不同產地來源蜂膠原膠與市售商品萃取液之化學分析

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邦军仇
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1 4: (2002) 不同產地來源蜂膠原膠與市售商品萃取液之化學分析 1 * 1 2 摘要 nm 360 nm * 19 th4420@ms36.hinet.net

2 前言 (1) (2) (3)(4) (5) (6) (7) (8) (9)(10) (11)(12) (13) (14) (15) Marcucci,1995 Muenstedt and Zygmunt, 2001 Hsu2002 NOEL 1,400 mg Burdock, 1998 flavonoids Greenaway et al., 1990 flavonols -- galangin Heo et al., 2001 Banskota et al.2001 Hegazi et al Ismailia Abd et al.2002 East Nile Delta Usia et al cinnamylchrysin 6-cinnamylchrysin Popova et al diterpene glycosides -- ent-8(17)-labden-15-o-alpha-l-rhamnoside ent-8(17)-labden-15-o- (3'-O-acetyl) -alpha- L-rhamnoside Popova et al ',3'-Dihydroxy-4,4'-dimethoxychalcone 2',3',4-trihydroxy-4'- methoxy- chalcone Ethanol Extracts of PropolisEEP spectophotometry 20

3 材料與方法 (1) (CE) (2) A (CG) B (CP) C (CW) D (CH) E (Ch) F (Cm) F (CM) G (Cs) H (CS) (3) (CT) (4) A. (CPC) B. (CLC) 1. 1 g 1 ml 9 ml rpm ml 105 w/v 21

4 ml 6 ml 95 U g 20 ml rpm10 min 80 8 ml Advantec No. 5A ml 2 AAlminum nitrateal(no 3 ) 3 9H 2 O 17.6 g 100 ml B1M Potassium acetatech 3 COOK g 100 ml 3 A 50 mg ml 200 µg/ml100 µg/ml50 µg/ml25 µg/ml12.5 µg/ml10 µg/ml 0.5 ml 1.5 ml ml 10AlNO 3 3 9H 2 O 0.1 ml 1M CH 3 COOK2.8ml nm Y X B 50 mg ml 200 µg/ml100 µg/ml50 µg/ml25 µg/ml12.5 µg/ml10 µg/ml 0.5 ml 1.5 ml ml 10AlNO 3 3 9H 2 O 0.1 ml 1M CH 3 COOK2.8ml nm Y X 4 A 0.5 ml 1.5 ml ml 10AlNO 3 3 9H 2 O0.1 ml 1M CH 3 COOK2.8ml nm B 0.5 ml 1.5 ml ml 10AlNO 3 3 9H 2 O0.1 ml 1M CH 3 COOK 22

5 2.8 ml nm 結果 Content(%) R e g i o n Fig 1. Ethanolic extracts content of crude propolis from the different regions. 23

6 (3) (2) Content(%) (23) (7) (2) 4.79 (2) (1) (4) 9.60 (1) 0 R e g i o n Fig 2. Average ethanolic extracts content of ethanolic extracts propolis from the different regions of commercial products with various number of samples; Sample number

7 Fig 3. Flavonols and flavones contents existed in ethanol from curde propolis from the different regions. 8 (Cm-22) 25

8 80.87 (CM-45) (CT-66) (CW-13) (CPC-62) (CPC-60) (17.95) 2 26

9 Table 1. Ethanolic extracts in non-ethanolic extracts, tablets and capsules of commercial propolis products from the different regions. Sample Region Ethanolic extracts (%) Ch-34 Cm-22 CM-45 CPC-59 CPC-61 CT-67 CT-68 CT-72 CM-41 Cs21 CW-13 CP-29 CP-30 CPC-57 CT-66 CT-70 CT-69 CP-28 CPC-60 CPC-62 CT-75 CT-74 CM-12 CP-11 CP-53 CPC-58 CT-73 CH-56 CPC-65 CT-71 CG-46 CLC-64 CLC-63 America America New Zealand New Zealand Germany Germany CGcommercial glycerol extract products containing propolischcommercial honey dew extract products containing propolischcommercial honey extract products containing propoliscmcommercial menthol oil extract products containing propoliscscommercial cough drop syrup extract products containing propoliscwcommercial water extract products containing propoliscmcommercial many solution extract products containing propolis CP commercial propylalcohol extract products containing propolis CLC commercial preparation of liquid capsule products containing propoliscpccommercial preparation of powder capsule products containing. propolisctcommercial preparation of tablet products containing propolis. 27

