oxidase on oral bacteria antimicrobial agents and chemotherapy. Antimicrob Agents Chemother 48:3390–3395CrossRefPubMedPubMedCentralGoogle Scholar
  16. 16.
    Cai L, Wu CD (1996) Compounds from Syzigium aromaticum possessing growth inhibitory activity against oral pathogens. J Nat Prod 59:987–990CrossRefPubMedGoogle Scholar
  17. 17.
    De Britto J, Manickam VS, Gopalakrishnan S, Ushioda T, Tanaka N (1995) Determination of aglycone chirality in dihydroflavonol 3-O-α-L-rhamnosides by 1H-NMR spectroscopy. Chem Pharm Bull 43:338–339CrossRefGoogle Scholar
  18. 18.
    Guo J, Feng Q, Jainxin L, Qiang X, Ting C (2007) Identifi cation of a new metabolite of astilbin, 3′-O-methylastilbin, and its immunosuppresive activity against contact dermatitis. Clin Chem 53:465–471CrossRefPubMedGoogle Scholar
  19. 19.
    Du Q, Lei L, Gerold J (2005) Purification of astilbin and isoastilbin of Smilax glabra rhizome by high speed-counter current chromatography. J Chromatogr 1007:98–101CrossRefGoogle Scholar
  20. 20.
    Hwang JK, Shim JS, Pyun YR (2000) Antibacterial activity of xanthorrhizol from Curcuma xanthorrhiza against oral pathogens. Fitoterapia 71:321–323CrossRefPubMedGoogle Scholar
  21. 21.
    Lee EH, Kim Hyoung JK, Yun Seon S, Changbae J, Kyung-Tae L, Jungsook C, Yong Sup L (2003) Constituents of the stems and fruits of Opuntia ficus-indica var. saboten. Arch Pharm Res 26: 1018–1023CrossRefPubMedGoogle Scholar
  22. 22.
    Chaca M, Bojase-Moleta G, Majindra RRT (2005) Antimicrobial and radical scavenging flavonoids from the stem wood of Erythrina latissima. Phytochemistry 66:99–104CrossRefGoogle Scholar
  23. 23.
    Tsuchiya H, Sato M, Miyazaki T, Fujiwara S, Tanigki S, Ohyama M, Tanaka T, Linuma M (1996) Comparative study on the antibacterial activity of phytochemical flavanones against methicillinresistant Staphyllococcus aeureus. J Ethnopharmacol 50:27–34CrossRefPubMedGoogle Scholar

Copyright information

© The Japan Wood Research Society 2009

Authors and Affiliations

  • Harlinda Kuspradini
    • 1
    • 2
  • Tohru Mitsunaga
    • 1
    Email author
  • Hideo Ohashi
    • 1
  1. 1.Department of Applied Life Science, Faculty of Biological ScienceGifu UniversityGifuJapan
  2. 2.Department of Forest Product Technology, Faculty of ForestryMulawarman UniversitySamarindaIndonesia

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