KR102549973B1 - Method for extracting ingredient of Artemisia montana - Google Patents

Method for extracting ingredient of Artemisia montana Download PDF

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KR102549973B1
KR102549973B1 KR1020210025893A KR20210025893A KR102549973B1 KR 102549973 B1 KR102549973 B1 KR 102549973B1 KR 1020210025893 A KR1020210025893 A KR 1020210025893A KR 20210025893 A KR20210025893 A KR 20210025893A KR 102549973 B1 KR102549973 B1 KR 102549973B1
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ethanol
wild
extracting
present
eucalyptol
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KR20220121969A (en
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김주영
황인현
이원웅
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우석대학교 산학협력단
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    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C7/00Purification; Separation; Use of additives
    • C07C7/10Purification; Separation; Use of additives by extraction, i.e. purification or separation of liquid hydrocarbons with the aid of liquids
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C13/00Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
    • C07C13/02Monocyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
    • C07C13/16Monocyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with a six-membered ring
    • C07C13/20Monocyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with a six-membered ring with a cyclohexene ring
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    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/74Separation; Purification; Use of additives, e.g. for stabilisation
    • C07C29/76Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment
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    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C35/00Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring
    • C07C35/22Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a condensed ring system
    • C07C35/23Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a condensed ring system with hydroxy on a condensed ring system having two rings
    • C07C35/28Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a condensed ring system with hydroxy on a condensed ring system having two rings the condensed ring system containing seven carbon atoms
    • C07C35/29Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a condensed ring system with hydroxy on a condensed ring system having two rings the condensed ring system containing seven carbon atoms being a (2.2.1) system
    • C07C35/30Borneol; Isoborneol
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    • C07C49/00Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/385Saturated compounds containing a keto group being part of a ring
    • C07C49/417Saturated compounds containing a keto group being part of a ring polycyclic
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    • C07C49/427Saturated compounds containing a keto group being part of a ring polycyclic a keto group being part of a condensed ring system having two rings
    • C07C49/433Saturated compounds containing a keto group being part of a ring polycyclic a keto group being part of a condensed ring system having two rings the condensed ring system containing seven carbon atoms
    • C07C49/437Camphor; Fenchone
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    • C07D493/00Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/02Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
    • C07D493/08Bridged systems
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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    • Y02ATECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
    • Y02A50/00TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
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Abstract

본 발명은 산약쑥 성분의 추출 방법에 관한 것으로, 구체적으로 산약쑥을 90%(v/v) 이상의 에탄올로 추출하는 단계;를 포함하는 산약쑥으로부터 알파-피넨(α-Pinene), 유칼립톨(eucalyptol), 캠퍼(camphor) 및 보르네올(borneol)의 추출 방법에 관한 것이다.
본 발명에 따르면 산약쑥으로부터 알파-피넨, 유칼립톨, 캠퍼 및 보르네올을 효율적으로 추출할 수 있다.
The present invention relates to a method for extracting components of wild medicinal mugwort, and specifically, extracting the wild medicinal mugwort with 90% (v/v) or more ethanol; α-Pinene, eucalyptol ( eucalyptol), camphor and borneol extraction methods.
According to the present invention, alpha-pinene, eucalyptol, camphor and borneol can be efficiently extracted from wild wormwood.

Description

산약쑥 성분의 추출 방법{Method for extracting ingredient of Artemisia montana}Method for extracting ingredients of wild wormwood {Method for extracting ingredient of Artemisia montana}

본 발명은 산약쑥 성분의 추출 방법에 관한 것으로, 구체적으로 산약쑥을 90%(v/v) 이상의 에탄올로 추출하는 단계;를 포함하는 산약쑥으로부터 알파-피넨(α-Pinene), 유칼립톨(eucalyptol), 캠퍼(camphor) 및 보르네올(borneol)의 추출 방법에 관한 것이다.The present invention relates to a method for extracting components of wild medicinal mugwort, and specifically, extracting the wild medicinal mugwort with 90% (v/v) or more ethanol; α-Pinene, eucalyptol ( eucalyptol), camphor and borneol extraction methods.

산약쑥(Artemisia montana Pampan.)은 쌍떡잎식물 초롱꽃목 국화과의 여러해살이풀로 산쑥이라고도 불린다. 산지에서 자라며 주로 어린순을 나물로 먹고 잎은 말려서 뜸쑥으로 사용한다. 이러한 산약쑥의 생리활성에 대해서는 추출물의 항산화 효과, 항염증 효과 등이 보고된 바 있다. Artemisia montana Pampan.) is a perennial plant of the dicotyledonous plant Asteraceae and is also called wild sagebrush. It grows in mountainous areas and mainly eats young shoots as herbs, and dried leaves are used as moxa. Antioxidant and anti-inflammatory effects of the extract have been reported for the physiological activity of this wild artemisia.

