KR20240079156A - Method of shikimic acid extraction using Conifer - Google Patents
Method of shikimic acid extraction using Conifer Download PDFInfo
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- KR20240079156A KR20240079156A KR1020230161223A KR20230161223A KR20240079156A KR 20240079156 A KR20240079156 A KR 20240079156A KR 1020230161223 A KR1020230161223 A KR 1020230161223A KR 20230161223 A KR20230161223 A KR 20230161223A KR 20240079156 A KR20240079156 A KR 20240079156A
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- shikimic acid
- coniferous
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- pine
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- JXOHGGNKMLTUBP-HSUXUTPPSA-N shikimic acid Chemical compound O[C@@H]1CC(C(O)=O)=C[C@@H](O)[C@H]1O JXOHGGNKMLTUBP-HSUXUTPPSA-N 0.000 title claims abstract description 77
- 238000000034 method Methods 0.000 title claims abstract description 22
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
- A23L33/105—Plant extracts, their artificial duplicates or their derivatives
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/43—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/47—Separation; Purification; Stabilisation; Use of additives by solid-liquid treatment; by chemisorption
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C62/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C62/30—Unsaturated compounds
- C07C62/32—Unsaturated compounds containing hydroxy or O-metal groups
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2200/00—Function of food ingredients
- A23V2200/30—Foods, ingredients or supplements having a functional effect on health
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2200/00—Function of food ingredients
- A23V2200/30—Foods, ingredients or supplements having a functional effect on health
- A23V2200/318—Foods, ingredients or supplements having a functional effect on health having an effect on skin health and hair or coat
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2200/00—Function of food ingredients
- A23V2200/30—Foods, ingredients or supplements having a functional effect on health
- A23V2200/324—Foods, ingredients or supplements having a functional effect on health having an effect on the immune system
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2250/00—Food ingredients
- A23V2250/20—Natural extracts
- A23V2250/21—Plant extracts
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Life Sciences & Earth Sciences (AREA)
- Mycology (AREA)
- Botany (AREA)
- Health & Medical Sciences (AREA)
- Nutrition Science (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
본 발명은 침엽수 추출물로부터 시킴산을 수득하는 방법에 관한 것으로, 구체적으로는 국내 원료인 잣나무 부산물을 이용하여 간편하고 저렴한 방법을 이용하여 고농도 고수율로 시킴산을 수득할 수 있는 방법에 관한 것이다.The present invention relates to a method of obtaining shikimic acid from coniferous extract, and specifically, to a method of obtaining shikimic acid in high concentration and high yield using a simple and inexpensive method using pine tree by-products, a domestic raw material.
Description
본 발명은 침엽수 추출물로부터 시킴산을 수득하는 방법에 대한 것이다.The present invention relates to a method for obtaining shikimic acid from coniferous extract.
시킴산(shikimic acid)(α, 4α, 5β-트리히드록시-1-시클로헥산-1-카르복실산)은 식물이나 미생물의 중요한 생화학 반응 중간체이며, 일본식물인 Illicium religiosum(Shikimi-no-ki)의 과일로부터 1885년 처음으로 분리되어 신종플루 H5N1에 대항하는 항바이러스성 약으로 널리 사용되고 있는 타미플루 합성의 원료가 되는 물질이다. 시킴산의 성분을 살펴보면, 아스코르빈산, 카로틴, 테르펜, 수지, 탄닌류, 시킴산 등이 존재하고 있다.Shikimic acid (α, 4α, 5β-trihydroxy-1-cyclohexane-1-carboxylic acid) is an important biochemical reaction intermediate in plants and microorganisms, and is used in the Japanese plant Illicium religiosum (Shikimi-no-ki). ) It is a material used as a raw material for the synthesis of Tamiflu, which was first isolated in 1885 from the fruit and is widely used as an antiviral drug against H5N1 swine flu. Looking at the components of shikimic acid, ascorbic acid, carotene, terpene, resin, tannins, shikimic acid, etc. exist.
상기 시킴산은 생체 내에서 특정 항원에 대한 세포성 및 체액성 면역반응을 강화시켜 주기 위해 항원과 함께 사용하는 물질이다. 현재까지 시판되는 백신에 사용되는 면역증강제로는 약 70년전 개발된 Alum이라는 물질이 가장 널리 사용되고 있으나, 최근 선천성 면역에 대한 연구가 활발히 진행되면서, 선천성 면역 유발인자를 활용하여 우수한 효과를 보이는 면역증강제가 개발되어 사용되고 있다.The shikimic acid is a substance used together with an antigen to strengthen cellular and humoral immune responses to a specific antigen in vivo. As an adjuvant used in commercially available vaccines to date, a substance called Alum, developed about 70 years ago, is the most widely used. However, as research on innate immunity has recently become active, an adjuvant that shows excellent effectiveness by utilizing innate immunity triggers has been developed. has been developed and is being used.
