Abstract
The demand for new alternative “low calorie” sweeteners for dietetic and diabetic purposes has increased worldwide. Although the currently developed and commercially used highly sweet sucrose substitutes are mostly synthetic compounds, the search for such compounds from natural sources is continuing. As of mid-2002, over 100 plant-derived sweet compounds of 20 major structural types had been reported, and were isolated from more than 25 different families of green plants. Several of these highly sweet natural products are marketed as sweeteners or flavoring agents in some countries as pure compounds, compound mixtures, or refined extracts. These highly sweet natural substances are reviewed herein.
Similar content being viewed by others
References
Anonymous, FDA approves new sweetener.Chem. Eng. News, July 15, 30 (2002).
Amoldi, A., Bassoli, A., Borgonovo, G. and Merlini, L., Synthesis and sweet taste of optically active (-)-haematoxylin and of some (±)-haematoxylin derivatives.J. Chem. Soc., Perkin Trans. 1, 2447–2453 (1995).
Auerbach, M. H., Locke, G. and Hendrick, M. E., Alitame. In O’Brien Nabors, L. (Ed.).Alternative Sweeteners: Third Edition, Revised and Expanded. Marcel Dekker, New York, pp. 31–40 (2001).
Ayafor, J. F. and Connolly, J. D., 2R,3R-(+)-Acetoxy-4’,5-dihydr-oxy-7-methoxyflavanone and 2R,3R-(+)-acetoxy-4’,5,7-trihydr-oxyflavonone: two new 3-acetylated dihydroflavonols fromAframomum pruinosum Gagnepain (Zingiberaceae).J. Chem. Soc, Perkin Trans. 1, 1750–1754 (1981).
Baek, N.-I., Chung, M.-S., Shamon, L., Kardono, L. B. S., Tsauri, S., Padmawinata, K., Pezzuto, J. M., Soejarto, D. D. and Kinghorn, A. D., Selligueain A, a novel highly sweet proanthocyanidin from the rhizomes ofSelliguea feei. J. Nat. Prod., 56, 1532–1538 (1993).
Baek, N.-I., Kennelly, E. J., Kardono, L. B. S., Tsauri, S., Padmawinata, K., Soejarto, D. D. and Kinghorn, A. D., Flavonoids and a proanthocyanidin from rhizomes o.Selliguea feei. Phytochemistry, 36, 513–518 (1994).
Bassoli, A., Borgonovo, G., Merlini, L. and Morini, G. Design and synthesis of taste active monatin analogues. 2nd IUPAC-International Symposium on Sweeteners, Hiroshima, Japan, November 13–17, 2001, Abstract P-15.
Bassoli, A., Merlini, L. and Morini, G., Isovanillyl sweeteners. From molecules to receptors.Pure Appl. Chem., 74, 1181–1187 (2002).
Bopp, B. A. and Price, P., Cyclamate. In O’Brien Nabors, L. (Ed.).Alternative Sweeteners: Third Edition, Revised and Expanded. Marcel Dekker, New York, pp. 63–85 (2001).
Borrego, F. and Montijano, H., Neohesperidin dihydrochalcone. In O’Brien Nabors, L. (Ed.).Alternative Sweeteners: Third Edition, Revised and Expanded. Marcel Dekker, New York, pp. 87–104 (2001).
Butchko, H. H., Stargel, W. W., Comer, C. P., Mayhew, D. A. and Andress, S. E., Aspartame. In O’Brien Nabors, L. (Ed.).Alternative Sweeteners: Third Edition, Revised and Expanded. Marcel Dekker, New York, pp. 41–61 (2001).
Choi, Y.-H., Hussain, R. A., Pezzuto, J. M., Kinghorn, A. D. and Morton, J. F.,Abrusosides A-D, four novel sweet-tasting triterpene glycosides from the leaves ofAbrus precatorius. J. Nat. Prod., 52, 1118–1127 (1989a).
Choi, Y.-H., Kinghorn, A. D., Shi, Z., Zhang, H. and Teo, B. K., Abrusoside A: a new type of highly sweet triterpene glycoside. J. Chem. Soc., Chem. Commun., 887–888 (1989b).
