KR100958375B1 - Process for mass production of d-pinitol - Google Patents
Process for mass production of d-pinitol Download PDFInfo
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- KR100958375B1 KR100958375B1 KR1020080028067A KR20080028067A KR100958375B1 KR 100958375 B1 KR100958375 B1 KR 100958375B1 KR 1020080028067 A KR1020080028067 A KR 1020080028067A KR 20080028067 A KR20080028067 A KR 20080028067A KR 100958375 B1 KR100958375 B1 KR 100958375B1
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- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01H—NEW PLANTS OR NON-TRANSGENIC PROCESSES FOR OBTAINING THEM; PLANT REPRODUCTION BY TISSUE CULTURE TECHNIQUES
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- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C35/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C35/02—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring monocyclic
- C07C35/08—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring monocyclic containing a six-membered rings
- C07C35/14—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring monocyclic containing a six-membered rings with more than one hydroxy group bound to the ring
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Abstract
본 발명은 D-피니톨(D-pinitol)의 대량 생산방법에 관한 것으로, 본 발명에 따라 콩나물 종자를 파종한 지 2일째부터 3일 동안 염을 처리함으로써 당뇨병 치료제로서 유용한 D-피니톨을 보다 대량으로 생산할 수 있다.The present invention relates to a method for mass-producing D-pinitol, and to treating D-pinitol, which is useful as a therapeutic agent for diabetes, by treating the salt for 2 to 3 days after sowing bean seed according to the present invention. Can produce.
당뇨병, D-피니톨, 염, NaCl Diabetes, D-Pinitol, Salt, NaCl
Description
본 발명은 D-피니톨(D-pinitol)의 대량 생산방법에 관한 것으로, 보다 상세하게는 콩나물의 재배시 염을 처리함으로써 D-피니톨을 보다 대량으로 생산하는 방법에 관한 것이다. The present invention relates to a method for mass production of D-pinitol, and more particularly, to a method for producing D-pinitol in larger quantities by treating salts when growing soybean sprouts.
D-피니톨(3-0-methyl-D-chiro-inositol) 또는 D-카이로-이노시톨(D-chiro-inositol)은 미오-이노시톨(myo-inositol)의 유도체로서 최근 식물체에서 이의 역할이 밝혀지고 있다. D-피니톨은 식물체가 스트레스(가뭄 또는 염도)를 받는 경우 수분유지를 위해 삼투 용질로서 축적되는 것으로 보고된 바 있다 (Loewus and Murthy, 2000).D- pinitol (3- 0 -methyl-D-chiro -inositol) or D- Cairo-inositol (D- chiro -inositol) is myo-the role thereof in the plant as recently derivatives of inositol (myo -inositol) is turning out to . D-pinitol has been reported to accumulate as an osmotic solute to retain moisture when plants are under stress (drought or salinity) (Loewus and Murthy, 2000).
D-피니톨 또는 D-카이로-이노시톨은 여러 식물체에 다양하게 분포되어 있는데, 식용작물 중에서는 콩과식물 특히 콩나물에 다량으로 존재하고 있는 것으로 알려졌다(Hong and Pak, 1999).D-pinitol or D-chiro-inositol is widely distributed in various plants, and it is known that edible crops are present in large amounts in legumes, especially bean sprouts (Hong and Pak, 1999).
식물체에서 D-피니톨의 합성경로가 밝혀졌는데 그 경로는 하기 반응식 1과 같다.The synthetic route of D-pinitol in the plant was found, the route is shown in Scheme 1 below.
최근 D-피니톨 또는 D-카이로-이노시톨이 혈당조절의 신호전달 과정 중에 관여하는 인자로서의 역할이 밝혀지면서 많은 주목을 받고 있다. 인슐린 비의존성 당뇨인 경우 D-피니톨 또는 D-카이로-이노시톨의 투여로 인해 혈당강하 효과가 있는 것으로 밝혀졌다(Pak et al., 1993; Asplin et al., 1993). 이에 따라 D-피니톨 또는 D-카이로-이노시톨이 인슐린 비의존성 당뇨인 경우에 하나의 지표로서 이용되고 있다(Pak et al., 1998).Recently, D-pinitol or D-chiro-inositol has attracted much attention as the role of the factor involved in the signaling process of glycemic control. In the case of insulin-independent diabetes, administration of D-pinitol or D-chiro-inositol has been shown to have a hypoglycemic effect (Pak et al., 1993; Asplin et al., 1993). Accordingly, D-pinitol or D-chiro-inositol is used as an indicator in the case of insulin-independent diabetes (Pak et al., 1998).