현재 새로운 바이러스가 계속 생기면서 인체질병예방을 위한 천연물 추출물을 활용한 새로운 치료제 개발에 도움이 되는 기능성 소재의 개발이 필요하다. 그러나, 천연물을 기반으로 한 기능성 소재는 한정된 분야에서만 사용되며, 인체로 유입된 바이러스 제거에 대한 기능과 안전성에 대한 연구 결과가 미흡한 실정이다. Currently, as new viruses continue to emerge, there is a need to develop functional materials that can help develop new treatments using natural product extracts to prevent human diseases. However, functional materials based on natural products are used only in limited fields, and research results on their function and safety in removing viruses introduced into the human body are insufficient.
최근 천연물로부터 간단한 단계만을 거쳐 합성되는 천연물의약품 중 가장 대표적이며 시장성을 확보하고 있는 물질이 오셀타미비르 항바이러스제이다. 자연적인 변이를 통해 발병한 신종 바이러스에 대항하는 항바이러스제의 생산을 위해 식물자원에서 제한적인 양으로 생산되는 원료(시킴산)를 안정적으로 원활하게 생산함으로써, 환경친화적이고 안정된 방법을 이용하여 천연물의약품의 원료가 되는 물질이 생산 가능하다.Among the natural medicines recently synthesized from natural products through simple steps, the most representative and marketable substance is oseltamivir, an antiviral agent. For the production of antiviral agents against new viruses that have arisen through natural mutations, natural medicinal products are produced using an environmentally friendly and stable method by stably and smoothly producing raw materials (shikimic acid) produced in limited quantities from plant resources. Materials that serve as raw materials can be produced.
또한, 시킴산을 이용한 피부 미백 효과의 기능을 테스트하여 시킴산이 피부 미백 효과에 뛰어난 역할을 하는 화장품 원료로서의 가능성을 보여준 연구가 발표된 바 있고, 시킴산으로부터 합성되는 물질들이 암 세포주 (급성 림프구성백혈병, 유방암, 간세포암, 전립선암, 경부암)에 대해 항암효과가 탁월하다는 연구 결과들이 발표되고 있다. In addition, a study was published that tested the skin whitening effect using shikimic acid and showed the possibility of shikimic acid as a cosmetic raw material that plays an excellent role in skin whitening effect, and that substances synthesized from shikimic acid were used in cancer cell lines (acute lymphocytic Research results have been published showing that it has excellent anticancer effects against leukemia, breast cancer, hepatocellular carcinoma, prostate cancer, and cervical cancer.
따라서, 시킴산은 훨씬 광범위하고 다양한 천연물 의약품으로 개발 가능한 잠재력을 지닌 물질로써 앞으로의 잠재적 수요가 더욱 기대되는 물질로서 이를 원활하게 공급하는 것에 대한 연구가 필요한 실정이다.Therefore, shikimic acid is a substance that has the potential to be developed into a much wider and more diverse range of natural medicines, and is expected to have greater potential demand in the future, so research is needed to smoothly supply it.
한편, 잣나무는 소나무과 소나무속에 속하는 늘푸른 바늘잎 큰키나무로, 학명은 Pinus koraiensis Siebold & Zuccarine이라 한다. 잣은 건강식품으로 으뜸이며, 우리나라에서 생산된 잣은 맛이 향기롭고 고소함이 세계적이라 할 수 있다. 일반적으로, 몸이 허약할 때 잣죽을 먹으며, 여성의 미용, 병후쇠약, 변비, 기침, 비만에도 사용되며, 특히 잣송이 구과는 경기가 심한 유아 방에 걸어두면 안정을 취하기도 하고 항균, 항염증 등의 다양한 효능이 알려져있다. Meanwhile, Pine Tree is a tall tree with evergreen needle leaves belonging to the Pinus genus of the Pine family, and its scientific name is Pinus koraiensis Siebold & Zuccarine. Pine nuts are the best health food, and the pine nuts produced in Korea have a fragrant and world-class taste. In general, pine porridge is eaten when the body is weak, and it is used for women's beauty, weakness after illness, constipation, cough, and obesity. In particular, pine pine cones are used to provide relief when hung in a child's room when the economy is strong, and have antibacterial and anti-inflammatory properties. Various effects are known.