산약쑥은 한방에서 애엽이라고 표현하는 쑥의 종류에 포함되며, 일반적으로 황해쑥, 쑥, 산약쑥(산쑥), 약쑥 등이 애엽에 포함된다.Mountain medicinal mugwort is included in the type of mugwort that is expressed as Aeyeop in oriental medicine.

이러한 애엽 중 약쑥의 추출물을 솔잎 등과 함께 피부외용제로 사용할 경우 피부소양증을 완화하는데 효과적인 것으로 알려져 있다(한국등록특허 제10-0875075호). 여기에 포함되는 다양한 성분들이 복합적으로 작용하여 이러한 효과를 나타내는 것으로 추측되지만, 약쑥의 경우 알파-피넨, 유칼립톨, 캠퍼 및 보르네올을 주요 성분으로 제시할 수 있다. 따라서 이러한 성분들을 보다 효과적으로 추출할 수 있다면 상기와 같은 효과를 높일 수 있을 것이다.Among these leaves, it is known that the extract of wormwood is effective in relieving skin pruritus when used as an external skin agent together with pine needles (Korean Patent Registration No. 10-0875075). It is presumed that the various components included here act in combination to produce these effects, but in the case of wormwood, alpha-pinene, eucalyptol, camphor, and borneol can be suggested as the main components. Therefore, if these components can be extracted more effectively, the above effects can be enhanced.

상기와 같은 약쑥의 주요성분은 산약쑥에도 존재한다. 따라서 산약쑥으로부터 상기 주요성분들을 효과적으로 추출할 수 있는 방법을 개발하고자 하였다.The main components of medicinal mugwort as described above are also present in wild medicinal mugwort. Therefore, it was attempted to develop a method for effectively extracting the main components from wild artemisia.

한국등록특허 제10-0875075호Korean Patent Registration No. 10-0875075

따라서 본 발명의 주된 목적은 산약쑥으로부터 알파-피넨, 유칼립톨, 캠퍼 및 보르네올을 효율적으로 추출할 수 있는 방법을 제공하는데 있다.Accordingly, the main object of the present invention is to provide a method for efficiently extracting alpha-pinene, eucalyptol, camphor and borneol from wormwood.

본 발명의 한 양태에 따르면, 본 발명은 산약쑥을 90%(v/v) 이상의 에탄올로 추출하는 단계;를 포함하는 산약쑥으로부터 알파-피넨, 유칼립톨, 캠퍼 및 보르네올의 추출 방법을 제공한다.According to one aspect of the present invention, the present invention provides a method for extracting alpha-pinene, eucalyptol, camphor and borneol from wild wormwood comprising the step of extracting wild wormwood with 90% (v / v) or more ethanol do.

본 발명의 추출 방법에 있어서, 산약쑥 1g에 대해 90%(v/v) 이상의 에탄올 20 내지 30㎖로 추출하는 것이 바람직하다.In the extraction method of the present invention, it is preferable to extract with 20 to 30 ml of 90% (v / v) or more ethanol based on 1 g of wild artemisia.

본 발명의 추출 방법에 있어서, 상기 추출은 상온에서 18시간 이상 이루어지는 것이 바람직하다.In the extraction method of the present invention, the extraction is preferably performed at room temperature for 18 hours or more.

본 발명에 따르면 산약쑥으로부터 알파-피넨, 유칼립톨, 캠퍼 및 보르네올을 효율적으로 추출할 수 있다.According to the present invention, alpha-pinene, eucalyptol, camphor and borneol can be efficiently extracted from wild wormwood.

본 발명의 추출 방법은 산약쑥으로부터 알파-피넨(α-Pinene), 유칼립톨(eucalyptol), 캠퍼(camphor) 및 보르네올(borneol)을 추출하는 방법으로, 산약쑥을 90%(v/v) 이상의 에탄올로 추출하는 단계;를 포함하는 것을 특징으로 한다.The extraction method of the present invention is a method of extracting α-Pinene, eucalyptol, camphor and borneol from wild wormwood, 90% (v/v) of wild wormwood It is characterized in that it comprises; the step of extracting with more than ethanol.

