KR100900725B1 - A preparation method of artemisia extract containing high content of eupatilin - Google Patents
A preparation method of artemisia extract containing high content of eupatilin Download PDFInfo
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Abstract
Description
쑥( Artemisia mongolica , A. asiatica , A. princeps var . orientalis , A. argyi, A. montana 등)은 국화과에 속하는 다년생 약초로서 예로부터 강장보혈, 부인병, 설사치료제로 사용되어 왔으며 규명된 화학성분으로서 이소쿠마린, 쿠마린, 디테르펜락톤 등이 있으며 유파틸린, 자세오시딘 등의 플라보이노이드 성분 등도 확인되었다.Wormwood ( Artemisia mongolica , A. asiatica , A. princeps var . orientalis , A. argyi, A. montana Etc.) is a perennial herb belonging to the Asteraceae family and has been used for the treatment of tonic blood, gynecological diseases, and diarrhea from ancient times. And so on.
대한약전외 한약(생약)규격집에서는 상기 쑥의 잎 및 어린줄기를 일컬어 애엽(艾葉, Artemisiae argyi Herb)이라 지칭하고 있다.In the herbal medicine standard (Korean herbal medicine) standard collection, the leaves and young stems of the mugwort are referred to as Artemisiae argyi Herb.
이 중 플라보노이드 성분인 유파틸린(eupatilin)은 항알러지 효과(일본 공개특허공보 소59-155314호)가 알려진 바 있으며 최근 국내에서도 위장질환 치료제로서의 효용성에 대해서도 밝혀진 바 있다. (대한민국 특허등록 127777) 더불어, 또 다른 플라보노이드 성분인 자세오시딘(jaseocidin) 역시 동일한 위장질환 치료제로서 사용 가능함이 특허로 등록된 바 있다. (대한민국 특허등록 181751)Among them, eupatilin, a flavonoid component, has been known to have an anti-allergic effect (Japanese Patent Laid-Open No. 59-155314) and has recently been found to be useful as a gastrointestinal disease treatment agent in Korea. (Korean Patent Registration 127777) In addition, another flavonoid ingredient, jaseocidin, has also been registered in the patent for use as a treatment for the same gastrointestinal diseases. (Korea Patent Registration 181751)
한편, 대한민국 특허등록 181751에서는, 쑥으로부터 정제한 유파틸린 또는 자세오시딘의 항위염 효과에 비해 쑥 추출물 자체의 항위염 효과가 더욱 뛰어나 해 당 추출물 중 미지의 물질들이 항위염 효과를 상승시키는 것으로 추정 기술하고 있다.Meanwhile, in Korean Patent Registration 181751, the anti-gastritising effect of the wormwood extract itself is more excellent than the anti-gastritising effect of eupatillin or postiosidine purified from mugwort, and it is estimated that unknown substances among the extracts increase the anti-gastritising effect. It is describing.
상기한 바와 같이, 쑥 추출물 자체가 유효 개별성분인 유파틸린 또는 자세오시딘에 비해 그 효과가 높다 하더라도 대한민국 등록특허 181751에서 보듯이, 쑥 추출물 중 개별 유효성분의 함유율이 높을수록 비례적으로 위병변 억제효과가 높아지는 경향이 명확하게 나타나 있어 해당 추출물 중 유효성분 함유량을 증가시키는 것은 그 치료효과를 더욱 상승시킬 수 있는 기회를 확보할 수 있다 하겠다.As described above, even though the effect of the mugwort extract itself is higher than that of the active individual component, eupatillin or postioscidin, as shown in the Republic of Korea Patent 181751, the higher the content of the individual active ingredient in the mugwort extract proportionally gastric lesion The inhibitory effect is clearly shown a tendency to increase, so increasing the content of the active ingredient in the extract can secure an opportunity to further increase the therapeutic effect.
