Chemistry and in vivo profile of ent-kaurene glycosides of Stevia rebaudiana Bertoni-an overview

Natural Product Radiance

Volumn 8, Issue 2, 2009, Pages 181-189

  Sharma, Manishika ^a   Thakral, Naveen Kr ^b   Thakral, Seema ^c  

^a GVM College of Pharmacy   (India)

^b Laborate Pharmaceutical India Ltd   (India)

^c PDM College of Pharmacy   (India)

Author keywords

Ent kaurene glycosides; Stevia; Stevia rebaudiana; Structure sweetness relationship; Sweeteners

Indexed keywords

STEVIA REBAUDIANA;

EID: 67650759653     PISSN: 0972592X     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Review

References (68)

1. Elkins R, Stevia: Nature's Sweetener, Woodland Publishing, Orem, 1997.
2. Kinghorn AD and Soejarto DD, Intensely sweet compounds of natural origin, Med Res Rev, 1989, 9, 91-115.
3. www.dweckdata.com/Published-papers/Rainforest-Plants.pdf
4. Garcia PA, Oliveira AB and Batista R, Occurrence, biological activities and synthesis of kaurene diterpenes and their glycosides, Molecules, 2007, 12, 455-483.
5. Mosettig E, Beglinger U, Dolder F, Lichti H, Quitt P and Waters JA, The absolute configuration of steviol and isosteviol, J Am Chem Soc., 1963, 83, 3163-3164.
6. Pasquel A, Meireles MAA, Marques MOM and Petenate AJ, Extraction of glycosides with carbon dioxide + water and carbon dioxide+ Ethanol, Braz J Chem Eng, 2000, 17, 3.
7. Soejarto DD, Kinghorn AD and Farnsworth NR, Potential sweetening agents of plant origin. III. Organoleptic evaluation of Stevia leaf herbarium samples for sweetness, J Nat Prod, 1982, 45, 590-599.
8. Kinghorn AD, Stevia: The genus Stevia, Medicinal and Aromatic Plants-Industrial Profiles, Vol. 19, R Hardman (Ed), Taylor and Francis, London, UK, 2002.
9. Kinghorn AD, Soejarto DD, Nanayakkara NPD, Compadre CM, Makapugay HC and Brown JM, Aphytochemical screening procedure for sweet ent-kaurene glycosides in the genus Stevia, J Nat Prod, 1984, 47, 439-444.
10. Dolder F, Lichti H, Mosetti E and Quirt P, The structure and stereochemistry of steviol and isosteviol, J Am Chem Soc, 1960, 82, 246-247.
11. Crammer B and Ikan R, Sweet glycosides from Stevia plant, Chem Br, 1986, 22, 915-918.
12. Shibata H, Sonoke S, Ochiai H, Nishihashi H and Yamada M, Glucosylation of steviol and steviol-glucosides in extracts from Stevia rebaudiana Bertoni, Plant Physiol, 1991, 95, 152.
13. Sholichin M, Yamasaki K, Miyama R, Yahara S and Tanaka O, Labdane-type diterpenes from Stevia rebaudiana, Phytochemistry, 1980, 19, 326-327.
14. Ishima M and Katayama O, Sensory evaluation of stevioside as a sweetener, Rep Nat Food Res Inst (Japan), 1976, 31, 80-85.
15. Application A540-Steviol Glycosides as Intense Sweeteners Final Assessment Report submitted to Food Standards Australia New Zealand (FSANZ).
16. Yokoyama Y, New invention on sweeteners - Stevia sweetener, Food Processing, 1981, 16, 44-55.
17. Shizuka H, Current status of stevioside and its application in food processing, Japan Food Sci, 1982, 21, 24-30.
18. Bakal AI and O'Brien Nabors L, Stevioside, In: Alternative Sweeteners, Nabors, O Brien and RC Gelardi (Eds), Marcel Dekker, Inc., New York, 1986, pp. 295-307.
19. Wu CD, Johnson SA, Sriakantha R and Kinghorn AD, Intense natural sweetener and their effect on cariogenic bacteria, J Dental Res, 1998, 77, 283.
20. Kawaide H, Sassa T and Kamiya Y, Functional analysis of the two interacting cyclase domains in ent-kaurene synthase from the fungus Phaeosphaeria sp. L487 and a comparison with cyclases from higher plants, J Biol Chem, 2000, 275, 2276-2280.
21. Duncan JD and West CA, Properties of kaurene synthetase from Marah macrocarpus endosperm: evidence for the participation of separate but interacting enzymes, Plant Physiol, 1981, 68, 1128-1134.
22. Mori K and Matsui M, Totalsynthesisofmethyl-8α- carboxymethylpodocarpan-13-one-4β-carboxylate, a degradation product of steviol, Tetrahedron Lett, 1965, 2347-2350:
23. Nakhara Y, Mori K and Matsui M, Diterpenoid total synthesis, Part XVI, Alternative synthetic routes to steviol and -kaur-l6-en-19-oic-acid, Agric Biol Chem, 1971, 35, 918-928.
