KR101605122B1 - Method for producing citrus fruits extract with high nobiletin or tangeretin content and use thereof - Google Patents
Method for producing citrus fruits extract with high nobiletin or tangeretin content and use thereof Download PDFInfo
- Publication number
- KR101605122B1 KR101605122B1 KR1020150180305A KR20150180305A KR101605122B1 KR 101605122 B1 KR101605122 B1 KR 101605122B1 KR 1020150180305 A KR1020150180305 A KR 1020150180305A KR 20150180305 A KR20150180305 A KR 20150180305A KR 101605122 B1 KR101605122 B1 KR 101605122B1
- Authority
- KR
- South Korea
- Prior art keywords
- citrus
- extract
- nobiletin
- tangeretin
- present
- Prior art date
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- MRIAQLRQZPPODS-UHFFFAOYSA-N nobiletin Chemical compound C1=C(OC)C(OC)=CC=C1C1=CC(=O)C2=C(OC)C(OC)=C(OC)C(OC)=C2O1 MRIAQLRQZPPODS-UHFFFAOYSA-N 0.000 title claims abstract description 47
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- ULSUXBXHSYSGDT-UHFFFAOYSA-N tangeretin Chemical compound C1=CC(OC)=CC=C1C1=CC(=O)C2=C(OC)C(OC)=C(OC)C(OC)=C2O1 ULSUXBXHSYSGDT-UHFFFAOYSA-N 0.000 title claims description 68
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
- A61K31/352—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom condensed with carbocyclic rings, e.g. methantheline
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- A23V2300/14—Extraction
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Abstract
본 발명은 노빌레틴 또는 탄제레틴 함량이 높은 감귤류 추출물의 제조방법에 관한 것으로서, 더욱 상세하게는 먼저 감귤류의 과실을 염기성용액으로 세척한 후 회수물을 알콜 수용액으로 추출하여 기존 방법보다 노빌레틴 또는 탄제레틴 함량이 높은 추출물을 제조하는 방법과 그 용도에 관한 것이다.
상기와 같은 본 발명에 따르면, 간단한 방법으로 노빌레틴 또는 탄제레틴 함량이 높은 감귤류 추출물을 추출함과 동시에 비용을 절감하는 효과가 있다. 노빌레틴 또는 탄제레틴 함량이 높은 감귤류 추출물을 유효성분으로 함유하는 높은 상품성의 기억력 증진, 치매 예방, 항암, 항염증, 아토피 개선, 가려움증 개선, 항비만, 지질대사 질병 개선, 치주염 개선, 골다공증을 포함한 골대사성 질환 개선 및 지방간 개선 효과가 있는 조성물 및 약학 조성물을 제공한다.The present invention relates to a method for producing citrus extract having high content of novelletin or a resorcinol. More specifically, citrus fruit is first washed with a basic solution and then extracted with an alcohol aqueous solution. The present invention relates to a method for producing an extract having a high content of retin and its use.
According to the present invention as described above, citrus extract having a high content of nobiletin or enamel retin is extracted by a simple method, and the cost is reduced. The present invention relates to a pharmaceutical composition containing a high-potency citrus extract having a high content of novirretin or tamsuletin as an active ingredient, for improving memory, dementia prevention, anti-cancer, antiinflammatory, atopic improvement, itching improvement, anti-obesity, lipid metabolic disease improvement, And to provide a composition and a pharmaceutical composition that have an effect of improving bone metabolism and improving fatty liver.
Description
본 발명은 감귤류에서 노빌레틴 및 탄제레틴 함량이 높은 추출물을 추출하는 방법과 그 용도에 관한 것이다.
The present invention relates to a method for extracting an extract having a high content of novelletine and resorcinol in citrus fruits and a use thereof.
최근 여러 가지 화학물질을 식품이나 의약품으로 이용할 때 부작용과 지나친 자극을 줄이기 위해 천연물을 사용한 식품 및 약품 조성물이 다양하게 개발되고 있으며, 천연재료는 부작용이 적을 뿐만 아니라 소비자들의 호응이 높아 약품과 화장품의 원료로써 개발가치가 증가하고 있는 추세이다.Recently, various foods and pharmaceutical compositions using natural materials have been developed in order to reduce adverse effects and excessive stimulation when various chemicals are used as food or medicine. Natural materials have a low side effect and are highly popular with consumers, The value of development as a raw material is increasing.
