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Official Journal of the Japan Wood Research Society

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Antioxidant activity and constituents of extracts from the root of Garcinia multiflora

Abstract

The methanolic extract of the root of Garcinia multiflora and its derived soluble fractions, namely those soluble in ethyl acetate (EtOAc), n-butanol, and water, were screened for their antioxidant activities. Among them, the EtOAc-soluble fraction exhibited the highest scavenging activity against the 1,1-dipheny1,2-picrylhydrazyl radical, the highest superoxide radical scavenging activity, and the strongest reducing power. In addition, according to the bioactivity-guided isolation, 26 specific phytocompounds, including 3 aromatics, 3 benzophenones, 3 flavonoids, 3 isocoumarins, 1 phloroglucinol, 6 steroids, and 7 xanthones, were isolated from the EtOAc-soluble fraction and identified. Of these, 2,4,3′,4′-tetrahydroxy-6-methoxybenzophenone and 1,3,6,7-tetrahydroxyxanthone were found to be the major bioactive constituents, present in the crude extract in concentrations of 3.9 and 15.6 mg/g, respectively. These two compounds had similar antioxidant activities to (+)-catechin, a well-known antioxidant.

References

  1. Cerutti PA (1991) Oxidant stress and carcinogenesis. Eur J Clin Invest 21:1–11

    Article  CAS  PubMed  Google Scholar 

  2. Lai LS, Chou ST, Chao WW (2001) Studies on antioxidative activities of Hsian-tsao (Mesona procumbens Hemsl) leaf gum. J Agric Food Chem 49:963–968

    Article  CAS  PubMed  Google Scholar 

  3. Mathew S, Abraham TE (2006) In vitro antioxidant activity and scavenging effects of Cinnamomum verum leaf extract assayed by different methodologies. Food Chem Toxicol 44:198–206

    Article  CAS  PubMed  Google Scholar 

  4. Halliwell B (1997) Antioxidants and human diseases: a general introduction. Nutr Rev 55:S44–S52

    Article  CAS  PubMed  Google Scholar 

  5. Aruoma OI (1998) Free radicals, oxidative stress, and antioxidants in human health and disease. J Am Oil Chem Soc 75:199–212

    Article  CAS  Google Scholar 

  6. Ames BN, Gold LS, Willet WC (1995) The causes and prevention of cancer. Proc Natl Acad Sci USA 92:5258–5265

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  7. Cao L, Liang F, Yao ZS (2000) The species and protection of wildly rare and endangered medicinal plants in Jinggangshan. Lishizhen Med Materia Medica Res 11:189–190

    Google Scholar 

  8. Chiang YM, Kuo YH, Oota S, Fukuyama Y (2003) Xanthones and benzophenones from the stems of Garcinia multiflora. J Nat Prod 66:1070–1073

    Article  CAS  PubMed  Google Scholar 

  9. Lin YM, Anderson H, Flavin MT, Pai YHS (1997) Anti-HIV activity of biofavonoids isolated from Rhus succedanea and Garcinia multiflora. J Nat Prod 60:884–888

    Article  CAS  PubMed  Google Scholar 

  10. Minami H, Kinoshita M, Fukuyama Y, Kodama M, Yoshizawa T, Sugiura M, Nakagawa K, Tago H (1994) Antioxidant xanthones from Garcinia subelliptica. Phytochemistry 36:501–506

    Article  CAS  Google Scholar 

  11. Takaki K, Shimasaki Y, Shishido T, Takehira K (2002) Selective oxidation of phenols to hydroxybenzaldehydes and benzoquinones with dioxygen catalyzed by polymer-supported copper. Bull Chem Soc Jpn 75:311–318

    Article  CAS  Google Scholar 

  12. Miyazawa M, Oshima T, Koshio K, Itsuzaki Y, Anzai J (2003) Tyrosinase inhibitor from black rice bran. J Agric Food Chem 51:6953–6956

    Article  CAS  PubMed  Google Scholar 

  13. Hirashima SI, Hashimoto S, Masaki Y, Itoh A (2006) Aerobic photo-oxidation of alcohols in the presence of a catalytic inorganic bromo source. Tetrahedron 62:7887–7891

    Article  CAS  Google Scholar 

  14. Atkinson JG, Gupta P, Lewis JR (1969) Some phenolic constituents of Gentiana lutea. Tetrahedron 25:1507–1511

    Article  CAS  PubMed  Google Scholar 

  15. Ito C, Itoigawa M, Miyamoto Y, Onoda S, Rao KS, Mukainaka T, Tokuda H, Nishino H, Furukawa H (2003) Polyprenylated benzophenones from Garcinia assigu and their potential cancer chemopreventive activities. J Nat Prod 66:206–209