10 Table 2. Ethanolic extracts in non-ethanolic extracts, tablets and capsules of commercial propolis products with the different formulations. Sample Region Ethanolic extracts (%) CLC-63 CLC-64 CM-12 CM-41 CM-45 CP-11 CP-28 CP-29 CP-30 CP-53 CPC-57 CPC-58 CPC-59 CPC-60 CPC-61 CPC-62 CPC-65 CT-66 CT-67 CT-68 CT-69 CT-70 CT-71 CT-72 CT-73 CT-74 CT-75 CG-46 Ch-34 CH-56 Cm-22 Cs21 CW-13 Germany Germany New Zealand America America New Zealand CGcommercial glycerol extract products containing propolischcommercial honey dew extract products containing propolischcommercial honey extract products containing propoliscm commercial menthol oil extract products containing propoliscscommercial cough drop syrup extract products containing propoliscwcommercial water extract products containing propolis CMcommercial many solution extract products containing propoliscpcommercial propylalcohol extract products containing propolisclc commercial preparation of liquid capsule products containing propolis CPC commercial preparation of powder capsule products containing. propolisctcommercial preparation of tablet products containing propolis. 28

11 (CPC-74) (CPC-75) (CM-12) (CP-11) (CH-56) (CT-73) (CT-71) 5.35 (CPC-65) (CG-46) 88.03(CLC-63) (CLC-64) (CLC) (CM) (CP) (CPC) (CT) (CG) (Ch) (CH) (Cm)(Cs) (CW) 2 CLC-63 CLC CM CM CP CP CPC CPC CT CT (CPC)35.75 (CM)35.07 (CT)30.35 (CW) 5.82 UVM (UVM) UVM 360 nm-390 nm 390 nm 230 nm 380 nm 365 nm 360 nm UVM 390 nm 375 nm 370 nm UVM360 nm 29

12 Table 3. Maximum of wave length in UV spectrum for ethanol extracts solution from crude propolis solutions from the different regions. Region Thailand TaiwanTainan TaiwanNantou TaiwanHualien Hwa-nan area Hwa-pei area Maximum of wave length (nm) UVMR UVM 44 UVMR UVM 2 UVMR nm 23UVMR nm nm 195 nm 44 UVM 2 UVM200 nm 7 UVMR nm nm nm UVM 315 nm UVMR UVM UVMR UVM 300 nm 4 UVMR nm 1 1 UVM 210 nm 205nm 300 nm 30

13 Fig 4. Major ranges or maximum of wave length in UV spectrum for ethanol extracts solut from commercial products with ethanolic extracts propolis from the different regions. Region 23 3 Taiwan7 Major ranges or maximum wave lengths (nm) America Czech Republic1 210 Germany1 335 Thailand1 205 Sample number UVM UVM 2 UVM 330 nm 205 nm 3 UVM UVM 205 nm 195 nm 8 UVM UVM 340 nm 200 nm 4 UVM UVM 375 nm 235 nm 8 UVM UVM 365 nm 205 nm 4 UVM UVM 360 nm 200 nm 2 UVM UVM 370 nm 205 nm 2 UVM UVM 205 nm 200 nm UVM UVM CPC nm CG nm 31

14 Table 5. Maximum of wave length in UV spectrum for ethanol extracts solution from commercial products with non-ethanolic extract, tablet and capsule propolis from the Sample Region Maximum of wave length(nm) CT-74 CT-75 CLC-63 CLC-64 CG-46 CP-30 CP-29 CPC-57 CT-66 CT-70 CM-41 Cs21 CW-13 CP-28 CPC-60 CPC-62 CT-69 CPC-59 CPC-61 CT-72 CT-67 CT-68 CM-45 Ch-34 Cm-22 CP-11 CP-53 CPC-58 CM-12 CPC-65 CT-71 CT-73 CH-56 America America Germany Germany New Zealand New Zealand

15 Table 6. Favonols and flavones contents existed in ethanol extracts with commercial products of ethanolic extracts propolis from the different regions. Region Flavonols (%) Flavones (%) Total (%) (23) 3 Taiwan7 America2 2 Czech Republic2 Germany1 4 Thailand Sample number 33

16 (CLC) (CM) (CP) (CPC) (CT) (CG) (Ch) (CH) (Cm) (Cs) (CW) (CPC) 7 (Cm) 1 (CT10) (Cm) 1 (CPC) 7 (CP) (CPC) 7 (CP) 5 (CT10) Ghisalberti 1979 resin

