KR100444368B1 - The manufacturing process for the specific ginsenoside from panax ginseng hairy roots by heat treatment - Google Patents
The manufacturing process for the specific ginsenoside from panax ginseng hairy roots by heat treatment Download PDFInfo
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Abstract
본원 발명은 인삼모상근을 조직배양하여 대량 수득한 다음, 이 모상근을 특정 조건하에서 열처리하여 약리 효과가 뛰어난 진세노사이드-Rg₃, Rh₁, Rh₂를 다량 제조하는 방법에 관한 것이다.The present invention relates to a method for producing a large amount of ginsenoside-Rg₃, Rh₁, Rh₂ having excellent pharmacological effect by obtaining a large amount of ginseng hairy root by tissue culture, and then heat-treating the hairy root under specific conditions.
Description
본 발명은 인삼(Panax ginsengC.A.Meyer)의 모상근(Hairy roots)을 조직배양하여 대량 수득하고, 이 모상근을 열처리하여 약리효과가 뛰어난 진세노사이드(Ginsenoside)-Rg₃, Rh₁, Rh₂를 제조하는 방법에 관한 것이다.The present invention is obtained by mass-cultured hair roots (Hairy roots) of Panax ginseng CAMeyer, and heat-treating the hair roots to a method for producing ginsenoside-Rg₃, Rh₁, Rh₂ with excellent pharmacological effects. It is about.
최근 진세노사이드(Ginsenoside)의 약리기작이 밝혀지면서, 특정 진세노사이드의 대량 생산 필요성이 대두되고 있는 실정이다. 홍삼은 수삼을 장기간 저장할 목적으로 증숙하여 인삼의 전분을 호화시켜 건조한 것을 말하며, 이때 카라멜화에 의해서 적갈색을 나타내고 있어 홍삼이라 하고 증숙과정에서 홍삼특유의 진세노사이드가 생성된다(Park JD,1996, Korean J. Ginseng Sci. 20 ; 389-415).Recently, as the pharmacological mechanism of ginsenoside has been revealed, the necessity of mass production of a specific ginsenoside is emerging. Red ginseng is steamed for long-term storage of ginseng and gelatinized starch of ginseng and dried. At this time, it is reddish brown by caramelization, and it is called red ginseng. Ginsenosides unique to red ginseng are produced during steaming process (Park JD, 1996, Korean J. Ginseng Sci. 20; 389-415).
홍삼의 진세노사이드는 대부분 백삼과 공통된 것도 있지만 홍삼 특유의 진세노사이드가 존재하는데, 홍삼의 가공과정을 거치는 동안 사포제닌(Sapogenin)의 C-20에서 글리코실(Glycosyl)잔기가 떨어져 나가거나, 하이드록실 그룹(Hydroxyl Group)의 에피머라이제이션(Epimerization)에 의해 홍삼특유의 진세노사이드 성분인 20(S)-진세노사이드 Rg2, 20(S)-진세노사이드 Rg₃,진세노사이드 Rh2등이 생성된다.(Park JD, 1996).Although most ginsenosides of red ginseng are common to white ginseng, there are ginsenosides unique to red ginseng. During the processing of red ginseng, glycosyl residues are released from C-20 of sapogenin, 20 (S) -ginsenoside Rg 2 , 20 (S) -ginsenoside Rg₃, ginsenoside Rh 2 which are the ginsenoside components unique to red ginseng by epimerization of the hydroxyl group And the like (Park JD, 1996).
이들 진세노사이드는 원료 수삼중의 일부 사포닌 성분이 홍삼의 특수한 증숙 공정을 거치는 과정에서 변환되어 2 차 적으로 생성된 성분들로서 백삼, 수삼 및 배양삼에는 거의 존재하지 않으며, 홍삼에 다량 존재하는 진세노사이드로서 그 약리 효능이 높은 것으로 알려지고 있다.These ginsenosides are secondary components produced by the conversion of some saponin components of raw ginseng during the special steaming process of red ginseng, and are rarely present in white ginseng, fresh ginseng, and cultured ginseng. It is known that its pharmacological efficacy is high as senoside.