본 발명에서 산약쑥은 학명이 'Artemisia montana Pampan.'인 것으로, 산쑥으로도 불린다. 본 발명에서 산약쑥은 잎, 줄기, 뿌리 등 산약쑥을 이루는 임의의 부위를 사용할 수 있으며, 바람직하게는 지상부, 보다 바람직하게는 잎 부위를 사용한다.In the present invention, the scientific name of wild wormwood is ' Artemisia montana Pampan.', and is also called wild wormwood. In the present invention, the wild medicinal mugwort may use any part constituting the living medicinal mugwort such as leaves, stems, and roots, preferably the aerial part, more preferably the leaf part.

본 발명에서 산약쑥은 수확한 상태 그대로, 즉 별도의 가공 과정 없이 추출에 사용할 수 있으며, 또한 임의의 크기로 절단하거나 분말화, 예를 들어 동결건조 분말화하여 사용할 수 있다.In the present invention, wild artemisia can be used for extraction as it is harvested, that is, without a separate processing process, and can also be cut into arbitrary sizes or powdered, for example, freeze-dried and powdered.

또한 바람직하게는 산약쑥 표면의 이물질을 제거하기 위한 세척 과정, 예를 들어 물 세척 과정과 물기를 제거하기 위한 건조 과정, 예를 들어 자연 건조 또는 열풍 건조 과정을 수행한다. 만약 산약쑥을 절단하여 사용하는 경우 절단 과정 이전에 세척 과정을 수행하는 것이 바람직하며, 분말화하여 사용하는 경우 분말화 과정 이전에 세척 과정을 수행한다.In addition, preferably, a washing process for removing foreign substances on the surface of wild artemisia, for example, a water washing process and a drying process for removing moisture, for example, a natural drying or hot air drying process, are performed. If wild artemisia is cut and used, it is preferable to perform a washing process before the cutting process, and when powdered and used, a washing process is performed before the powdering process.

본 발명에서는 추출 용매로 90%(v/v) 이상의 에탄올, 즉 90 내지 100%(v/v)의 에탄올을 사용한다. 이때 에탄올 이외의 나머지는 바람직하게는 물이다. 바람직하게는 95%(v/v) 이상의 에탄올, 즉 95 내지 100%(v/v)의 에탄올을 사용하며, 보다 바람직하게는 96%(v/v) 이상의 에탄올, 즉 96 내지 100%(v/v)의 에탄올, 보다 바람직하게는 97%(v/v) 이상의 에탄올, 즉 97 내지 100%(v/v)의 에탄올, 보다 바람직하게는 98%(v/v) 이상의 에탄올, 즉 98 내지 100%(v/v)의 에탄올, 보다 바람직하게는 99%(v/v) 이상의 에탄올, 즉 99 내지 100%(v/v)의 에탄올, 보다 바람직하게는 100%(v/v)의 에탄올을 사용한다.In the present invention, 90% (v/v) or more ethanol, that is, 90 to 100% (v/v) ethanol is used as the extraction solvent. At this time, the remainder other than ethanol is preferably water. Preferably, 95% (v / v) or more ethanol, that is, 95 to 100% (v / v) ethanol is used, more preferably 96% (v / v) or more ethanol, that is, 96 to 100% (v / v) /v) ethanol, more preferably 97% (v/v) or more ethanol, i.e. 97 to 100% (v/v) ethanol, more preferably 98% (v/v) or more ethanol, i.e. 98 to 100% (v/v) ethanol 100% (v/v) ethanol, more preferably 99% (v/v) or more ethanol, i.e. 99 to 100% (v/v) ethanol, more preferably 100% (v/v) ethanol Use

본 발명에서 추출은 바람직하게는 상온, 예를 들어 15 내지 25℃에서 이루어진다. 또한 바람직하게는 18시간 이상, 예를 들어 18 내지 48시간 동안, 예를 들어 18 내지 24시간 동안 이루어진다.Extraction in the present invention is preferably carried out at room temperature, for example, 15 to 25 ℃. It is also preferably made for 18 hours or more, for example 18 to 48 hours, for example 18 to 24 hours.

본 발명에서 추출 용매는 바람직하게는 산약쑥 1g에 대해 20 내지 30㎖의 비율로 사용한다. 예를 들어, 산약쑥이 1kg인 경우 99%(v/v) 이상의 에탄올 20 내지 30ℓ를 첨가하여 추출한다.In the present invention, the extraction solvent is preferably used in an amount of 20 to 30 ml per 1 g of wild artemisia. For example, when 1 kg of wild artemisia is extracted by adding 20 to 30 liters of 99% (v/v) or more ethanol.