Chung, M.-S., Kim, N.-C., Long, L., Shamon, L., Ahmad, W.-Y., Sagrero-Nieves, L., Kardono, L. B. S., Kennelly, E. J., Pezzuto, J. M., Soejarto, D. D. and Kinghorn, A. D., Dere-plication of saccharide and polyol constituents of candidate sweet-tasting plants: isolation of the sesquiterpene glycoside mukurozioside lib as a sweet principle o.Sapindus rarak. Phytochem. Anal., 8, 49–54 (1997).
Dalton, L., Licorice. Root is used worldwide as a flavor and a medicine.Chem. Eng. News, August 12, 37 (2002).
de Klerk, G. J., Nieuwenhuis, M. G. and Beutler, J. J., Lesson of the week: hypokalaemia and hypertension associated with use of liquorice flavoured chewing gum.BMJ, 314, 731–732 (1997).
DeRider, M. L., Kuloglu, E. S., Abildgaard, F., Aceti, D. J., Assadi-Porter, F B., West-Nielsen, M. and Markley, J. L. Brazzein, a potential low-calorie protein sweetener: high-resolution solution structure of the protein determined from multi-dimensional, multi-nuclear magnetic resonance spectroscopy. 2nd IUPAC-International Symposium on Sweeteners, Hiroshima, Japan, November 13–17, 2001, Abstract PL-08.
DuBois, G. E., Nonnutritive sweeteners.Annu. Rep. Med. Chem., 17, 323–332 (1982).
DuBois, G. E., Bunes, L. A., Dietrich, P. S. and Stephenson, R. A., Diterpenoid sweeteners. Synthesis and sensory evaluation of biologically stable analogues of stevioside.J. Agric. Food Chem., 32, 1321–1325 (1984).
Duffy, V. B. and Anderson, G. H., Position of the American Dietetic Association: use of nutritive and nonnutritive sweeteners.J. Am. Diet. Assoc., 98, 580–587 (1998).
Esaki, S., Tanaka, R. and Kamiya, S., Synthesis and taste of certain steviol glycosides.Agric. Biol. Chem., 48, 1831–1834 (1984).
Fenwick, G. R., Lutomski, J. and Nieman, C., Liquorice.Gly-cyrrhiza glabra L. - composition, uses, and analysis.Food Chem., 38, 119–143 (1990).
Fischer, C. M., Harper, H. J., Henry Jr., W. J., Mohlenkamp Jr., M. J., Romer, K. and Swaine Jr., R. L. (1994). Sweet beverages and sweetener compositions, PCT patent application, WO94-US1690, Feb. 14, 1994.
Fukunaga, Y., Miyata, T., Nakayasu, N., Mizutani, K., Kasai, R. and Tanaka, O., Enzymatic transglucosylation products of stevioside: separation and sweetness evaluation.Agric. Biol. Chem., 53, 1603–1607 (1989).
Fullas, F., Choi, Y.-H., Kinghorn, A. D. and Bunyapraphatsara, N., Sweet-tasting triterpene glycoside constituents o.Abrus fruticulosus. Planta Med., 56, 332–333 (1990).
Fullas, F., Hussain, R. A., Bordas, E., Pezzuto, J. M., Soejarto, D. D. and Kinghorn, A. D., Gaudichaudiosides A-E, five novel diterpene glycoside constituents from the sweet-tasting plant, Bacchahs gaudichaudiana.Tetrahedron, 47, 8515–8522 (1991).
Gao, F., Wang, H., Mabry, T. J. and Kinghorn, A. D., Dihydroflavonol sweeteners and other constituents fro.Hymenoxys turneri. Phytochemistry, 29, 2865–2869 (1990).
Gibbs, B. F., Alli, I. and Mulligan, C., Sweet and taste-modifying proteins: a review.Nutr. Res. (N. Y), 16, 1619–1630 (1996).
Goldsmith, L. A. and Merkel, C. M., Sucralose. In O’Brien Nabors, L. (Ed.).Alternative Sweeteners: Third Edition, Revised and Expanded. Marcel Dekker, New York, pp. 185–207 (2001).