    Article  CAS  PubMed  Google Scholar 

  16. Barros DAD, Alvarenga MAD, Gottlieb OR, Gottlieb HE (1982) Naringenin coumaroylglucosides from Mabea caudate. Phytochemistry 21:2107–2110

    Article  CAS  Google Scholar 

  17. Miyazawa M, Hisama M (2003) Antimutagenic activity of flavonoids from Chrysanthemum morifolium. Biosci Biotechnol Biochem 67:2091–2099

    Article  CAS  PubMed  Google Scholar 

  18. Ding HY, Chen YY, Chang WL, Lin HC (2004) Flavonoids from the flowers of Pueraria lobata. J Chin Chem Soc 51:1425–1428

    Article  CAS  Google Scholar 

  19. Anderson JR, Edwards RL, Whalley AJS (1983) Metabolites of the higher fungi. Part 21. 3-Methyl-3,4-dihydroisocoumarins and related compounds from the ascomycete family Xylariaceae. J Chem Soc Perkin Trans 1 pp 2185–2192

    Article  Google Scholar 

  20. Lee TH, Chiou JL, Lee CK, Kuo YH (2005) Separation and determination of chemical constituents in the roots of Rhus javanica L. var. roxburghiana. J Chin Chem Soc 52:833–842

    Article  CAS  Google Scholar 

  21. Roux D, Hadi HA, Thoret S, Guenard D, Thoison O, Pais M, Sevenet T (2000) Structure-activity relationship of polyisoprenyl benzophenones from Garcinia pyrifera on the tubulin/microtubule system. J Nat Prod 63:1070–1076

    Article  CAS  PubMed  Google Scholar 

  22. Das B, Srinivas KVNS (1992) Minor C29-steroids from the marine red alga, Gracilaria edulis. Phytochemistry 31:2427–2430

    Article  CAS  Google Scholar 

  23. Shu Y, Jones SR, Kinney WA, Selinsky BS (2002) The synthesis of spermine analogs of the shark aminosterol squalamine. Steroids 67:291–304

    Article  CAS  PubMed  Google Scholar 

  24. Iida T, Tamura T, Matsumoto T (1981) Stigmastanol in the seeds of Trichosanthes cucumeroide. Phytochemistry 20:857

    Article  CAS  Google Scholar 

  25. Barrero AF, Sanchez JF, Alvarez-Manzaneda EJ, Dorado MM, Haidour A (1993) Terpenoids and sterols from the wood of Abies pinsapo. Phytochemistry 32:1261–1266

    Article  CAS  Google Scholar 

  26. Kuo YH, Lee YC (1997) Constituents of the bark of Ficus microcarpa L.f. J Chin Chem Soc 44:321–325

    Article  CAS  Google Scholar 

  27. Hattori M, Shu YZ, Tomimori T, Kobashi K, Namba T (1989) A bacterial cleavage of the c-glucosyl bond of mangiferin and bergenin. Phytochemistry 28:1289–1290

    Article  CAS  Google Scholar 

  28. Li WK, Chan CL, Leung HW, Yeung HW, Xiao PG (1998) Xanthones and flavonoids of Polygala caudata. Pharm Pharmacol Commun 4:415–417

    CAS  Google Scholar 

  29. Tisdale EJ, Slobodov I, Theodorakis EA (2003) Biomimetic total synthesis of forbesione and desoxymorellin utilizing a tandem Claisen/Diels-Alder/Claisen rearrangement. Org Biomol Chem 24:4418–4422

    Article  Google Scholar 

  30. Mak NK, Li WK, Zhang M, Wong RNS, Tai LS, Yung KKL, Leung HW (2000) Effects of euxanthone on neuronal differentiation. Life Sci 66:347–354

    Article  CAS  PubMed  Google Scholar 

  31. Rocha L, Marton A, Kaplan MAC, Stoeckli-Evans H, Thull U, Testa B, Hostettmann K (1994) An antifungal g-pyrone and xanthones with monoamine oxidase inhibitory activity from Hypericum brasiliense. Phytochemistry 36:1381–1386

    Article  CAS  PubMed  Google Scholar 

  32. Iinuma M, Ito T, Tosa H, Tanaka T, Miyake R, Chelladurai V (1997) New linear pyranoxanthones from Calophyllum apetalum. Heterocycles 45:299–308