본 발명에서 상기 추출하는 단계 이후 여과하는 단계를 추가로 포함할 수 있다. 이때 여과는 추출 이후 잔사를 제거하는데 사용되는 통상의 여과 방법, 예를 들어 여과지를 사용하는 방법으로 달성할 수 있다.In the present invention, a filtering step may be further included after the extracting step. At this time, filtration can be achieved by a conventional filtration method used to remove residues after extraction, for example, a method using filter paper.

여과하는 단계 이후에는 선택적으로 농축하는 단계, 예를 들어, 감압 농축하는 단계를 더 포함할 수 있다.After the step of filtering, a step of selectively concentrating, for example, a step of concentrating under reduced pressure may be further included.

이하, 실시예를 통하여 본 발명을 더욱 상세히 설명하기로 한다. 이들 실시예는 단지 본 발명을 예시하기 위한 것이므로, 본 발명의 범위가 이들 실시예에 의해 제한되는 것으로 해석되지는 않는다.Hereinafter, the present invention will be described in more detail through examples. Since these examples are intended to illustrate the present invention only, the scope of the present invention is not to be construed as being limited by these examples.

[실시예][Example]

실시예 1Example 1

산약쑥 2g을 100㎖ 비커에 담고, 100% 에탄올 50㎖를 첨가하여 18시간 동안 상온 추출한 다음, 여과지로 여과하여 추출잔사가 제거된 추출물을 제조하였다.2 g of wild medicinal mugwort was placed in a 100 ml beaker, 50 ml of 100% ethanol was added and extracted at room temperature for 18 hours, and then filtered with filter paper to prepare an extract from which extraction residues were removed.

이때 산약쑥은 지상부를 건조하여 5㎝ 정도로 절단한 것을 사용하였다.At this time, the aerial part of wild artemisia was dried and cut to about 5 cm.

비교예 1Comparative Example 1

상기 실시예 1과 동일하게 실시하되, 100% 에탄올 대신 6%(v/v) 에탄올(1차 증류수 94㎖ 및 100% 에탄올 6㎖ 혼합)을 사용하여 추출물을 제조하였다.An extract was prepared in the same manner as in Example 1, but using 6% (v/v) ethanol (a mixture of 94 ml of primary distilled water and 6 ml of 100% ethanol) instead of 100% ethanol.

비교예 2Comparative Example 2

상기 비교예 1과 동일하게 실시하되, 18시간 동안의 상온 추출 대신 중탕으로 80ㅀC에서 3시간 동안 추출하여 추출물을 제조하였다.The extract was prepared in the same manner as in Comparative Example 1, but instead of extraction at room temperature for 18 hours, extraction was performed at 80°C for 3 hours in a water bath.

비교예 3Comparative Example 3

상기 실시예 1과 동일하게 실시하되, 100% 에탄올 대신 95%(v/v) n-헥산(n-hexane)을 사용하여 추출물을 제조하였다.An extract was prepared in the same manner as in Example 1, but using 95% (v/v) n-hexane instead of 100% ethanol.

비교예 4Comparative Example 4

상기 비교예 3의 추출물 50㎖과 건조된 레진(Amberliteㄾ XAD7HP) 1.0041g을 함께 100㎖ 삼각 플라스크에 넣고 입구를 밀봉한 후, 25℃에서 115rpm으로 6시간 교반하였다. 교반 후 걸러진 레진을 100㎖ 삼각 플라스크에 넣고 100% 에탄올 50㎖와 함께 25℃에서 115rpm으로 18시간 교반하였다. 여과지로 여과하여 레진이 제거된 추출물을 제조하였다.50 ml of the extract of Comparative Example 3 and 1.0041 g of dried resin (Amberlite® XAD7HP) were put together in a 100 ml Erlenmeyer flask, the inlet was sealed, and stirred at 25° C. at 115 rpm for 6 hours. After stirring, the filtered resin was put into a 100 ml Erlenmeyer flask and stirred with 50 ml of 100% ethanol at 25° C. at 115 rpm for 18 hours. Filtered with a filter paper to prepare an extract from which the resin was removed.

