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(12) United States Patent (10) Patent No.: US 8,829,205 B2 Jeon Et Al

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(12) United States Patent (10) Patent No.: US 8,829,205 B2 Jeon Et Al USOO8829205B2 (12) United States Patent (10) Patent No.: US 8,829,205 B2 Jeon et al. (45) Date of Patent: Sep. 9, 2014 (54) METHOD FOR PREPARING COUMESTROL (58) Field of Classification Search AND COUMESTROL PREPARED BY SAME USPC ........................................... 549/279; 435/119 See application file for complete search history. (75) Inventors: Hee Young Jeon, Yongin-si (KR); Dae Bang Seo, Yongin-si (KR); Si Young (56) References Cited Cho, Seoul (KR); Sang Jun Lee, U.S. PATENT DOCUMENTS Seongnam-si (KR) 3,564,019 A * 2/1971 Holmlund et al. ............ 549,279 (73) Assignee: Amorepacific Corporation, Seoul (KR) 6,129,937 A 10/2000 Zurbriggen et al. (*) Notice: Subject to any disclaimer, the term of this FOREIGN PATENT DOCUMENTS patent is extended or adjusted under 35 EP 1357,807 B1 3, 2007 U.S.C. 154(b) by 226 days. JP 2008-120729. A 5/2008 KR 10-0360306 B1 11, 2002 (21) Appl. No.: 13/575,267 KR 10-0706279 B1 4/2007 KR 10-0778.938 B1 11, 2007 (22) PCT Filed: Jan. 31, 2011 WO WOO1f97769 A1 12/2001 OTHER PUBLICATIONS (86). PCT No.: PCT/KR2O11AOOO673 S. M. Boué et al., “Induction of the Soybean Phytoalexins S371 (c)(1), Coumestrol and Glyceollin by Aspergillus,” J. Agric. Food Chem. (2), (4) Date: Jul. 25, 2012 vol. 48, No. 6, pp. 2167-2172, 2000. X. Hao et a... "Analysis of Coumestrol Content in Soybean.” Journal (87) PCT Pub. No.: WO2011/093686 of Beijing University of Agriculture, vol. 23, No. 3, pp. 7-9, 2008. PCT Pub. Date: Aug. 4, 2011 * cited by examiner (65) Prior Publication Data Primary Examiner — Nizal Chandrakumar US 2012/O2897 14 A1 Nov. 15, 2012 (74) Attorney, Agent, or Firm - Dickstein Shapiro LLP (51) Int. Cl (57) ABSTRACT cod 193/00 (2006.01) The present invention relates to a method for preparing CI2P 17/18 (200 6. 01) coumestrol, comprising a step in which beans are germinated and a step in which the beans are fermented, and to (52) is: C. CI2P 17/181 (2013.01) coumestrol prepared by the method. USPC ........................................... 549/279; 435/119 6 Claims, 9 Drawing Sheets U.S. Patent Sep. 9, 2014 Sheet 1 of 9 US 8,829,205 B2 Figure 1 3 Ow -X-Wariety 25 ----Wariety 2 2 15 10 re 5 - ------------ 0 - reer O 2 4. 6 8 Germination period (days) U.S. Patent Sep. 9, 2014 Sheet 2 of 9 US 8,829,205 B2 Figure 2 35 -X-Wariety - d - Wariety 2 2 4 6 Germination period (days) U.S. Patent Sep. 9, 2014 Sheet 3 of 9 US 8,829,205 B2 Figure 3 250 G b 2 200 -X-Wariety 1 a 150 -- Wariety 2 o hm t 2 100 o 8 / 5 1 50 1. -1 3 - -- O -éla O 2 4 6 S Germination period (days) U.S. Patent Sep. 9, 2014 Sheet 4 of 9 US 8,829,205 B2 Figure 4 140 120 as s s 100 -X-Wariety 1 Sg SO --- Wariety 2 y o W 60 A 5c y 3 , M c 40 ? -- 1. 20 1. o 1. Y t --k O --- () 2 4 6 S Germination period (days) U.S. Patent Sep. 9, 2014 Sheet 5 of 9 US 8,829,205 B2 Figure 5 120 - G r t s 100 - e -X-Wariety ----Wariety 2 - 60 hu d S 40 - / 8 / H ^ 4U2O / ^ 3 0. --- ---- O 2 4 6 8 Germination period (days) U.S. Patent Sep. 9, 2014 Sheet 6 of 9 US 8,829,205 B2 Figure 6 225 2OO 175 :: 150 125 OO 75 50 Pungsan-namul kong Sowon kong U.S. Patent Sep. 9, 2014 Sheet 7 Of 9 US 8,829,205 B2 Figure 7 400 350 300 28.7 250 2OO 83.3 150 O5.8 Non-treated 1% sucrose 1% glucose % SRT U.S. Patent Sep. 9, 2014 Sheet 8 of 9 US 8,829,205 B2 Figure 8 350 OO contro O.O.5% 0.1% 0.5% 0.75% 1.00% 25% Concentration of Aspergillus oryzae (%) U.S. Patent Sep. 9, 2014 Sheet 9 Of 9 US 8,829,205 B2 Figure 9 3500 - 3OOO 2500 500 OOO . 500 364.2 Non-treated 1% sucrose US 8,829,205 B2 1. 2 METHOD FOR PREPARING COUMESTROL FIG. 8 shows the content of coumestrol depending on the AND COUMESTROL PREPARED BY SAME concentration of fungus; and FIG. 9 shows the content of coumestrol under the opti TECHNICAL FIELD mized condition. The present disclosure relates to a method for producing MODE FOR INVENTION coumestrol and coumestrol produced thereby. Coumestrol (CMS: 3,9-dihydroxy-6H-benzofuro(3.2-c) BACKGROUND ART (1)benzopyran-6-one CHOs, MW: 268.2) is a coumarin 10 like compound structurally similar to the natural estrogen Bean is of great nutritional value and contains various estradiol or stilbestrol. It has a structure of the chemical physiologically active and functional Substances. Especially, formula 1: since the phytoestrogens contained in bean are similar to the estrogen of mammals including human in structure, they have the effect of preventing chronic diseases such as hormonal 15 chemical formula 1 disorders. The phytoestrogens include in general isoflavone, coumestan and lignan. DISCLOSURE Technical Problem HO The present disclosure is directed to providing a method for producing coumestrol and coumestrol produced thereby. 