더불어, 대한민국 특허공개 2006-0002639에서는, 쑥에 함유되어 있는 혈액응고억제 성분 즉, 쿠마린(coumarin)류가 포함되어 있으며 특히, 이 가운데 디쿠마롤(Dicoumarol) 성분이 추출 과정에서 포함된다고 적시하고 있다. 선행기술에 기술된 바와 같이 디쿠마롤은 소량의 투약으로도 혈소판 수를 급격히 감소시킬 수 있고 간독성도 보고된 바 있어 의학적 용도로 사용할지라도 매우 신중을 기해 투약되어야 하는 성분에 해당한다. 더욱이, 위염 또는 위궤양 환자는 위장 손상에 의한 위출혈이 동반되는 경우가 허다하므로 이 같은 성분은 반드시 제거되어야만 약효 증가를 더욱 기대할 수 있다 하겠다.In addition, Korean Patent Publication No. 2006-0002639 indicates that the anticoagulant component of wormwood, that is, coumarin, is included, and in particular, the dicoumarol component is included in the extraction process. . Dicoumarol, as described in the prior art, can dramatically reduce platelet counts even with small doses, and hepatotoxicity has also been reported, corresponding to ingredients that must be administered with great care, even when used for medical purposes. Moreover, gastritis or gastric ulcer patients are often accompanied by gastrointestinal bleeding due to gastrointestinal damage, so such components must be removed to increase the efficacy.
또한, 상기 선행기술에서는, 기존의 대한민국 특허등록 181751에 따른 알코올 또는 알코올 수용액 추출물에서는 이 성분의 제거가 용이하지 않음을 적시하고 있으며 이를 제거할 수 있는 방법으로서, 1) 애엽 잎을 알코올 또는 알코올 수용액으로 추출하는 단계(단계1), 2) 상기 단계1에서 얻어진 추출물에 알칼리 용액을 첨가하고 80℃에서 1시간 이상 반응시키는 단계(단계2), 3) 상기 단계2에서 얻어진 추출물에 산성 용액을 첨가하여 중화시키는 단계(단계3) 및 4) 상기 단계3에서 얻어진 추출물을 감압농축한 후 동결건조하는 단계(단계4)를 포함하는 제조방법을 제공하고 있다. 즉, 선행기술에 단계2 및 단계3의 알칼리 처리 및 이의 중화 과정을 포함시킴으로써 디쿠마롤 성분을 용이하게 제거할 수 있음을 알 수 있다.In addition, in the prior art, it is indicated that the removal of this component is not easy in the alcohol or alcohol aqueous solution extract according to the existing Korean patent registration 181751, and a method for removing the same, 1) leaf leaves alcohol or aqueous alcohol solution Extracting step (step 1), 2) adding an alkaline solution to the extract obtained in step 1 and reacting at 80 ° C. for at least 1 hour (step 2), 3) adding an acidic solution to the extract obtained in step 2 Neutralizing by step (step 3) and 4) it provides a manufacturing method comprising the step (step 4) of lyophilizing and then concentrated under reduced pressure of the extract obtained in step 3. That is, it can be seen that the dicoumarol component can be easily removed by including the alkali treatment of step 2 and step 3 and its neutralization process in the prior art.
본 발명에서는 기존 추출법과 달리 추출 용매를 에탄올에서 프로판올로 치환할 경우, 예상치 않게 높은 유파틸린 함량을 확보할 수 있음과 더불어 별도의 추가 공정을 거치지 않더라도, 혈액응고억제성분인 디쿠마롤이 포함되지 않는 것을 발견하여 본 발명을 완성하였다.In the present invention, unlike the conventional extraction method, when the extraction solvent is replaced with ethanol to propanol, it is possible to secure an unexpectedly high eupatillin content and does not include dicoumarol, which is a blood coagulation inhibitor, even without additional processing. The present invention was found to be complete.
본 발명은 위병변 억제 효과를 나타내는 유파틸린이 고함량으로 함유되고 별도의 제거공정을 거치지 않더라도 혈액응고성분인 디쿠마롤이 포함되지 않는 쑥 추출물의 제조방법을 확보하는 것을 목적으로 한다.It is an object of the present invention to ensure a method for preparing a mugwort extract, which contains a high content of eupatyline showing a gastric lesion suppression effect and does not include dicoumarol, which is a blood coagulation component, without undergoing a separate removal process.