또한, D-피니톨과 D-카이로-이노시톨에서 유도되는 이노시톨 포스포글리칸(inositol phosphoglycan)은 인슐린 작용에 잠재적으로 중요한 수용체 후 중개자(postreceptor mediator), 즉, 인슐린이 수용체에 신호를 전달한 후 세포 내로의 하부(downstream) 신호전달에 관여하는 신호전달 중재자로서, 생리적 농도의 인슐린에 반응하여 빠르게 생성되며 생체내(in vivo)에서 인슐린과 유사한 효과를 갖는다. 제2형 당뇨병의 주요 특징 중의 하나가 인슐린 저항성인데, 당뇨병에 걸린 환자에게서 D-피니톨 또는 D-카이로-이노시톨의 역할을 조사한 결과 소변 내의 D-피니톨 또는 D-카이로-이노시톨 농도가 당뇨병 환자에서 증가하였다고 보고되었 다(Asplin, et al., 1993).Inositol phosphoglycans, also derived from D-pinitol and D-chiro-inositol, are postreceptor mediators that are potentially important for insulin action, i.e., after insulin delivers signals to the receptor and into the cell. of the lower (downstream) as signaling mediators involved in signal transduction, is rapidly generated in response to physiological concentration of insulin in vivo (in have a similar effect to insulin in vivo ). One of the main features of type 2 diabetes is insulin resistance, and the investigation of the role of D-pinitol or D-chiro-inositol in diabetic patients resulted in increased levels of D-pinitol or D-chiro-inositol in diabetic patients. Has been reported (Asplin, et al., 1993).
인슐린 비의존성 당뇨에 의한 다낭성 난소질환(polycystic ovary syndrome)인 경우도 D-피니톨 또는 D-카이로-이노시톨의 투여로 인해 정상적인 배란이 일어나는 것으로 보고되었다(Nestler et al., 1999). 이러한 결과들은 D-카이로-이노시톨이 당뇨병 전증(prediabetic) 환자 및 인슐린 저항성 당뇨병에 걸린 환자의 치료에 유용할 것임을 보여준다. D-카이로-이노시톨의 생체내에서의 생성이 증명된 바 있지만 현재는 D-카이로-이노시톨의 메틸화된 유도체인 D-피니톨의 식사 중 섭취가 주된 대사적 원천이다. D-피니톨은 콩과 식물과 귤에서 주로 발견되며 대두박(soy meal) 건중량의 1%를 차지한다. Polycystic ovary syndrome caused by insulin-independent diabetes has also been reported to result in normal ovulation due to the administration of D-pinitol or D-chiro-inositol (Nestler et al., 1999). These results show that D-chiro-inositol may be useful in the treatment of prediabetic patients and patients with insulin resistant diabetes. In vivo production of D-chiro-inositol has been demonstrated, but ingestion of D-pinitol, a methylated derivative of D-chiro-inositol, is currently the main metabolic source. D-Pinitol is found primarily in legumes and tangerines and accounts for 1% of the dry weight of soy meal.
이에 본 발명자들은 당뇨병 치료제로서 유용한 D-피니톨을 콩과식물로부터 보다 대량으로 생산할 수 있는 방법을 개발하기 위해 계속 연구를 진행하던 중, 콩과식물 중 특히 콩나물 재배시에 염을 특정조건으로 처리함으로써 D-피니톨을 대량으로 생산할 수 있음을 발견하여 본 발명을 완성하였다.Therefore, the present inventors are continuing to develop a method for producing a larger amount of D-pinitol from legumes, which is useful as a diabetes treatment agent, and by treating salts in legumes, especially when growing bean sprouts, under specific conditions. The present invention was completed by the discovery that D-finitol can be produced in large quantities.
본 발명의 목적은 당뇨병 치료제로서 유용한 D-피니톨을 대량으로 생산하는 방법을 제공하기 위한 것이다.It is an object of the present invention to provide a method for producing large amounts of D-pinitol useful as a therapeutic agent for diabetes.
상기 목적을 달성하기 위하여, 본 발명에서는 콩나물 종자를 파종한 지 2일째되는 날부터 3일 동안 염을 처리하는 것을 특징으로 하는, 콩나물로부터 D-피니톨을 생산하는 방법을 제공한다.In order to achieve the above object, the present invention provides a method for producing D-pinitol from soybean sprouts, characterized in that the salt treatment for 3 days from the second day of sowing sprouts seeds.
본 발명에서 사용가능한 염으로는 NaCl, KCl 또는 CaCl2를 예로 들 수 있으며, 이중 특히 NaCl가 바람직하다. 이러한 염의 농도는 30 내지 70mM가 바람직하며, 특히 70mM가 바람직하다. Salts usable in the present invention include, for example, NaCl, KCl or CaCl 2 , of which NaCl is particularly preferred. The concentration of such salts is preferably 30 to 70 mM, particularly preferably 70 mM.
