Abstract
This review article presents 342 aromatic glycosides, isolated from and identified in plants and microorganisms, that demonstrate different biological activities. They are of great interest, especially for the medicinal and/or pharmaceutical industries. These biologically active natural sufactants are good prospects for the future chemical preparation of compounds useful as antioxidant, anticancer, antimicrobial, and antibacterial agents. These glycosidic compounds have been classified into several groups, including simple aromatic compounds, stilbenes, phenylethanoids, phenylpropanoids, naphthalene derivatives, and anthracene derivatives.
Article PDF
Similar content being viewed by others
Abbreviations
- D-GalN:
-
D-galactosamine
- EC50 :
-
the median effect concentration, being a statistically derived concentration of a substance that can be expected to cause (i) an adverse reaction in 50% of organisms or (ii) a 50% reduction in growth or in the growth rate of organisms
- GI50 :
-
the concentration needed to reduce the growth of treated cells to half that of untreated (i.e., control) cells
- HUVEC:
-
human umbilical vein endothelial cells
- IC50 :
-
concentration at which growth or activity is inhibited by 50% (applies to ligand and growth inhibition)
- K1 :
-
prolyl hydroxylase activity, expressed as mol/mg protein
- LLC:
-
Lewis lung carcinoma
- LPS:
-
lipopolysaccharide
- MIC:
-
minimum inhibitory concentration of an antibiotic that inhibitts a bacterium
- MPP+ :
-
1-methyl-4-phenylpyridinium ion
- OLE:
-
olive leaf extract
- SDG:
-
seciosolariciresinol diglycoside 245
- TNF-α:
-
tumor necrosis factor α
References
Dembitsky, V.M. (2005) Astonishing Diversity of Natural Surfactants. 4. Fatty Acid Amide Glycosides, Their Analogs and Derivatives, Lipids 40, 641–660.
Dey, P.M., and Harborne, J.B. (1997) Plant Biochemistry, Academic Press, 554 pp.
Karakaya, S. (2004) Bioavailability of Phenolic Compounds, Crit. Rev. Food Sci. Nutr. 44, 453–464.
Dell' Agli, M., Busciala, A., and Bosisio, E. (2004) Vascular Effects of Wine Polyphenols, Cardiovasc. Res. 63, 593–602.
Kris-Etherton, P.M., Hecker, K.D., Bonanome, A., Coval, S.M., Binkoski, A.E., Hilpert, K.F., Griel, A.E., and Etherton, T.D. (2002) Bioactive Compounds in Foods: Their Role in the Prevention of Cardiovascular Disease and Cancer, Am. J. Med. 113 (Suppl. 9B), 71S-88S.
Cai, Y., Luo, Q., Sun, M., and Corke, H. (2004) Antioxidant Activity and Phenolic Compounds of 112 Traditional Chinese Medicinal Plants Associated with Anticance, Life Sci. 74, 2157–2184.
Duthie, G., and Crozier, A. (2000) Plant-Derived Phenolic Antioxidants, Curr. Opin. Clin. Nutr. Metab. Care 3, 447–451.
Bravo, L. (1998) Polyphenols: Chemistry, Dietary Sources, Metabolism, and Nutritional Significance, Nutr. Rev. 56, 317–333.
Gubitz, G.M., and Paulo, A.C. (2003) New Substrates for Reliable Enzymes: Enzymatic Modification of Polymers, Curr. Opin. Biotechnol. 14, 577–582.
King, A., and Young, G. (1999) Characteristics and Occurrence of Phenolic Phytochemicals, J. Am. Diet. Assoc. 99, 213–218.
Plomion, C., Leprovost, G., and Stokes, A. (2001) Wood Formation in Trees, Plant Physiol. 127, 1513–1523.
Rabinovich, M.L., Bolobova, A.V., and Vasil'chenko, L.G. (2004) Decomposition of Natural Aromatic Structures and Xenobiotics by Fungi, Prikl. Biokhim. Mikrobiol. 40, 5–23.
Ros Barcelo, A. (1997) Lignification in Plant Cell Walls, Int. Rev. Cytol. 176, 87–132.
Wallace, G., and Fry, S.C. (1994) Phenolic Components of the Plant Cell Wall, Int. Rev. Cytol. 151, 229–267.
Brennan, P.J. (1989) Structure of Mycobacteria: Recent Developments in Defining Cell Wall Carbohydrates and Proteins, Rev. Infect. Dis., (Suppl. 2), S420-S430.
Dembitsky, V.M. (2004) Chemistry and Biodiversity of Biologically Active Natural Glycosides, Chem. Biodivers. 1, 673–781.
Dembitsky, V.M. (2005) Astonishing Diversity of Natural Surfactants. 2. Polyether Glycosidic Ionophores and Macrocyclic Glycosides, Lipids 40, 219–248.
Figueroa-Espinoza, M.C., and Villeneuve, P. (2005) Phenolic Acids Enzymatic Lipophilization, J. Agric. Food Chem. 53, 2779–2787.
Oak, M.H., El Bedoui, J., and Schini-Kerth, V.B. (2005) Antiangiogenic Properties of Natural Polyphenols from Red Wine and Green Tea, J. Nutr. Biochem. 16, 1–8.
De la Lastra, C.A., and Villegas, I. (2005) Resveratrol as an Anti-inflammatory and Anti-aging Agent: Mechanisms and Clinical Implications, Mol. Nutr. Food Res. 49, 405–430.
Pervaiz, S. (2004) Chemotherapeutic Potential of the Chemopreventive Phytoalexin Resveratrol, Drug Resist. Updat. 7, 333–344.
Gescher, A. (2004) Polyphenolic Phytochemicals Versus Nonsteroidal Anti-inflammatory Drugs: Which Are Better Cancer Chemopreventive Agents? J. Chemother. (Suppl. 4), 3–6.
Lambert, J.D., and Yang, C.S. (2003) Cancer Chemopreventive Activity and Bioavailability of Tea and Tea Polyphenols, Mutat. Res. 523–524, 201–208.
Lopez-Velez, M., Martinez-Martinez, F., and Del Valle-Ribes, C. (2003) The Study of Phenolic Compounds as Natural Antioxidants in Wine, Crit. Rev. Food Sci. Nutr. 43, 233–244.
Stark, A.H., and Madar, Z. (2002) Olive Oil as a Functional Food: Epidemiology and Nutritional Approaches, Nutr. Rev. 60, 170–176.
Hollman, P.C., and Katan, M.B. (1999) Health Effects and Bioavailability of Dietary Flavonols, Free Radic. Res. 31 (Suppl.) S75-S80.
Orsini, F., Pelizzoni, F., Bellini, B., and Miglierini, G. (1997) Synthesis of Biologically Active Polyphenolic Glycosides (combretastatin and resveratrol series), Carbohydr. Res. 301, 95–109.
Cheynier, V. (2005) Polyphenols in Foods Are More Complex Than Often Thought, Am. J. Clin. Nutr. 81 (Suppl. 1), 223S-229S.
Lee, K.H. (1999) Novel Antitumor Agents from Higher Plants, Med. Res. Rev. 19, 569–596.
Tan, B.K.H., and Vanitha, J. (2004) Immunomodulatory and Antimicrobial Effects of Some Traditional Chinese Medicinal Herbs: A Review, Curr. Med. Chem. 11, 1423–1430.
Wojcikowski, K., Johnson, D.W., and Gobe, G. (2004) Medicinal Herbal Extracts—Renal Friend or Foe? Part One: The Toxicities of Medicinal Herbs, Nephrology 9, 313–318.
Pittler, M.H., and Ernst, E. (2003) Systematic Review: Hepatotoxic Events Associated with Herbal Medicinal Products, Aliment. Pharmacol. Therapeut. 18, 451–471.
Parojcic, D. (2003) A Historical Overview of the Discovery of Aspirin with Some New Aspects on Its Development, Arh. Farm. (Belgr.) 53, 51–70.
Weissmann, G. (1991) Aspirin, Sci. Am. 264, 84–90.
Alstaedter, R. (ed.) (1984) Aspirin, the Medicine of the Century, Bayer AG, Leverkusen, Germany.
Rainsford, K.D. (1984) Aspirin and the Salicylates, Butterworths, London.
Gross, M., and Greenburg, L.A. (1948) The Salicylates: A Critical Bibliographical Review, Hillhouse, New Haven, CT.
Brewer, S. (2000) The Relationship Between Natural Products and Synthetic Chemistry in the Discovery Process, Spec. Pub. Royal Soc. Chem. 257, 59–65.
Malterud, K.E. (2000) Medicines from Nature, Kjemi 60, 10–15.
Nahrstedt, A. (1990) Use of Plant Secondary Metabolites by Animals and Humans, Dtsch. Apoth. Ztg. 130, 2155–2161.
Lukic, P. (1967) Natural Sources of Anglgesics, Arh. Farm. (Berlgr.) 17, 261–270.
Bridel, M. (1919) Application of the Biochemical Method to the Branches and Barks of Various Species of the Genus Populus, J. Pharma. Chim. (France) 19, 429–434
Bridel, M., and Picard, P. (1928) Primeveroside of Salicylic Acid, Bull. Soc. Chim. Biol. 10, 381–385.
Vane, J.R. (1971) Salicylates, Nature 231, 232.
Thieme, H. (1963) The Phenolic Glycosides of the Salicaeae. I. General Review (discovery, elucidation of structure, synthesis, occurrence), Pharmazie 18, 770–774.
Yunes, R.A., Filho, V.C., Ferreira, J., and Calixto, J.B. (2005) The Use of Natural Products as Sources of New Analgesic Drugs, Stud. Nat. Prod. Chem. Bioact. Nat. Prod. 30, 191–212.
