Skip to main content
Erschienen in: Journal of Natural Medicines 3/2018

28.02.2018 | Original Paper

Enzyme linked immunosorbent assay for total potent estrogenic miroestrol and deoxymiroestrol of Pueraria candollei, a Thai herb for menopause remedy

verfasst von: Gorawit Yusakul, Tharita Kitisripanya, Thaweesak Juengwatanatrakul, Seiichi Sakamoto, Hiroyuki Tanaka, Waraporn Putalun

Erschienen in: Journal of Natural Medicines | Ausgabe 3/2018

Einloggen, um Zugang zu erhalten

Abstract

Miroestrol and deoxymiroestrol are the most potent phytoestrogens of Pueraria candollei var. mirifica, having been proved as an effective herb for menopausal symptoms in folk medicines and clinical trials. To ensure efficacy and safety of P. candollei var. mirifica involved in nutraceutical products being available worldwide, the content of potent phytoestrogens as active ingredients should be specified. Therefore, in this study, we produced a monoclonal antibody for total analysis of potent estrogenic miroestrol and deoxymiroestrol, for which an analytical method was developed using a procedure for an indirect competitive enzyme-linked immunosorbent assay. The antibody exhibited equal reactivity against miroestrol and deoxymiroestrol. The sensitivity of determination was in the range of 31.3–500 ng/ml with high precision. The analytical parameters, such as accuracy (99.6–106% recovery) and high correlation with a HPLC–UV method, indicated the reliability of analysis. This method is of high performance, and it is cheap to control optimal miroestrol and deoxymiroestrol doses of P. candollei var. mirifica nutraceutical products.
Anhänge
Nur mit Berechtigung zugänglich
Literatur
1.
Zurück zum Zitat Ingham JL, Tahara S, Dziedzic SZ (1989) Minor isoflavones from the roots of Pueraria mirifica. Z Naturforsch C Bio Sci 44:724–726CrossRef Ingham JL, Tahara S, Dziedzic SZ (1989) Minor isoflavones from the roots of Pueraria mirifica. Z Naturforsch C Bio Sci 44:724–726CrossRef
2.
Zurück zum Zitat Ingham JL, Tahara S, Dziedzic SZ (1988) Coumestans from the roots of Pueraria mirifica. Z Naturforsch C Bio Sci 43:5–10CrossRef Ingham JL, Tahara S, Dziedzic SZ (1988) Coumestans from the roots of Pueraria mirifica. Z Naturforsch C Bio Sci 43:5–10CrossRef
3.
Zurück zum Zitat Chansakaow S, Ishikawa T, Seki H, Sekine K, Okada M, Chaichantipyuth C (2000) Identification of deoxymiroestrol as the actual rejuvenating principle of “Kwao Keur”, Pueraria mirifica. The known miroestrol may be an artifact. J Nat Prod 63(2):173–175CrossRef Chansakaow S, Ishikawa T, Seki H, Sekine K, Okada M, Chaichantipyuth C (2000) Identification of deoxymiroestrol as the actual rejuvenating principle of “Kwao Keur”, Pueraria mirifica. The known miroestrol may be an artifact. J Nat Prod 63(2):173–175CrossRef
4.
Zurück zum Zitat Matsumura A, Ghosh A, Pope GS, Darbre PD (2005) Comparative study of oestrogenic properties of eight phytoestrogens in MCF7 human breast cancer cells. J Steroid Biochem Mol Biol 94(5):431–443CrossRef Matsumura A, Ghosh A, Pope GS, Darbre PD (2005) Comparative study of oestrogenic properties of eight phytoestrogens in MCF7 human breast cancer cells. J Steroid Biochem Mol Biol 94(5):431–443CrossRef
5.
Zurück zum Zitat Dalal PK, Agarwal M (2015) Postmenopausal syndrome. Indian J Psychiatry 57(Suppl 2):S222–S232CrossRef Dalal PK, Agarwal M (2015) Postmenopausal syndrome. Indian J Psychiatry 57(Suppl 2):S222–S232CrossRef
6.
Zurück zum Zitat Virojchaiwong P, Suvithayasiri V, Itharat A (2011) Comparison of Pueraria mirifica 25 and 50 mg for menopausal symptoms. Arch Gynecol Obstet 284(2):411–419CrossRef Virojchaiwong P, Suvithayasiri V, Itharat A (2011) Comparison of Pueraria mirifica 25 and 50 mg for menopausal symptoms. Arch Gynecol Obstet 284(2):411–419CrossRef