17 Table 7. Flavonols and flavones contents in ethanol extracts with commercial products of non-ethanolic extract, tablet and capsule propolis from the different regions. Sample Region Flavonols (%) Flavones (%) Total (%) Ch-34 CM-45 Cm-22 CPC-61 CPC-59 CT-67 CT-68 CT-72 CP-30 CP-29 CT-66 CT-70 CM-41 CPC-57 Cs21 CW-13 CPC-60 CPC-62 CP-28 CT-69 CT-75 CT-74 CP-53 CP-11 CM-12 CPC-58 CH-56 CT-73 CT-71 CPC-65 CG-46 CLC-64 CLC-63 America America New Zealand New Zealand Germany Germany CGcommercial glycerol extract products containing propolischcommercial honey dew extract products containing propolischcommercial honey extract products containing propoliscm commercial menthol oil extract products containing propoliscscommercial cough drop syrup extract products containing propoliscwcommercial water extract products containing propoliscm commercial many solution extract products containing propoliscpcommercial propylalcohol extract products containing propolisclc commercial preparation of liquid capsule products containing propoliscpccommercial preparation of powder capsule products containing. propolisct commercial preparation of tablet products containing propolis. 35

18 Table 8. Flavonols and flavones contents in ethanol extracts with commercial products of non-ethanolic extract, tablet and capsule propolis with the different formulations. Sample Region Flavonols (%) Flavones (%) Total (%) CP-29 CP-30 CP-28 CP-11 CP-53 CPC-59 CPC-61 CPC-57 CPC-60 CPC-62 CPC-58 CPC-65 CT-67 CT-68 CT-72 CT-66 CT-70 CT-69 CT-74 CT-75 CT-73 CT-71 CM-12 CM-41 CM-45 CLC-63 CLC-64 CG-46 Ch-34 CH-56 Cm-22 Cs21 CW-13 Germany America America New Zealand Germany New Zealand CGcommercial glycerol extract products containing propolischcommercial honey dew extract products containing propolischcommercial honey extract products containing propoliscm commercial menthol oil extract products containing propoliscscommercial cough drop syrup extract products containing propolis CW commercial water extract products containing propoliscmcommercial many solution extract products containing propoliscpcommercial propylalcohol extract products containing propolisclc commercial preparation of liquid capsule products containing propolis CPC commercial preparation of powder capsule products containing. propolisctcommercial preparation of tablet products containing propolis. 36

19 ferulic acids Velikova et al., 2000 Bankova et al.2002 Sicily diterpenic acids Bonvehi et al. (1994) 15 Tomas-Barberan et al. (1993) diterpenes Bankova et al., 1998a, b Negri et al.1998 Sorkun et al g/100 g 19.8 g/100 g 20Velikova et al., Hollman and Katan, Marcucci, 1995 Walker and Crane (1987) Woisky Salatino(1998) % 37

20 12 1 quercetin-2 chrysin- 3 tectochrysin- (4) isalpinin -(5) galangin- (6) kaempferol- (7)kaempfeid -(8) rutin - 9 3, 5, 7-3, 5, 7-trihydroxyflavone - (10)5, 7-5, 7-dihydroxyflavone-(11)5, 7, 8-5, 7, 8-trimethoxyflavanone-(12)6-6-fluorflavanone- Hsu2002 GC-MS Bankova et al., 1992 Seifert and Haslinger, 1991 Ackermann, 1991 RPHPTLC RPHPLC GC-MS 12 Park et al., 2002 spectrophotometry Franco and Kurebayashi, 1986 Woisky et al. (1998) Japan Association of Health and Nutrition Foods,1995 chrysin (1) flavanones(2) flavones(3) flavonols(4) isoflavones(5) anthocyanins(6) flavans Oezcan, 1999 El-Khatib et al., 2002 Banskota et al., Hsu2002 Midorikawa et al., 2002 Woisky et al. (1998) (1) (2) (3) (4) Menezes et al. (1997) Sawaya et al.,