Brubacher, J.R., and Hoffman, R.S. (1996) Salicylism from Topical Salicylates: Review of the Literature, J. Toxicol. Clin. Toxicol. 34, 431–436.
Smith, M.J.H., and Smith, P.K. (eds.) (1966) The Salicylates: A Critical Bibliographical Review, Wiley Interscience, New York, 313 pp.
Paris, R.A., and Pointet, M. (1953) Presence of a Monotropitoside in the Bark of Ostryopsis davidiana, Ann. Pharm. Fr. 11, 346–348.
Towers, G.H.N., Tse, A., and Maass, W.S.G. (1966) Phenolic Acids and Phenolic Glycosides of Gaultheria Species, Phytochemistry 5, 677–681.
Boas, F. (1966) Kwakiutl Ethnobotany, (Codere, H., ed.), The University of Chicago Press, Chicago.
Thieme, H. (1965) Isolation and Structural Clarification of Spiraein, a Phenol Glycoside from Filipendula ulmaria, Pharmazie 20, 113–114.
Meier, B., Lehmann, D., and Sticher, O. (1987) Salicylate in Medicinal Plants. Screening Methods (HPLC, TLC) for Detection, Dtsch. Apoth. Zeit. (Germany) 127, 2401–2417.
Kanchanapoom, T., Kamel, M.S., Kasai, R., Picheansoonthon, C., Hiraga, Y., and Yamasaki, K. (2001) Benzoxazinoid Glucosides from Acanthus ilicifolius Phytochemistry 58, 637–640.
Itoh, A., Tanahashi, T., and Nagakura, N. (1993) Two Phenolic Glucosides and an Iridoid Glucoside from Alangium platanifolium var. trilobum, Phytochemistry 33, 161–164.
Wei, S., Zhou, Y., and Chang, Y. (1985) Phenolic Glucosides and Phenolic Acids from the Bark of Several Poplar Species, Linchan Huaxue Yu Gongye 5, 1–8.
Steele, J.W., Weitzel, P.F., and Audette, R.C.S. (1972) Phytochemistry of the Salicaceae. IV. Bark of Salix petiolaris (S. gracilis var. textoris), J. Chromatogr. 71, 435–441.
Tolonen, A., Pakonen, M., Hohtola, A., and Jalonen, J. (2003) Phenylpropanoid Glycosides from Rhodiola rosea, Chem. Pharm. Bull. (Tokyo) 51, 467–470.
Itoh, A., Tanahashi, T., Nagakura, N., Inoue, K., Kuwajima, H., and Wu, H.X. (2001) Glycosides of Benzyl and Salicyl Alcohols from Alangium chinense, Chem. Pharm. Bull. (Tokyo) 49, 1343–1345.
Delaquis, P.J., Stanich, K., Girard, B., and Mazza, G. (2002) Antimicrobial Activity of Individual and Mixed Fractions of Dill, Cilantro, Coriander and Eucalyptus Essential Oils, Int. J. Food Microbiol. 74, 101–109.
Singh, G., Kapoor, I.P., Pandey, S.K., Singh, U.K., and Singh, R.K. (2002) Studies on Essential Oils: Part 10: Antibacterial Activity of Volatile Oils of Some Species, Phytother. Res. 16, 680–682.
Yazdanparast, R., and Alavi, M. (2001) Antihyperlipidaemic and Antihypercholesterolaemic Effects of Anethum graveolens Leaves After the Removal of Furocoumarins, Cytobios 105, 185–191.
Ishikawa, T., Kudo, M., and Kitajima, J. (2002) Water-Soluble Constituents of Dill, Chem. Pharm. Bull. (Tokyo) 50, 501–507.
Society of Japanese Pharmacopoeia (2001) Japanese Pharmacopoeia, 14th edn., pp. 2708–2709, 2869–2871, Hirokawa Publishing, Tokyo.
Kitajima, J., Kamoshita, A., Ishikawa, T., Takano, A., Fukuda, T., Isoda, S., and Ida, Y. (2003) Glycosides of Atractylodes japonica, Chem. Pharm. Bull. (Tokyo) 51, 152–157.
Ishikawa, T., Kondo, K., and Kitajima, J. (2003) Water-Soluble Constituents of Coriander, Chem. Pharm. Bull. (Tokyo) 51, 32–39.
Kitajima, J., and Ishikawa, T. (2003) Water-Soluble Constituents of Amomum Seed, Chem. Pharm. Bull. (Tokyo) 51, 890–893.
Morikawa, T., Tao, J., Ueda, K., Matsuda, H., and Yoshikawa, M. (2003) Medicinal Foodstuffs. XXXI. 1). Structures of New Aromatic Constituents and Inhibitors of Degranulation in RBL-2H3 Cells from a Japanese Folk Medicine, the Stem Bark of Acer nikoense, Chem. Pharm. Bull. (Tokyo) 51, 62–67.
Ravi, K., Sivagnanam, K., and Subramanian, S. (2004) Antidiabetic Activity of Eugenia jambolana Seed Kernels on Streptozotocin-Induced Diabetic Rats, J. Med. Food 7, 187–191.
Ravi, K., Sekar, D.S., and Subramanian, S. (2004) Hypoglycemic Activity of Inorganic Constituents in Eugenia jambolana Seed on Streptozotocin-Induced Diabetes in Rats, Biol. Trace Elem. Res. 99, 145–155.
Chandrasekaran, M., and Venkatesalu, V. (2004) Antibacterial and Antifungal Activity of Syzygium jambolanum Seeds, J. Ethnopharmacol. 91, 105–108.
Bokesch, H.R., Young, S.M., McKee, T.C., Blunt, J.W., and Boyd, M.R. (1998) Lambertianoside, a Novel Phenylglycoside from Eugenia lambertiana, Nat. Prod. Lett. 11, 211–216.
Hase, K., Kadota, S., Basnet, P., Namba, T., and Takahashi, T. (1996) Hepatoprotective Effects of Traditional Medicines. Isolation of the Active Constituent from Seeds of Celosia argentea, Phytother. Res. 10, 387–392.
Xia, H.C., Li, F., Li, Z., and Zhang, Z.C. (2003) Purification and Characterization of Moschatin, a Novel Type I Ribosome-inactivating Protein from the Mature Seeds of Pumpkin (Cucurbita moschata), and Preparation of Its Immunotoxin Against Human Melanoma Cells, Cell Res. 13, 369–374.
Koke, K., Li, W., Liu, L., Hata, E., and Nikaido, T. (2005) New Phenolic Glycosides from the Seeds of Cucurbita moschata, Chem. Pharm. Bull. (Tokyo) 53, 225–228.
Jung, M.J., Kang, S.S., Jung, Y.J., and Choi, J.S. (2004) Phenolic Glycosides from the Stem Bark of Albizzia julibrissin, Chem. Pharm. Bull. (Tokyo) 52, 1501–1503.
De Leo, M., Braca, A., De Tommasi, N., Norscia, I., Morelli, I., Battinelli, L., and Mazzanti, G. (2004) Phenolic Compounds from Baseonema acuminatum Leaves: Isolation and Antimicrobial Activity, Planta Med. 70, 841–846.
Cottiglia, F., Bonsignore, L., Casu, L., Deidda, D., Pompei, R., Casu, M., and Floris, C. (2005) Phenolic Constituents from Ephedra nebrodensis, Nat. Prod. Res. 19, 117–123.
Braham, H., Mighri, Z., Jannet, H.B., Matthew, S., and Abreu, P.M. (2005) Antioxidant Phenolic Glycosides from Moricandia arvensis, J. Nat. Prod. 68, 517–522.
Liu, G.-W. (2001) Chinese Herbal Medicine, HuaXia Publishing House, Beijing (in Chinese).
Shri, N.G., Laxmi, N.M., and Shantosh, K.A. (1989) Corchioiside A, an Orcinol Glycoside from Curculigo orchioides, Phytochemistry 28, 1771–1772.
Xu, J.P., and Xu, R.S. (1992) Phenyl Glycosides from Curculigo orchioides, Yao Xue Xue Bao 27, 353–357.
Li, N., Zhao, Y., Jia, A., Liu, Y., and Zhou, J. (2003) Study on the Chemical Constituents of Curculigo orchioides, Tianran Chanwu Yanjiu Yu Kaifa 15, 208–211.
Lu, H., Zhu, B., and Liang, Y. (2002) Determination of Curculigoside in Curculigo orchioides by HPLC, Zhongguo Zhongyao Zashi 27, 192–194.
Palazzino, G., Galeffi, C., Federici, E., Delle Monache, F., Francesca Cometa, M., and Palmery, M. (2000) Benzylbenzoate and Norlignan Glucosides from Curculigo pilosa: Structural Analysis and in vitro Vascular Activity, Phytochemistry 55, 411–417.
Chen, C., Ni, W., and Mei, W. (1999) Glycosides from Curculigo orchioides, Yunnan Zhi Wu Yan Jiu 21, 521–524.
Fu, D.-X., Lei, G.-Q., Cheng, X.-W., Chen, J.-K., and Zhou, T.-S. (2004) Curculigoside C, a New Phenolic Glucoside from Rhizomes of Curculigo orchioides, Acta Bot. Sin. 46, 621–624.
Wu, H., Liu, Y., and Chen, Y. (1999) Determination of Curculigoside in Rhizomes of Curculigo orchioides Gaertn. by HPLC, Yaowu Fenxi Zazhi 19, 105–107.
Li, N., Tan, N.-H., and Zhou, J. (2004) New Chlorine-Containing Phenoloid from Curculigo capitulate, J. Asian Nat. Prod. Res. 6, 7–10.