진세노사이드-Rg₃는 암세포전이 억제작용, 혈소판 응집 억제 및 항혈전작용, 혈관이완작용, 실험적 간 상해 억제작용, 항암제의 내성 억제작용등이 있으며(Mochizuki et al., 1995, Proc. '95 Korean-Japan Ginseng Symp. : 41-44), 진세노사이드-Rh₁은 실험적 간 상해 억제작용, 종양세포(F9 cells)분화촉진, 혈소판 응집억제 및 선용활성화 작용이 알려지고 있다(Lee et al., 1993, Proc 6th Int'l Ginseng Symp., Korea : 127-131).Ginsenoside-Rg₃ has inhibitory effects on cancer cell metastasis, platelet aggregation and antithrombotic activity, vascular relaxation, experimental liver injury inhibition, and anticancer drug resistance (Mochizuki et al., 1995, Proc. '95 Japan Ginseng Symp .: 41-44), Ginsenoside-Rh® has been known to inhibit experimental liver injury, promote differentiation of tumor cells (F9 cells), inhibit platelet aggregation, and inhibit activation (Lee et al., 1993). , Proc 6th Int'l Ginseng Symp., Korea: 127-131).
또한 진세노사이드 Rh₂는 암세포증식 억제작용, 종양증식억제작용, 항암제의 항암활성 증대작용등 여러 가지 효과(Odashima et al., 1979, Europ J. Cancer 15 : 885-892 ; Kim et al., 1996, '96 Korean-Japan Ginseng Symp : 102-116) 때문에 인삼의 중요한 진세노사이드이다.In addition, ginsenoside Rh₂ has various effects such as inhibiting cancer cell proliferation, inhibiting tumor growth, and increasing anticancer activity of anticancer drugs (Odashima et al., 1979, Europ J. Cancer 15: 885-892; Kim et al., 1996 , '96 Korean-Japan Ginseng Symp: 102-116) is an important ginsenoside of ginseng.
하지만 인삼의 재배는 매년 경작지가 감소되고 있는 실정이어서 앞으로 원료공급에 지장을 초래할 가능성이 있으며, 특정 진세노사이드-Rg₃, Rh₁, Rh₂의 대량생산을 위해서는 홍삼원료가 많이 소비되기 때문에 경제성을 맞출 수가 없는 형편이다.However, as the cultivation of ginseng is decreasing every year, there is a possibility that it may interfere with the supply of raw materials, and red ginseng raw materials are consumed for mass production of certain ginsenoside-Rg₃, Rh₁, and Rh₂. There is no way.
한편, 본원 발명의 출원인의 특허출원 1997-0233470(진세노사이드 Rg₃의 제조방법)에는 진세노사이드 Rb₁, Rb₂, Rc, Rd등 프로토파낙사다이올사포닌이 함유된 사포닌 혼합물 또는 인삼추출물을 완충용액 중에서 효소 락타제와 반응시켜 진세노사이드 Rg₃를 제조하는 방법이 기술되어 있다.Meanwhile, the applicant's patent application 1997-0233470 (method of preparing ginsenoside Rg₃) contains saponin mixture or ginseng extract containing protofanaxadiol saponin such as ginsenoside Rb₁, Rb₂, Rc, and Rd as a buffer solution. The method for preparing ginsenoside Rg 3 by reacting with enzyme lactase is described.
또한 본원 발명의 출원인이 특허출원 1998-0062265(20(에스)-진세노사이드 알에취투의 제조방법)에는 진세노사이드 Rg₃를 수성용매 중에서 효소 나린지나제와 베타갈락토시다제 중에서 선택한 효소와 반응시켜 20(S)-진세노사이드 Rh₂를 제조하는 방법이 나와 있다.In addition, the applicant of the present invention patent application 1998-0062265 (method of preparing 20 (S) -ginsenoside R. et al.) And ginsenoside Rg 3 and the enzyme selected from the enzyme naringinase and beta galactosidase in an aqueous solvent and Reaction shows a method for preparing 20 (S) -ginsenoside Rh2.
