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.
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Cerutti PA (1991) Oxidant stress and carcinogenesis. Eur J Clin Invest 21:1–11
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
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
Halliwell B (1997) Antioxidants and human diseases: a general introduction. Nutr Rev 55:S44–S52
Aruoma OI (1998) Free radicals, oxidative stress, and antioxidants in human health and disease. J Am Oil Chem Soc 75:199–212
Ames BN, Gold LS, Willet WC (1995) The causes and prevention of cancer. Proc Natl Acad Sci USA 92:5258–5265
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
Chiang YM, Kuo YH, Oota S, Fukuyama Y (2003) Xanthones and benzophenones from the stems of Garcinia multiflora. J Nat Prod 66:1070–1073
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
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
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
Miyazawa M, Oshima T, Koshio K, Itsuzaki Y, Anzai J (2003) Tyrosinase inhibitor from black rice bran. J Agric Food Chem 51:6953–6956
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
Atkinson JG, Gupta P, Lewis JR (1969) Some phenolic constituents of Gentiana lutea. Tetrahedron 25:1507–1511
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
Barros DAD, Alvarenga MAD, Gottlieb OR, Gottlieb HE (1982) Naringenin coumaroylglucosides from Mabea caudate. Phytochemistry 21:2107–2110
Miyazawa M, Hisama M (2003) Antimutagenic activity of flavonoids from Chrysanthemum morifolium. Biosci Biotechnol Biochem 67:2091–2099
Ding HY, Chen YY, Chang WL, Lin HC (2004) Flavonoids from the flowers of Pueraria lobata. J Chin Chem Soc 51:1425–1428
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
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
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
Das B, Srinivas KVNS (1992) Minor C29-steroids from the marine red alga, Gracilaria edulis. Phytochemistry 31:2427–2430
Shu Y, Jones SR, Kinney WA, Selinsky BS (2002) The synthesis of spermine analogs of the shark aminosterol squalamine. Steroids 67:291–304
Iida T, Tamura T, Matsumoto T (1981) Stigmastanol in the seeds of Trichosanthes cucumeroide. Phytochemistry 20:857
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
Kuo YH, Lee YC (1997) Constituents of the bark of Ficus microcarpa L.f. J Chin Chem Soc 44:321–325
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
Li WK, Chan CL, Leung HW, Yeung HW, Xiao PG (1998) Xanthones and flavonoids of Polygala caudata. Pharm Pharmacol Commun 4:415–417
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
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
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
Iinuma M, Ito T, Tosa H, Tanaka T, Miyake R, Chelladurai V (1997) New linear pyranoxanthones from Calophyllum apetalum. Heterocycles 45:299–308
Ikeya Y, Sugama K, Okada M, Mitsuhashi H (1991) Two xanthones from Polygala tenuifolia. Phytochemistry 30:2061–2065
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
Kirby AJ, Schmidt RJ (1997) The antioxidant activity of Chinese herbs for eczema and of placebo herbs-1. J Ethnopharmacol 56:103–108
Oyaizu M (1986) Studies on product of browning reaction prepared from glucose amine. Jpn J Nutr 44:307–315
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
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
Soares JR, Dinis TCP, Cunha AP, Ameida LM (1997) Antioxidant activity of some extracts of Thymus zygis. Free Radic Res 26:469–478
Halliwell B, Gutteridge JMC (1985) Free radicals, ageing, and disease. Free radicals in biology and medicine. Clarendron, Oxford, UK
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
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
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
Gordon MH (1990) The mechanism of the antioxidant action in vitro. In: Hudson BJF (ed) Food antioxidants. Elsevier, New York, pp 1–18
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
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
Kumaran A, Karunakaran RJ (2006) Antioxidant and free radical scavenging activity of an aqueous extract of Coleus aromaticus. Food Chem 97:109–114
Wangensteen H, Samuelsen AB, Malterud KE (2004) Antioxidant activity in extracts from coriander. Food Chem 46:4113–4117
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
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
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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