Day, J.D., and Saunders, E. (2004) Glycosidation of Chlorophenols by Lemna minor, Environ. Toxicol. Chem. 23, 613–620.
Rothley, D., and Oelschlaeger, H. (1982) Unequivocal Determination of Glucuronides, in Particular of Clofibric β-Glucuronide, Arch. Pharm. (Weinheim) 315, 457–462.
Miller, L.P. (1957) Monosaccharide Components of an Induced Glycoside of Trichloroethyl Alcohol from Dandelion Tops, Contrib. Boyce Thompson Inst. 19, 113–115.
Day, J.A., III (2002) Formation and Fate of Chlorophenol Glycosides in an Aquatic Plant Enviroment, Georgia Institute of Technology, Atlanta, 255 pp. [abstracted in Diss. Abstr. Int. B 63, 5435 (2003)].
Chang, W.-L., Chen, C.-H., and Lee, S.-S. (1999) Three Novel Constituents from Curculigo capitulata, and Revision of C-2 Stereochemistry in Nyasicoside, J. Nat. Prod. 62, 734–739.
Galeffi, C., Federici, E., Palazzino, G., and Nicoletti, M. (1997) Research on African Medicinal Plants. XXXVIII. Further Norlignans from Hypoxis obtusa Burch, Gazz. Chim. Ital. 127, 501–504.
Marini Bettolo, G.B., Patamia, M., Nicoletti, M., Galeffi, C., and Messana, I. (1982) Research on African Medicinal Plants. II. Hypoxoside, a New Glycoside of Uncommon Structure from Hypoxis obtusa Busch, Tetrahedron 38, 1683–1687.
Chang, P.C., and Wu, C.C. (1979) Herbs of Taiwan in Color, Vol. 1, Nan Cun (South Villa) Trade Co., Taipei, Republic of China, p. 99.
Morikawa, H., Kasai, R., Otsuka, H., Shinzato, T., Aramoto, M., and Takeda, Y. (2004) Terpenic and Phenolic Glycosides from Leaves of Breynia officinalis HEMSL, Chem. Pharm. Bull. (Tokyo) 52, 1086–1090.
Perry, L.M. (1980) Medicinal Plants of East and Southeast Asia: Attributed Properties and Uses, The MIT Press, Cambridge.
Kim, J.S., Shim, S.H., Xu, Y.N., Kang, S.S., Son, K.H., Chang, H.W., Kim, H.P., and Bae, K. (2004) Phenolic Glycosides from Pyrola japonica, Chem. Pharm. Bull. (Tokyo) 52, 714–717.
Li, L.M., Liao, X., Peng, S.L., and Ding, L.S. (2005) Chemical Constituents from the Seeds of Ziziphus jujube var. spinosa (Bunge) Hu, J. Integrative Plant Biol. (formerly Acta Bot. Sin.) 47, 494–498.
Ouyang, M.-A., He, Z.-D., and Wu, C.-L. (2003) Anti-oxidative Activity of Glycosides from Ligustrum sinense, Nat. Prod. Res. 17, 381–387.
Nagatani, Y., Warashina, T., and Noro, T. (2002) Studies on the Constituents from the Aerial Part of Baccharis dracunculifolia DC. II, Chem. Pharm. Bull. (Tokyo) 50, 583–589.
Zhang, W., Chen, W., Wang, Y., Liu, W., Kong, D., and Li, H. (2001) Two New Glycosides from Erigeron breviscapus (Vant.) Hand.-Mazz, Zhongguo Zhongyao Zazhi 26, 689–690.
Chen, X.C., and Jia, Z.J. (2000) Two New Glycosides from Rubus amabilis, Chin. Chem. Lett. 11, 897–900.
Zhang, W., Tam, H.A., Thi, B., Chen, W., Kong, D., Li, H., Wang, Y., and Fouraste, I. (2000) Two New Glycosides from Erigeron breviscapus, J. Chinese Pharmaceut. Sci. 9, 122–124.
Kitajima, J., Ishikawa, T., and Tanaka, Y. (1998) Water-Soluble Constituents of Fennel. II. Four erythro-Anethole Glycol Glycosides and Two p-Hydroxyphenylpropylene Glycol Glycosides, Chem. Pharm. Bull. (Tokyo) 46, 1591–1594.
Yoshikawa, K., Eiko, K., Mimura, N., Kondo, Y., and Arihara, S. (1998) Hovetrichosides C-G, Five New Glycosides of Two Auronols, Two Neolignans, and a Phenylpropanoid from the Bark of Hovenia trichocarea, J. Nat. Prod. 61, 786–790.
Rashid, M.A., Gustafson, K.R., Cardellina, J.H., II, and Boyd, M.R. (1996) A Benzoic Acid Glycoside from Geniostoma antherotrichum, Phytochemistry 41, 1205–1207.
Xiao, K., Xuan, L., Xu, Y., and Bai, D. (2002) Novel Stilbene Glycosides from Polygonum multiflorum, Acta Bot. Sin. 44, 1491–1494.
Heitzman, M.E., Neto, C.C., Winiarz, E., Vaisberg, A.J., and Hammond, G.B. (2005) Ethnobotany, Phytochemistry and Pharmacology of Uncaria (Rubiaceae), Phytochemistry 66, 5–29.
Kong, J.M., Goh, N.K., Chia, L.S., and Chia, T.F. (2003) Recent Advances in Traditional Plant Drugs and Orchids, Acta Pharmacol. Sin. 24, 7–21.
Lu, Y.R., and Foo, L.Y. (2002) Polyphenolics of Salvia—A Review, Phytochemistry 59, 117–140.
Lovkova, M.Ya., Buzuk, G.N., Sokolova, S.M., and Kliment'eva, N.I. (2001) Chemical Features of Medicinal Plants (review), Appl. Biochem. Microbiol. 37, 229–237.
Agarwal, S.K., Singh, S.S., Lakshmi, V., Vermam, S., and Kumar, S. (2001) Chemistry and Pharmacology of Rhubarb (Rheum species)—A Review, J. Scient. Indust. Res. 60, 1–9.
Von Kruedener, S., Schneider, W., and Elstner, E. (1995) A Combination of Populus tremula, Solidago virgaurea and Fraxinus excelsior as an Antiinflammatory and Antirheumatic Drug—A Short Review, Arzneim. Forsch./Drug Res. 45, 169–171.
Ahmad, Y.U., and Rahman, A. (1994) Handbook of Natural Products Data, Vol. 2, Elsevier, Amsterdam, The Netherlands.
Bandyukova, V.A. (1983) Plant Phenol Acids, Their Esters and Glycosides, Khim. Prirod. Soed. (USSR) 3, 263–273.
Miller, L.P. (1973) Glycosides, Phytochemistry 1, 297–375.
Hopkinson, S.M. (1969) Chemistry and Biochemistry of Phenolic Glycosides, Quart. Rev. Chem. Soc. 23, 98–124.
Kompantsev, V.A. (1969) Phenolic Glycosides from Salix pentandroides, Khim. Prirod. Soed. (USSR) 5, 183–201.
Psenak, M. (1967) Phenol Glycosides: Their Significance and Structure, Biologia (Bratislava) 22, 704–714.
Kondratyuk, T.P., and Pezzuto, J.M. (2004) Natural Product Polyphenols of Relevance to Human Health, Pharmaceut. Biol. 42 (Suppl. S.), 46–63.
Matsuda, H., Kageura, T., Morikawa, T., Toguchida, I., Harima, S., and Yoshikawa, M. (2000) Effects of Stilbene Constituents from Rhubarb on Nitric Oxide Production in Lipopolysaccharide-Activated Macrophages, Bioorg. Med. Chem. Lett. 10, 323–327.
Nicolaou, K.C., Roecker, A.J., Barluenga, S., Pfefferkorn, J.A., and Cao, G.-Q. (2001) Discovery of Novel Antibacterial Agents Active Against Methicillin-Resistant Staphylococcus aureus from Combinatorial Benzopyran Libraries, Chem-BioChem 2, 460–465.
Schultz, T.P., Hubbard, T.F., Jr., Jin, L., Fisher, T.H., and Nicholas, D.D. (1990) Role of Stilbenes in the Natural Durability of Wood—Fungicidal Structure-Activity Relationships, Phytochemistry 29, 1501–1507.
Shen, F., Chen, S.-J., Dong, X.-J., Zhong, H., Li, Y.-T., and Cheng, G.-F. (2003) Suppression of IL-8 Gene Transcription by Resveratrol in Phorbol Ester Treated Human Monocytic Cells, J. Asian Nat. Prod. Res. 5, 151–157.
Boonlaksiri, C., Oonanant, W., Kongsaeree, P., Kittakoop, P., Tanticharoen, M., and Thebtaranonth, Y. (2000) An Antimalarial Stilbene from Artocarpus integer, Phytochemistry 54, 415–417.
Banwell, M.G., Bezos, A., Chand, S., Dannhardt G., Kiefer, W., Nowe, U., Parish, C.R., Savage, G.P., and Ulbrich, H. (2003) Convergent Synthesis and Preliminary Biological Evaluations of the Stilbenolignan (+/−)-Aiphanol and Various Congeners, Org. Biomol. Chem. 1, 2427–2429.
Orsini, F., Pelizzoni, F., Verotta, L., Aburjai, T., and Roger, C.B. (1997) Isolation, Synthesis, and Antiplatelet Aggregation Activity of Resveratrol 3-O-β-d-Glucopyranoside and Related Compounds, J. Nat. Prod. 60, 1082–1087.
Pacher, T., Seger, C., Engelmeier, D., Vajrodaya, S., Hofer, O., and Greger, H. (2002) Antifungal Stilbenoids from Stemona collinsae, J. Nat. Prod. 65, 820–827.