본 발명의 목적은 침엽수로부터 시킴산을 효율적으로 수득하는 방법을 제공하는 것을 목적으로 하며, 침엽수 부산물에 처리되는 알부민 용액의 처리 농도와 수확시기, 부위별 비교를 통한 시킴산 생산 최적 조건을 탐색하고, 생산 최적조건 하에서 다양한 시킴산 추출방법을 통해 최대량의 시킴산을 수득하는 방법을 제공하는 데에 있다. The purpose of the present invention is to provide a method for efficiently obtaining shikimic acid from coniferous trees, and to explore the optimal conditions for producing shikimic acid by comparing the treatment concentration, harvest time, and site of the albumin solution treated with coniferous by-products, The aim is to provide a method of obtaining the maximum amount of shikimic acid through various shikimic acid extraction methods under optimal production conditions.
상기 과제를 해결하기 위하여, 본 발명은 침엽수를 이용한 시킴산 추출 방법으로, 구체적으로In order to solve the above problems, the present invention is a shikimic acid extraction method using coniferous trees, specifically
(i) 침엽수 부산물을 증류수를 처리하여 농축시키는 단계; (i) concentrating the coniferous by-product by treating it with distilled water;
(ii) 농축된 추출물 속 탄닌 성분 분리하는 단계; (ii) separating the tannin component in the concentrated extract;
(iii) 음이온 및 양이온 교환수지에 통과시켜 세척하는 단계; (iii) washing by passing through an anion and cation exchange resin;
(iv) 세척된 침엽수 추출물을 진공 농축하는 단계; 및(iv) vacuum concentrating the washed coniferous extract; and
(v) 농축된 침엽수 추출물을 냉동 및 재결정화하여 분말을 만드는 단계;를 포함한다.(v) freezing and recrystallizing the concentrated coniferous extract to produce powder.
본 발명의 침엽수 추출물로부터 시킴산을 수득하는 방법에 따르면, 국내 원료인 잣나무 부산물을 이용하여 간편하고 저렴한 방법으로 높은 수율의 시킴산을 수득할 수 있으며, 특히, 추출방법은 증류수를 이용하여 침엽수 부산물에서 고농도 고수율의 시킴산을 추출할 수 있다.According to the method of obtaining shikimic acid from coniferous tree extract of the present invention, high yield of shikimic acid can be obtained in a simple and inexpensive way using pine tree by-products, which are domestic raw materials. In particular, the extraction method uses distilled water to obtain shikimic acid by-products from coniferous trees. Shikimic acid can be extracted in high concentration and high yield.
또한, 본 발명의 방법에 따라 추출된 시킴산 추출물은 항산화, 미백, 또는 항염증 목적의 의약품, 건강기능식품 분야에 다양하게 활용될 수 있다.In addition, the shikimic acid extract extracted according to the method of the present invention can be used in various fields such as pharmaceuticals and health functional foods for antioxidant, whitening, or anti-inflammatory purposes.
도 1은 본 발명의 일 실시에 따른 침엽수를 이용한 시킴산 추출 단계를 나타낸 흐름도이다.Figure 1 is a flowchart showing the steps of extracting shikimic acid using coniferous trees according to an embodiment of the present invention.
이하, 본 발명을 보다 상세히 설명하도록 한다.Hereinafter, the present invention will be described in more detail.
본 발명은 침엽수 추출물로부터 시킴산을 수득하는 방법에 대한 것으로, 다음의 단계를 포함하는 것을 특징으로 한다:The present invention relates to a method for obtaining shikimic acid from coniferous extract, characterized by comprising the following steps:
(i) 침엽수 부산물을 증류수를 처리하여 농축시키는 단계; (i) concentrating the coniferous by-product by treating it with distilled water;
(ii) 농축된 추출물 속 탄닌 성분 분리하는 단계; (ii) separating the tannin component in the concentrated extract;
(iii) 음이온 및 양이온 교환수지에 통과시켜 세척하는 단계; (iii) washing by passing through an anion and cation exchange resin;
(iv) 세척된 침엽수 추출물을 진공 농축하는 단계; 및(iv) vacuum concentrating the washed coniferous extract; and
(v) 농축된 침엽수 추출물을 냉동 및 재결정화하여 분말을 만드는 단계.(v) Freezing and recrystallizing the concentrated coniferous extract to make a powder.
