Anti-diabetic Activities of Chalcones Derived from Ashitaba
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1 456 Nippon Shokuhin Kagaku Kogaku Kaishi Vol. /1, No. ++,./0.0- (,*+*) 10 Anti-diabetic Activities of Chalcones Derived from Ashitaba Tatsuji Enoki, Hiromu Ohnogi, Eiji Kobaashi and Hiroaki Sagawa Biotechnolog Research Laboratories, Takara Bio Inc., -. +, Seta, Otsu, Shiga /,*,+3- Ashitaba, ( Angelica keiskei), is a perennial belonging to Umbelliferae and has been taken as a healthpromoting vegetable around the Hachijo Island area. Ashitaba has been known to contain about,* kinds of chalcones, and two major chalcones such as xanthoangelol (XA) and.-hdroxderricin (. HD) are more abundantl included than other chalcones. We previousl found that these two chalcones have insulin-like activities such as the induction of adipocte di# erentiation and the enhancement of glucose uptake. Moreover,. HD especiall showed stronger promoting activit of glucose uptake and preventive e# ect on the progression of diabetes in geneticall diabetic mice than the XA. In this report, we tested whether. HD can reduce the blood glucose levels of mice which developed hperglcemia associated with insulin resistance, and the structure-activit relationships of chalcones on glucose uptake using other Ashitaba chalcones and snthetic chalcones. As a result,. HD showed a lowering e# ect of blood glucose levels of diabetic mice, probabl due to the enhancement of glucose uptake. Thus, it is suggested that. HD exert a hpoglcemic action via an insulin-independent pathwa. In the structure-activit relationship, both. - methox group and --large substituted group, such as prenl, geranl, farnesl and benzl of A ring were considered to be essential for glucose uptake promoting activit. (Received Jun.,/,,*+* ; Accepted Jul. +,,,*+*) Kewords : Ashitaba, Angelica keiskei, chalcone, insulin-like activit, diabetes : : Angelica keiskei Koidzumi,- ++ +, * + -,*,,+* + +-,* QOL : xanthoangelol : XA. +. Qualit of Life. -hdroxderricin :. HD. / XA. HD, XA +*. HD /,*, Corresponding author enokit@takara-bio.co.jp,
2 11 : 457. HD, -hdrox-- -methl-. - KK-A methox-ap c,,. -dihdrox---methl-ap. HD 1* +, +*, -hdrox-- -farnesl-. -methox-ap d a, -hdrox-- -benzl-. -methox-ap e. HD b XA. HD AP.-hdroxbenzaldehde AP BP, -hdrox-. -methox- AP - mmol.-hdroxbenzaldehde - mmol +-ml +.*1/ g.*,* +.,, -dihdrox-. -methoxchalcone DHMC +//., AP ae BP a / kg +/ L.,,,. -trihdrox- --farneslchalcone THFC b.,,,. -trihdrox- - -benzl-,/ +.* C+2-OPN chalcone THBC,2./ c.,, -dihdrox- - -methl-. -methoxchalcone DHMMC,.0. -*.* 1/ d.,, -dihdrox-- -farnesl-. -methoxchalcone +** 1/ DHFMC./.. e.,, -dihdrox--- BW--** SP, benzl-. -methoxchalcone DHBMC,3.. : +* : /. NMR F XA-F, 1.+ mg. HD, +2/ mg XA - /3- mg IBC, 0- mg. -T-L - +.* -T--L+ DS : /* / : + -T- -L+ +* DS,** M H XA-H, -0 mg + D-MEM -1 / CO NMR 2*, - +, +* - Lonza,** M + AP D-MEM D-MEM,,. -dihdrox-- -farnesl-ap a,,. -dihdrox- FBS *,/. M +* AP, M KOH gml */. mm farnesl bromide, / g +/./ ml D-MEMFBS,. XA. HD,,. -dihdrox---benzl-ap b,,. -dihdrox-ap benzl bromide +* +.,
3 458 /1 ++,*+* / / -T- -L+ PBS 1 : - :, KK-A Ta E-Test +, CE-, +, 0, / -T--L + *+. D-. HD */. MEM D-MEMBSA. HD + +,** mgkg D-MEMBSA +. +/ HEPES HBSS HBSS./ + gml -* - */. CimL, +,,- H Ameri- can Radiolabeled Chemicals +** M, +. HD XA +*.* M B - + A B XA. HD PBS + NP-.* PBS KK-A + XA. HD XA. HD A B C:XA D:. HD E:XA F:. HD N. * p*.*/ ** p*.*+ v.s. Ctr. Tuke b