Likhitwitayawuid, K., and Sritularak, B. (2001) A New Dimeric Stilbene with Tyrosinase Inhibitory Activity from Artocarpus gomezianus, J. Nat. Prod. 64, 1457–1459.
Dai, J.R., Hallock, Y.F., Cardellina, J.H., and Boyd, M.R. (1998) HIV-Inhibitory and Cytotoxic Oligostilbenes from the Leaves of Hopea malibato, J. Nat. Prod. 61, 351–353.
Hazai, L., and Hornyak, G. (1998) Photochemical Reactions of Stilbenes and Their Heterocyclic Derivatives—A Review, Ach.-Model, Chem. 135, 493–514.
Hagen, S., and Hopf, H. (1998) Modern Routes to Extended Aromatic Compounds, Carbon Rich Compounds 1, Topic. Curr. Chem. 196, 45–89.
Bai, L., Masukawa, N., Yamaki, M., and Takagi, S. (1997) Two Bibenzyl Glucosides from Pleione bulbocodioides, Phytochemistry 44, 1565–1567.
Toshio, M., and Akira, U. (1991) Ionone and Bibenzyl Glycosides from Epimedium grandiflorum var. thunbergianum, Phytochemistry 30, 1727–1728.
Bae, K.H. (2002) Medicinal Plants of Korea, Kyo-Hak Publishing Co., Seoul, pp. 302.
Yang, H., Sung, S.H., and Kim, Y.C. (2005) Two New Hepatoprotective Stilbene Glycosides from Acer mono Leaves, J. Nat. Prod. 68, 101–103.
Rahman, A., Naz, H., Fadimatou, Makhmoor, T., Yasin, A., Fatima, N., Ngounou, F.N., Kimbu, S.F., Sondengam, B.L., and Choudhary, M.I. (2005) Bioactive Constituents from Boswellia papyrifera, J. Nat. Prod. 68, 189–193.
Roggero, J.P., and Archier, P. (1994) Quantitative Determination of Resveratrol and of One of Its Glycosides in Wines, Sci. Aliments 14, 99–107.
Vastano, B.C., Chen, Y., Zhu, N., Ho, C.T., Zhou, Z., and Rosen, R.T. (2000) Isolation and Identification of Stilbenes in Two Varieties of Polygonum cuspidatum, J. Agric. Food Chem. 48, 253–256.
Shi, Y.Q., Fukai, T., Sakagami, H., Kuroda, J., Miyaoka, R., Tamura, M., Yoshida, N., and Nomura, T. (2001) Cytotoxic and DNA Damage-Inducing Activities of Low Molecular Weight Phenols from Rhubarb, Anticancer Res. 21, 2847–2853.
Kimura, Y. (2003) Pharmacological Studies on Resveratrol, Methods Find. Exp. Clin. Pharmacol. 25, 297–310.
Nonaka, G., Minami, M., and Nishioka, I. (1977) Studies on Rhubarb (Rhei rhizoma). III. Stilbene Glycosides, Chem. Pharm. Bull. (Tokyo) 25, 2300–2305.
Gromova, A.S., Lutskii, V.I., and Tyukavkina, N.A. (1979) Stilbenes from the Bark of Some Pinaceae Species, Koksnes Kimija 3, 103–109.
Pearson, T.W., Kriz, G.S., Jr., and Taylor, R.J. (1977) Absolute Identification of Hydroxystilbenes, Chemical Markers in Engelmann spruce, Wood Sci. 10, 93–98.
Gromova, A.S., Tyukavkina, N.A., Lutskii, V.I., Kalabin, G.A., and Kushnarev, D.F. (1975) Hydroxystilbenes of the Inner Bark of Pinus sibiricd, Khim. Prirod. Soed. (USSR) 11, 677–682.
Bombardelli, E., Martinelli, E.M., and Mustich, G. (1975) Plants of Mozambique. IX. New Hydroxystilbene Glycoside from Terminalia sericea, Fitoterapia 46, 199–200.
Nkiliza, J. (2003) Rhubarb Extract, Compositions Obtained from This Extract, Procedure for Obtaining, and Uses, French Patent: FR 2835185, 20 pp
Kimura, Y., and Okuda, H. (2000) Effects of Naturally Occurring Stilbene Glucosides from Medicinal Plants and Wine, on Tumor Growth and Lung Metastasis in Lewis Lung Carcinoma-Bearing Mice, J. Pharm. Pharmacol. 52, 1287–1295.
Zhang, L., Li, L., and Li, Y. (2004) Mechanism of the Protection of Effective Component of Tuber Fleeceflower Root Stilbene Glycoside on Nerve Cells, Zhongguo Linchuang Kangfu 8, 118–120.
Chen, W., Li, L., Yin, X., Yang, G., Qiao, C., Zhang, W., and Chen, H. (2001) Tetrahydroxy-diphenylethylene Glycosides for Preventing and Treating Cardiovascular and Cerebrovascular Diseases, Chinese Patent: CN 1303858, 11 pp.
Matsuda, H., Tewtrakul, S., Morikawa, T., and Yoshikawa, M. (2004) Anti-allergic Activity, of Stilbenes from Korean Rhubarb (Rheum undulatum L.): Structure Requirements for Inhibition of Antigen-Induced Degranulation and Their Effects on the Release of TNF-α and IL-4 in RBL-2H3 Cells, Bioorg. Med. Chem. 12, 4871–4876.
Pan, H., and Lundgren, L.N. (1995) Phenolic Extractives from Root Bark of Picea abies, Phytochemistry 39, 1423–1428.
Fuendjiep, V., Wandji, J., Tillequin, F., Mulholland, D.A., Budzikiewicz, H., Fomum, Z.T., Nyemba, A.M., and Koch, M. (2002) Chalconoid and Stilbenoid Glycosides from Guibourtia tessmanii, Phytochemistry 60, 803–806.
Ali, Z., Ito, T., Tanaka, T., Nakaya, K.I., Murata, J., Darnaedi, D., and Iinuma, M. (2004) Acetophenone C-Glucosides and Stilbene O-Glucosides in Upuna borneensis, Phytochemistry 65, 2141–2146.
Waffo-Teguo, P., Lee, D., Cuendet, M., Merillon, J.-M., Pezzuto, J.M., and Kinghorn, A.D. (2001) Two New Stilbene Dimer Glucosides from Grape (Vitis vinifera) Cell Cultures, J. Nat. Prod. 64, 136–138.
Ito, T., Akao, Y., Tanaka, T., Iinuma, M., and Nozawa, Y. (2002) Vaticanol C, a Novel Resveratrol Tetramer, Inhibits Cell Growth Through Induction of Apoptosis in Colon Cancer Cell Lines, Biol. Pharm. Bull. 25, 147–148.
Iliya, I., Tanaka, T., Furusawa, M., Ali, Z., Nakaya, K., Iinuma, M., Shirataki, Y., Murata, J., and Darnaedi, D. (2001) Four New Glucosides of Stilbene Oligomers from the Stem of Gnetum gnemonoides, Heterocycles 55, 2123–2130.
Iliya, I., Tanaka, T., Iinuma, M., Furusawa, M., Ali, Z., Nakaya, K.I., Murata, J., and Darnaedi, D. (2002) Five Stilbene Glucosides from Gnetum gnemonoides and Gnetum africanum, Helv. Chim. Acta. 85, 2394–2402.
Iliya, I., Ali, Z., Tanaka, T., Iinuma, M., Furusawa, M., Nakaya, K., Murata, J., Darnaedi, D., Matsuura, N., and Ubukata, M. (2003) Stilbene Derivatives from Gnetum gnemon Linn, Phytochemistry 62, 601–606.
Xiao, K., Xuan, L., Xu, Y., Bai, D., Zhong, D., Wu, H., Wang, Z., and Zhang, N. (2002) Dimeric Stilbene Glycosides from Polygonum cuspidatum, Eur. J. Org. Chem. 3, 564–568.
Ono, M., Ito, Y., Kinjo, J., Yahara, S., Nohara, T., and Niiho, Y. (1995) Four New Glycosides of Stilbene Trimer from Foeniculi fructus (fruit of Foeniculum vulgare Miller), Chem. Pharm. Bull. (Tokyo) 43, 868–871.
Xiao, K., Xuan, L., Xu, Y., and Bai, D. (2000) Stilbene Glycoside Sulfates from Polygonum cuspidatum, J. Nat. Prod. 63, 1373–1376.
Ashton, P.S. (1982) Flora Malesiana, in Spermatophyta, Series 1, Vol. 9 (Steenis C.G.G.J., ed.), Martivus Nijhoff Publishers, Leiden, The Netherlands, pp. 337–340.
Ito, T., Ali, Z., Iliya, I., Furusawa, M., Tanaka, T., Nakaya, K.C., Takahashi, Y., Sawa, R., Murata, J., Darnaedi, D., et al. (2005) Occurrence of Stilbene Glucosides in Upuna borneensis, Helv. Chim. Acta 88, 23–34.
Taskova, R.M., Gotfredsen, C.H., and Jensen, S.R. (2005) Chemotaxonomic Markers in Digitalideae (Plantaginaceae), Phytochemistry 66, 1440–1447.
Li, Y., and Ohizumi, Y. (2004) Search for Constituents with Neurotrophic Factor-Potentiating Activity from the Medicinal Plants of Paraguay and Thailand, Yakugaku Zasshi 124, 417–424.
Jimenez, C., and Riguera, R. (1994) Phenylethanoid Glycosides in Plants: Structure and Biological Activity, Nat. Prod. Rep. 11, 591–606.
Mel'nikov, V.N., Bugorskii, P.S., and Medvedkova, V.V. (1975) β-Phenethyl-β-d-glucopyranoside from the Flowers of Rosa gallica, Khim. Prirod. Soed. (USSR) 11, 807–809.