이하, 각 단계의 구성을 설명한다.Below, the configuration of each step will be described.
(i) 침엽수 부산물을 증류수를 처리하여 농축시키는 단계(i) Concentrating softwood by-products by treating them with distilled water
본 발명의 일 실시형태에서, 상기 침엽수의 종류는 소나무, 메타세콰이아, 푸른구상, 전나무, 개잎갈나무, 눈측백, 잎갈나무, 일본잎갈나무, 분비나무, 개비자나무, 섬잣나무, 잣나무, 리기다소나무, 노간주나무, 향나무, 낙엽송, 곰솔(흑송), 낙우송, 편백나무 등을 사용하며, 상기 침엽수 중 적어도 하나에 국한되지 않으나, 이중 잣나무를 사용하는 것이 바람직하다. In one embodiment of the present invention, the types of coniferous trees include pine, metasequoia, blue globular, fir, Japanese larch, snow arborvitae, larch, Japanese larch, secretion tree, giraffe tree, Japanese pine tree, Japanese pine tree, and Rigida pine tree. , juniper, juniper, larch, black pine, taxidermy, cypress, etc. are used. It is not limited to at least one of the above conifers, but it is preferable to use pine.
본 발명에서 침엽수 중 잣나무를 사용하는 경우, 잣나무 부산물은 잣을 탈각 후의 구과(잣송이)의 인편, 잣나무(Pinus koraiensis)로부터 얻어지는 가지, 미성숙구과 및 성숙구과, 잣나무 뿌리 중 적어도 하나를 사용하며, 잣나무 부산물은 테르펜(terpene), 페놀화합물(phenolics), 탄닌(tannin)등의 정유성분과 엽록소성분, 무기 및 유기성분, 비타민 등의 다양한 성분이 함유되어 있다.When using pine trees among conifers in the present invention, pine tree by-products include at least one of the scales of cones (pine pine) after shelling pine nuts, branches obtained from pine trees (Pinus koraiensis), immature and mature cones, and pine roots. By-products contain essential oil components such as terpenes, phenolics, and tannin, as well as various components such as chlorophyll, inorganic and organic components, and vitamins.
본 발명의 일 실시형태에서, 상기 침엽수 부산물을 추출 및 농축하는 것이 바람직하다.In one embodiment of the present invention, it is desirable to extract and concentrate the softwood by-product.
상기 추출은 끓는 용매를 이용해 추출하는 방법(boiling)이나 오븐을 이용해 추출하는 방법 (microwave)을 이용하여 수행될 수 있으며, 이에 한정되는 것은 아니다.The extraction may be performed using a boiling solvent extraction method (boiling) or an oven extraction method (microwave), but is not limited thereto.
상기 추출은 침엽수 부산물에 물, 메탄올 및 에탄올 중 하나 이상의 용매를 가하여 중탕하고(Extraction(boiling)), 이를 추출(Filtration and dray), 여과 및 농축한 다음, 원심분리(Centrifuge)한 후 상등액을 재여과하는 과정을 포함할 수 있다.The extraction involves adding one or more solvents of water, methanol, and ethanol to the coniferous by-product and boiling it (Extraction (boiling)), extracting (filtrating and draying) it, filtering and concentrating it, and then centrifuging (Centrifuge) the supernatant. It may include a filtration process.
(ii) 농축된 추출물 속 탄닌 성분 분리하는 단계(ii) Separating the tannin component in the concentrated extract
본 발명의 일 실시형태에서, 상기 침엽수 부산물을 증류수로 처리하여 추출 및 농축한 후 40 내지 70℃의 온도에서 1% 알부민 용액을 투입하여 탄닌을 침전시키고 및 분리하여 탄닌을 제거하는 공정을 수행하는 것이 바람직하다. 상기 온도는 70℃인 것이 보다 바람직하다.In one embodiment of the present invention, the coniferous by-product is treated with distilled water, extracted and concentrated, and then a 1% albumin solution is added at a temperature of 40 to 70 ° C. to precipitate tannin and separate to remove tannin. It is desirable. It is more preferable that the temperature is 70°C.
상기 알부민 용액 외에 탄닌을 침전시키기 위한 용도로 사용되는 물질이라면 이에 제한되지 않고 사용할 수 있으며, 예를 들면 카제인, 젤라틴 등을 사용하는 것이 바람직하다.Any substance used for precipitating tannin other than the albumin solution may be used without limitation, and for example, casein, gelatin, etc. are preferably used.