실험예 1Experimental Example 1

상기 실시예 1, 비교예 1 내지 4 각 추출물의 알파-피넨, 유칼립톨, 캠퍼 및 보르네올의 함량을 Agilent Technologies사(Palo Alto, CA, USA)의 7890B gas chromatograph/7000C mass spectrometer와 J&W Scientific사(Folsom, CA, USA)의 DB5-MS 컬럼을 이용하여 분석하였다.The contents of alpha-pinene, eucalyptol, camphor and borneol in each of the extracts of Example 1 and Comparative Examples 1 to 4 were measured using a 7890B gas chromatograph/7000C mass spectrometer from Agilent Technologies (Palo Alto, CA, USA) and a mass spectrometer from J&W Scientific. (Folsom, CA, USA) was analyzed using a DB5-MS column.

이의 결과, 아래의 표 1과 같이, 실시예 1의 추출물에서 알파-피넨, 유칼립톨, 캠퍼 및 보르네올 모두의 함량이 가장 높은 것으로 나타났다.As a result, as shown in Table 1 below, the extract of Example 1 showed the highest content of alpha-pinene, eucalyptol, camphor, and borneol.

알파-피넨alpha-pinene 유칼립톨eucalyptol 캠퍼camper 보르네올Borneol 실시예1Example 1 0.46±0.04 ㎍/㎖0.46±0.04 μg/mL 25.80±1.35 ㎍/㎖25.80±1.35 μg/mL 1.93±0.17 ㎍/㎖1.93±0.17 μg/mL 9.04±0.83 ㎍/㎖9.04±0.83 μg/mL 비교예1Comparative Example 1 -- 4.57±0.43 ㎍/㎖4.57±0.43 μg/mL 0.41±0.04 ㎍/㎖0.41±0.04 μg/mL 1.76±0.14 ㎍/㎖1.76±0.14 μg/mL 비교예2Comparative Example 2 -- 3.88±0.20 ㎍/㎖3.88±0.20 μg/mL 1.09±0.04 ㎍/㎖1.09±0.04 μg/mL 6.20±0.34 ㎍/㎖6.20±0.34 μg/mL 비교예3Comparative Example 3 0.11±0.01 ㎍/㎖0.11±0.01 μg/mL 1.89±0.51 ㎍/㎖1.89±0.51 μg/mL 0.10±0.01 ㎍/㎖0.10±0.01 μg/mL 0.44±0.03 ㎍/㎖0.44±0.03 μg/mL 비교예4Comparative Example 4 -- -- -- 0.16±0.15 ㎍/㎖0.16±0.15 μg/mL

Claims (3)

산약쑥(학명: 'Artemisia montana Pampan.')을 99%(v/v) 이상의 에탄올로 상온에서 추출하는 단계;를 포함하는 산약쑥으로부터 알파-피넨, 유칼립톨, 캠퍼 및 보르네올의 추출 방법.A method for extracting alpha-pinene, eucalyptol, camphor and borneol from wild wormwood, comprising: extracting wild wormwood (scientific name: ' Artemisia montana Pampan.') with 99% (v/v) or more ethanol at room temperature. 제1항에 있어서,
산약쑥 1g에 대해 99%(v/v) 이상의 에탄올 20 내지 30㎖로 추출하는, 방법.
According to claim 1,
A method of extracting with 20 to 30 ml of 99% (v / v) or more ethanol for 1 g of wild artemisia.
제1항에 있어서,
상기 추출은 상온에서 18시간 이상 이루어지는, 방법.
According to claim 1,
Wherein the extraction is performed at room temperature for 18 hours or more.
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JP2005022988A (en) * 2003-06-30 2005-01-27 Takeda Food Products Ltd Composition for promoting sugar transport of muscle cell comprising mugwort as active ingredient
JP2006045082A (en) * 2004-08-02 2006-02-16 Takeda Food Products Ltd Antifatigue agent and food and drink containing the same

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KR100875075B1 (en) 2008-05-01 2008-12-18 하호원 A composition of plants extract for alleviation of pruritis
KR101080648B1 (en) * 2009-02-26 2011-11-09 서울대학교산학협력단 A method for isolating and producing highly-concentrated Eupatilin and Jaceosidine from the extract of Artemisia species by using Centrifugal Partition Chromatography

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JP2005022988A (en) * 2003-06-30 2005-01-27 Takeda Food Products Ltd Composition for promoting sugar transport of muscle cell comprising mugwort as active ingredient
JP2006045082A (en) * 2004-08-02 2006-02-16 Takeda Food Products Ltd Antifatigue agent and food and drink containing the same

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