Kimura, T., Utida, M., Nakajima, H., and Dombou, M. (2000) Enzymatic Synthesis of Phenethyl Glycoside and Its Application, J. Appl. Glycosci. 47, 55–59.
Nicoletti, M., Galeffi, C., Messana, I., Garbarino, J.A., Gambaro, V., Nyandat, E., and Marini-Bettolo, G.B. (1986) New Phenylpropanoid Glucosides from Calceolaria hypericina, Gazz. Chim. Ital. 116, 431–433.
Ersoz, T., Ozalp, M., Ekizoglu, M., and Calis, I. (2002) Antimicrobial Activities of the Phenylethanoid Glycosides from Scutellaria galericulata, Hacettepe Univ. Eczacilik Fak. Derg. (Turkey) 22, 1–8.
Miyase, T., Ishino, M., Akahori, C., Ueno, A., Ohkawa, Y., and Tanizawa, H. (1991) Phenylethanoid Glycosides from Plantago asiatica, Phytochemistry 30, 2015–2018.
Liu, D.-L., Zhang, Y., Xu, S.-X., Xu, Y., and Wang, Z.-X. (1998) Phenylethanoid Glycosides from Forsythia suspensa Vahl, J. Chinese Pharmaceut. Sci. 7, 103–105.
Wang, H., Sun, Y., Ye, W.-C., Xiong, F., Wu, J.-J., Yang, C.-H., and Zhao, S.-X. (2004) Antioxidative Phenylethanoid and Phenolic Glycosides from Picrorhiza scrophulariiflora, Chem. Pharm. Bull. (Tokyo) 52, 615–617.
Pettit, G.R., Numata, A., Takemura, T., Ode, R.H., Narula, A.S., Schmidt, J.M., Cragg, G.M., and Pase, C.P. (1990) Antineoplastic Agents, 107. Isolation of Acteoside and Isoacteoside from Castilleja linariaefolia, J. Nat. Prod. 53, 456–458.
Diaz, A.M., Abad, M.J., Fernandez, L., Silvan, A.M., De Santos, J., and Bermejo, P. (2004) Phenylpropanoid Glycosides from Scrophularia scorodonia: In vitro Anti-inflammatory Activity, Life. Sci. 74, 2515–2526.
Chiou, W.-F., Lin, L.-C., and Chen, C.-F. (2003) The Antioxidant and Free Radical Scavenging Properties of Acteoside, Chin. Pharm. J. (Taipei) 55, 347–353.
Boje, K., Lechtenberg, M., and Nahrstedt, A. (2003) New and Known Iridoid- and Phenylethanoid Glycosides from Harpagophytum procumbens and Their in vitro Inhibition of Human Leukocyte Elastase, Planta Med. 69, 820–825.
Lee, J.Y., Woo, E.-R., and Kang, K.W. (2005) Inhibition of Lipopolysaccharide-Inducible Nitric Oxide Synthase Expression by Acteoside Through Blocking of AP-1 Activation, J. Ethnopharmacol. 97, 561–566.
Zhang, F., Jia, Z., Deng, Z., Fan, J., Chen, J., Wu, H., Zhao, C., and Wei, Y. (2002) Inhibition of Verbascoside on the Telomerase Activity of Human Gastric Adenocarcinoma Cell NKN45, Shijie Huaren Xiaohua Zazhi 10, 366–367.
Nagao, T., Abe, F., and Okabe, H. (2001) Antiproliferative Constituents in the Plants. 7. Leaves of Clerodendron bungei and Leaves and Bark of C. trichotomum, Biol. Pharm. Bull. 24, 1338–1341.
Xiong, Q., Hase, K., Tezuka, Y., Namba, T., and Kadota, S. (1999) Acteoside Inhibits Apoptosis in d-Galactosamine and Lipopolysaccharide-Induced Liver Injury, Life Sci. 65, 421–430.
Schapoval, E.E.S., Winter de Vargas, M.R., Chaves, C.E.G., Bridi, R., Zuanazzi, J.A., and Henriques, A.T. (1998) Antiinflammatory and Antinociceptive Activities of Extracts and Isolated Compounds from Stachytarpheta cayennensis, J. Ethnopharmacol. 60, 53–59.
Kang, K.H., Jang, S.K., Kim, B.K., and Park, M.K. (1994) Antibacterial Phenylpropanoid Glycosides from Paulownia tomentosa Steud, Arch. Pharm. Res. 17, 470–475.
Pu, X., Li, X., Li, H., Tu, P., Song, Z., and Li, C. (2001) Campneoside II of Cistanche tubulosa (Schenk) R. Wight Protects Neurons from Apoptosis Induced by Neurotoxin 1-Methyl-4-phenylpyridinium (MPP+), Beijing Daxue Xuebao, Yixueban 33, 217–220.
Jimenez, C., Villaverde, M.C., Riguera, R., Castedo, L., and Stermitz, F.R. (1987) Three Phenylpropanoid Glycosides from Mussatia, Phytochemistry 26, 1805–1810.
Jimenez, C., Villaverde, M.C., Riguera, R., Castedo, L., and Stermitz, F.R. (1988) Five Phenylpropanoid Glycosides from Mussatia, Phytochemistry 27, 2947–2951.
Jimenez, C., Villaverde, M.C., Riguera, R., Castedo, L., and Stermitz, F. (1989) Phenylpropanoid Glycosides from Mussatia hyacinthine, J. Nat. Prod. 52, 408–410.
Cano, E., Veiga, M., Jimenez, C., and Riguera, R. (1990) Pharmacological Effects of Three Phenylpropanoid Glycosides from Mussatia, Planta Med. 56, 24–26.
Salib, J.Y., and Michael, H.N. (2004) Cytotoxic Phenylethanol Glycosides from Psidium guaijava Seeds, Phytochemistry 65, 2091–2093.
Kikuchi, M., and Yamauchi, Y. (1986) Structural Analysis on the Constituents of Syringa Species. II. Structures of Components from the Leaves of Syringa reticulata (Blume) Hara, Ann. Rep. Tohoku Coll. Pharm. 33, 63–68.
Kikuchi, M., Yamauchi, Y., Takahashi, Y., and Sugiyama, M. (1989) Studies on the Constituents of Syringa Species. VIII. Isolation and Structures of Phenylpropanoid Glycosides from the Leaves of Syringa reticulata (Blume) Hara, Yakugaku Zasshi 109, 366–371.
Shen, Y.-C., Lin, S.-L., Hsieh, P.-W., and Chein, C.-C. (1996) Secoiridoid Glycosides from Jasminum polyanthum, J. Chinese Chem. Soc. (Taipei) 43, 171–176.
Shen, Y.-C., Lin, S.-L., and Chein, C.-C. (1996) Jaspolyside, a Secoiridoid Glycoside from Jasminum polyanthum, Phytochemistry 42, 1629–1631.
Damtoft, S., Franzyk, H., and Jensen, S.R. (1997) Iridoid Glucosides from Picconia excelsa, Phytochemistry 45, 743–750.
Machida, K., Kaneko, A., Hosogai, T., Kakuda, R., Yaoita, Y., and Kikuchi, M. (2002) Studies on the Constituents of Syringa Species. X. Five New Iridoid Glycosides from the Leaves of Syringa reticulata (Blume) Hara, Chem. Pharm. Bull. (Tokyo) 50, 493–497.
Fukuyama, Y., Koshino, K., Hasegawa, T., Yamada, T., and Nakagawa, K. (1987) New Secoiridoid Glucosides from Ligustrum japonicum, Planta Med. 53, 427–431.
LaLonde, R.T., Wong, C., and Tsai, A.I.-M. (1976) Polyglucosidic Metabolites of Oleaceae. The Chain Sequence of Oleoside Aglucon, Tyrosol, and Glucose Units in Three Metabolites from Fraxinus americana, J. Am. Chem. Soc. 98, 3007–3013.
Jensen, S.R., Franzyk, H., and Wallander, E. (2002) Chemotaxonomy of the Oleaceae: Iridoids as Taxonomic Markers, Phytochemistry 60, 213–231.
Kikuchi, M., and Yamauchi, Y. (1985) Studies on the Constituents of Osmanthus Species. III. On the Components of the Leaves of Osmanthus ilicifolius (Hassk.) Mouillefert, Yakugaku Zasshi 105, 442–448.
Kuwajima, H., Uemura, T., Takaishi, K., Inoue, K., and Inouye, H. (1988) Monoterpene Glucosides and Related Natural Products. Part 60. A Secoiridoid Glucoside from Olea europaea, Phytochemistry 27, 1757–1759.
Ryan, D., Antolovich, M., Herlt, T., Prenzler, P.D., Lavee, S., and Robards, K. (2002) Identification of Phenolic Compounds in Tissues of the Novel Olive Cultivar Hardy's Mammoth, J. Agric. Food Chem. 50, 6716–6724.
Ryan, D., Prenzler, P.D., Lavee, S., Antolovich, M., and Robards, K. (2003) Quantitative Changes in Phenolic Content During Physiological Development of the Olive (Olea europaea) Cultivar Hardy's Mammoth, J. Agric. Food Chem. 51, 2532–2538.
Lee-Huang, S., Zhang, L., Huang, P.L., Chang, Y.-T., and Huang, P.L. (2003) Anti-HIV Activity of Olive Leaf Extract (OLE) and Modulation of Host Cell Gene Expression by HIV-1 Infection and OLE Treatment, Biochem. Biophys. Res. Commun. 307, 1029–1037.