7.
Zurück zum Zitat Okamura S, Sawada Y, Satoh T, Sakamoto H, Saito Y, Sumino H, Takizawa T, Kogure T, Chaichantipyuth C, Higuchi Y, Ishikawa T, Sakamaki T (2008) Pueraria mirifica phytoestrogens improve dyslipidemia in postmenopausal women probably by activating estrogen receptor subtypes. Tohoku J Exp Med 216(4):341–351CrossRef Okamura S, Sawada Y, Satoh T, Sakamoto H, Saito Y, Sumino H, Takizawa T, Kogure T, Chaichantipyuth C, Higuchi Y, Ishikawa T, Sakamaki T (2008) Pueraria mirifica phytoestrogens improve dyslipidemia in postmenopausal women probably by activating estrogen receptor subtypes. Tohoku J Exp Med 216(4):341–351CrossRef
8.
Zurück zum Zitat Lamlertkittikul S, Chandeying V (2004) Efficacy and safety of Pueraria mirifica (Kwao Kruea Khao) for the treatment of vasomotor symptoms in perimenopausal women: phase II study. J Med Assoc Thai 87(1):33–40PubMed Lamlertkittikul S, Chandeying V (2004) Efficacy and safety of Pueraria mirifica (Kwao Kruea Khao) for the treatment of vasomotor symptoms in perimenopausal women: phase II study. J Med Assoc Thai 87(1):33–40PubMed
9.
Zurück zum Zitat Chandeying V, Lamlertkittikul S (2007) Challenges in the conduct of Thai herbal scientific study: efficacy and safety of phytoestrogen, Pueraria mirifica (Kwao Keur Kao), phase I, in the alleviation of climacteric symptoms in perimenopausal women. J Med Assoc Thai 90(7):1274–1280PubMed Chandeying V, Lamlertkittikul S (2007) Challenges in the conduct of Thai herbal scientific study: efficacy and safety of phytoestrogen, Pueraria mirifica (Kwao Keur Kao), phase I, in the alleviation of climacteric symptoms in perimenopausal women. J Med Assoc Thai 90(7):1274–1280PubMed
10.
Zurück zum Zitat Manonai J, Chittacharoen A, Theppisai U, Theppisai H (2007) Effect of Pueraria mirifica on vaginal health. Menopause 14(5):919–924CrossRef Manonai J, Chittacharoen A, Theppisai U, Theppisai H (2007) Effect of Pueraria mirifica on vaginal health. Menopause 14(5):919–924CrossRef
11.
Zurück zum Zitat Manonai J, Chittacharoen A, Udomsubpayakul U, Theppisai H, Theppisai U (2008) Effects and safety of Pueraria mirifica on lipid profiles and biochemical markers of bone turnover rates in healthy postmenopausal women. Menopause 15(3):530–535CrossRef Manonai J, Chittacharoen A, Udomsubpayakul U, Theppisai H, Theppisai U (2008) Effects and safety of Pueraria mirifica on lipid profiles and biochemical markers of bone turnover rates in healthy postmenopausal women. Menopause 15(3):530–535CrossRef
12.
Zurück zum Zitat Chandeying V, Sangthawan M (2007) Efficacy comparison of Pueraria mirifica (PM) against conjugated equine estrogen (CEE) with/without medroxyprogesterone acetate (MPA) in the treatment of climacteric symptoms in perimenopausal women: phase III study. J Med Assoc Thai 90(9):1720–1726PubMed Chandeying V, Sangthawan M (2007) Efficacy comparison of Pueraria mirifica (PM) against conjugated equine estrogen (CEE) with/without medroxyprogesterone acetate (MPA) in the treatment of climacteric symptoms in perimenopausal women: phase III study. J Med Assoc Thai 90(9):1720–1726PubMed
13.
Zurück zum Zitat Eisenberger A, Westhoff C (2014) Hormone replacement therapy and venous thromboembolism. J Steroid Biochem Mol Biol 142(Supplement C):76–82CrossRef Eisenberger A, Westhoff C (2014) Hormone replacement therapy and venous thromboembolism. J Steroid Biochem Mol Biol 142(Supplement C):76–82CrossRef
14.