본 발명은 쑥(애엽)을 프로판올로 추출, 농축하여 고농도의 유파틸린을 함유하는 쑥 프로판올 추출물에 대한 것으로 추출, 농축 과정에서 혈액응고억제 물질 즉, 디쿠마롤을 제거하기 위한 별도의 공정을 포함시키지 않더라도 디쿠마롤을 함유하지 않는 것을 특징으로 하고 있다.The present invention relates to a mugwort propanol extract containing a high concentration of eupatillin by extracting and concentrating mugwort (lobster) with propanol, and includes a separate process for removing blood coagulation inhibitors, that is, dicumarols in the extraction and concentration process. It is characterized by not containing dicoumarol even if it is not made.
본 발명에 사용되는 쑥은 황해쑥(Artemisia argyi), 쑥(A. princeps var. orientalis, A. asiatica), 산쑥(A. montana), 참쑥(A. mongolica) 및 대한약전외 한약(생약)규격집에 정의된 동속식물을 포함한다. The mugwort used in the present invention is Artemisia argyi, mugwort (A. princeps var. Orientalis, A. asiatica), mountain mugwort (A. montana), sesame seed (A. mongolica) and Korean herbal medicine (medicinal herbs) Includes homologous plants as defined in
본 발명에서 사용되는 프로판올은 1-프로판올(n-프로판올) 또는 2-프로판올(이소프로판올)을 포함한다.Propanol used in the present invention includes 1-propanol (n-propanol) or 2-propanol (isopropanol).
본 발명은, 쑥에 상기 프로판올을 가해 통상의 생약추출물 즉, 침지법, 환류법을 통해 추출 및/또는 재추출하여 이를 적절한 방법으로 여과한 뒤 별도의 추가 공정 없이 바로 농축하여 쑥 프로판올 추출물을 최종 확보한다.The present invention, by adding the propanol to the mugwort extract, and extracting and / or re-extracted through a conventional herbal extract, that is, dipping, reflux, and filtered in a suitable manner and concentrated immediately without any additional process to finalize the mugwort propanol extract Secure.
침지법을 사용하는 경우, 쑥에 프로판올을 가해 충분한 시간 동안 침지하고 이를 적절한 방법으로 여과한 뒤 감압농축하여 추출물을 획득한다.When immersion is used, propanol is added to the mugwort, it is immersed for a sufficient time, and it is filtered by an appropriate method and concentrated under reduced pressure to obtain an extract.
환류법을 사용할 경우, 여과병에 쑥을 넣고 이 병에 프로판올을 계속 환류시켜 추출액을 얻은 뒤 마찬가지로 적절한 방법으로 여과한 뒤 감압농축하여 최종 추출물을 획득한다.In the case of using the reflux method, the mugwort is added to the filter bottle and the reflux solution is continuously refluxed to obtain an extract, and then, filtered in a suitable manner and concentrated under reduced pressure to obtain the final extract.
본 발명을 통해 고함량의 유파틸린을 함유할 뿐만 아니라 약효가 더욱 개선되고 특히, 별도의 추가 제거공정을 포함하지 않더라도 혈액응고억제성분이 포함되지 않는 쑥 추출물을 확보할 수 있다.Through the present invention, not only contains a high content of eupatillin, but the drug efficacy is further improved, and in particular, even without a separate additional removal process, it is possible to obtain a mugwort extract containing no blood coagulation inhibitor.