그러나 이들은 효소적 방법에 의해 진세노사이드 Rh₃ 또는 Rh₂를 제조하는 방법에 관한 것으로서, 본원 발명의 열처리와는 그 기술구성이 다른 발명들이다.However, these relate to a method for producing ginsenoside Rh 3 or Rh 2 by an enzymatic method, which is different from the heat treatment of the present invention.
한편, 한국특허출원 10-1999-002120(진세노사이드 Rg₃ 및/ 또는 Rg5의 제조방법)에는 인삼을 110 내지 180℃의 온도에서 0.5 내지 20시간 동안 가열처리하고, 수득된 가공인삼을 알콜, 헥산, 에테르, 및 그들의 혼합용매로 이루어진 군으로부터 선택되는 유기용매로 추출한 후에 추출물을 크로마토그라피 처리하고 진세노사이드 Rg₃ 및/ 또는 Rg5를 분리수득하는 단계를 포함함을 특징으로 하여 진세노사이드 Rg₃ 및/ 또는 Rg5를 제조하는 방법이 기재되어 있다.On the other hand, Korean Patent Application No. 10-1999-002120 (method of preparing ginsenoside Rg₃ and / or Rg 5 ) is heat-treated with ginseng at a temperature of 110 to 180 ℃ for 0.5 to 20 hours, and the processed ginseng is alcohol, Extracting with an organic solvent selected from the group consisting of hexane, ether, and mixed solvents thereof, followed by chromatographic treatment of the extract and separating and obtaining ginsenoside Rg₃ and / or Rg 5 . And / or a method of producing Rg 5 is described.
그러나, 본원 발명에서 사용하고 있는 인삼모상근이 아닌 일반 인삼을 사용하고 있어서 그 원료 수득에 제한이 있고, 수득물 또한 Rg₃와 Rg5로서 본원발명에서 목적하는 Rg₃, Rh₁, Rh₂와는 수득성분이 다르며 수득율이 낮은 단점이 있다.However, since the ginseng is used in the present invention rather than the ginseng hair root root, there is a limitation in obtaining the raw material, and the obtained product is also Rg₃ and Rg 5 , and the obtained components are different from those of Rg₃, Rh₁, and Rh₂ which are intended in the present invention. This has a low disadvantage.
본 발명의 목적은 일반 재배삼이 아닌, 인삼 모상근을 조직배양을 통해 대량 수득하고 , 이것을 열처리 하여 약리효과가 우수한 진세노사이드 Rg₃, Rh₁, Rh₂를 대량으로 제조하는데 있다.An object of the present invention is to obtain a large amount of ginsenosides Rg ₃, Rh ₁, Rh ₂ having excellent pharmacological effect by obtaining a large amount of ginseng hairy roots through tissue culture, not the general cultivated ginseng.
도1은 진세노사이드 Rg₃의 구조식1 is a structural formula of ginsenoside Rg₃
도2는 진세노사이드 Rh₂의 구조식2 is a structural formula of ginsenoside Rh₂
본 발명은 인삼 모상근을 대량으로 조직배양하여 수득한 다음, 수득된 모상근을 적정 조건하에서 열처리하는 것으로 구성된다.The present invention consists in obtaining tissue culture of ginseng hairy roots in bulk, and then heat-treating the hairy root obtained under appropriate conditions.
인삼 모상근을 온도 및 시간을 달리하여 열처리한 결과 진세노사이드의 성분별 함량차이가 현저하게 다름을 발견하고, 여러 번의 실험을 통하여 그 중에서 최적의 조건을 찾아냄으로써 본 발명을 완성하게 되었다.As a result of heat-treating ginseng hairy roots at different temperatures and times, the content difference of each component of ginsenosides was found to be remarkably different, and the present invention was completed by finding the optimal conditions therefrom through several experiments.
조직배양하여 수득한 인삼 모상근을 온도 105 ℃에서 60 분 ~ 180 분간 처리할 경우, 진세노사이드-Rg₃, Rh₁, Rh₂의 생성량이 많았으며, 특히 105 ℃에서 120 분간 처리할 경우 목적하는 진세노사이드의 함량이 가장 높았다.When ginseng hairy roots obtained by tissue culture were treated at a temperature of 105 ° C. for 60 minutes to 180 minutes, the amount of ginsenoside-Rg₃, Rh₁, and Rh₂ was high, especially when treated at 105 ° C. for 120 minutes. The content of was the highest.