Sugiyama, M., Machida, K., Matsuda, N., and Kikuchi, M. (1993) Studies on the Constituents of Osmanthus Species. Part 15. A Secoiridoid Glycoside from Osmanthus asiaticus, Phytochemistry 34, 1169–1170.
Kikuchi, M., and Kakuda, R. (1999) Studies on the Constituents of Ligustrum species. XIX. Structures of Iridoid Glucosides from the Leaves of Ligustrum lucidum AIT, Yakugaku Zasshi (J. Pharm. Soc. Japan) 119, 444–450.
Tattini, M., Galardi, C., Pinelli, P., Massai, R., Remorini, D., and Agati, G. (2004) Differential Accumulation of Flavonoids and Hydroxycinnamates in Leaves of Ligustrum vulgare Under Excess Light and Drought Stress, New Phytol. 163, 547–561.
Kikuchi, M., and Yamauchi, Y. (1985) Studies on the Constituents of Ligustrum Species. XI. On the Secoiridoids of the Fruits of Ligustrum japonica Thunb. and L. lucidum Ait, Yakugaku Zasshi 105, 142–147.
Park, H.J., Lee, M.S., Lee, K.T., Sohn, I.C., Han, Y.N., and Miyamoto, K. (1999) Studies on Constituents with Cytotoxic Activity from the Stem Bark of Syringa velutina, Chem. Pharm. Bull. (Tokyo) 47, 1029–1031.
Tanahashi, T., Shimada, A., Nagakura, N., and Nayeshiro, H. (1992) Jasamplexosides A, B and C: Novel Dimeric and Trimeric Secoiridoid Glucosides from Jasminum amplexicaule, Planta Med. 58, 552–555.
Tanahashi, T., Shimada, A., Nagakura, N., Inoue, K., Kuwajima, H., Takashi, K., and Chen, C.C. (1993) A Secoiridoid Glucoside from Fraxinus insularis, Phytochemistry 33, 397–400.
Iossifova, T., Mikhova, B., and Kostova, I. (1995) A Secoiridoid Dilactone from Fraxinus ornus Bark, Monatsh. Chem. 126, 1257–1264.
Benkrief, R., Ranarivelo, Y., Skaltsounis, A.-L., Tillequin, F., Koch, M., Pusset, J., and Sevenet, T. (1998) Monoterpene Alkaloids, Iridoids and Phenylpropanoid Glycosides from Osmanthus austrocaledonica, Phytochemistry 47, 825–832.
Tanahashi, T., Watanabe, H., Itoh, A., Nagakura, N., Inoue, K., Ono, M., Fujita, T., and Chen, C.C. (1992) A Secoiridoid Glucoside from Fraxinus formosana, Phytochemistry 31, 2143–2145.
He, Z.D., Ueda, S., Inoue, K., Akaji, M., Fujita, T., and Yang, C. (1994) Secoiridoid Glucosides from Fraxinus malacophylla, Phytochemistry 35, 177–181.
Ivanovska, N., Iossifova, T., and Kostova, I. (1996) Complement-Mediated Anti-inflammatory action of Extracts and Pure Secoiridoids Isolated from Fraxinus species, Phytotherapy Res. 10, 555–558.
Kuwajima, H., Morita, M., Takaishi, K., Inoue, K., Fujita, T., He, Z.D., and Yang, C.R. (1992) Secoiridoid, Coumarin and Secoiridoid-Coumarin Glucosides from Fraxinus chinensis, Phytochemistry 31, 1277–1280
Damtoft, S., Franzyk, H., and Jensen, S.R. (1995) Biosynthesis of Iridoids in Syringa and Fraxinus: Carbocyclic Iridoid Precursors, Phytochemistry 40, 785–792.
Asaka, Y., Kamikawa, T., Tokoroyama, T., and Kubota, T. (1970) The Structure and Absolute Configuration of Syringopicroside. A New Iridoid Glucoside from Syringa vulgaris L., Tetrahedron 26, 2365–2370.
Kikuchi, M., Yamauchi, Y., and Sugiyama, M. (1989) The Constituents of Syringa species. IX. Structure of Oxidative Products from Syringopicroside with Perbenzoic Acid, Ann. Rep. Tohoku Coll. Pharm. 36, 97–104.
Shen, Y.C., and Chen, C.H. (1989) Novel Secoiridoid Lactones from Jasminum multiflorum, J. Nat. Prod. 52, 1060–1070.
Shen, Y.-C., and Chen, C.-H. (1994) A New Secoiridoid Lactone from Jasminum multiflorum, J. Chin. Chem. Soc. 41, 473–476.
Kurkin, V.A. (2003) Phenylpropanoids from Medicinal Plants: Distribution, Classification, Structural Analysis, and Biological Activity, Chem. Nat. Comp. 39, 123–153.
Pan, J., Yuan, C., Lin, C., Jia, Z., and Zheng, R. (2003) Pharmacological Activities and Mechanisms of Natural Phenyl-propanoid Glycosides, Pharmazie 58, 767–775.
Milkowska-Leyck, K., Borkowski, B., and Strzelecka, H. (2001) Selected Polyphenol Compounds. Part IV. Characteristics and Occurrence of Phenylpropanoid Glycosides, Herba Polonica 47, 225–244.
Sawabe, A., Kumamoto, H., and Matsubara, Y. (1998) Bioactive Glycosides in Citrus Fruit Peels, Kinki Daigaku Nogaku Sogo Kenkyusho Hokoku 6, 57–67.
Cometa, F., Tomassini, L., Nicoletti, M., and Pieretti, S. (1993) Phenylpropanoid Glycosides. Distribution and Pharmacological Activity, Fitoterapia 64, 195–217.
He, Z., and Yang, C. (1989) The Advances of Phenylpropanoid Glycosides in Plants, Tianran Chanwu Yanjiu Yu Kaifa 1, 29–41.
Kucinskaite, A., Briedis, V., and Savickas, A. (2004) Experimental Analysis of Therapeutic Properties of Rhodiola rosea L. and Its Possible Application in Medicine, Medicina (Kaunas) 40, 614–619.
Sokolov, S.Ya., Ivashin, V.M., Zapesochnaya, G.G., Kurkin, V.A., and Shchavlinskii, A.N. (1985) Studies of Neurotropic Activity of New Compounds Isolated from Rhodiola rosea, Khim.Farmatsev. Z. (USSR) 19, 1367–1371.
Sawabe, A., Matsubara, Y., Iizuka, Y., and Okamoto, K. (1988) Physiologically Active Substances in Citrus Fruit Peels. XIII. Structure and Physiological Activity of Phenyl Propanoid Glycosides in the Lemon (Citrus limon Burm. f.), Unshiu (Citrus unshiu), and Kinkan (Fortunella japonica), Nippon Nogeikagaku Kaishi 62, 1067–1071.
Matsubara, Y., Kumamoto, H., Sawabe, A., Iizuka, Y., and Okamoto, K. (1985) Structure and Physiological Activity of Phenyl Propanoid Glycosides in Lemon, Unshiu and Orange Peelings, Kinki Daigaku Igaku Zasshi 10, 51–58.
Sawabe, A. (1996) Bioactive Compounds in Citrus Fruit Peels, Foods Food Ingred. J. Japan. 169, 37–44.
Matsubara, Y., Yusa, T., Sawabe, A., Iizuka, Y., and Okamoto, K. (1991) Studies on Physiologically Active Substances in Citrus Fruit Peel. Part XX. Structure and Physiological Activity of Phenyl Propanoid Glycosides in Lemon (Citrus limon Burm. f.) Peel, Agric. Biol. Chem. 55, 647–650.
Afifi, M.S., Lahloub, M.B., El-Khayaat, S.A., Anklin, C.G., Ruegger, H., and Sticher, O. (1993) Crenatoside: A Novel Phenylpropanoid Glycoside from Orobanche crenata, Planta Med. 59, 359–362.
Nakanishi, T., Iida, N., Inatomi, Y., Murata, H., Inada, A., Murata, J., Lang, F.A., Iinuma, M., and Tanaka, T. (2004) New Neolignan and Phenylpropanoid Glycosides in Juniperus communis var. depressa, Heterocycles 63, 2573–2580.
Sosa, A. (1934) Biochemical Study of Betula alba L. A New Heteroside: Betuloside, and Its Prosthetic Group, Betuligenol, Rev. Acad. Cienc. (Madrid) 31, 81–100.
Kiem, P.V., Minh, C.V., Dat, N.T., Cai, X.F., Lee, J.J., and Kim, Y.H. (2003) Two New Phenylpropanoid Glycosides from the Stem Bark of Acanthopanax trifoliatus, Arch. Pharm. Res. 26, 1014–1017.
Miyazawa, M. (2001) Biotransformation of Lignans and Neolignans, Curr. Org. Chem. 5, 975–986.
Ramos, A.C., De Clairac, R.P.L., and Medarde, M. (1999) Heterolignans, Heterocycles 51, 1443–1469.
Damayanthi, Y., and Lown, J.W. (1998) Podophyllotoxins: Current Status and Recent Developments, Curr. Med. Chem. 5, 205–252.
Begum, A.N., Nicolle, C., Mila, I., Lapierre, C., Nagano, K., Fukushima, K., Heinonen, S., Adlercreutz, H., Remesy, C., and Scalbert, A. (2004) Dietary Lignins Are Precursors of Mammalian Lignans in Rats, J. Nutr. 134, 120–127.
Wang, L.Q. (2002) Mammalian Phytoestrogens: Enterodiol and Enterolactone, J. Chromatogr. B 777, 289–309.
Qu, H.Y., Madl, R.L., Takemoto, D.J., Baybutt, R.C., and Wang, W.Q. (2005) Lignans Are Involved in the Antitumor Activity of Wheat Bran in Colon Cancer SW480 Cells, J. Nutr. 135, 598–602.