4 13 : 459,. HD XA. HD / M XA,* M,. HD XA A. -,. HD KK-A. HD,. HD KK-A KK-A. HD. HD N/ ** p **+. v.s. Ctr. t KK-A -F. HD XA-F. HD IBCXA-H. HD. +2 DHMC,. HD - DHMMC HD +. A -.. HD XA - A -. HD XA. A - - XA-F - A. HD A - XA.. IBC - C. HD. XA. A ; DHFMC, B ; DHBMC, C ; THBC, D ; THFC,. HD, XA, XA-F. HD XA, A. XA-H - B. HD XA-F DHFMC DHBMC. HD, -. HD - THBC THFC -D;DHMC -. -E ; DHMMC
5 460 /1 ++,*+* XA-F A XA-H B, IBC C DHMC D, DHMMC E F N0 * p**/. ** p**+. v.s. Ctr. Tuke b. HD KK-A + +, +. +* KK-A. HD,. HD. HD KK-A in vivo +*. HD
6 15 : 461. DHFMC A DHBMC B, THBC C, THFC D E N0 ** p**+. v.s. Ctr. Tuke b B.. -. HD XA HD XA XA-F IBC XA-F. HD. IBC -. HD XA-F A. XA IBC A. A. -. / B A,
7 462 /1 ++,*+* / A. - XA,. HD XA-F. HD A -. XA. HD XA-F XA-F HD. HD KK-A. HD KK-A + Akihisa, T., Tokuda, H., Ukia, M., Iizuka, M., Schneider, S., Ogasawara, K., Mukainaka, T., Iwatsuki, K., Suzuki, T. and Nishino, H., Chalcones, coumarins, and flavanones from the exudates of Angelica keiskei and their chemopreventive e# ects. Cancer Lett.,,*+, (,**-)., Kozawa, M., Morita, N., Baba, K. and Hata, K., The structure of xanthoangelol, a new chalcone from the roots of Angelica keiskei KOIDZUMI (Umbelliferae). Chem. Pharm. Bull.,,/, /+/ /+0 ( +311). - Foods Food Ingredients J. Jpn., +12, /, 0* Shimizu, E., Haashi, A., Takahashi, R., Aoagi, Y., Murakami, T. and Kimoto, K., E# ects of angiotensin I-converting enzme inhibitor from Ashitaba ( Angelica keiskei) on blood pressure of spontaneousl hpertensive rats. J. Nutr. Sci. Vitaminol.,./, -1/ -2- ( +333). / Kimura, Y. and Baba, K., Antitumor and antimetastatic activities of Angelica keiskei roots, part + : isolation of an active substance, xanthoangelol. Int. J. Cancer., +*0,.,3.-1 (,**-). 0 Kimura, Y., Taniguchi, M. and Baba, K., Antitumor and Antimetastatic activities of.-hdroxderricin isolated from Angelica keiskei roots. Planta Med., 1*,,++,+3 (,**.). 1 Ogawa, H., Ohno, M. and Baba, K., Hpotensive and lipid regulator actions of.-hdroxderricin, a chalcone from Angelica keiskei, in stroke-prone spontaneousl hpertensive rats. Clin. Exp. Pharmacol. Phsiol., -, ( +,), +3,- (,**/). 2 Murakami, S., Kijima, H., Isobe, Y., Muramatsu, M., Aihara, H., Otomo, S., Baba, K. and Nozawa, M., Inhibi- 3 +* ++ tion of gastric H, K -ATPase b chalcone derivatives, xanthoangelol and.-hdroxderricin, from Angelica keiskei Koidzumi. J. Pharm. Pharmacol.,.,, 1,-1,0 ( +33* ). Inamori, Y., Baba, K., Tsujibo, H., Taniguchi, M., Nakata, K. and Kozawa, M., Antibacterial activit of two chal- cones, xanthoangelol and.-hdroxderricin, isolated from the root of Angelica keiskei KOIDZUMI. Chem. Pharm. Bull., -3, +0*. +0*/ ( +33+ ). Enoki, T., Ohnogi, H., Nagamine, K., Kudo, Y., Sugiama, K., Tanabe, M., Kobaashi, E., Sagawa, H. and Kato, I., Antidiabetic activities of chalcones isolated from a Japanese herb, Angelica keiskei. J. Agric. Food Chem., //, 0*+-0*+1 (,**1). Saltiel, A.R. and Kahn, R., Insulin signalling and the regulation of glucose and lipid metabolism. Nature,.+., 1332*0 (,**+).
8 17 : 463 +, Zimmet, P., Alberti, K.G.M.M. and Shaw, J., Global and HD societal implications of the diabetes epidemic. Nature, -/ 0.100*,**2.+., 12, 121 (,**+). +1 Kadowaki, T., Yamauchi, T., Kubota, N., Hara, K., Ueki, K. and Tobe, K., Adiponectin and adiponectin receptors +. Tripathi, B.K. and Srivastava, A.K., Diabetes mellitus : in insulin resistance, diabetes, and the metabolic sn- Complications and therapeutics. Med. Sci. Monit., +,, RA drome. J. Clin. Invest., ++0, , (,**0). +-* +.1 (,**0). +2 +/ Rubin, C.S., Hirsch, A., Fung, C. and Rosen, O.M., Devel- opment of hormone receptors and hormonal responsive- New Food Industr, /+ ( +* ), ++,+,**3 ness in vitro. J. Biol. Chem.,,/-, 1/1* 1/12 ( +312). +0.,, 0,/,, 1 +,
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