* Sweetness Characteristics of the Triterpene Glycosides in Siraitia grosvenori

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1 1 Nippon Shokuhin Kagaku Kogaku Kaishi Vol. /-, No.+*, /,1/-- (,**0) 527 *, ** * * * ** ** * ** Sweetness Characteristics of the Triterpene Glycosides in Siraitia grosvenori Yuji Murata*, **, Shinichi Yoshikawa*, Yasushi A. Suzuki*, Masaki Sugiura*, Hiroshi Inui** and Yoshihisa Nakano** * Biochemical Laboratory, Saraya Co. Ltd.,,.+, Tamate-cho, Kashiwara, Osaka /2,**,2 ** Division of Applied Life Sciences, Graduate School of Life and Environment Sciences, Osaka Prefecture University, ++ Gakuen-cho, Nakaku, Sakai, Osaka /332/-+ The aim of this study was to evaluate the sweetness characteristics of a plant-derived sweetener from Siraitia grosvenori that contains triterpene glycosides. Sweetness qualities of four triterpene glycosides were found to be superior to rebaudioside A in stevia, dipotassium glycyrrhizinate in licorice, and saccharin sodium. Using ripe S. grosvenori fruits as starting materials, a single-step chromatographic procedure at an industrial level yielded a concentrated extract in which four triterpene glycosides accounted for -/. The obtained extract showed excellent sweetness-quality. When the young fruits were utilized instead, the sweetness-quality of the obtained extract was inferior to the one obtained from the ripe fruits. Mogroside V, one of the main sweetness components of S. grosvenori, was trans-glycosylated by cyclodextrin glucanotransferase, before being partially hydrolyzed by glucoamylase to produce mogroside V derivatives to which + to - glucose residues were conjugated. The sweetness intensity of the derivatives was found to decrease as the number of additional glucoses increased. The sweetness-quality, however, was improved in the tri glucose-conjugated derivative compared with mogroside V. In conclusion, the S. grosvenori extract is a potential source of sweeteners for various foods. In addition, when approved as a food additive, mogroside V derivatives are expected to expand the market for sweeteners. (Received Apr..,,**0 ; Accepted Jun.,,,,**0) * /2,**,2,.+, ** /332/-+ ++ Corresponding author murata@saraya.com +0 mogrol / mogroside -** oxo-mogroside mogroside siamenoside

2 528 /- +*,**0 +* 2 mogroside a mogroside +* mogroside +- mogroside + Guilin S&TNewTech. Company mogroside ++-oxomogroside mogroside siamenoside +* ww /* ml ODS LiChroprep RP-+2, Merck, f-0 mm--* mm /** ml,* vv /** ml,*2* vv, *** ml, +./ mlmin,*- nm ODS mogroside ++oxo-mogroside mogroside siamenoside 30 mogrol +- mogroside / g mogroside 0* +** m mol/l, ph. /* ml AC+** + g.*,. +* ODS.* vv HPLC : Nucleosil +**-/C+2 f,* mm,/* mm, :.* vv : 0.* ml HPLC 2* mogroside 2/ mogroside 3/ mogroside mogroside mogroside mogroside A3-3* A:.2 : 2 3/ 33, +* ++ - Guilin S & T New Tech. Company A B C +* *.. YMC : ODS-A+,*S- +/* *.- m - 1/ vv C D - mogroside Mogroside +* mogroside a Bacillus macerans CGTase mogroside a a - mogroside +- : mogroside+ glc, mogrosidev, glc, mogrosidev- glc : 3/. +/ 0

3 3 : * wv + Pauli N i.0 - n, Do Du gr gl kl Eo Em Eu S EoDoi,grin EuDui,klin EmEoEu, SN+**Em / ++ +* wv +/ * 2 1 *0 * +, -. / Pauli + + mogroside -12 siamenoside.0/ mogroside -** ++-oxo-mogroside 02 +, mogroside mogroside +3/ mogroside mogroside mogroside mogroside,, 2 2 2,. mogroside ++oxo-mogroside mogroside siamenoside 2 -.** ** -.-2.* ;,/./ mogroside - ++-oxo-mogroside mogroside siamenoside mogroside..,* -.* A 2

4 530 /- +*,**0 +* 4 + /.,*..,1..,1..,* A ,.3.,.*./ A, ODS + - A, B, C mogroside C +3.. A +*.2 +. C -/.+ A +0.* mogroside A 01./ C //.- - C