본 발명의 방법에서는 콩나물 종자를 파종한 지 2일째부터 3일동안 염을 처리하는 것이 특징이며, 특히 2일 동안 염을 처리하는 것이 바람직하다. In the method of the present invention, it is characterized by treating the salts for 2 to 3 days after sowing of the bean sprout seeds, and particularly, the salts are treated for 2 days.
본 발명은 콩나물로부터 D-피니톨을 생산하는 방법을 제공하기 위한 것으로서, 콩나물 종자를 적당한 재배용기에 파종한 후 기존의 방법에 따라 콩나물을 재배하되, 종자 파종 2 일째부터 3일 동안 염을 처리하는 것을 특징으로 하며, 이러한 방법에 따라 재배된 콩나물로부터 D-피니톨의 양을 측정함으로써 D-피니톨의 대량생산을 위한 최적의 염처리 조건을 분석하였다. The present invention is to provide a method for producing D-pinitol from soybean sprouts, soybean sprouts are seeded in a suitable cultivation container and cultivated soybean sprouts according to the existing method, but the salt treatment for 2 to 3 days seed sowing The optimum salt treatment conditions for mass production of D-pinitol were analyzed by measuring the amount of D-pinitol from the bean sprouts grown according to this method.
본 발명에 따르면, 콩나물 종자를 처음 파종한 시점을 1일로 정하고 2일째부터 3일동안 염을 처리하고, 염 처리는 예를 들면, 매일 2시간에 한 번씩 수행할 수 있다.According to the present invention, the first seeding time of the bean sprout seed is set to 1 day and the salt is treated for 2 to 3 days, and the salt treatment may be performed once every two hours, for example.
염 처리된 콩나물은, 처리된 날짜별로 수확하고 공지된 방법에 따라 수확된 콩나물 샘플로부터 생리활성물질을 추출하고 가스크로마토그래피 방법을 이용하여 에 D-피니톨의 양을 분석할 수 있다. Salt-treated bean sprouts can be harvested by date of treatment and extracted bioactive substances from harvested bean sprout samples according to known methods and analyzed for the amount of e-D-pinitol using gas chromatography.
본 발명에 따라 콩나물을 재배함으로써 당뇨병 치료제로서 유용한 D-피니톨을 대량으로 생산할 수 있다.By cultivating bean sprouts according to the present invention, it is possible to produce large amounts of D-pinitol useful as a therapeutic agent for diabetes.
이하, 본 발명을 하기 실시예에 의해 보다 구체적으로 설명하고자 한다. 단, 하기 실시예는 본 발명을 예시하기 위한 것일 뿐, 본 발명의 범위가 이들만으로 한정되는 것은 아니다.Hereinafter, the present invention will be described in more detail with reference to the following examples. However, the following examples are only for illustrating the present invention, and the scope of the present invention is not limited thereto.
실시예 1: 콩나물 재배Example 1 Cultivation of Bean Sprouts
콩나물 종자 풍산콩(입수처: 한국종자협회) 20 g을 식물배양전용 용기(Phytohealth 310120)에 파종하고, 온도는 37℃, 습도는 80%를 유지하면서 5 내지 7일 동안 콩나물을 재배하였다. 하루 24시간을 1시간씩 나누어 1시간을 기준으로 수분제공시간은 20분으로 하였으며, 스프링쿨러를 통해 물을 제공하고 40분 동안은 수분제공 없이 온도와 습도를 일정하게 유지시켰다. 물의 온도는 14℃를 유지하여 고온으로 인한 세균증식을 억제하였다.Sprouts Seed Pungsan soybeans (obtained from Korea Seed Association) were sown in a plant culture container (Phytohealth 310120), and sprouts were grown for 5 to 7 days while maintaining a temperature of 37 ° C. and a humidity of 80%. The water supply time was divided into 1 hour 24 hours a day and 20 minutes per hour. Water was supplied through the sprinkler and the temperature and humidity were kept constant for 40 minutes without water supply. The temperature of water was maintained at 14 ℃ to suppress bacterial growth due to high temperature.
실시예 2: 생리활성물질 증가조건 Example 2: Bioactive substance increasing conditions
실시예 1에서 하루동안 재배된 콩나물을 파종 2일째부터 각각 NaCl를 30 mM 및 70 mM의 2개의 농도 군으로 나누어 수분이 제공되지 않는 40분 사이에 매일 2시간 간격으로 50 ml씩 3일 동안 처리하였다. Soybean sprouts grown for one day in Example 1 were divided into two concentration groups of 30 mM and 70 mM, respectively, from the second day of sowing, and treated with 50 ml at a daily interval of 2 hours for 2 days between 40 minutes without water. It was.