<실시예1>Example 1
쑥 (Artemisia princeps Pamp. var. orientalis) 2kg에 2-프로판올 20kg을 가해 약 24시간 동안 환류추출하고 이를 400mesh 천으로 여과한다. 잔류물에 2-프로판올 46kg을 추가로 가해 이를 400mesh 천으로 여과하여 합친 뒤, 49℃ 부근을 유지하며 감압농축하여 프로판올 쑥 추출물 100g을 얻었다. (수득율 20:1)20 kg of 2-propanol is added to 2 kg of Artemisia princeps Pamp. Var. Orientalis and refluxed for about 24 hours and filtered through a 400 mesh cloth. 46 kg of 2-propanol was further added to the residue, and the resultant was filtered through a 400mesh cloth, combined, and concentrated under reduced pressure while maintaining the vicinity of 49 ° C. to obtain 100 g of propanol mugwort extract. (Yield 20: 1)
<실시예2>Example 2
쑥 (Artemisia princeps Pamp. var. orientalis) 2kg에 2-프로판올 20kg을 가해 약 24시간 동안 침지추출하고 이를 1500mesh 천으로 여과한다. 잔류물에 2-프로판올 46kg을 추가로 가해 이를 400mesh 천으로 여과하여 합친 뒤, 47-48℃ 부근을 유지하며 감압농축하여 프로판올 쑥 추출물 100g을 얻었다. (수득율 20:1)20 kg of 2-propanol is added to 2 kg of Artemisia princeps Pamp.var.orientis and dipping for about 24 hours and filtered with a 1500mesh cloth. 46 kg of 2-propanol was further added to the residue, and the resultant was filtered through a 400mesh cloth, combined, and concentrated under reduced pressure maintaining 47-48 ° C. to obtain 100 g of propanol mugwort extract. (Yield 20: 1)
<실시예3>Example 3
쑥 (Artemisia princeps Pamp. var. orientalis) 2kg에 1-프로판올 20kg을 가해 약 24시간 동안 환류추출하고 이를 1500mesh 천으로 여과한다. 잔류물에 2-프로판올 46kg을 추가로 가해 이를 400mesh 천으로 여과하여 합친 뒤, 47-48℃ 부근을 유지하며 감압농축하여 프로판올 쑥 추출물 100g을 얻었다. (수득율 20:1)20 kg of 1-propanol is added to 2 kg of Artemisia princeps Pamp. Var. Orientalis and refluxed for about 24 hours and filtered with a 1500mesh cloth. 46 kg of 2-propanol was further added to the residue, and the resultant was filtered through a 400mesh cloth, combined, and concentrated under reduced pressure while maintaining around 47-48 ° C. to obtain 100 g of propanol mugwort extract. (Yield 20: 1)
<실시예4>Example 4
쑥 (Artemisia princeps Pamp. var. orientalis) 3kg에 2-프로판올 39kg을 가해 약 24시간 동안 환류추출하고 이를 3㎛ 멤브레인 필터로 여과한다. 잔류물에 2-프로판올 7.5kg을 추가로 가해 이를 3㎛ 멤브레인 필터로 여과하여 합친 뒤, 49-57℃ 부근을 유지하며 감압농축하여 프로판올 쑥 추출물 150g을 얻었다. (수득율 20:1)39 kg of 2-propanol was added to 3 kg of Artemisia princeps Pamp. Var. Orientalis and refluxed for about 24 hours and filtered through a 3 μm membrane filter. 7.5 kg of 2-propanol was further added to the residue, and the resultant was filtered through a 3 μm membrane filter, combined, and concentrated under reduced pressure while maintaining the vicinity of 49-57 ° C. to obtain 150 g of propanol mugwort extract. (Yield 20: 1)
<비교예1>Comparative Example 1
쑥 (A. asiatica) 1kg에 에탄올(약전) 10kg을 가해 약 24시간 동안 추출하고 이를 400mesh 천으로 여과한다. 잔류물에 에탄올(약전) 23kg을 추가로 가해 이를 400mesh 천으로 여과하여 합친 뒤, 49℃ 부근을 유지하며 감압농축하여 에탄올 쑥 추출물 50g을 얻었다. (수득율 20:1)Add 10 kg of ethanol (pharmaceutical) to 1 kg of mugwort (A. asiatica), extract for about 24 hours, and filter it with 400mesh cloth. 23 kg of ethanol (pharmaceutical) was added to the residue, and the resultant was filtered through a 400mesh cloth, and then combined, and concentrated under reduced pressure while maintaining the vicinity of 49 ° C. to obtain 50 g of ethanol mugwort extract. (Yield 20: 1)
<실험예1> 추출용매에 따른 유파틸린 함량 비교<Experimental Example 1> Comparison of Eupatillin Contents According to Extraction Solvents
상기 실시예 및 비교예와 동일한 제조방법으로 추가적으로 1 batch씩을 제조하여 얻은 쑥 추출물 중 약효성분인 유파틸린의 함유량은 다음과 같다.The content of the eutectilin as an active ingredient of the mugwort extract obtained by additionally preparing one batch by the same preparation method as the above Examples and Comparative Examples is as follows.