5 wxῌy : z{p }~ '(% T 5 X ῌ -.,*..**!"#$%&'()* 531 PQ -RS '(DEK, '(% TU, VWX NY Z[\#$%&'(%#F -. +, -. -/ / 9: ]?@A C + 5 ^_`abc de+f g ;8+, -. < => /?@A C '(%B/ C' hijk+lm- T?@A DX. n op/ mogrosideῐ (DE#FG mogrosideῐ HIJK +3.. #F / HIJK '(DELMHIJ# -/.+ N; mogroside, - O5 /!"#$% qr - Ts +X. tu/ siamenoside B^_`abc de#v. &'()*+ mogrosideῌ

6 532 /- +*,**0 +* 6 + A B C D mogroside V +*42 +24/ oxo-mogroside V mogroside IV * 04, *43 siamenoside I,4+.4* / *,34, -/4+ /-4* /0 +*+ +,, +10 /-.* D C + C +- mogroside ++-oxo-mogroside mogroside siamenoside mogroside A B 2..,*/.-- C + mogroside mogroside mogroside A, B, C mogroside mogroside mogroside A, B mogroside + - mogroside +.+0 mogroside CGTase mogroside mogroside +* mogroside +- mogroside +/ Pauli mogroside -12 mogroside + glc mogroside, glc mogrosideglc /- mogroside. - mogroside mogroside-glc mogroside -/ - +- mogroside -, ,3.1 mogrosideglc,/./ mogroside +1 mogroside mogrosideglc /*

7 7 : 533. mogroside ++-oxo-mogroside mogroside siamenoside A : -/ mogroside mogroside mogroside +- mogroside-glc mogroside + Prog. Med.,,*,,,/-,,/1,***, Takeo, E., Yoshida, H., Tada, N., Shingu, T., Matsuura, H., Murata, Y., Yoshikawa, S., Ishikawa, T., Nakamura, H., Ohsuzu, F. and Kohda, H., Sweet elements of Siraitia grosvenori inhibit oxidative modification of lowdensity lipoprotein. J. Atheroscler. Thromb., 3, ++.+,*,**, - Takasaki, M., Konoshima, T., Murata, Y., Sugiura, M., Nishino, H., Tokuda, H., Matsumoto, K., Kasai, R. and Yamasaki, K., Anticarcinogenic activity of natural sweeteners, cucurbitane glycosides, from Momordica grosvenori. Cancer Letters, +32, -1.,,**-. Hossen, M.A., Shinmei, Y., Jiang, S., Takubo, M., Tsumuro, T., Murata, Y., Sugiura, M. and Kamei, C., E#ect of lo han kuo (Siraitia grosvenori Swingle) on nasal rubbing and scratching behavior in ICR mice. Biol. Pharm. Bull.,,2,,-2,.+,**/ / Suzuki, Y., Murata, Y., Inui, H., Sugiura, M. and Nakano, Y., Triterpene glycosides of Siraitia grosvenori inhibit rat intestinal maltase and suppress the rise in blood glucose level after single oral administration of maltose in rats. J. Agric. Food. Chem., /-,,3.+,3.0,**/ 0 Kamei, T. and Sugiura, M., New pharmacological functions of Luo Han Guo. FFI Journal,,+*,,..,/.,**/ 1 + +*- ++/+++/ , Sapogenin +*- ++//++/ Mogroside +* * Yoshikawa, S., Murata, Y., Sugiura, M., Kiso, T., Shizuma, M., Kitahata, S. and Nakano, H., Transglycosylation of mogrosidev, a triterpene glycoside in Siraitia grosvenori, by cyclodextrin glucanotransferase and improvement of the qualities of sweetness. J. Appl. Glycosci., /,,,.1,/,,**/ ++ + Pharm. Tech. Japan, +., +/+3+/, , Matsumoto, K., Kasai, R., Ohtani, K. and Tanaka, O., Minor cucurbitane-glycosides from fruits of Siraitia grosvenori (Cucurbitaceae). Chem. Pharm. Bull., -2 (1),,*-*,*-, +33* +- +, /+/2 +33/ +. Kitahata, S. and Okada, S., Comparison of action of cyclodextrin glucanotransferase from Bacillus megaterium, B. circulans, B. stearothermophilus and B. macerans. J. Jap. Soc. Starch. Sci.,,3, , +/ Foods. Food. Ingredients. J. Jpn., +22, -0.2,*** +0 Darise, M., Mizutani, K., Kasai, R., Tanaka, O., Kitahata, S., Okada, S., Ogawa, S., Murakami, F. and Chen, F.H., Enzymic transglucosylation of rubusoside and the structure-sweetness relationship of steviol-bisglycosides. Agric. Biol. Chem..2,,.2-, / ,,

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