Zurück zum Zitat Prentice RL (2014) Postmenopausal hormone therapy and the risks of coronary heart disease, breast cancer, and stroke. Semin Reprod Med 32(6):419–425CrossRef Prentice RL (2014) Postmenopausal hormone therapy and the risks of coronary heart disease, breast cancer, and stroke. Semin Reprod Med 32(6):419–425CrossRef
15.
Zurück zum Zitat Suwanvesh N, Manonai J, Sophonsritsuk A, Cherdshewasart W (2017) Comparison of Pueraria mirifica gel and conjugated equine estrogen cream effects on vaginal health in postmenopausal women. Menopause 24(2):210–215CrossRef Suwanvesh N, Manonai J, Sophonsritsuk A, Cherdshewasart W (2017) Comparison of Pueraria mirifica gel and conjugated equine estrogen cream effects on vaginal health in postmenopausal women. Menopause 24(2):210–215CrossRef
16.
Zurück zum Zitat Monthakantirat O, Sukano W, Umehara K, Noguchi H, Chulikhit Y, Matsumoto K (2014) Effect of miroestrol on ovariectomy-induced cognitive impairment and lipid peroxidation in mouse brain. Phytomedicine 21(11):1249–1255CrossRef Monthakantirat O, Sukano W, Umehara K, Noguchi H, Chulikhit Y, Matsumoto K (2014) Effect of miroestrol on ovariectomy-induced cognitive impairment and lipid peroxidation in mouse brain. Phytomedicine 21(11):1249–1255CrossRef
17.
Zurück zum Zitat Urasopon N, Hamada Y, Asaoka K, Cherdshewasart W, Malaivijitnond S (2007) Pueraria mirifica, a phytoestrogen-rich herb, prevents bone loss in orchidectomized rats. Maturitas 56(3):322–331CrossRef Urasopon N, Hamada Y, Asaoka K, Cherdshewasart W, Malaivijitnond S (2007) Pueraria mirifica, a phytoestrogen-rich herb, prevents bone loss in orchidectomized rats. Maturitas 56(3):322–331CrossRef
18.
Zurück zum Zitat Urasopon N, Hamada Y, Cherdshewasart W, Malaivijitnond S (2008) Preventive effects of Pueraria mirifica on bone loss in ovariectomized rats. Maturitas 59(2):137–148CrossRef Urasopon N, Hamada Y, Cherdshewasart W, Malaivijitnond S (2008) Preventive effects of Pueraria mirifica on bone loss in ovariectomized rats. Maturitas 59(2):137–148CrossRef
19.
Zurück zum Zitat Suthon S, Jaroenporn S, Charoenphandhu N, Suntornsaratoon P, Malaivijitnond S (2016) Anti-osteoporotic effects of Pueraria candollei var. mirifica on bone mineral density and histomorphometry in estrogen-deficient rats. J Nat Med 70(2):225–233CrossRef Suthon S, Jaroenporn S, Charoenphandhu N, Suntornsaratoon P, Malaivijitnond S (2016) Anti-osteoporotic effects of Pueraria candollei var. mirifica on bone mineral density and histomorphometry in estrogen-deficient rats. J Nat Med 70(2):225–233CrossRef
20.
Zurück zum Zitat Chatuphonprasert W, Udomsuk L, Monthakantirat O, Churikhit Y, Putalun W, Jarukamjorn K (2013) Effects of Pueraria mirifica and miroestrol on the antioxidation-related enzymes in ovariectomized mice. J Pharm Pharmacol 65(3):447–456CrossRef Chatuphonprasert W, Udomsuk L, Monthakantirat O, Churikhit Y, Putalun W, Jarukamjorn K (2013) Effects of Pueraria mirifica and miroestrol on the antioxidation-related enzymes in ovariectomized mice. J Pharm Pharmacol 65(3):447–456CrossRef
21.
Zurück zum Zitat Jearapong N, Chatuphonprasert W, Jarukamjorn K (2014) Miroestrol, a phytoestrogen from Pueraria mirifica, improves the antioxidation state in the livers and uteri of beta-naphthoflavone-treated mice. J Nat Med 68(1):173–180CrossRef Jearapong N, Chatuphonprasert W, Jarukamjorn K (2014) Miroestrol, a phytoestrogen from Pueraria mirifica, improves the antioxidation state in the livers and uteri of beta-naphthoflavone-treated mice. J Nat Med 68(1):173–180CrossRef
22.
Zurück zum Zitat Chivapat S, Chavalittumrong P, Rattanajarasroj S, Punyamung S (2005) Chronic toxicity of Pueraria mirifica in rats. Thai J Pharmacol 27(2–3):76–90 Chivapat S, Chavalittumrong P, Rattanajarasroj S, Punyamung S (2005) Chronic toxicity of Pueraria mirifica in rats. Thai J Pharmacol 27(2–3):76–90