Grenby, T. H., Prospects for sugar substitutes.Chem. Br., 27, 342–345 (1991).
Hirono, S., Chou, W.-H., Kasai, R., Tanaka, O. and Tada, T., Sweet and bitter diterpene-glucosides from leaves o.Rubus suavissimus.Chem. Pharm. Bull., 38, 1743–1744 (1990).
Hu, Z. and He, M., Studies on mabinlin, a sweet protein from the seeds o.Capparis masaikai Levl. I. Extraction, purification and some characteristics.Yunnan Zhiwu Yanjiu, 5, 207–212 (1991).
Huan, V. D., Ohtani, K., Kasai, R., Yamasaki, K. and Tuu, N. V., Sweet pregnane glycosides fro.Telosma procumbens.Chem. Pharm. Bull., 49, 453–460 (2001).
Hussain, R. A., Lin, Y.-M., Poveda, L. J., Bordas, E., Chung, B. S., Pezzuto, J. M., Soejarto, D. D. and Kinghorn, A. D., Plant-derived sweetening agents: saccharide and polyol constituents of some sweet-tasting plants.J. Ethnopharmacol., 28, 103–115 (1990a).
Hussain, R. A., Poveda, L. J., Pezzuto, J. M., Soejarto, D. D. and Kinghorn, A. D., Sweetening agents of plant origin: phenylpropanoid constituents of seven sweet-tasting plants.Econ. Bot., 44, 174–182 (1990b).
Huxtable, R. J., Pharmacology and toxicology of stevioside, rebaudioside A, and steviol. In Kinghorn, A. D. (Ed.).Stevia: the Genus Stevia. Taylor & Francis, London, pp. 161–177 (2002).
Ishikawa, H., Kitahata, S., Ohtani, K., Ikuhara, C. and Tanaka, O., Production of stevioside and rubusoside derivatives by transfructosylation of β-fructofuranosidase.Agric. Biol. Chem., 54, 3137–3143 (1990).
Kamiya, S., Konishi, F. and Esaki, S., Synthesis and taste of some analogs of stevioside.Agric. Biol. Chem., 43, 3553–3557 (1979).
Kaneda, N., Kasai, R., Yamasaki, K. and Tanaka, O., Chemical studies on sweet diterpene-glycosides o.Stevia rebaudiana: conversion of stevioside into rebaudioside A.Chem. Pharm. Bull., 25, 2466–2467 (1977).
Kaneda, N., Lee, I.-S., Gupta, M. P., Soejarto, D. D. and Kinghorn, A. D., (+)-4β-Hydroxyhernandulcin, a new sweet sesquiterpene from the leaves and flowers ofLippia dulcis. J. Nat. Prod., 55, 1136–1141 (1992).
Kasai, R., Fujino, H., Kuzuki, T., Wong, W.-H., Goto, C., Yata, N., Tanaka, O., Yasuhara, F. and Yamaguchi, S., Acyclic sesquiterpene oligosaccharides from pericarps o.Sapindus mukurossi.Phytochemistry, 25, 871–876 (1986).
Kasai, R., Hirono, S., Chou, W.-H., Tanaka, O. and Chen, F.-H., Sweet dihydroflavonol rhamnoside from leaves o.Engelhardtia chrysolepis, a Chinese folk medicine, Huang-qi.Chem. Pharm. Bull., 36, 4167–4170 (1988a).
Kasai, R., Hirono, S., Chou, W.-H., Tanaka, O. and Chen, F.-H., An additional sweet dihydroflavonol glycoside from leaves o. Engelhardtia chrysolepis, a Chinese folk medicine, Huang-qi.Chem. Pharm. Bull., 39, 1871–1872 (1991).
Kasai, R., Matsumoto, K., Nie, R. L., Zhou, J. and Tanaka, O., Glycosides from Chinese medicinal plants.Hemsleya panacisscandens, and structure-taste relationship of cucurbitane glycosides.Chem. Pharm. Bull., 36, 234–243 (1988b).