주재료인 인삼 모상근은 3년생 고려인삼(Parax girseng C.A.Meyer)의 주근에서 A.rhizogenes A4에 의하여 유도 선발된 모상근 세포주 KGHR-8(Yang et al., 1998), 또는 KGHR-8의 체세포변이체인 KGHR-8A가 바람직하나, 이에 한정하지 않고 조직배양된 인삼 모상근이면 모두 적용이 가능하다.The ginseng hairy root, the main ingredient, is KGHR-8 (Yang et al., 1998), or KGHR, a somatic variant of the hairy root cell line KGHR-8 (Yang et al., 1998) induced by A.rhizogenes A4 in the root of three-year-old Korean ginseng (Parax girseng CAMeyer). -8A is preferred, but is not limited thereto, and any ginseng hairy root of tissue culture may be applied.
이하 실시예를 들어 본 발명을 상세히 설명하지만 이에 의해 본원 발명이 제한되지는 않는다.Hereinafter, the present invention will be described in detail with reference to Examples, but the present invention is not limited thereto.
<실시예1> 인삼 모상근의 배양Example 1 Culture of Ginseng Hairy Roots
인삼 모상근 세포주로서 KGHR-8A를 사용하였다.KGHR-8A was used as a ginseng hairy root cell line.
(1) 모상근 세포주의 계대배양은 생체중 0.5g을 GB5(Gamborg et al., 1968) 액체배지와 비타민과 3% 수크로스(Sucrose)가 첨가된 MS(Murashige and Skoog, 1962, 40ml/100ml flask) 액체배지에서 3 주 간격으로 수행하였다.(1) For subculture of hairy root cell line, 0.5 g of live weight of MS (Murashige and Skoog, 1962, 40ml / 100ml flask) with GB5 (Gamborg et al., 1968) liquid medium and vitamin and 3% sucrose was added. The liquid medium was carried out at three week intervals.
(2) 열처리에 사용한 모상근은, 근단이 1.5cm인 모상근 생체 중 1g을 40㎖ MS/B5 액체배지가 들어있는 100㎖ 삼각플라스크에서 23℃로 4주간 암상태로 배양한 것을 사용하였다.(2) The hairy roots used for heat treatment were those in which 1 g of hairy roots of 1.5 cm root end were incubated in a 100 ml Erlenmeyer flask containing 40 ml MS / B5 liquid medium at 23 ° C. for 4 weeks in the dark.
(3) 배양 4주 후 주근의 길이는 8.7cm 로 성장하였고, 1차 측근의 갯수는 19개 정도였고 생장량은 건조중량(dry wt) 0.43g 이었다.(3) After 4 weeks of incubation, the length of main root grew to 8.7cm.
<실시예2> 모상근의 열처리Example 2 Heat Treatment of Hairy Roots
(1) 배양 후 수득한 모상근을 증류수로 2번 세척한 다음 물기를 제거하였다.(1) The hairy root obtained after the culture was washed twice with distilled water and then dried.
(2) 생체시료를 증기멸균기로 온도와 시간을 달리하여 열처리하였다. 각 열처리 온도 및 시간은 90℃에서 30분과 60분, 105℃에서 30분, 60분, 120분, 180분, 121℃에서 30분, 120분 동안 열처리하였다(표1 참조).(2) The biological sample was heat treated with steam sterilizer at different temperature and time. Each heat treatment temperature and time were heat-treated at 90 ° C. for 30 minutes and 60 minutes, at 105 ° C. for 30 minutes, 60 minutes, 120 minutes, 180 minutes, and at 121 ° C. for 30 minutes and 120 minutes (see Table 1).
(3) 열처리한 모상근은 60℃가 일정하게 유지되는 열풍건조기에서 건조하였다.(3) The heat-treated hairy roots were dried in a hot air dryer in which 60 ° C was kept constant.
< 실시예 3 > 진세노사이드의 추출 및 분석Example 3 Extraction and Analysis of Ginsenosides
(1) 진세노사이드의 추출은 n-BuOH 추출법에 의하여 추출하였다.(1) Ginsenoside extraction was carried out by the n-BuOH extraction method.