24. Ziegler FE and Kloek JA, 1-Hydroxy-7-methylene bicycle [3.2.1] octane: A gibbanesteviol C/D ring model, Tetrahedron Lett, 1971, 2201-2203.
25. Cook IF and Knox JR, The synthesis of 13-hydroxylated ent-kaur-16-ene derivatives using an acyloin like cyclization of keto esters, Tetrahedron, 1976, 32, 363-367.
26. Kaneda N, Kasai R, Yamasaki K and Tanaka O, Chemical synthesis on sweet diterpeneglycosides of Stevia rebaudiana: conversion of stevioside into rebaudioside-A, Chem Pharm Bull, 1977, 25, 2466-2467.
27. Kren V and Martínkova L, Glycosides in medicine: The role of glycosidic residue in biological activity, Curr Med Chem, 2001, 8, 1313-1337.
28. Fukunaga Y, Miyata T, Nakayasu N, Mizutani K, Kasai R and Tanaka O, Enzyme transglucosylation products of stevioside: separation and sweetness evaluation, Agric Biol Chem, 1989, 53, 1603-1607.
29. Ohatani K, Aikawa Y, Ishikawa H, Kasai R, Kitahata S, Mizutani K, Doi S, Nakamura M and Tanaka O, Further study on the 1, 4-α-transglucosylation of rubusoside, a sweet steviol bisglucoside from Rubus suavissimus, Agric Biol Chem, 1991, 55, 449-453.
30. Esaki S, Tanaka R and Kamiya S, Synthesis and taste of certain steviol glycosides, Agric Biol Chem, 1984, 48, 1831-1834.
31. Mizutani K, Miyata T, Kasai R, Tanaka O, Ogawa S and Doi S, Study on improvement of sweetness of steviol bisglycosides: selective enzymatic transglycosylation of 13-O-glycosyl moiety, Agric Biol Chem, 1989, 53, 395-398.
32. Ohtani K, Aikawa Y, Fujisawa Y, Kasai R, Tanaka O and Yamasaki K, Solubilisation of steviolbioside and steviolmonoside with γ-cyclodextrin and its application to selective synthesis of better sweet glycosides from stevioside and rubusoside, Chem Pharm Bull, 1991, 39, 3172-3174.
33. Kitahata S, Ishikawa S, Miyata T and Tanaka O, Production of rubusoside derivatives by transgalactosylation of various a-galactosidases, Agric Biol Chem, 1989, 53, 2929-2934.
34. Pezzuto JM, Chemistry, metabolism and biological activity of steviol, the aglycone of stevioside. In: New Trends in Natural Product Chemistry, by A Rahman and PW Quesne (Eds), Elsevier Sciences, Amsterdam, 1986, p. 371.
35. Phillips KC, Stevia: Step in developing a new sweetener. In: Developments in Sweetners, by TH Grenby (Ed), Elsevier Applied Science, London, 1987, pp. 1-43.
36. Hanson JR and De Oliveira BH, Stevioside and related sweet diterpenoid glycosides, Nat Prod Rep, 1993, 10, 301-309.
37. Genus JMC, Buyse J, Vankeirsbilck A and Temme EHM, Metabolism of stevioside by healthy subjects, Exp Biol Med, 2007, 232, 164-173.
38. 131-stevioside and its metabolites, Nuclear Med Biol, 1996, 23, 97.
39. Vignais PV, Duee ED, Vignais PM and Huet J, Effects of atractyligenin and its structural analogues on oxidative phosphorylation and on the translocation of adenine nucleotides in mitochondria, Biochem Biophys Acta, 19.66, 118, 465-483.
40. Toskulkao C, Deechakawan W, Leardkamolkarn V, Glinsukon T and Buddhasukh D, The low calorie natural sweetener stevioside - Nephrotoxicity and its relationship to urinary enzyme excretion in the rat, Phytother Res, 1994, 8, 281-286.
41. Yamamoto NS, Kelmer Bracht AM, Ischii EL, Kemmelmeier FS, Alvarez M and Bracht A, Effect of steviol and its structural analogues on glucose production and oxygen uptake in rat renal tubules, Experientia, 1985, 41, 55.
42. Ischii EL, Schwab AJ and Bracht A, Inhibition of monosaccharide transport in the intact rat liver by stevioside, Biochem Pharmacol, 1987, 36, 1417-1433.
43. Toskulkao C and Sytheerawattananon M, Effects of Stevioside, a natural sweetener, on intestinal glucose absorption in hamsters, Nutr Res, 1994, 14, 1711-1720.
44. Suanarunsawat T and Chaiyabutr N, The effect of stevioside on glucose metabolism in rat, Can J Physiol Pharmacol, 1997, 75, 976-982.
45. Oviedo CA, Fronciana G, Moreno R and Maas LC, Acute hypoglycemic activity of Stevia rebaudiana, Excerpta Medica, 1970, 209, 92.