(iii) 음이온 및 양이온 교환수지에 통과시켜 세척하는 단계(iii) Washing by passing through an anion and cation exchange resin.
본 발명의 일 실시형태에서, 상기 탄닌이 제거된 침엽수 추출물을 강산성 양이온 교환수지 및 약염기성 음이온 교환수지를 통과시킨 후, 브롬티몰(Bromthymol)청알림액이 음성일 때까지 증류수로 세척하는 것이 바람직하다. In one embodiment of the present invention, it is preferable to pass the coniferous extract from which the tannins have been removed through a strongly acidic cation exchange resin and a weakly basic anion exchange resin, and then wash it with distilled water until the bromthymol blue alim solution is negative. do.
(iv) 세척된 침엽수 추출물을 진공 농축하는 단계 (iv) vacuum concentrating the washed coniferous extract.
본 발명의 일 실시형태에서, 상기 (iii) 단계에서 세척된 침엽수 추출물을 초산용액을 이용해 탈착한 후 진공 농축하여 엑기스화하고, 알코올 용액에 24 내지 72 시간 동안 용해하는 것이 바람직하다. In one embodiment of the present invention, it is preferable to desorb the coniferous extract washed in step (iii) using an acetic acid solution, extract it by vacuum concentration, and dissolve it in an alcohol solution for 24 to 72 hours.
상기 알코올은 메타놀(Methanol)을 사용하는 것이 보다 바람직하고, 상기 용해 시간은 48시간 동안 수행되는 것이 보다 바람직하다.It is more preferable to use methanol as the alcohol, and the dissolution time is more preferably 48 hours.
(v) 냉동 및 재결정화하여 분말을 만드는 단계(v) Freezing and recrystallization to make powder
본 발명의 일 실시형태에서, 상기 (iv) 단계에서 진공 농축된 침엽수 추출물을 냉동 및 재결정화하여 시킴산 추출 분말을 제조하였다. In one embodiment of the present invention, shikimic acid extract powder was prepared by freezing and recrystallizing the vacuum-concentrated coniferous extract in step (iv).
본 발명의 일 실시형태에서, 상기 침엽수 부산물로부터 추출된 시킴산 추출물을 유효성분으로 함유하는 항산화, 미백, 또는 항염증 목적의 의약품, 건강기능식품 분야에 다양하게 활용될 수 있다.In one embodiment of the present invention, the shikimic acid extract extracted from the coniferous by-product can be used in a variety of fields in the fields of pharmaceuticals and health functional foods for antioxidant, whitening, or anti-inflammatory purposes, containing the shikimic acid extract as an active ingredient.
이하, 실시예에 의해 본 발명을 보다 구체적으로 설명하고자 한다. 이들 실시예는 오직 본 발명을 설명하기 위한 것으로, 본 발명의 범위가 이들 실시예에 국한되지 않는다는 것은 당업자에게 있어서 자명하다.Hereinafter, the present invention will be described in more detail through examples. These examples are only for illustrating the present invention, and it is obvious to those skilled in the art that the scope of the present invention is not limited to these examples.
실시예 1 : 침엽수 부산물로부터 시킴산 분리 및 추출Example 1: Separation and extraction of shikimic acid from coniferous by-products
실시예 1-1 : 잣나무 부산물로부터 시킴산 분리 및 추출Example 1-1: Separation and extraction of shikimic acid from pine tree by-products
잣나무 부산물을 증류수로 추출하여 농축한 후, 70℃ 고온에서 1% 알부민 용액을 투입하여 탄닌 침전 및 분리 제거하였다. 그런 다음, 강산성 양이온 교환수지 및 약염기성 음이온 교환수지를 통과시킨 후 브롬티몰청알림액이 음성일 때까지 증류수로 세척하였다. 세척 후, 1M 초산용액을 이용해 탈착한 후 진공 농축하여 엑기스화하고, 메타놀 용액에 48hr 동안 용해한 후 냉동 및 재결정화하여 분말을 제조하였다.Pine tree by-products were extracted and concentrated with distilled water, and then 1% albumin solution was added at a high temperature of 70°C to precipitate and separate tannin. Then, it was passed through a strongly acidic cation exchange resin and a weakly basic anion exchange resin, and then washed with distilled water until the bromthymol cyanide test result was negative. After washing, it was desorbed using a 1M acetic acid solution, concentrated under vacuum, converted into extract, dissolved in methanol solution for 48 hours, frozen, and recrystallized to prepare a powder.