건조분말 시료 1g을 취하여 60℃ 수욕조에서 80% MeOH로 추출하여 건조시킨 후, 에테르로 추출하여 탈지시켰다.1 g of a dry powder sample was taken, extracted with 80% MeOH in a 60 ° C. water bath, dried, extracted with ether and degreased.
그리고 수포화 1-BuOH 로 추출하고 증류수로 세척한 뒤, 1-BuOH 층을 건조시켜 TLC 및 HPLC 분석시료로 사용하였다.After extraction with saturated 1-BuOH and washing with distilled water, the 1-BuOH layer was dried and used as a TLC and HPLC analysis sample.
(2) 추출한 진세노사이드의 TLC 분석은 조사포닌 5 ㎕를 TLC 플레이트(silica gel 60 F, Merck)에 점적한 후, CHCl₃:MeOH:H2O(65:35:10, v/v)의 하층부로 전개하였으며, 30 % 황산을 분무하여 105 ℃ 건조기에서 발색하였다.(2) TLC analysis of the extracted ginsenosides was carried out by dropping 5 μl of irradiated saponinin onto a TLC plate (silica gel 60 F, Merck), followed by CHCl₃: MeOH: H 2 O (65:35:10, v / v). It developed to the lower layer, and sprayed 30% sulfuric acid, and it developed in 105 degreeC dryer.
(3) 진세노사이드의 정량분석은 HPLC를 이용하여 RI 검출기(Waters R401)로 분석하였으며, 컬럼은 LiChrospher-NH₂(Merk Co., 10㎛, 0.46 cm I.Dx25cm)을 사용하였고, 이동상은 acetonitrile/H2O/n-Butanol(80:20:10, v/v)와 acetonitrile/H2O(90:10, v/v)을 각각 사용하였다.(3) Quantitative analysis of ginsenosides was carried out using a RI detector (Waters R401) using HPLC, the column was LiChrospher-NH₂ (Merk Co., 10㎛, 0.46 cm I.Dx25cm), the mobile phase acetonitrile / H 2 O / n-Butanol (80:20:10, v / v) and acetonitrile / H 2 O (90:10, v / v) were used, respectively.
펌프는 워터스(Waters)사의 U6K를 사용하였고, 플로우 레이트는 0.3ml/min 과 2.0ml/min의 조건하에서 크로마토그램의 각 피크를 표준품과 비교하여 진세노사이드의 함량을 피크의 높이로 계산하였다.The pump used Waters U6K, and the flow rate calculated the content of ginsenoside as the height of the peak by comparing each peak of the chromatogram with a standard under the conditions of 0.3 ml / min and 2.0 ml / min.
<비교예1>Comparative Example 1
(1) 실시예1과 같은 방법으로 인삼모상근을 조직 배양하였다.(1) The ginseng hair root muscle was cultured in the same manner as in Example 1.
(2) 수득된 인삼모상근을 동결 건조 처리하였다.(2) The obtained ginseng hairy root was freeze-dried.
(3) 동결건조 처리한 인삼모상근을 실시예 3과 같이 진세노이드를 추출하고 분석하여 그 결과를 표1에 나타냈다.(3) The ginseng hair roots treated with lyophilized ginseng were extracted and analyzed as in Example 3, and the results are shown in Table 1.
< 실시예 및 비교예 분석 ><Example and Comparative Example Analysis>
상기 실시예 및 비교예의 결과를 표1에 나타냈다.Table 1 shows the results of the Examples and Comparative Examples.