감귤류 과일은 우리나라에서 많이 생산되는 과일이며 제주도에는 토종 감귤인 진귤(C.sunki hort. ex Tanaka)을 비롯해 다양한 품종의 감귤류 과일이 재배되고 있다. 감귤류 과일에 대해서 기존에는 비타민 C의 대명사로만 불리어 왔다. 하지만 감귤에는 몸에 이로운 다른 기능성 물질이 다양하게 있으며, 작은 분자량을 갖는 폴리페놀류 성분인 플라보노이드는 이러한 기능성 물질의 한 종류로서 감귤류 과일에는 60여 가지가 존재한다. 대부분의 플라보노이드 물질은 하이드록시기(-OH)를 가지며 이것이 항산화 등의 기능과 관련 있는 것으로 보인다. 하지만 노빌레틴(nobiletin)은 플라보노이드류 중 메톡실기(CH3O-)를 갖는 플라본 그룹에 속하며, 이는 하이드록시 플라본보다 적은 함량으로도 생물학적 활성이 높은 것으로 알려져 있다. 이에 해당하는 것은 노빌레틴(nobiletin)외에도 탄제레틴(tangeretin), 시넨시틴(sinensitin)이 있으며, 특히 이 성분들은 감귤류에서만 발견되는 물질로 알려져 있어서 천연재료로서 감귤류의 유용성을 알 수 있다.Citrus fruits are a lot of fruit produced in Korea, and citrus fruits such as C.sunki hort. Ex Tanaka are cultivated in Jeju Island. For citrus fruits, vitamin C has been said to be synonymous. However, citrus has a variety of other functional materials that are beneficial to the body. Flavonoids, a polyphenolic compound with a small molecular weight, are a kind of this functional substance, and there exist about 60 kinds of citrus fruit. Most flavonoids have a hydroxyl group (-OH), which appears to be related to antioxidant functions. However, nobiletin belongs to a flavonoid group having a methoxyl group (CH3O-) among flavonoids, which is known to have a high biological activity even at a content lower than that of hydroxyflavone. In addition to nobiletin, there are also tangeretin and sinensitin. Especially, these ingredients are known to be found only in citrus fruits, so the usefulness of citrus fruits as a natural ingredient can be known.
감귤류의 노빌레틴(nobiletin), 탄제레틴(tangeretin) 및 다른 폴리메톡시플라보노이드(PMF)에 대해서 항암, 항염증, 면역조절, 신경보호, 기억력손상 회복 효과 작용(Li, R. W., Theriault, A. G., Au, K., Douglas, T. D., Casaschi, A., Kurowska, E. M. and Mukherjee, R., Citrus polymethoxylated flavones improve lipid and glucose homeostasis and modulate adipocytokines in fructose-induced insulin resistant hamsters., Life Sciences 79: 365-373, 2006)이 보고된 바 있다. 또한 간기능 개선 효과(Satomi Onoue et al., Physicochemical and biopharmaceutical characterization of amorphous solid dispersion of nobiletin, a citrus polymethoxylated flavone, with improved hepatoprotective effects, European Journal of Pharmaceutical Sciences 49: 453-460, 2013), 항비만 효과(Young-Sil Lee et al., Nobiletin improves obesity and insulin resistance in high-fat diet-induced obese mice, Journal of Nutritional Biochemistry 24: 156?162, 2013), 치주염 개선 효과(Tsukasa Tominari et al., Polymethoxy Flavonoids, Nobiletin and Tangeretin, Prevent Lipopolysaccharide-Induced Inflammatory Bone Loss in an Experimental Model for Periodontitis, Journal of Pharmacological Sciences 119: 390?394, 2012), 골다공증을 포함한 골대사성 질환 개선 효과(Suguru Harada et al., Nobiletin, a Polymethoxy Flavonoid, Suppresses Bone Resorption by Inhibiting NFκB-Dependent Prostaglandin E Synthesis in Osteoblasts and Prevents Bone Loss Due to Estrogen Deficiency, Journal of Pharmacological Sciences 115: 89-93, 2011), 가려움증 개선 효과(Se-Eun Jang et al., Nobiletin and tangeretin ameliorate scratching behavior in mice by inhibiting the action of histamine and the activation of NF-κB, AP-1 and p38, International Immunopharmacology 17: 502?507, 2013), 지질대사 이상 개선 효과(Yuguang Lin et al., Molecular Structures of Citrus Flavonoids Determine Their Effects on Lipid Metabolism in HepG2 Cells by Primarily Suppressing ApoB Secretion Journal of