실시예 1-2 : 잣나무 부산물로부터 시킴산 분리 및 추출Example 1-2: Separation and extraction of shikimic acid from pine tree by-products
70℃에서 1% 알부민 용액을 투입하는 대신 40℃에서 투입하는 것을 제외하고는, 상기 실시예 1-1과 동일한 방법으로 시킴산을 분리 및 추출하여 분말을 제조하였다. Powder was prepared by separating and extracting shikimic acid in the same manner as Example 1-1, except that instead of adding the 1% albumin solution at 70°C, it was added at 40°C.
실시예 1-3 : 잣나무 부산물로부터 시킴산 분리 및 추출Example 1-3: Separation and extraction of shikimic acid from pine tree by-products
70℃에서 1% 알부민 용액을 투입하는 대신 50℃에서 투입하는 것을 제외하고는, 상기 실시예 1-1과 동일한 방법으로 시킴산을 분리 및 추출하여 분말을 제조하였다. Powder was prepared by separating and extracting shikimic acid in the same manner as Example 1-1, except that instead of adding the 1% albumin solution at 70°C, it was added at 50°C.
실시예 1-4 : 잣나무 부산물로부터 시킴산 분리 및 추출Example 1-4: Separation and extraction of shikimic acid from pine tree by-products
70℃에서 1% 알부민 용액을 투입하는 대신 60℃에서 투입하는 것을 제외하고는, 상기 실시예 1-1과 동일한 방법으로 시킴산을 분리 및 추출하여 분말을 제조하였다. Shikimic acid was separated and extracted in the same manner as Example 1-1, except that instead of adding the 1% albumin solution at 70°C, it was added at 60°C to prepare powder.
실시예 1-5 : 잣나무 부산물로부터 시킴산 분리 및 추출Example 1-5: Separation and extraction of shikimic acid from pine tree by-products
메타놀 용액시간을 48hr 대신 24hr로 수행하는 것을 제외하고는, 상기 실시예 1-1과 동일한 방법으로 시킴산을 분리 및 추출하여 분말을 제조하였다. Powder was prepared by separating and extracting shikimic acid in the same manner as Example 1-1, except that the methanol solution time was 24 hours instead of 48 hours.
실시예 1-6 : 잣나무 부산물로부터 시킴산 분리 및 추출Example 1-6: Separation and extraction of shikimic acid from pine tree by-products
메타놀 용액시간을 48hr 대신 72hr로 수행하는 것을 제외하고는, 상기 실시예 1-1과 동일한 방법으로 시킴산을 분리 및 추출하여 분말을 제조하였다. Powder was prepared by separating and extracting shikimic acid in the same manner as Example 1-1, except that the methanol solution time was 72 hours instead of 48 hours.
실시예 2 : 소나무 부산물로부터 시킴산 분리 및 추출Example 2: Separation and extraction of shikimic acid from pine byproducts
잣나무 부산물 대신 소나무 부산물을 사용하는 것을 제외하고는, 상기 실시예 1-1과 동일한 방법으로 시킴산을 분리 및 추출하여 분말을 제조하였다.Powder was prepared by separating and extracting shikimic acid in the same manner as Example 1-1, except that pine byproducts were used instead of pine byproducts.
실시예 3 : 전나무 부산물로부터 시킴산 분리 및 추출Example 3: Separation and extraction of shikimic acid from fir by-products
잣나무 부산물 대신 전나무 부산물을 사용하는 것을 제외하고는, 상기 실시예 1-1과 동일한 방법으로 시킴산을 분리 및 추출하여 분말을 제조하였다.Powder was prepared by separating and extracting shikimic acid in the same manner as Example 1-1, except that fir by-products were used instead of pine tree by-products.
실시예 4 : 눈측백나무 부산물로부터 시킴산 분리 및 추출Example 4: Separation and extraction of shikimic acid from arborvitae by-products
잣나무 부산물 대신 눈측백나무 부산물을 사용하는 것을 제외하고는, 상기 실시예 1-1과 동일한 방법으로 시킴산을 분리 및 추출하여 분말을 제조하였다.Powder was prepared by separating and extracting shikimic acid in the same manner as Example 1-1, except that arborvitae by-products were used instead of pine by-products.