Kasai, R., Nie, R.-L., Nashi, K., Ohtani, K., Zhou, J., Tao, G.-D. and Tanaka, O., Sweet cucurbitane glycosides from fruits o.Siraitia siamensis (“hi-zi lou-han-kuo”).Agric. Biol. Chem., 53, 3347–3349 (1989).
Kennelly, E. J., Cai, L., Kim, N.-C. and Kinghorn, A. D., Abrusoside E., a further sweet-tasting cycloartane glycoside from the leaves ofAbrus precatorius.Phytochemistry, 41, 1381–1383 (1996a).
Kennelly, E. J., Cai, L., Long, L., Shamon, L., Zaw, K., Zhou, B.- N., Pezzuto, J. M. and Kinghorn, A. D., Novel highly sweet secodammarane glycosides fro.Pterocarya paliurus.J. Agric. Food Chem., 43, 2602–2607 (1995).
Kennelly, E. J., Suttisri, R. and Kinghorn, A. D., Novel sweet-tasting saponins of the cycloartane, oleanane, secodammarane, and steroidal types. In Waller, G. R. and Yamasaki, K. (Eds.).Saponins Used in Food and Agriculture. Plenum Press, New York, pp. 13–24 (1996b).
Kim, J., Choi, Y. H. and Choi, Y.-H., Use of stevioside and cultivation ofStevia rebaudiana in Korea. In Kinghorn, A. D. (Ed.).Stevia: the Genus Stevia. Taylor & Francis, London, pp. 196–202 (2002).
Kim, J. and Kinghorn, A. D., Further steroidal and flavonoid constituents of the sweet plant, Polypodium glycyrrhiza.Phytochemistry, 28, 4, 1225–1228 (1989).
Kim, J., Pezzuto, J. M., Soejarto, D. D., Lang, F. A. and Kinghom, A. D., Polypodoside A, an intensely sweet constituent of the rhizomes ofPolypodium glycyrrhiza.J. Nat. Prod., 51, 1166–1172 (1988).
Kim, J. H., Lim, H. J. and Cheon, S. H., Synthesis of (-)-hernan-dulcin and (+)-hemandulcin.Tetrahedron Lett., 43, 4721–4722 (2002).
Kim, N.-C., Kim, D. S. H. L. and Kinghorn, A. D., New triter-penoids from the leaves o.Abrus precatorius.Nat. Prod. Left., 16, 261–266 (2002).
Kim, N.-C., Kinghorn, A. D. and Kim, D. S. H. L., Semisynthesis of abrusoside A methyl ester.Org. Lett., 1, 223–224 (1999).
Kinghorn, A. D., Overview. In Kinghorn, A. D. (Ed.).Stevia: the Genus Stevia. Taylor & Francis, London, pp. 1–17 (2002).
Kinghorn, A. D. and Compadre, C. M., Less common high-potency sweeteners. In O’Brien Nabors, L. (Ed.).Alternative Sweeteners: Third Edition, Revised and Expanded. Marcel Dekker, New York, pp. 209–233 (2001).
Kinghorn, A. D., Fullas, F. and Hussain, R. A., Structure-activity relationships of highly sweet natural products. In Atta-ur-Rahman (Ed.).Studies in Natural Product Chemistry. Elsevier Science Publishers, Amsterdam, pp. 3–41 (1995).
Kinghorn, A. D., Kaneda, N., Baek, N.-I., Kennelly, E. J. and Soejarto, D. D., Noncariogenic intense natural sweeteners.Med. Res. Rev., 18, 347–360 (1998).
Kinghorn, A. D. and Kennelly, E. J., Discovery of highly sweet compounds from natural sources.J. Chem. Educ., 72, 676–680 (1995).
Kinghorn, A. D., Kim, N.-C. and Kim, D. S. H. L., Terpenoid glycoside sweeteners. In Ikan, R. (Ed.).Naturally Occurring Glycosides: Chemistry, Distribution and Biological Properties. John Wiley and Sons, Chichester, U.K., pp. 399–429 (1999).
Kinghorn, A. D. and Soejarto, D. D., Sweetening agents of plant origin.CRC Crit. Rev. Plant Sci., 4, 79–120 (1986).