Ranich, T., Bhathena, S.J., and Velasquez, M.T. (2001) Protective Effects of Dietary Phytoestrogens in Chronic Renal Disease, J. Ren. Nutr. 11, 183–193.
Kitts, D.D., Yuan, Y.V., Wijewickreme, A.N., and Thompson, L.U. (1999) Antioxidant Activity of the Flaxseed Lignan Secoisolariciresinol Diglycoside and Its Mammalian Lignan Metabolites Enterodiol and Enterolactone, Mol. Cell. Biochem. 202, 91–100.
Yahara, S., Nakazono, M., Tutumi, H., and Nohara, T. (1992) Lignans from Leaves of Laurus nobilis L, Shoyakugaku Zasshi 46, 184–186.
Yuan, Z., Tezuka, Y., Fan, W., Kadota, S., and Li, X. (2002) Constituents of the Underground Parts of Glehnia littoralis, Chem. Pharm. Bull. (Tokyo) 50, 73–77.
Min, B.-S., Na, M.-K., Oh, S.-R., Ahn, K.-S., Jeong, G.-S., Li, G., Lee, S.-K., Joung, H., and Lee, H.-K. (2004) New Furofuran and Butyrolactone Lignans with Antioxidant Activity from the Stem Bark of Styrax japonica, J. Nat. Prod. 67, 1980–1984.
Tan, X.Q., Chen, H.-S., Liu, R.-H., Tan, C.-H., Xu, C.-L., Xuan, W.-D., and Zhang, W.-D. (2005) Lignans from Trachelospermum jasminoides, Planta Med. 71, 93–95.
Tanaka, T., Ikeda, T., Kaku, M., Zhu, X.-H., Okawa, M., Yokomizo, K., Uyeda, M., and Nohara, T. (2004) A New Lignan Glycoside and Phenylethanoid Glycosides from Strobilanthes cusia Bremek, Chem. Pharm. Bull. 52, 1242–1245.
Kraft, C., Jenett-Siems, K., Kohler, I., Tofern-Reblin, B., Siems, K., Bienzle, U., and Eich, E. (2002) Antiplasmodial Activity of Sesquilignans and Sesquineolignans from Bonamia spectabilis, Phytochemistry 60, 167–173.
Su, B., Zhu, Q., Gao, K., Yuan, C., and Jia, Z. (1999) Lignan and Phenylpropanoid Glycosides from Lancea tibetica and Their Antitumor Activity, Planta Med. 65, 558–561.
Kuriyama, K., Tsuchiya, K., and Murui, T. (1995) Generation of New Lignan Glucosides During Germination of Sesame Seeds, Nippon Nogeikagaku Kaishi 69, 685–693.
Haensel, R., Schulz, H., and Leuckert, C. (1964) The Lignane Glycoside Arctiin as a Chemotaxonomic Characteristic in the Compositae Family, Z. Naturforsch B 19, 727–734.
Jang, Y.P., Kim, S.R., and Kim, Y.C. (2001) Neuroprotective Dibenzylbutyrolactone Lignans of Torreya nucifera, Planta Med. 67, 470–472.
Wang, C.Z., and Jia, Z.J. (1996) Neolignan Glucosides from Pedicularis torta, Chin. Chem. Lett. 7, 145–148.
Wang, C., and Jia, Z. (1997) Lignan, Phenylpropanoid and Iridoid Glycosides from Pedicularis torta, Phytochemistry 45, 159–166.
El Gamal, A.A., Takeya, K., Itokawa, H., Halim, A.F., Amer, M.M., and Saad, H.-E.A. (1997) Lignan Bis-glucosides from Galium sinaicum, Phytochemistry 45, 597–600.
Morikawa, T., Sun, B., Matsuda, H., Wu, L.J., Harima, S., and Yoshikawa, M. (2004) Bioactive Constituents from Chinese Natural Medicines. XIV. New Glycosides of β-Carboline-Type Alkaloid, Neolignan, and Phenylpropanoid from Stellaria dichotoma L. var. lanceolata and Their Antiallergic Activities, Chem. Pharm. Bull. (Tokyo) 52, 1194–1199.
Lee, I.G.,Lee, S.J., Yoo, I.D., Yoo, I.J., and Yoon, B.S. (2001) Novel Lignan Glycoside Having Inhibition Activity of Lipid Peroxidation, Korean Patent KR 2001002647.
Kawagishi, S., Oosawa, T., and Katsuzaki, H. (1994) Pinoresinol Glycoside, Sesame Seed Extract Containing the Glycoside, and Its Use for Preventing Oxidation of Lipids, Japanese Patent JP 06116282, 5 pp.
Katsuzaki, H., Kawakishi, S., and Osawa, T. (1993) Structure of Novel Antioxidative Lignan Triglucoside Isolated from Sesame Seed, Heterocycles 36, 933–936.
Hou, C.C., Lin, S.J., Cheng, J.T., and Hsu, F.L. (2003) Antidiabetic Dimeric Guianolides and a Lignan Glycoside from Lactuca indica, J. Nat. Prod. 66, 625–629.
Cho, J.Y., Kim, A.R., and Park, M.H. (2001) Lignans from the Rhizomes of Coptis japonica Differentially Act as Anti-inflammatory Principles, Planta Med. 67, 312–316.
Ward, R.S. (1999) Lignans, Neolignans and Related Compounds, Nat. Prod. Rep. 16, 75–96.
Zainullin, R.A., Kukovinets, O.S., Kunakova, R.V., and Tolstikov, G.A. (2001) Naphthalene Oxidation and Reduction Reactions: A Review, Petroleum Chem. (Russia) 41, 143–158.
Simon, M.A., Bonner, J.S., McDonald, T.J., and Autenrieth, R.L. (1999) Bioaugementation for the Enhanced Bioremediation of Petroleum in a Wetland, Polycyc. Aromat. Comp. 14, 231–239.
Bode, H.B., Wegner, B., and Zeeck, A. (2000) Biosynthesis of Cladospirone Bisepoxide, a Member of the Spirobisnaphthalene Family, J. Antibiot. 53, 153–157.
Watanabe, A., and Ebizuka, Y. (2002) A Novel Hexaketide Naphthalene Synthesized by a Chimeric Polyketide Synthase Composed of Fungal Pentaketide and Heptaketide Synthases, Tetrahedron Lett. 43, 843–846.
Davis, P.H. (1988) Flora of Turkey and the East Aegean Islands, University Press, Edinburgh, United Kingdom.
Kuruüzüm, A., Demirezer, L.Ö., Bergère, I., and Zeeck, A. (2001) Two New Chlorinated Naphthalene Glycosides from Rumex patentia, J. Nat. Prod. 64, 688–690.
Cichewicz, R.H., and Nair, M.G. (2002) Isolation and Characterization of Stelladerol, a New Antioxidant Naphthalene Glycoside, and Other Antioxidant Glycosides from Edible Daylily (Hemerocallis) Flowers, J. Agric. Food Chem. 50, 87–91.
Demirezer, Ö., Kuruüzüm, A., Bergere, I., Schiewe, H.J., and Zeeck, A. (2001) Five Naphthalene Glycosides from the Roots of Rumex patientia, Phytochemistry 56, 399–402.
Choi, J.S., Jung, J.H., Lee, H.J., Lee, J.H., and Kang, S.S. (1995) A Naphthalene Glycoside from Cassia tora, Phytochemistry 40, 997–999.
Cichewicz, R.H., Lim, K.C., McKerrow, J.H., and Nair, M.G. (2002) Kwanzoquinones A-G and Other Constituents of Hemerocallis fulva ‘Kwanzo’ Roots and Their Activity Against the Human Pathogenic Trematode Schistosoma mansoni, Tetrahedron 58, 8597–8606.
Pathak, A., Kulshreshtha, D.K., and Maurya, R. (2004) Coumaroyl Triterpene Lactone, Phenolic and Naphthalene Glycoside from Stem Bark of Diospyros angustifolia, Phytochemistry 65, 2153–2158.
Wessels, P.L., Holzapfel, C.W., van Wyk, B.-E., and Marais, W. (1996) Plicataloside, an O,O-Diglycosylated Naphthalene Derivative from Aloe plicatilis, Phytochemistry 41, 1547–1551.
Cai, L., Wei, G.-X., Van der Bijl, P., and Wu, C.D. (2000) Namibian Chewing Stick, Diospyros lycioides, Contains Antibacterial Compounds Against Oral Pathogens, J. Agric. Food Chem. 48, 909–914.
Rauwald, H.W., and Just, H.D. (1983) Study of the Constituents of Buckthorn Cortex. III. A New Lactonic Naphthalene Glycoside from the Cortex of Rhamnus catharticus L, Arch. Pharm. (Weinheim) 316, 409–412.
Lin, C.N., and Wei, B.L. (1994) The Constituents of Formosan Rhamnus Species. 8. Flavonol and Naphthalene Glycosides from Rhamnus nakaharai, J. Nat. Prod. 57, 294–297.
Lemli, J., Toppet, S., Cuveele, J., and Janssen, G. (1981) Naphthalene Glycosides in Cassia senna and Cassia angustifolia. Studies in the Field of Drugs Containing Anthracene Derivatives. XXXII, Planta Med. 43, 11–17.
Liou, M.-J., Teng, C.-M., and Wu, T.-S. (2002) Constituents from Rubia ustulata Diels and R. yunnanensis Diels and Their Antiplatelet Aggregation Activity, J. Chin. Chem. Soc. (Taipei) 49, 1025–1030.
Auvray, P., Bichat, F., and Genne, P. (2000) Preclinical Evaluation of Aromatase Inhibitors Antitumor Activity, Bull. Cancer 87, 7–22.