23.
Zurück zum Zitat Malaivijitnond S (2012) Medical applications of phytoestrogens from the Thai herb Pueraria mirifica. Front Med 6(1):8–21CrossRef Malaivijitnond S (2012) Medical applications of phytoestrogens from the Thai herb Pueraria mirifica. Front Med 6(1):8–21CrossRef
24.
Zurück zum Zitat Yusakul G, Putalun W, Udomsin O, Juengwatanatrakul T, Chaichantipyuth C (2011) Comparative analysis of the chemical constituents of two varieties of Pueraria candollei. Fitoterapia 82(2):203–207CrossRef Yusakul G, Putalun W, Udomsin O, Juengwatanatrakul T, Chaichantipyuth C (2011) Comparative analysis of the chemical constituents of two varieties of Pueraria candollei. Fitoterapia 82(2):203–207CrossRef
25.
Zurück zum Zitat Udomsuk L, Juengwatanatrakul T, Putalun W, Jarukamjorn K (2012) Bimodal action of miroestrol and deoxymiroestrol, phytoestrogens from Pueraria candollei var. mirifica, on hepatic CYP2B9 and CYP1A2 expressions and antilipid peroxidation in mice. Nutr Res 32(1):45–51CrossRef Udomsuk L, Juengwatanatrakul T, Putalun W, Jarukamjorn K (2012) Bimodal action of miroestrol and deoxymiroestrol, phytoestrogens from Pueraria candollei var. mirifica, on hepatic CYP2B9 and CYP1A2 expressions and antilipid peroxidation in mice. Nutr Res 32(1):45–51CrossRef
26.
Zurück zum Zitat Udomsin O, Juengwatanatrakul T, Yusakul G, Putalun W (2015) Chromene stability: the most potent estrogenic compounds in White Kwao Krua (Pueraria candollei var mirifica) crude extract. J Funct Foods 19(Part A):269–277CrossRef Udomsin O, Juengwatanatrakul T, Yusakul G, Putalun W (2015) Chromene stability: the most potent estrogenic compounds in White Kwao Krua (Pueraria candollei var mirifica) crude extract. J Funct Foods 19(Part A):269–277CrossRef
27.
Zurück zum Zitat Shimokawa S, Kumamoto T, Ishikawa T, Takashi M, Higuchi Y, Chaichantipyuth C, Chansakaow S (2013) Quantitative analysis of miroestrol and kwakhurin for standardisation of Thai miracle herb ‘Kwao Keur’ (Pueraria mirifica) and establishment of simple isolation procedure for highly estrogenic miroestrol and deoxymiroestrol. Nat Prod Res 27(4–5):371–378CrossRef Shimokawa S, Kumamoto T, Ishikawa T, Takashi M, Higuchi Y, Chaichantipyuth C, Chansakaow S (2013) Quantitative analysis of miroestrol and kwakhurin for standardisation of Thai miracle herb ‘Kwao Keur’ (Pueraria mirifica) and establishment of simple isolation procedure for highly estrogenic miroestrol and deoxymiroestrol. Nat Prod Res 27(4–5):371–378CrossRef
28.
Zurück zum Zitat Yusakul G, Udomsin O, Juengwatanatrakul T, Tanaka H, Chaichantipyuth C, Putalun W (2013) High performance enzyme-linked immunosorbent assay for determination of miroestrol, a potent phytoestrogen from Pueraria candollei. Anal Chim Acta 785(Supplement C):104–110CrossRef Yusakul G, Udomsin O, Juengwatanatrakul T, Tanaka H, Chaichantipyuth C, Putalun W (2013) High performance enzyme-linked immunosorbent assay for determination of miroestrol, a potent phytoestrogen from Pueraria candollei. Anal Chim Acta 785(Supplement C):104–110CrossRef
29.
Zurück zum Zitat Yusakul G, Udomsin O, Juengwatanatrakul T, Tanaka H, Chaichantipyuth C, Putalun W (2013) Highly selective and sensitive determination of deoxymiroestrol using a polyclonal antibody-based enzyme-linked immunosorbent assay. Talanta 114(Supplement C):73–78CrossRef Yusakul G, Udomsin O, Juengwatanatrakul T, Tanaka H, Chaichantipyuth C, Putalun W (2013) Highly selective and sensitive determination of deoxymiroestrol using a polyclonal antibody-based enzyme-linked immunosorbent assay. Talanta 114(Supplement C):73–78CrossRef