Kinghorn, A. D. and Soejarto, D. D., Intensely sweet compounds of natural origin.Med. Res. Rev., 9, 91–115 (1989).
Kinghorn, A. D. and Soejarto, D. D., Discovery of terpenoid and phenolic sweeteners from plants.Pure Appl. Chem., 74, 1169–1179 (2002).
Kinghorn, A. D., Wu, C. D. and Soejarto, D. D., Stevioside. In O’Brien Nabors, L. (Ed.).Alternative Sweeteners: Third Edition, Revised and Expanded. Marcel Dekker, New York, pp. 167–183 (2001).
Kinjo, J. and Nohara, T., Hepatoprotective oleanane glucuronides in Fabaceae. In Ageta, H., Aimi, N., Ebizuka, Y., Fujita, T. and Honda, G. (Eds.).Towards Natural Medicine Research in the 21st Century. Elsevier, Amsterdam, pp. 237–248 (1998).
Kitagawa, I., Licorice root. A natural sweetener and an important ingredient in Chinese medicine.Pure Appl. Chem., 74, 1189–1198 (2002).
Kitagawa, I., Sakagami, M., Hashiuchi, F., Zhou, J. L., Yoshikawa, M. and Ren, J., Apioglycyrrhizin and araboglycyrrhizin, two new sweet oleanane-type triterpene oligoglycosides from the root o. Glycyrrhiza inflata.Chem. Pharm. Bull., 37, 551–553 (1989).
Ko, T.-P., Day, J., Greenwood, A. and McPherson, A., Structures of three crystal forms of the sweet protein thaumatin.Acta Crystallogr.D. Biol. Crystallogr., 50D, 813–825 (1994).
Kohda, H., Kasai, R., Yamasaki, K., Murakami, K. and Tanaka, O., New sweet diterpene glycosides fro. Stevia rebaudiana.Phytochemistry, 15, 981–983 (1976).
Kohmura, M. and Ariyoshi, Y., Chemical synthesis and characterization of the sweet protein mabinlin II.Biopolymers, 46, 215–223 (1998).
Kohmura, M., Mizukoshi, T., Nio, N., Suzuki, E.-I. and Ariyoshi, Y., Structure-taste relationships of the sweet protein monellin.Pure Appl. Chem., 74, 1235–1242 (2002).
Kohmura, M., Ota, M., Izawa, H., Ming, D., Hellekant, G. and Ariyoshi, Y., Assignment of the disulfide bonds in the sweet protein brazzein.Biopolymers, 38, 553–556 (1996).
Konoshima, T. and Takasaki, M., Cancer-chemopreventive effects of natural sweeteners and related compounds.Pure Appl. Chem., 74, 1309–1316 (2002).
Koyama, E., Kitazawa, K., Ohori, Y., Sakai, N., Izawa, O., Kakegawa, K., Fujino, A. and Ui, M. Intestinal degradation, absorption, and hepatic metabolism of the glycosidic sweeteners, Stevia mixtures. 2nd IUPAC-International Symposium on Sweeteners, Hiroshima, Japan, 2001, Abstract P-12.
Kubo, H., Ohtani, K., Kasai, R., Yamasaki, K., Nie, R.-L. and Tanaka, O., Cucurbitane glycosides fro.Hemsleya panacisscandens rhizomes.Phytochemistry, 41, 1169–1174 (1996).
Kurihara, Y., Characterization of antisweet substance, sweet proteins, and sweetness-inducing proteins.Crit. Rev. Food Sci.Nutr., 32, 231–252 (1992).
Masuda, H., Ohtani, K., Mizutani, K., Ogawa, S., Kasai, R. and Tanaka, O., Chemical study o.Haematoxylon campechianum: a sweet principle and new dibenz[b, d]oxocin derivatives.Chem. Pharm. Bull., 39, 1382–1384 (1991).
Matsui, M., Sofuni, T. and Nohmi, T., Regionally targeted mutagenesis by metabolically-activated steviol; DNA sequence analysis of steviol-induced mutants of guanine phosphori-bosyltransferase (gpt) gene o.Salmonella typhimurium TM677.Mutagenesis, 11, 565–572 (1996).