21 Abd, El., F. K. Hady, and A. G. Hegazi Egyptian propolis: 2. Chemical composition, antiviral and antimicrobial activities of East Nile Delta propolis. Z. Naturforsch 57: Ackermann, T Fast chromatographic study of propolis crudes. Food Chem. 42: Bankova, V., G. Boudourova-Krasteva, S. Popov, J. M. Sforcin, and S. R. C. Funari Seasonal variations of the chemical composition of ian propolis. Apidologie 29: Bankova, V., M. Popova, S. Bogdanov, and A. G. Sabatini Chemical composition of European propolis: expected and unexpected results. Z. Naturforsch. 57: Bankova, V.; A. Dyulgerov, S. Popov, L. Evstatieva, L. Kuleva, O. Pureb, and Z. Zamjansan Propolis produced in Bulgaria and Mongolia: Phenolic compounds and plant origin. Apidologie. 23: Bankova, V.; G. Boudourova-Krasteva, S. Popov, J. M. Sforcin, and S. R. C. Funari Seasonal variations in essential oil from ian propolis. J. Essent. Oil Res. 10: Banskota A. H., Y. Tezuka, and S. Kadota Recent progress in pharmacological research of propolis. Phytother Res. 15: Banskota, A. H., T. Nagaoka, L. Y. Sumioka, Y. Tezuka, S. Awale, K. Midorikawa, K. Matsushige, and S. Kadota Antiproliferative activity of the Netherlands propolis and its active principles in cancer cell lines. J. Ethnopharmacol. 80: Bonvehi, J S.; F. V. Coll, and R. E. Jorda The composition, active components and bacteriostatic activity of propolis in dietetics. J. Am. Oil. Chem. Soc. 71: Bonvehi, J. S.; F. V. Coll, and R. E. Jorda The composition, active components and bacteriostatic activity of propolis in dietetics. J. Am. Oil Chem. Soc. 71: Burdock, G. A Review of the biological properties and toxicity of bee propolis. Food Chem. Toxicol. 36: El-Khatib, A. S., A. M. Agha, L. G. Mahran, and M. T. Khayya Prophylactic effect of aqueous propolis extract against acute experimental hepatotoxicity in vivo. Z. Naturforsch. 57: Franco, T. T., and A. K. Kurebayashi Isolation of active principles of propolis through bidimensional paper chromatography and spectrophotometric determination. Rev. Inst. Adolfo lutz. 46: 39

22 Ghisalberti, E. L Propolis: a review. Bee World. 60: Greenaway, W., T. Scaysbrook, and F. R. Whatley The composition and plant origins of propolis : A report of work at Oxford. Bee World 71: Hegazi, A. G., El. Abd, and F. K. Hady Egyptian propolis: 3. Antioxidant, antimicrobial activities and chemical composition of propolis from reclaimed lands. Z. Naturforsch. 57: Heo, M. Y., S. J. Sohn, and W. W. Au Anti-genotoxicity of galangin as a cancer chemopreventive agent candidate. Rev. Mut. Res. 488: Hollman, P. C. H., and M. B. Katan Dietary flavonoids: intake, health effects and bioavailability. Food Chem. Toxicol. 37: Hsu, T. H The relationship between bioactivity and bioactive ingredients of propolis. (in Chinese and in submission) Japan Association of Health and Nutrition Foods Guideline and specification for propolis as foods and processed foods. Japan Association of Health and Nutrition Foods.Japan.(in Japanese ) Marcucci, M. C Propolis: Chemical composition, biological properties and therapeutic activity. Apidologie 26: Menezes, H., M. Jr. Bacci, S. D. Oliveira, and F. C. Pagnocca Antibacterial properties of propolis and products containing propolis from. Apidologie 28: Midorikawa, K., A. H. Banskota, Y. Tezuka, T. Nagaoka, K. Matsushige, D. Message, A. A. Huertas, and S. Kadota Liquid chromatography-mass spectrometry analysis of propolis. Phytochem. Anal. 12: Muenstedt, K., and M. Zygmunt Propolis - current and future medical uses. Am. Bee J. 141: Negri, G.; M. C. Marcucci, A. Salatino, and M. L. F. Salatino Hydrocarbons and monoesters of propolis waxes from. Apidologie 29: Oezcan, M Antifungal properties of propolis. Grasas. Aceitesvol. 50: Park, Y. K., S. M. Alencar, and C. L. Aguiar Botanical origin and chemical composition of ian propolis. J Agric. Food Chem. 50: Popova, M., V. Bankova, I. Tsvetkova, C. Naydenski, and M. V. Silva The first glycosides isolated from propolis: diterpene rhamnosides..z. Naturforsch. 56: Popova, M., V. Bankova, S. Spassov, I. Tsvetkova, C. Naydenski, M. V. Silva, and M. Tsartsarova New bioactive chalcones in propolis from El Salvador. Z. Naturforsch. 56: Sawaya, A. C., A. M. Palma, F. M. Caetano, M. C. Marcucci, I. B. da Silva Cunha, C. E. Araujo, 40