참조예 1 : 시킴산의 분석Reference Example 1: Analysis of shikimic acid
Agilent(USA) 1200 series를 이용하여 시킴산 분석을 시행하였다. 컬럼은 250×4.6mm waters NH2 5㎛였으며, 이동상은 isocratic 조건으로 0.1%의 인산을 포함한 Acetonitrile 90%을 이용하였다. flow rate은 분당 1mL이 흐르도록 하였으며, 파장 215nm의 UV검출기를 통해 시킴산 피크를 확인하였다.(HPLC system : Agilent(USA) 1200 series, Detector : UV-DAD, Column : waters (250*4.6mm, 5um), Mobile phase : Isocratic (0.1% )water.(0.1%)acetonitrile= 1.9, Flow rate : 1ml/min, UV wavelength : 215nm, Sample size : 10uL, Total run time : 20min, Retention time : 6.5min)Shikimic acid analysis was performed using the Agilent (USA) 1200 series. The column was 250×4.6mm waters NH 2 5㎛, and the mobile phase was 90% Acetonitrile containing 0.1% phosphoric acid under isocratic conditions. The flow rate was set at 1 mL per minute, and the shikimic acid peak was confirmed through a UV detector with a wavelength of 215 nm. (HPLC system: Agilent (USA) 1200 series, Detector: UV-DAD, Column: waters (250*4.6mm, 5um), Mobile phase: Isocratic (0.1% )water.(0.1% )acetonitrile= 1.9, Flow rate: 1ml/min, UV wavelength: 215nm, Sample size: 10uL, Total run time: 20min, Retention time: 6.5min)
검량선은 10, 50, 100, 500, 1000㎍/mL 농도의 표준물질로 구했으며, r2 값은 ≥0.999으로 나왔다. retention time은 6.5min으로 확인되었으며 시료들은 UV spectrum을 통해 시킴산임을 재확인했다. The calibration curve was obtained using standard substances at concentrations of 10, 50, 100, 500, and 1000㎍/mL, and the r2 value was ≥0.999. The retention time was confirmed to be 6.5min, and the samples were reconfirmed to be shikimate through UV spectrum.
분리된 시킴산은 냉동건조 또는 고압증류장치를 이용하면 분말상태로 정제된다.The separated shikimic acid is purified into powder form by freeze-drying or using a high-pressure distillation device.
실험예 1 : 침엽수 종류별 시킴산 함량 측정Experimental Example 1: Measurement of shikimic acid content by coniferous tree type
상기 실시예의 방법 중 침엽수 종류별로 시킴산을 농축/추출한 후 시킴산 함량을 비교하였으며, 각 처리당 총 3반복의 실험을 수행하였다.In the method of the above example, shikimic acid was concentrated/extracted for each type of coniferous tree and the shikimic acid content was compared, and a total of three experiments were performed for each treatment.
상기 표 1을 참고하면, 침엽수 부산물 종류별로 시킴산을 추출하였을 때 잣나무 부산물에서 월등히 많은 시킴산이 추출된다는 것을 확인하였다. 결과적으로, 침엽수 부산물 중 잣나무 부산물에서 시킴산 함량이 가장 높게 나온 것을 확인하였다.Referring to Table 1 above, it was confirmed that when shikimic acid was extracted for each type of coniferous by-product, significantly more shikimic acid was extracted from pine tree by-product. As a result, it was confirmed that among coniferous by-products, pine tree by-products had the highest shikimic acid content.
실험예 2 : 추출온도별, 시킴산 함량 측정Experimental Example 2: Measurement of shikimic acid content by extraction temperature
침엽수 부산물의 시킴산 추출량이 많은 잣나무 부산물을 이용하여 상기 실시예 1의 방법 중 증류수로 추출/농축한 후 처리온도별 시킴산 함량을 측정하여 표 2에 나타내었다.Pine tree by-products, which contain a large amount of shikimate extract from coniferous tree by-products, were extracted/concentrated with distilled water in the method of Example 1, and then the shikimic acid content was measured at each treatment temperature, and is shown in Table 2.
상기 표 2를 참고하면, 잣나무 부산물을 이용하여 추출 및 농축한 후 알부민 용액을 이용해 탄닌을 침전 및 분리시키기 위해 추출온도별로 시킴산 함량을 측정한 결과 70℃에서 높은 시킴산 함량을 확인하였다.Referring to Table 2, after extraction and concentration using pine tree by-products, the shikimic acid content was measured at each extraction temperature to precipitate and separate tannin using an albumin solution, and a high shikimic acid content was confirmed at 70°C.