표1. 열처리 및 동결건조 처리에 의한 진세노사이드의 성분량Table 1. Component amounts of ginsenosides by heat treatment and lyophilization
Ginsenoside contents according to temperature and time of heat treatment in ginseng hairy roots.(KGHR-8A)Ginsenoside contents according to temperature and time of heat treatment in ginseng hairy roots. (KGHR-8A)
FD: Freeze dried hairy root, T: Trace, PD: Ginsenoside-Rb1+Rb2+Rc+Rd+Rh2+Rg3, PT: Ginsenoside-Re+Rf+Rg1+Rg2+Rh1, *: %/Total ginsenosideFD: Freeze dried hairy root, T: Trace, PD: Ginsenoside-Rb 1 + Rb 2 + R c + Rd + Rh 2 + Rg 3 , PT: Ginsenoside-Re + Rf + Rg 1 + Rg 2 + Rh 1 , * :% / Total ginsenoside
일반 수삼이나 백삼에 많이 존재하는 진세노사이드-Rb₁, Rb₂, Rc, Rd, Re, Rf, Rg₁의 함량은, 비교예인 동결건조 처리했을 때가 열처리했을 때 보다 함량이 높았다.The content of ginsenoside-Rb₁, Rb2, Rc, Rd, Re, Rf, and Rg 하는, which is present in a lot of common ginseng and white ginseng, was higher than that of the comparative freeze-drying treatment.
목적하는 진세노사이드-Rg₃, Rh₁, Rh₂의 함량은 비교예인 동결건조 처리시 거의 생성되지 않았다.The desired contents of ginsenoside-Rg 3, Rh₁, and Rh₂ were hardly produced during the lyophilization treatment as a comparative example.
목적하는 진세노사이드-Rg₃, Rh₁, Rh₂의 함량은, 열처리시 온도 105 ℃에서 60 분~180 분 처리할 때 높았으며, 특히 120 분 처리할 때 함량이 가장 높았다.The contents of the desired ginsenoside-Rg₃, Rh₁, and Rh₂ were high at 60 ° C. to 180 min at 105 ° C. during heat treatment, and were highest at 120 min.
조직배양을 통해 대량 생산된 인삼 모상근을 원료로 사용함으로써 경제성을 높이고, 수득된 인삼 모상근을 열처리를 통해 약리활성이 뛰어난 진세노사이드-Rg₃, Rh₁, Rh₂를 대량 제조하는 방법이 제공된다.By using ginseng hairy roots mass-produced through tissue culture as a raw material, economic efficiency is provided, and a method of mass-producing ginsenoside-Rg₃, Rh₁, Rh₂ having excellent pharmacological activity through heat treatment of the obtained ginseng hairy roots is provided.
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62158490A (en) * | 1986-01-08 | 1987-07-14 | Nitto Electric Ind Co Ltd | Treatment of panax ginseng |
| KR19990000457A (en) * | 1997-06-05 | 1999-01-15 | 박명규 | Method for preparing trace ginsenosides |
| KR100228510B1 (en) * | 1995-11-22 | 2000-03-15 | 손경식 | A process for the preparation of ginsenoside Rg3 and/or Rg5 |
| KR20000044063A (en) * | 1998-12-30 | 2000-07-15 | 박명규 | Manufacturing method of ginsenoside rg1 using ginseng hairy root kghr-8 |
| KR20000045694A (en) * | 1998-12-30 | 2000-07-25 | 박명규 | Method for producing 20(s)-ginsenoside rh2 |
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Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62158490A (en) * | 1986-01-08 | 1987-07-14 | Nitto Electric Ind Co Ltd | Treatment of panax ginseng |
| KR100228510B1 (en) * | 1995-11-22 | 2000-03-15 | 손경식 | A process for the preparation of ginsenoside Rg3 and/or Rg5 |
| KR19990000457A (en) * | 1997-06-05 | 1999-01-15 | 박명규 | Method for preparing trace ginsenosides |
| KR20000044063A (en) * | 1998-12-30 | 2000-07-15 | 박명규 | Manufacturing method of ginsenoside rg1 using ginseng hairy root kghr-8 |
| KR20000045694A (en) * | 1998-12-30 | 2000-07-25 | 박명규 | Method for producing 20(s)-ginsenoside rh2 |
Non-Patent Citations (4)
| Title |
|---|
| 식물조직배양학회지 Vol.27(6) pp.461-468, 2000 * |
| 식물조직배양학회지 Vol.27(6) pp.485-489, 2000 * |
| 식물조직배양학회지 Vol.27(6):485-489(2000) * |
| 식물학회지 Vol.39(1) p.63-69, 1996 * |
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