결과적으로, 에탄올 추출물에 비해 프로판올 추출물에서 약효성분인 유파틸린이 약 2배 가량 증가한 결과를 나타내었다.As a result, the eupantilin, an active ingredient in the propanol extract, increased about two times as compared to the ethanol extract.
더욱이, 도1에서와 같이 유파틸린뿐만 아니라 기타 성분도 유사 비율로 증가한 결과를 나타내어, 선행기술에서 공지된 바와 같이 단일 약효성분이 아닌 추출물 자체의 약효가 더욱 증가되었다는 점을 감안할 때, 본 발명은 기타 약효성분의 함유율도 크게 증가시킨 쑥 추출물을 확보할 수 있음을 개시한다고 할 수 있다.Furthermore, as shown in FIG. 1, not only eupatillin but also other components are shown to increase in similar proportions, and as the known effect of the present invention is increased, the effect of the extract itself, which is not a single active ingredient, is further increased. It can be said that it is possible to obtain a mugwort extract with a significantly increased content of the active ingredient.
<실험예2> 혈액응고억제 성분인 디쿠마롤 측정Experimental Example 2 Measurement of Dicoumarol, a Blood Coagulation Inhibition Component
본 발명에 따른 프로판올추출물 중 디쿠마롤 성분 함유 여부를 확인하기 위해 다음과 같은 시험법으로 측정하였다.Propanol extract according to the present invention was measured by the following test method to determine whether or not containing dicummarol component.
시험법 고속액체크로마토그래프법 (HPLC법)High speed liquid chromatography (HPLC method)
컬럼 캅셀팩 C18 (4.6 x 250mm; 5㎛)Column capsule pack C18 (4.6 x 250 mm; 5 μm)
유속 1.0mL/minFlow rate 1.0mL / min
검출 UV 350nmDetection UV 350nm
주입량 10㎕
이동상 이동상 A 5mM 메탄설폰산나트륨 및 10mM 인산칼륨 혼Mobile phase Mobile phase A 5 mM sodium methanesulfonic acid and 10 mM potassium phosphate horn
액(pH 3.0)Liquid (pH 3.0)
이동상 B 아세토니트릴Mobile phase B acetonitrile
이동상 그라디에이션(gradiation)Mobile phase gradation
도2에 기재된 시험결과에서와 같이, 실시예 1 및 3의 추출물에서 디쿠마롤 성분이 전혀 검출되지 않았다. As in the test results described in FIG. 2, no dicumarole component was detected in the extracts of Examples 1 and 3.
따라서, 본 발명에 따른 쑥 프로판올 추출물은 프로판올을 이용한 추출 공정 이외에 별도의 추가 공정을 가하지 않더라도 기존 에탄올 추출물과 달리 디쿠마롤 성분이 포함되지 않음을 알 수 있다.Therefore, it can be seen that the mugwort propanol extract according to the present invention does not contain dicumarole components, unlike the existing ethanol extract, even if an additional process is not added in addition to the extraction process using propanol.
<실험예3> 쑥 프로판올 추출물의 위염병변 억제 효과Experimental Example 3 Inhibitory Effect of Mugwort Propanol Extract on Gastritis
실시예1에 따라 제조된 쑥 추출물을 약 1.5배에 해당하는 부형제(마이크로셀락)에 가해 희석, 건조하여 이 희석건조물을 대상으로 통상의 염산-에탄올 유발 위 손상 랫드(rat) 모델에서 위점막보호 효과를 평가하였다. 대조군으로서는, 비교예1에 따라 제조된 쑥 에탄올 추출물을 함유하는 동아제약 스티렌정을 분말화하여 사용하였다.Mugwort extract prepared in Example 1 by diluting and drying about 1.5 times the excipient (microcell lock) corresponding to about 1.5 times to protect the gastric mucosa in the conventional hydrochloric acid-ethanol induced gastric injury rat model The effect was evaluated. As a control, Dong-A Pharmaceutical styrene tablets containing mugwort ethanol extract prepared according to Comparative Example 1 were used as powder.