실험예 3 : 메타놀 용해 시간별 시킴산 함량 측정Experimental Example 3: Measurement of shikimic acid content according to methanol dissolution time
침엽수 부산물의 시킴산 추출량이 많은 잣나무 부산물을 이용하여 상기 실시예 1-1의 방법 중 메타놀 용액을 이용하여 용해시간대별 시킴산 함량을 측정하여 표 3에 나타내었다.Using pine tree by-products, which contain a large amount of shikimate extract from coniferous tree by-products, the shikimic acid content was measured for each dissolution time using methanol solution in the method of Example 1-1, and is shown in Table 3.
상기 표 3을 참고하면, 메타놀 용액을 용해 시간별로 시킴산 함량을 측정한 결과 48시간에서 높은 시킴산 함량을 확인하였다.Referring to Table 3 above, as a result of measuring the shikimic acid content of the methanol solution at each dissolution time, a high shikimic acid content was confirmed at 48 hours.
실험예 4 : 항산화 효과 측정Experimental Example 4: Measurement of antioxidant effect
상기 시킴산의 항산화 효과를 측정하기 위하여 ascorbic acid의 EC50을 측정 후 비교하여 항산화 효과를 측정하였다. ascorbic acid의 EC50 수치는 17.44 μg/mL임을 확인하였고, 본 발명에 따른 시킴산 추출물은 65.59 μg/mL로 나타나 ascorbic acid와 비교 시 약 25.59%의 항산화능을 보였다.In order to measure the antioxidant effect of shikimic acid, the EC 50 of ascorbic acid was measured and compared to measure the antioxidant effect. The EC 50 value of ascorbic acid was confirmed to be 17.44 μg/mL, and the shikimic acid extract according to the present invention was found to be 65.59 μg/mL, showing an antioxidant activity of about 25.59% compared to ascorbic acid.
이상으로 본 발명의 특정한 부분을 상세히 기술하였는 바, 본 발명이 속한 기술분야에서 통상의 지식을 가진 자에게 있어서 이러한 구체적인 기술은 단지 바람직한 구현예일 뿐이며, 이에 본 발명의 범위가 제한되는 것이 아님은 명백하다. 본 발명이 속한 기술분야에서 통상의 지식을 가진 자라면 상기 내용을 바탕으로 본 발명의 범주 내에서 다양한 응용 및 변형을 행하는 것이 가능할 것이다.As the specific parts of the present invention have been described in detail above, it is clear to those skilled in the art that these specific techniques are merely preferred embodiments and do not limit the scope of the present invention. do. Anyone skilled in the art to which the present invention pertains will be able to make various applications and modifications within the scope of the present invention based on the above contents.
따라서, 본 발명의 실질적인 범위는 첨부된 특허청구범위와 그의 등가물에 의하여 정의된다고 할 것이다.Accordingly, the actual scope of the present invention will be defined by the appended claims and their equivalents.
Claims (7)
(ii) 농축된 추출물 속 탄닌 성분 분리하는 단계;
(iii) 음이온 및 양이온 교환수지에 통과시켜 세척하는 단계;
(iv) 세척된 침엽수 추출물을 진공 농축하는 단계; 및
(v) 농축된 침엽수 추출물을 냉동 및 재결정화하여 분말을 만드는 단계;를 포함하는 침엽수를 이용한 시킴산 추출 방법.(i) concentrating the coniferous by-product by treating it with distilled water;
(ii) separating the tannin component in the concentrated extract;
(iii) washing by passing through an anion and cation exchange resin;
(iv) vacuum concentrating the washed coniferous extract; and
(v) freezing and recrystallizing the concentrated coniferous extract to produce powder.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| KR100357651B1 (en) | 1998-05-13 | 2002-10-25 | 에프. 호프만-라 로슈 아게 | Process for the preparation of shikimic acid and its salts |
| KR101587717B1 (en) | 2013-08-09 | 2016-02-02 | 고려대학교 산학협력단 | Process for obtaining shikimic acid from Sicyos angultus |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| KR100357651B1 (en) | 1998-05-13 | 2002-10-25 | 에프. 호프만-라 로슈 아게 | Process for the preparation of shikimic acid and its salts |
| KR101587717B1 (en) | 2013-08-09 | 2016-02-02 | 고려대학교 산학협력단 | Process for obtaining shikimic acid from Sicyos angultus |
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