실시예 3: 생리활성물질 분리Example 3: Separation of Bioactive Material
염 처리된 콩나물을 처리된 날짜별로 수확하여 콩나물 샘플을 20 g씩 나누었다. 각각 샘플에 액화질소를 처리하여 급속으로 냉동시킨 후 식물분쇄용 막자사발을 이용하여 곱게 분쇄하였다. 분쇄된 분말에 50% 에탄올 30 ml을 첨가하고 70℃에서 1시간 동안 콩나물 샘플의 내용물을 전부 용출시켰다. 5000 rpm으로 원심 분리하여 콩나물 조직을 침전시켜 제거하고 25 ml의 상등액을 취한 후 진공펌프와 연결된 회전증발기를 이용하여 80℃에서 500 rpm으로 용액속의 에탄올을 완전히 제거하였다. 제거된 용액 13 ml을 다시 나노셉(nanosep) 3K 오메가(omega) 필터와 고속원심분리기를 이용하여 단백질 및 기타물질을 제거하여 콩나물에서 추출된 생리활성물질이 첨가된 용액 4 ml을 얻었다. 이중 1 ml를 다시 -70℃의 저온 냉장고에 1시간동안 냉동시킨 후 동결건조기를 이용하여 30 시간동안 건조시켰다. 건조된 샘플에 피리딘:3-메틸이미다졸=1:1(v/v)인 혼합용액 100 ㎕를 가하고 70℃의 고온가열기에서 30분 동안 열 반응시킨 후 반응시료를 준비하였으며, 준비된 시료 1㎕를 가스크로마토그래피에 주입하였다. 이때 가스크로마토그래피 초기온도는 150℃ 이었고 주입기(injector)의 온도는 250℃이며, 검출기(detector)의 온도는 300℃였다 (컬럼: DB1-HT, 용출가스: N2).Salt treated bean sprouts were harvested by date of treatment and divided into 20 g sample of bean sprouts. Each sample was treated with liquid nitrogen and rapidly frozen, and then finely ground using a mortar and pestle. 30 ml of 50% ethanol was added to the ground powder and the contents of the bean sprout sample were completely eluted at 70 ° C. for 1 hour. After centrifugation at 5000 rpm, the bean sprouts tissue was precipitated and removed. 25 ml of the supernatant was taken out, and ethanol in the solution was completely removed at 80 rpm at 500 rpm using a rotary evaporator connected to a vacuum pump. 13 ml of the removed solution was again removed using a nanoseop 3K omega filter and a high-speed centrifuge to remove proteins and other substances, thereby obtaining 4 ml of a solution containing bioactive substances extracted from bean sprouts. One ml of this was again frozen in a low temperature freezer at -70 ° C for 1 hour and then dried for 30 hours using a freeze dryer. 100 μl of a mixed solution of pyridine: 3-methylimidazole = 1: 1 (v / v) was added to the dried sample, followed by thermal reaction for 30 minutes in a high temperature heater at 70 ° C. to prepare a reaction sample. Μl was injected into gas chromatography. At this time, the initial temperature of gas chromatography was 150 ° C., the temperature of the injector was 250 ° C., and the temperature of the detector was 300 ° C. (column: DB1-HT, elution gas: N 2 ).
그 결과는 하기 표 1에 나타낸 바와 같다:The results are shown in Table 1 below:
상기 표 1에서 보듯이, 종자 파종 후 2일째부터 염 처리를 한지 2일째에 D-피니톨 함량이 콩나물 종자에 비해 약 200% 정도로 증가하여 D-피니톨이 매우 우수한 수율로 증가되었음을 확인할 수 있었으며, 염의 농도에 있어서는 30 mM 보다 70 mM에서 D-피니톨의 함량이 보다 증가됨을 알 수 있었다. 또한, 이 상태의 콩나물은 형태의 변화가 거의 없는 것으로 관찰되어 그 상품성에 있어서도 전혀 손색이 없음이 관찰되었다. As shown in Table 1, on the second day after the seed sowing, the D-pinitol content was increased by about 200% compared to the bean sprout seeds on the second day, and it was confirmed that D-pinitol was increased in a very good yield. The concentration of D-pinitol was found to be higher at 70 mM than at 30 mM. In addition, it was observed that the bean sprouts in this state had almost no change in form, and thus, there was no inferiority in the commerciality.
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| KR20020076095A (en) * | 2001-03-27 | 2002-10-09 | 아미코젠주식회사 | Method of recovering chiro-inositol and its derivatives from byproducts of soybean processing |
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| KR20020076095A (en) * | 2001-03-27 | 2002-10-09 | 아미코젠주식회사 | Method of recovering chiro-inositol and its derivatives from byproducts of soybean processing |
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