    Article  CAS  Google Scholar 

  33. Ikeya Y, Sugama K, Okada M, Mitsuhashi H (1991) Two xanthones from Polygala tenuifolia. Phytochemistry 30:2061–2065

    Article  CAS  Google Scholar 

  34. Gyamfi MA, Yonamine M, Aniya Y (1999) Free-radical scavenging action of medicinal herbs from Ghana Thonningia sanguinea on experimentally induced liver injuries. Gen Pharmacol 32:661–667

    Article  CAS  PubMed  Google Scholar 

  35. Kirby AJ, Schmidt RJ (1997) The antioxidant activity of Chinese herbs for eczema and of placebo herbs-1. J Ethnopharmacol 56:103–108

    Article  CAS  PubMed  Google Scholar 

  36. Oyaizu M (1986) Studies on product of browning reaction prepared from glucose amine. Jpn J Nutr 44:307–315

    Article  CAS  Google Scholar 

  37. Dinis TCP, Madeira VMC, Almeida LM (1994) Action of phenolic derivatives (acetaminophen, salicylate, and 5-aminosalicylate) as inhibitors of membrane lipid peroxidation and as peroxyl radical scavengers. Arch Biochem Biophys 315:161–169

    Article  CAS  PubMed  Google Scholar 

  38. Kujala TS, Loponen JM, Klika KD, Pihlaja K (2000) Phenolics and betacyanins in red beetroot (Beta vulgaris) root: distribution and effect of cold storage on the content of total phenolics and three individual compounds. J Agric Food Chem 48:5338–5342

    Article  CAS  PubMed  Google Scholar 

  39. Soares JR, Dinis TCP, Cunha AP, Ameida LM (1997) Antioxidant activity of some extracts of Thymus zygis. Free Radic Res 26:469–478

    Article  CAS  PubMed  Google Scholar 

  40. Halliwell B, Gutteridge JMC (1985) Free radicals, ageing, and disease. Free radicals in biology and medicine. Clarendron, Oxford, UK

    Google Scholar 

  41. Korycka-Dahl M, Richardson M (1978) Photogeneration of superoxide anion in serum of bovine milk and in model systems containing riboflavin and aminoacids. J Dairy Sci 61:400–407

    Article  CAS  Google Scholar 

  42. Yildirim A, Mavi A, Kara A (2001) Determination of antioxidant and antimicrobial activities of Rumex crispus L. extracts. J Agric Food Chem 49:4083–4089

    Article  CAS  PubMed  Google Scholar 

  43. Duh PD (1998) Antioxidant activity of burdock (Arctium lappa Linne): its scavenging effect on free-radical and active oxygen. J Am Oil Chem Soc 75:455–461

    Article  CAS  Google Scholar 

  44. Gordon MH (1990) The mechanism of the antioxidant action in vitro. In: Hudson BJF (ed) Food antioxidants. Elsevier, New York, pp 1–18

    Google Scholar 

  45. Shon MY, Choi SD, Kahng GG, Nam SH, Sung NJ (2004) Antimutagenic, antioxidant and free radical scavenging activity of ethyl acetate extracts from white, yellow and red onions. Food Chem Toxicol 42:659–666

    Article  CAS  PubMed  Google Scholar 

  46. Duh PD, Du PC, Yen GC (1999) Action of methanolic extract of mung hulls as inhibitors of lipid peroxidation and non-lipid oxidative damage. Food Chem Toxicol 37:1055–1061

    Article  CAS  PubMed  Google Scholar 

  47. Kumaran A, Karunakaran RJ (2006) Antioxidant and free radical scavenging activity of an aqueous extract of Coleus aromaticus. Food Chem 97:109–114

    Article  CAS  Google Scholar 

  48. Wangensteen H, Samuelsen AB, Malterud KE (2004) Antioxidant activity in extracts from coriander. Food Chem 46:4113–4117

    Google Scholar 

  49. Yen GC, Hsieh CL (1998) Antioxidant activity of extracts from Du-zhong (Eucommia ulmoides) toward various lipid peroxidation models in vitro. J Agric Food Chem 46:3952–3957

    Article  CAS  Google Scholar 

  50. Chang ST, Wu JH, Wang SY, Kang PL, Yang NS, Shyur LF (2001) Antioxidant activity of extracts from Acacia confusa bark and heartwood. J Agric Food Chem 49:3420–3424

    Article  CAS  PubMed  Google Scholar 

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Correspondence to Yueh-Hsiung Kuo.

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Wu, JH., Tung, YT., Chyu, CF. et al. Antioxidant activity and constituents of extracts from the root of Garcinia multiflora . J Wood Sci 54, 383–389 (2008). https://doi.org/10.1007/s10086-008-0961-9

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  • DOI: https://doi.org/10.1007/s10086-008-0961-9

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