23 and M. T. Shimizu Comparative study of in vitro methods used to analyse the activity of propolis extracts with different compositions against species of Candida. Lett. Appl. Microbiol. 35: Seifert, M., and E. Haslinger Constituents of the propolis. Liebigs. Ann. Chem. 2: Sorkun, K., B. Suer, and B. Salih Determination of chemical composition of Turkish propolis. Z. Naturforsch. 56: Tomas-Barberan, F. A.; C. Garcia-Viguera, P. Vit-Olivier, F. Ferreres, and F. Tomas-Lorente Phytochemical evidence for the botanical origin of tropical propolis from Venezuela. Phytochem. 34: Usia, T., A. H. Banskota, Y. Tezuka, K. Midorikawa, K. Matsushige, and S. Kadota Constituents of Chinese propolis and their antiproliferative activities. J. Nat. Prod. 65: Velikova, M., V. Bankova, K. Sorkun, S. Houcine, I. Tsvetkova, and A. Kujumgiev Propolis from the Mediterranean region: chemical composition and antimicrobial activity. Z. Naturforsch 55: Velikova, M., V. Bankova, M. C. Marcucci, I. Tsvetkova, and A. Kujumgiev Chemical composition and biological activity of propolis from ian meliponinae. Z. Naturforsch. 55: Walker, P., and E. Crane Constituents of propolis. Apidologie. 18: Woisky, R. G., and A. Salatino Analysis of propolis : some parameters and procedures for chemical quality control. J. Apic. Res. 37:

24 Chemical Analysis of Tinctures from Commercial Products and Crude Propolis with Different Sources Tai-Hao Hsu 1, Mei-Yueh Wang 1, and Shu-Young Chang 2 1 Department of Bioindustry Technology, Da-Yeh University 2 Bureau of Animal and Plant Health Inspection and Quarantine Council of Agriculture, Executive Yuan, Taiwan, ROC ABSTRACT Propolis is a resinous mixture with plant secretions and saliva produced by honeybee. It is well known for broadly bioactivity. Recently, the commercial products with different formulations and types containing propolis are popular in Taiwan. This study involved in determination of the content of ethanolic extracts, flavonols and flavones in the commercial product and crude propolis with different sources and formulations. In addition, the UV spectrum of tinctures from the related propolis by spectrophotometry evaluated for the possibility of differentiation from different sources. In the analyzed samples, the content average (42.51%)of ethanolic extracts from the crude Taiwan propolis was higher than the average (31.98%)of all nine different sources. The content average (29.14%) of ethanolic extracts from the Taiwan propolis tinctures of commercial products was higher than the average (26.77%)of all commercial products with the nine different sources. The content average (18.94%) of flavonols and flavones from the ethanolic extracts of crude Taiwan propolis was lower than the average (22.14%) of the all nine different sources. For the non-ethanolic commercial products, ignoring of the sample size and production source, the highest content average (35.75%)of ethanolic extracts was from the powder capsule, the second was from the solvent mixture (35.07%), and the third was from the tablet (30.35%). The major or maximum UV length of wave range of 44 propolis ethanolic tinctures was from nm. There was no specific type in the major or maximum UV length of wave range among them. The content average (8.07%) of flavonols and flavones from the Taiwan propolis tinctures of commercial products was higher than the average (7.91%) of all different sources. For the non-ethanolic commercial products, the highest content average (20.19%)of flavonols and flavones was from the powder capsule, the second was from the propylalcohol extracts (10.37%), and the third was from the tablet (8.54%). Key words: crude propolis, commercial propolis, chemical analysis, flavonols, flavones, flavonoids. 42

Microsoft Word - 3172-3176 20150628002高蓬勃-二校出3172、3173

Microsoft Word - 3172-3176 20150628002高蓬勃-二校出3172、3173 6 8 Vol. 6 No. 8 2015 8 Journal of Food Safety and Quality Aug., 2015 1, 高蓬勃 2, 徐响 2, 高丽苗 2, 孙丽萍 (1., 350002; 2., 100093) 1, 2* 摘要 :,,,,,,,,, 关键词 : ; ; Research progress in chemical component