30.
Zurück zum Zitat Kitisripanya T, Jutathis K, Inyai C, Komaikul J, Udomsin O, Tanaka H, Putalun W (2017) Development of an enzyme-linked immunosorbent assay for the detection of isomiroestrol, an identical marker, in White Kwao Krua using a monoclonal antibody. J Pharm Biomed Anal 137:229–234CrossRef Kitisripanya T, Jutathis K, Inyai C, Komaikul J, Udomsin O, Tanaka H, Putalun W (2017) Development of an enzyme-linked immunosorbent assay for the detection of isomiroestrol, an identical marker, in White Kwao Krua using a monoclonal antibody. J Pharm Biomed Anal 137:229–234CrossRef
31.
Zurück zum Zitat Kitisripanya T, Krittanai S, Udomsin O, Jutathis K, Komaikul J, Juengwatanatrakul T, Sakamoto S, Tanaka H, Morimoto S, Putalun W (2017) Development of an enzyme-linked immunosorbent assay for determination of miroestrol using an anti-miroestrol monoclonal antibody. Planta Med 83(10):855–861CrossRef Kitisripanya T, Krittanai S, Udomsin O, Jutathis K, Komaikul J, Juengwatanatrakul T, Sakamoto S, Tanaka H, Morimoto S, Putalun W (2017) Development of an enzyme-linked immunosorbent assay for determination of miroestrol using an anti-miroestrol monoclonal antibody. Planta Med 83(10):855–861CrossRef
32.
Zurück zum Zitat Kitisripanya T, Jutathis K, Inyai C, Komaikul J, Udomsin O, Yusakul G, Tanaka H, Putalun W (2016) Anti-miroestrol polyclonal antibodies: a comparison of immunogen preparations used to obtain desired antibody properties. J Nat Med 70(2):296–299CrossRef Kitisripanya T, Jutathis K, Inyai C, Komaikul J, Udomsin O, Yusakul G, Tanaka H, Putalun W (2016) Anti-miroestrol polyclonal antibodies: a comparison of immunogen preparations used to obtain desired antibody properties. J Nat Med 70(2):296–299CrossRef
33.
Zurück zum Zitat Rajesh K, Rana KV, Suri CR (2013) Characterization of hapten-protein conjugates: antibody generation and immunoassay development for pesticides monitoring. Bionanoscience 3(2):137–144CrossRef Rajesh K, Rana KV, Suri CR (2013) Characterization of hapten-protein conjugates: antibody generation and immunoassay development for pesticides monitoring. Bionanoscience 3(2):137–144CrossRef
34.
Zurück zum Zitat Lee JH, Kim JY, Cho S-H, Jeong JH, Cho S, Park HJ, Baek SY (2017) Determination of miroestrol and isomiroestrol from Pueraria mirifica (White Kwao Krua) in dietary supplements by LC–MS–MS and LC–Q-Orbitrap/MS. J Chromatogr Sci 55(3):214–221PubMed Lee JH, Kim JY, Cho S-H, Jeong JH, Cho S, Park HJ, Baek SY (2017) Determination of miroestrol and isomiroestrol from Pueraria mirifica (White Kwao Krua) in dietary supplements by LC–MS–MS and LC–Q-Orbitrap/MS. J Chromatogr Sci 55(3):214–221PubMed
35.
Zurück zum Zitat Sookvanichsilp N, Soonthornchareonnon N, Boonleang C (2008) Estrogenic activity of the dichloromethane extract from Pueraria mirifica. Fitoterapia 79(7–8):509–514CrossRef Sookvanichsilp N, Soonthornchareonnon N, Boonleang C (2008) Estrogenic activity of the dichloromethane extract from Pueraria mirifica. Fitoterapia 79(7–8):509–514CrossRef
Metadaten
Titel
Enzyme linked immunosorbent assay for total potent estrogenic miroestrol and deoxymiroestrol of Pueraria candollei, a Thai herb for menopause remedy
verfasst von
Gorawit Yusakul
Tharita Kitisripanya
Thaweesak Juengwatanatrakul
Seiichi Sakamoto
Hiroyuki Tanaka
Waraporn Putalun
Publikationsdatum
28.02.2018
Verlag
Springer Singapore
Erschienen in
Journal of Natural Medicines / Ausgabe 3/2018
Print ISSN: 1340-3443
Elektronische ISSN: 1861-0293
DOI
https://doi.org/10.1007/s11418-018-1194-x

Weitere Artikel der Ausgabe 3/2018

Journal of Natural Medicines 3/2018 Zur Ausgabe