46. Melis MS, Maciel RE and Sainati AR, Effect of two concentrations of stevioside on renal function and mean arterial pressure in rats, IRCS Med Sci, 1986, 14, 973.
47. Melis MS, Chronic administration of aqueous extract of Stevia rebaudiana in rats: renal effects, J Ethnopharmacol, 1995, 47 (3), 129-134.
48. Melis MS, A crude extract of Stevia rebaudiana increases the renal plasma flow of normal and hypertensive rats, Braz J Med Biol Res, 1996, 29, 669-675.
49. Melis MS, Renal excretion of stevioside in rats, J Nat Prod, 1992, 5, 688-690.
50. Planas GM and Kuc J, Contraceptive properties of Stevia rebaudiana, Science, 1968, 162, 1007.
51. Mori N, Sakanoue M, Takeuchi M, Shimpo K and Tanabe T, Effect of stevioside on fertility in rats, Shokuhin Eiseigaku Zasshi, 1981, 22, 409-414.
52. Prasad S, Jaykumar K, Honnegowda, Narayana K and Rao S, Male reproductive toxicity of Stevia rebaudiana (Bert.) in rats, Toxicol Int, 2005, 12 (1), 48.
53. Joint FAO/WHO Expert Committee on Food Additives. Toxicological Evaluation of Certain Food Additives, WHO Food Additives Series, Geneva, 1999, 42, 119-143.
54. Ishidate M, Sofuni T, Yoshikawa K, Hayashi M and Nohni T, Primary mutagenicity screening of food additives currently used in Japan, Food Chem Toxicol, 1984 22, 623-636.
55. Matsui M, Matsui K, Nohmi T, Mizusawa H and Ishidate M, Mutagenicity of steviol: an analytical approach using the southern blotting system, Bull Nat Inst Hygeine Sci Tokyo, 1989, 107, 83-87.
56. Pezutto JM, Nanayakkara NPD, Compadre CM, Swanson SM, Kinghorn AD and Guenthner TM, Characterization of bacterial mutagenesis mediated by 13-hydroxy-ent-kaurenoic acid and several structurally related derivatives and evaluation of potential to induce glutathione S-transferase in mice, Mutation Res, 1986, 169, 93-103.
57. Pezzuto JM, Compadre CM, Swanson SM, Nanayakkara NPD and Kinghorn AD, Metabolically activated steviol, the aglycone of stevioside is mutagenic, Proc Natl Acad Sci, 1985, 82, 2478-2482.
58. Matsui M, Matsui Kand Kawasaki Y, Evaluation of the genotoxicity of stevioside and steviol using six in vitro and one in vivo mutagenic assays, Mutagenesis, 1996, 11, 573-579.
59. Matsui M, Sofuni T and Nohmi T, Regionally targeted mutagenesis by metabolically activated steviol: DNA sequence analysis of steviol induced mutants of guanine phosphoribosyltransferase gene of Salmonella typhimurium TM 677, Mutagenesis, 1996, 11, 565.
60. Medon PJ, Pezzuto JM, Hovanec-Brown JM, Nanayakkara NP, Soejarto DD, Kamath SK and Kinghorn AD, Safety assessment ot some Stevia rebaudiana sweet principles, Fed Proc, 1982, 41, 1568.
61. Toskulkao C, Chaturat L, Temcharoen P and Glinsukon T, Acute toxicity of stevioside, a natural sweetener, and its metabolite, steviol, in several animal species, Drug Chem Toxicol, 1997, 20, 31.
62. 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, 1997, 35, 597-603.
63. Usami M, Sakemi K, Kawashima K, Tsuda M and Ohno Y, Teratogenicity study of stevioside in rats, Eisei Shikenjo Hokoku - Bull Nat Inst Hygienic Sci, 1995, 113, 31-35.
64. Wasuntarawat C, Temcharoen P, Toskulkao C, Mungkornkarn P, Suttajit M and Glusukon T, Developmental toxicity of steviol, a metabolite of stevioside in hamster, Drug Chem Toxicol, 1998, 21, 207-222.
65. Toskulkao C, Deechakawan W, Leardkamolkarn V, Glinsukon T and Buddhasukh D, The low calorie natural sweetner stevioside - nephrotoxicity and its relationship to urinary enzyme excretion in the rat, Phytother Res, 1994, 8, 281-286.
66. Panichkul T, Glinsukon T, Buddhasukh D, Cheuvchit P and Pimolsri U, The plasma levels of urea nitrogen, creatinine and uric acid and urine volume in rats and hamsters treated with stevioside, J Toxicol, 1998, 4, 47-52.
67. http://content.herbalgram.org/abc/herbclip/pdfs/090681-362.pdf.
68. Carakostas MC, Curry LL, Boileau AC and Brusick DJ, Overview: the history, technical function and safety of rebaudioside A, a naturally occurring steviol glycoside, for use in food and beverages, Food Chem Toxicol, 2008, 46, S1-S10.