Matsumoto, K., Kasai, R., Ohtani, K. and Tanaka, O., Minor cucurbitane glycosides from fruits o.Siraitia grosvenori (Cucurbitaceae).Chem. Pharm. Bull., 38, 2030–2032 (1990).
Ming, D. and Hellekant, G., Brazzein, a new high-potency thermostable sweet protein fromPentadiplandra brazzeana B.FEBS Lett., 355, 106–108 (1994).
Mizutani, K., Kambara, T., Masuda, H., Tamura, Y., Ikeda, T., Tanaka, O., Tokuda, H., Nishino, H., Kozuka, M., Konoshima, T. and Takasaki, M., Glycyrrhetic acid monoglucuronide (MGGR): biological activities. In Ageta, H., Aimi, N., Ebizuka, Y., Fujita, T. and Honda, G. (Eds.).Toward Natural Medicine Research in the 21st. Century. Elsevier, Amsterdam, pp. 225–235 (1998).
Mizutani, K., Kuramoto, T., Tamura, Y., Ohtake, N., Doi, S., Nakamura, M. and Tanaka, O., Sweetness of glycyrrhetic acid 3-O-β-D-monoglucuronide and the related glycosides.Biosci. Biotechnol. Biochem., 58, 554–555 (1994).
Mizutani, K., Miyata, T., Kasai, R., Tanaka, O., Ogawa, S. and Doi, S., Study on improvement of sweeteners of steviol bisglycosides: selective enzymatic transglucosylation of the 13-O-glycosyl moiety.Agric. Biol. Chem., 53, 395–398 (1989).
Mizutani, K. and Tanaka, O., Use ofStevia rebaudiana sweeteners in Japan. In Kinghorn, A. D. (Ed).Stevia: the Genus Stevia. Taylor & Francis, London, pp. 178–195 (2002).
Montmayeur, J.-P. and Matsunami, H., Receptors for bitter and sweet taste.Curr. Opin. Neurobiol., 12, 366–371 (2002).
Mori, K. and Kato, M., Synthesis of (6S,1S)-(+)-hemandulcin, a sweetener, and its stereoisomers.Tetrahedron, 42, 5895–5900 (1986).
Morimoto, S., Nonaka, G.-I. and Nishioka, I., Tannins and related compounds. XXXV. Proanthocyanidins with a doubly linked unit from the root bark o.Cinnamomum sieboldii Meisner.Chem. Pharm. Bull., 33, 4338–4345 (1985).
Nakamura, K., Baker, T J. and Goodman, M., The total synthesis of monatin.Org. Lett., 2, 2967–2970 (2000).
Nishizawa, M. and Yamada, H., Intensely sweet saponin osladin: synthetic and structural study. In Waller, G. R. and Yamasaki, K. (Eds.).Saponins Used in Food and Agriculture. Plenum Press, New York, pp. 25–36 (1996).
Nishizawa, M., Yamada, H., Yamaguchi, Y., Hatakeyama, S., Lee, I.-S., Kennelly, E. J., Kim, J. and Kinghorn, A. D., Structure revision of polypodoside A: major sweet principle ofPolypodium glycyrrhiza.Chem. Lett., 1555–1558, 1979 (1994).
O’Brien Nabors, L. (Ed.).Alternative Sweeteners: Third Edition, Revised and Expanded. Marcel Dekker, New York (2001).
Ogata, C. M., Gordon, P. F., De Vos, A. M. and Kim, S.-H., Crystal structure of a sweet-tasting protein, thaumatin, at 1.65 Å resolution.J. Mol. Biol., 228, 893–908 (1992).
Ohtani, K., Aikawa, Y., Kasai, R., Chou, W.-H., Yamasaki, K. and Tanaka, O., Minor diterpene glycosides from sweet leaves o.Rubus suavissimus. Phytochemistry, 31, 1553–1559 (1992).
Ohtani, K. and Yamasaki, K., Methods to improve the taste of the sweet principles ofStevia rebaudiana. In Kinghorn, A. D. (Ed.).Stevia: the Genus Stevia. Taylor & Francis, London, pp. 138–159 (2002).