Sendelbach, L.E. (1989) A Review of the Toxicity and Carcinogenicity of Anthraquinone Derivatives, Toxicology 57, 227–240.
Sissi, C., and Palumbo, M. (2004) Antitumor Potential of Azabioisosterism in Anthracenedione-Based Drugs, Curr. Top. Med. Chem. 4, 219–230.
De Witte, P. (1993) Metabolism and Pharmacokinetics of Anthranoids, Pharmacology 47 (Suppl. 1), 86–97.
Franz, G. (1993) The Senna Drug and Its Chemistry, Pharmacology 47 (Suppl. 1), 2–6.
Koyama, J., Morita, I., Kawanishi, K., Tagahara, K., and Kobayashi, N. (2003) Capillary Electrophoresis for Simultaneous Determination of Emodin, Chrysophanol, and Their 8-β-d-Glucosides, Chem. Pharm. Bull. (Tokyo) 51, 418–420.
Yin, J., and Guo, L. (1993) Modern Study of Chinese Drugs and Clinical Applications, Xueyuan Press, Beijing, China (in Chinese).
Frew, T., Powis, G., Berggren, M., Abraham, R.T., Ashendel, C.L., Zalkow, L.H., Hudson, C., Qazia, S., Gruszecka-Kowalik, E., and Merriman, R. (1994) A Multiwell Assay for Inhibitors of Phosphatidylinositol-3-kinase and the Identification of Natural Product Inhibitors, Anticancer Res. 14, 2425–2458.
Krenn, L., Presser, A., Pradhan, R., Bahr, B., Paper, D.H., Mayer, K.K., and Kopp, B. (2003) Sulfemodin 8-O-β-d-Glucoside, a New Sulfated Anthraquinone Glycoside, and Antioxidant Phenolic Compounds from Rheum emodi, J. Nat. Prod. 66, 1107–1109.
Koyama, J., Morita, I., Fujiyoshi, H., and Kobayashi, N. (2005) Simultaneous Determination of Anthraquinones, Their 8-β-d-Glucosides, and Sennosides of Rhei rhizoma by Capillary Electrophoresis, Chem. Pharm. Bull. (Tokyo) 53, 573–575.
Van Gorkom, B.A.P., Vries, E.G.E., Karrenbeld, A., and Kleibeuker, J.H. (1999) Review Article: Anthranoid Laxatives and Their Potential Carcinogenic Effects, Aliment. Pharmacol. Therapeut. 13, 443–452.
Newall, C.A., Anderson, L.A., and Phillipson, J.D. (1996) Herbal Medicines: A Guide for Health Care Professionals, The Pharmaceutical Press, London.
Wichtl, M., and Bisset, N.G. (eds., English transl. by Bisset, N.G.) (1994) Rhamni purshiani Cortex—Cascara Bark, in Herbal Drugs and Phytopharmaceuticals, pp. 90–91, CRC Press, Stuttgart.
Van Os, F.H. (1976) Anthraquinone Derivatives in Vegetable Laxatives, Pharmacology 14 (Suppl. 1), 7–17.
Che, Q.M., Akao, T., Hattori, M., Tsuda, Y., Namba, T., and Kobashi, K. (1991) Barbaloin Stimulates Growth of Eubacterium sp. Strain BAR, a Barbaloin-Metabolizing Bacterium from Human Feces, Chem. Pharm. Bull. (Tokyo) 39, 757–760.
Alves, D.S., Perez-Fons, L., Estepa, A., and Micol, V. (2004) Membrane-Related Effects Underlying the Biological Activity of the Anthraquinones Emodin and Barbaloin, Biochem. Pharmacol. 68, 549–561.
Hernandez-Medel, M.R., and Pereda-Miranda, R. (2002) Cytotoxic Anthraquinone Derivatives from Picramnia antidesma, Planta Med. 68, 556–558.
Qhotsokoane-Lusunzi, M.A., and Karuso, P. (2001) Secondary Metabolites from Basotho Medicinal Plants. II, Bulbine capitata, Aust. J. Chem. 54, 427–430.
Palm, C., Bjork, O., Bjorkholm, M., and Eksborg, S. (2001) Quantification of Doxorubicin in Plasma—A Comparative Study of Capillary and Venous Blood Sampling, Anticancer Drugs 12, 859–864.
Demirezer, L.O., Kuruuzum-Uz, A., Bergere, I., Schiewe, H.-J., and Zeeck, A. (2001) The Structures of Antioxidant and Cytotoxic Agents from Natural Source: Anthraquinones and Tannins from Roots of Rumex patientia, Phytochemistry 58, 1213–1217.
Qhotsokoane-Lusunzi, M.A., and Karuso, P. (2001) Secondary Metabolites from Basotho Medicinal Plants. I. Bulbine narcisifolia, J. Nat. Prod. 64, 1368–1372.
Tunman, T. (1907) Alder Buckthorn Bark and Its Glucoside, Chem. Zentralbl. (Germany) 48, 99–103.
Schmidt, E. (1909) Contributions on the Rhamnosides, Arch. Pharm. (Germany) 246, 214–224.
Krasovskii, N. (1913) Rhamnoxanthin from Rhamnus cathartica and Frangulin from Rhamnus frangula, Zh. Russ. Fiziko-Khim, Obshchest. (Russia) 45, 188–193.
Koch, W. (2001) Studies on Biologically Active Substances of Hypericum L. Species, Farmatsevt. Zh. (Kiev) 4, 50–55.
Muhlemann, H. (1955) Anthraquinone and Anthraquinine Glycosides. XVII, Pharm. Acta Helv. 30, 350–355.
Francis, G.W., Aksnes, D.W., and Holt, O. (1998) Assignment of the 1H and 13C NMR Spectra of Anthraquinone Glycosides from Rhamnus frangula, Magnet. Reson. Chem. 36, 769–772.
Chung, M.I., Gan, K.H., Lin, C.N., Ko, F.N., and Teng, C.M. (1993) Antiplatelet Effects and Vasorelaxing Action of Some Constituents of Formosan Plants, J. Nat. Prod. 56, 929–934.
Wei, B.L., Lu, C.M., Tsao, L.T., Wang, J.P., and Lin, C.N. (2001) In vitro Anti-inflammatory Effects of Quercetin 3-O-Methyl Ether and Other Constituents from Rhamnus Species, Planta Med. 67, 745–747.
Uesato, S., Tokunaga, T., and Takeuchi, K. (1998) Novel Angucycline Compound with Both Antigastrin and Gastric Mucosal Protective Activities, Bioorg. Med. Chem. Lett. 8, 1969–1972.
Drautz, H., Zahner, H., Rohr, J., and Zeeck, A. (1986) Metabolic Products of Microorganisms. 234. Urdamycins, New Angucycline Antibiotics from Streptomyces fradiae. I. Isolation, Characterization and Biological Properties, J. Antibiol. 39, 1657–1669.
Rohr, J., and Zeeck, A. (1987) Metabolic Products of Microorganisms. 240. Urdamycins, New Angucycline Antibiotics from Streptomyces fradiae. II. Structural Studies of Urdamycins B to F, J. Antibiot. 40, 459–467.
Henkel, T., Rohr, J., Beale, J.M., and Schwenen, L. (1990) Landomycins, New Angucycline Antibiotics from Streptomyces sp. I. Structural Studies on Landomycins A-D, J. Antibiot. 43, 492–503.
Matseliukh, B.P., Konovalova, T.A., Polishchuk, L.V., and Bambura, O.I. (1998) The Sensitivity to Landomycins A and E of streptomycetes, Producers of Polyketide Antibiotics, Mikrobiol. Zh. (Kiev) 60, 31–36.
Liu, H.-W., Sherman, D.H., and Zhao, L. (2002) Recombinant Bacteria Producing Substances with Altered Sugar Moieties and Their Use for Production of These Substances, U.S. Patent Application A2 20020411, 174 pp.
Ishimaru, T., Kanamaru, T., Takahashi, T., Ohta, K., and Okazaki, H. (1982) Inhibition of Prolyl Hydroxylase Activity and Collagen Biosynthesis by the Anthraquinone Glycoside, P-1894B, an Inhibitor Produced by Streptomyces albogriseolus, Biochem. Pharmacol. 31, 915–919.
Bechthold, A., Domann, S., Faust, B., Hoffmeister, D., Stockert, S., Trefzer, A., Weitnauer, G., and Westrich, L. (1999) Glycosylated Natural Products: Perspectives for Combinatorial Biosynthesis, Chemother. J. 8, 130–135.
Singh R., Geetanjali, Chuhan SMS. (2004) 9,10-Anthraquinones and Other Biologically Active Compounds from the Genus Rubia, Chem. Biodiver. 1, 1241–1264.
Krenn, L., Pradhan, R., Presser, A., Reznicek, G., and Kopp, B. (2004) Anthrone C-Glucosides from Rheum emodi, Chem. Pharm. Bull. (Tokyo) 52, 391–393.
Muhlemann, H. (1949) Anthraquinone and Anthraquinone Glycoside. VI. Anthrone and Anthranol Glycosides, Pharm. Acta Helv. 24, 343–351.
Fairbairn, J.W. (1949) Active Constituents of Vegetable Purgatives Containing Anthracene Derivatives. I. Glycosides and Aglycones, J. Pharm. Pharmacol. 1, 683–692.
Author information
Authors and Affiliations
Corresponding author
Additional information
For the previous article in this series, see Reference 1.
About this article
Cite this article
Dembitsky, V.M. Astonishing diversity of natural surfactants: 5. Biologically active glycosides of aromatic metabolites. Lipids 40, 869–900 (2005). https://doi.org/10.1007/s11745-005-1449-2
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/s11745-005-1449-2