도3에 도시된 바와 같이 실시예1에 따라 제조된 쑥 프로판올 추출물은 위손 상 억제효과가 뚜렷하였고 그 효과는 투여용량에 비례한 결과를 나타내었다.As shown in Figure 3, the mugwort propanol extract prepared according to Example 1 had a clear inhibitory effect on gastric injury and the effect was proportional to the dose.
특히, 쑥 에탄올 추출물을 함유하여 시판되고 있는 스티렌정과 추출물로서 동량을 투약한 그룹 3 및 그룹 5를 비교할 때, 위병변 억제 효과가 더욱 개선되었음을 알 수 있다. In particular, when comparing the styrene tablets containing the mugwort ethanol extract and Group 3 and Group 5 dosed as the extract, it can be seen that the effect of inhibiting gastric lesions was further improved.
도 1은 실시예1 및 비교예1에 따라 제조된 각 추출물에 대한 액체크로마토그래프법에 따른 크로마토그램이다.1 is a chromatogram according to the liquid chromatograph method for each extract prepared according to Example 1 and Comparative Example 1.
도 2a 및 2b는 실시예1 및 실시예3에 따라 제조된 쑥 프로판올 추출물에 대한 혈액응고억제 물질, 디쿠마롤(Dicoumarol) 함유 유무를 확인한 크로마토그램이다. 2a and 2b are chromatograms of the presence of anticoagulant, Dicoumarol (Dicoumarol) containing the mugwort propanol extract prepared according to Examples 1 and 3.
도 3a 및 3b는 실시예1에 따라 제조된 추출물에 대한 위병변 억제 효과를 나타내는 도이다.3a and 3b is a diagram showing the effect of inhibiting gastric lesions on the extract prepared according to Example 1.
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WO2016208926A1 (en) * | 2015-06-24 | 2016-12-29 | 대원제약주식회사 | Pharmaceutical composition comprising isopropanol extract of artemisiae argyi folium |
KR20190075872A (en) * | 2011-07-26 | 2019-07-01 | 지엘팜텍주식회사 | An animal feed form with poultry productivity improvement |
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KR101292741B1 (en) * | 2011-09-29 | 2013-08-02 | 경희대학교 산학협력단 | Novel use of eupatilin |
KR20150085330A (en) * | 2014-01-15 | 2015-07-23 | 동아에스티 주식회사 | A method for preparing artemisia extract with a reduced content of hazardous substance for treatment of gastrointestinal disorders |
CN105232603A (en) * | 2015-10-10 | 2016-01-13 | 宁波绿之健药业有限公司 | Folium artemisiae argyi extract preparation method |
CN106668110A (en) * | 2015-11-06 | 2017-05-17 | 沈阳药科大学 | Artemisia argyi extract, eupatilin, jaceosidin and preparation method and application thereof |
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WO2017146309A1 (en) * | 2016-02-22 | 2017-08-31 | (주)오스티오뉴로젠 | Novel use of eupatilin as pharmaceutical composition for preventing and treating fibrosis by using epithelial-mesenchymal transition inhibitory activity thereof |
CN107550965A (en) * | 2017-08-28 | 2018-01-09 | 杨凌萃健生物工程技术有限公司 | A kind of preparation method of Folium Artemisiae Argyi extract |
KR101871166B1 (en) * | 2018-02-27 | 2018-07-02 | (주)오스티오뉴로젠 | Novel compound and composition for prevention, improvement or treatment of fibrosis or non-alcoholic steatohepatitis comprising the same |
KR102091464B1 (en) * | 2019-08-30 | 2020-03-20 | (주)오스티오뉴로젠 | Composition for anti-inflammation |
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KR0181751B1 (en) * | 1994-12-30 | 1999-05-01 | 유충식 | The extract of artemisia spps for treating gastric disease |
KR20060002639A (en) * | 2004-07-03 | 2006-01-09 | 동아제약주식회사 | Dicoumarol-removed-extract of artemisia, preparation and pharmaceutical compositions thereof |
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