Oobayashi, K., Yoshikawa, K. and Arihara, S., Structural revision of bryonoside and structure elucidation of minor saponins fro.Bryonia dioica.Phytochemistry, 31, 943–946 (1992).
Pearson, R. L., Saccharin. In O’Brien Nabors, L. (Ed.).Alternative Sweeteners: Third Edition, Revised and Expanded. Marcel Dekker, New York, pp. 147–165 (2001).
Pezzuto, J. M., Compadre, C. M., Swanson, S. M., Nanayakkara, N. P. D. and Kinghorn, A. D., Metabolically activated steviol, the aglycone of stevioside, is mutagenic.Proc. Natl. Acad. Sci. U. S. A., 82, 2478–2482 (1985).
Seewald, N., Replacement. A steady diet of growth of sweeteners and fat substitutes.Chem. Week, June 7, 41 (2000).
Shibasato, M., Current status of Stevia sweeteners and its application.Japan Food Sci., 51–58 (1995).
Shu, R. G., Xu, C. R. and Li, L. N., Studies on the sweet principles from the leaves o.Cyclocarya paliurus (Batal.) Iljinsk.Acta Pharmaceutica Sinica, 30, 757–761 (1995).
Stargel, W. W., Mayhew, D. A., Comer, C. P., Andress, S. E. and Butchko, H. H., Neotame. In O’Brien Nabors, L. (Ed.).Alternative Sweeteners: Third Edition, Revised and Expanded. Marcel Dekker, New York, pp. 129–145 (2001).
Starratt, A. N., Kirby, C. W., Pocs, R. and Brandle, J. E., Rebaudioside F., a diterpene glycoside fromStevia rebaudiana.Phytochemistry, 59, 367–370 (2002).
Subamas, A. and Wagner, H., Analgesic and anti-inflammatory activity of the proanthocyanidin shelligueain A fro. Poly-podium feei METT.Phytomedicine, 7, 401–405 (2000).
Suttisri, R., Chung, M.-S., Kinghorn, A. D., Sticher, O. and Hashimoto, Y., Periandrin V, a further sweet triterpene glycoside fromPeriandra dulcis.Phytochemistry, 34, 405–408 (1993).
Suttisri, R., Lee, I.-S. and Kinghorn, A. D., Plant-derived triterpenoid sweetness inhibitors.J. Ethnopharmacol., 47, 9–26 (1995).
Takemoto, T., Arihara, S., Nakajima, T. and Okuhira, M., Studies on the constituents of Fructus Momordicae. I. On the sweet principle.Yakugaku Zasshi, 103, 1151–1154 (1983a).
Takemoto, T., Arihara, S., Nakajima, T. and Okuhira, M., Studies on the constituents o. Gynostemma pentaphyllum Makino. II. Structures of gypenoside XV-XXI.Yakugaku Zasshi, 103, 1015–1023 (1983b).
Tanaka, N., Orii, R., Ogasa, K., Wada, H., Murakami, T., Sakai, Y. and Chen, CM., Chemical and chemotaxonomical studies of ferns. LXXX. Proanthocyanidins o.Arachniodes sporadosora Nakaike andA. exilis Ching.Chem. Pharm. Bull., 39, 55–59 (1991).
Tanaka, O., Improvement of taste of natural sweeteners.Pure Appl. Chem., 69, 675–683 (1997).
Terai, T., Ren, H., Mori, G., Yamaguchi, Y. and Hayashi, T., Mutagenicity of steviol and its oxidative derivatives i.Salmonella typhimurium TM677.Chem. Pharm. Bull., 50, 1007–1010 (2002).
Toyoda, K., Matsui, H., Shoda, T., Uneyama, C., Takada, K. and Takahashi, M., Assessment of the carcinogenicity of stevioside in F344 rats.Food Chem. Toxicol., 35, 597–603 (1997).