25 Since the estrogenic activity of coumestrol is 30-100 times Technical Solution higher as compared to isoflavone which is known to have estrogenic activity, it is very useful in alleviating the Symp In one general aspect, the present disclosure provides a toms of uterine cancer, bone marrow cancer, breast cancer, method for producing coumestrol, including: germinating brain cancer or menopausal disorders. The estrogenic activity bean; and fermenting the bean. 30 of coumestrol is thought to be attributable to its structure. In another general aspect, the present disclosure provides Coumestrol is known to be present in very Small amounts coumestrol produced by the above method. in bean or other plants in the family Fabaceae. Accordingly, it is necessary to effectively produce the coumestrol which is Advantageous Effects very useful but is contained in bean in trace amount. 35 Hereinafter, the present disclosure will be described in The method for producing coumestrol according to the more detail. present disclosure enables production of a large amount of In an aspect, the present disclosure provides a method for coumestrol from bean at high yield by increasing the content producing coumestrol, comprising: a germinating process of of coumestrol in the bean. The method can produce a large germinating bean; and a fermenting process offermenting the amount of coumestrol which is very expensive. The produced 40 bean. coumestrol may be used usefully in the fields of pharmaceu In an aspect of the present disclosure, the bean may be any ticals, foods or cosmetics. plant in the family Fabaceae that synthesizes coumestrol. For DESCRIPTION OF DRAWINGS example, the bean that can be used in the present disclosure 45 includes those for paste, bean curd, bean sprouts, bean-mixed FIG. 1 shows the content of coumestrol (mg/kg dry weight) rice or unripe bean. The bean species for paste(Jang) or bean extracted from bean germinated in an automatic watering curd include daepung, hojang, jangwon, daehwang, Sodam, apparatus at 30°C.; Songhak, daewon, jinpum, danbaek, duyu, sinpaldal, taeg FIG.2 shows the content of coumestrol (mg/kg dry weight) Wang, manri, jangsu, muhan, baekun, saeal. hwanggeum and extracted from bean germinated after contacting with 50 jangyeop. The species for bean sprouts include sinhwa, Aspergillus niger, SOWon, anpyeong, Seonam, dachae, Sorok, Soho. Somyeong, FIG.3 shows the content of coumestrol (mg/kg dry weight) dawon, pungsan-namul, iksan-namul, Sobaek-namul, gwan extracted from bean germinated in liquid medium (potato gan, danyeop and eunha. The species for bean-mixed rice dextrose broth) at 30° C. after contacting with Aspergillus include cheongja, heukcheong, galmi, Seonheuk, geomjeong niger, 55 kong and ilpumgeomjeong-kong. Also, the species for unripe FIG. 4 shows the content of coumestrol (mg/kg dry weight) bean include daol, sinrok, Saeeul, geomjeongeul, Seokryang extracted from bean germinated in liquid medium (potato putkong, hwaeom-putkong and keuneul. dextrose broth) at 30° C. after inoculating with Aspergillus In another aspect of the present disclosure, the bean may be Sojae, one that can germinate and is resistant to damage from disease FIG.5 shows the content of coumestrol (mg/kg dry weight) 60 and harmful insects. Examples may include Sinhwa-kong, extracted from bean germinated in liquid medium (potato SOWon-kong, anpyeong, Seonam, dachae, Sorok, Soho, Somy dextrose broth) at 30° C. after inoculating with Bifidobacte eong, dawon, pungsan-kongnamul, iksan-kongnamul, rium infantis, Sobaek-kongnamul, gwangan, danyeop and eunha. FIG. 6 shows the content of coumestrol in different variet The method for producing coumestrol according to the ies of bean: 65 present disclosure comprises a germinating process of germi FIG. 7 shows the content of coumestrol depending on nating bean. The germinating process may be conducted by medium additives; contacting the bean at least partly with oxygen or air. US 8,829,205 B2 3 4 The method for producing coumestrol according to the on the total weight of the medium. The saccharides include present disclosure also comprises a fermenting process of common monosaccharides, disaccharides or polysaccha fermenting the bean. Columestrol is known as a phytoalexin rides, specifically include Sucrose, glucose or SRT. synthesized by the plants in the family Fabaceae to protect In an aspect of the present disclosure, the process may be themselves from attack of fungi or other pathogenic micro conducted by adding 1-50 vol%, specifically 5-20 vol%.
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