Tsopmo, A., Tchuendem, M. H., Ayafor, J. F., Tillequin, F., Koch, M. and Anke, H., 3-Acetoxy-5,7-dihydroxy-4’-methoxyflavanone, a new cytotoxic dihydroflavanol fromAframomum hanburyi K. Schum.Nat. Prod. Lett., 9, 33–37 (1996).
Van der Wel, H., Isolation and characterization of the sweet principles fro.Dioscoreophyllum cumminsii.FEBS Lett., 21, 88–90 (1972).
Van der Wel, H., Larson, G., Hladik, A., Hladik, C. M., Hellekant, G. and Glaser, D., Isolation and characterization of pentadin, the sweet principle o.Pentadiplandra brazzeana.Chem. Senses, 14, 75–79 (1989).
Van der Wel, H. and Loeve, K., Isolation and characterization of thaumatin I and II, the sweet-tasting proteins fro.Thaumatococcus daniellii.Eur. J. Biochem., 31, 221–225 (1972).
Van Rossum, T. G. J., De Jong, F. H., Hop, W. C. J., Boomsma, F. and Schalm, S. W., “Pseudoaldosteroidism” induced by intravenous glycyrrhizin treatment of chronic hepatitis C patients.Neth. J. Gastroenterol. Hepatol., 16, 789–795 (2001).
Vasaenge, M., Liu, B., Welch, C. J., Rolfsen, W. and Bohlin, L., The flavonoid constituents of two Polypodium species (Calaguala) and their effect on the elastase release in human neutrophils.Planta Med., 63, 511–517 (1997).
Vleggaar, R., Ackerman, L. G. J. and Steyn, R S., Structure elucidation of monatin, a high-intensity sweetener isolated from the plantSchlerochiton ilicifolius.J. Chem. Soc., Perkin Trans. 7, 3095–3098 (1992).
von Rymon Lipinski, G.-W. and Hanger, L. Y., Acesulfame-K. In O’Brien Nabors, L. (Ed.).Alternative Sweeteners: Third Edition, Revised and Expanded. Marcel Dekker, New York, pp. 13–30 (2001).
Walters, D. E., Prakash, I. and Desai, N., The active conformations of neotame and other high-potency sweeteners.J. Med. Chem., 43, 1242–1245 (2000).
Yamada, H. and Nishizawa, M., Syntheses of sweet tasting diterpene glycosides, baiyunoside and analogs.Tetrahedron, 48, 3021–3044 (1992).
Yamashita, H., Theerasilp, S., Aiuchi, T., Nakaya, K., Nakamura, Y. and Kurihara, Y., Purification and complete amino acid sequence of a new type of sweet protein with taste-modifying activity, curculin.J. Biol. Chem., 265, 15770–15775 (1990).
Yang, D. J., Zhong, Z. C. and Xie, Z. M., Studies on the sweet principles from the leaves o.Cyclocarya paliurus (Batal.) Iljinskaya.Yao Hsueh Hsueh Pao, 27, 841–844 (1992).
Yoshikawa, M., Morikawa, T., Nakano, K., Pongpiriyadacha, Y., Murakami, T. and Matsuda, H., Characterization of new sweet triterpene saponins fro.Albizia myriophylla.J. Nat. Prod., 65, 1638–1642 (2002).
Yoshikawa, M., Murakami, T., Ueda, T., Shimoda, H., Yamahara, J. and Matsuda, H., Development of bioactive functions i.Hydrangea dulcis folium. VII. Absolute stereostructures of 3S-phyllodulcin, 3R- and 3S-phyllodulcin glycosides, and3R-and 3S-thunberginol H glycosides from the leaves ofHydrangea macrophylla Seringe var.thunbergii Makino.Heterocycles, 50, 411–418 (1999).
Author information
Authors and Affiliations
Corresponding author
Additional information
Dedicated to Professor Kazuo Yamasaki, Graduate School of Biomedical Sciences, Hiroshima University, Hiroshima, Japan, on the occasion of his retirement.
Rights and permissions
About this article
Cite this article
Kim, N.C., Kinghorn, A.D. Highly sweet compounds of plant origin. Arch Pharm Res 25, 725–746 (2002). https://doi.org/10.1007/BF02976987
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF02976987