Agricultural, Food Chemistry 59: 4496-4503, 2011) 등 여러 약리 작용이 최근 잇달아 보고된 바 있다.Anti-cancer, anti-inflammatory, immunomodulatory, neuroprotective, and memory-restorative effects (Li, RW, Theriault, AG, Au) on citrus nobiletin, tangeretin and other polymethoxy flavonoids , K., Douglas, TD, Casaschi, A., Kurowska, EM and Mukherjee, R., Citrus polymethoxylated flavones to improve lipid and glucose homeostasis and modulate adipocytokines in fructose-induced insulin resistant hamsters. Life Sciences 79: 365-373, 2006) have been reported. In addition, the effect of improving liver function (Satomi Onoue et al., Physicochemical and biopharmaceutical characterization of amorphous solid dispersion of nobiletin, a citrus polymethoxylated flavone, improved hepatoprotective effects, European Journal of Pharmaceutical Sciences 49: 453-460, 2013) (Tsukasa Tominari et al., Polymethoxy Flavonoids (2004)). In addition, the present inventors have found that the use of the polymethoxy flavonoids , Nobiletin and Tangeretin, Prevent Lipopolysaccharide-Induced Inflammatory Bone Loss in an Experimental Model for Periodontitis, Journal of Pharmacological Sciences 119: 390-394, 2012), the effect of improving bone metabolic diseases including osteoporosis (Suguru Harada et al., Nobiletin, Polymethoxy Flavonoid, Suppresses Bone Resorption by Inhibiting NFκB-Dependent Prostaglandin E Synthesis in Osteoblasts and Prevents Bone Loss Due to Estrogen Deficiency, Jou (NF-κB, AP-1, and NF-κB) inhibited the action of histamine and the tangeretin ameliorate scratching behavior in mice (Sei Eun Jang et al., Rnal of Pharmacological Sciences 115: 89-93, 2011) and p38, International Immunopharmacology 17: 502-507, 2013), lipid metabolism abnormality improvement effect (Yuguang Lin et al., Molecular Structures of Citrus Flavonoids Determine their Effects on Lipid Metabolism in HepG2 Cells by Primarily Suppressing ApoB Secretion Journal of Agricultural, Chemistry 59: 4496-4503, 2011) have been recently reported.
이러한 약리 작용 때문에 감귤류의 노빌레틴과 탄제레틴에 대한 수요가 증가하고 있는데, 노빌레틴과 탄제레틴을 다량 함유하는 원재료 감귤류에서 저비용으로 높은 함량을 가지는 추출물의 제조방법의 필요성이 높아지고 있다. 감귤류, 특히 진귤(C.sunki hort. ex Tanaka)은 제주에서 자생하는 12종의 자생 토종귤 중의 하나이며 진귤의 과피를 건조시킨 진피는 한의약재로 사용되어 왔다. 한라봉(C.hybrid Shiranuhi)은 제주에서 생산하는 고급 품종의 감귤인데 진귤과 한라봉에는 노빌레틴과 탄제레틴 추출이 보고된 바 있다. 특히 한라봉을 이용한 과자, 음료 등을 생산할 때 착즙 후의 잔여물이 다량 남기 때문에 이 잔여물의 효과적인 재활용이 필요하다. Due to this pharmacological action, there is a growing demand for nonyltetin and benzetretin in citrus, and there is a growing need for a method for producing extracts having a high content at low cost from raw citrus fruits containing a large amount of nobiletin and resorcinol. Citrus fruits, especially C.sunki hort. Ex Tanaka, are one of 12 indigenous native mandarins native to Jeju. The dermis, which has dried the skin of the mandarin orange, has been used as a medicinal herb. C. hybrid Shiranuhi is a high-grade citrus fruit produced in Jeju. Jeju and Halabong have been reported to extract Novartin and Tangerine extract. Especially, it is necessary to effectively recycle these residues since the residues after the juice are left in large quantities when producing confectionery and beverage using hara ram.
특히 노빌레틴(nobiletin) 및 탄제레틴(tangeretin)은 과육에도 많지만 착즙 잔여물에 다량 들어있는 것이 보고되었는데, 감귤 착즙 잔여물의 이러한 가능성에도 불구하고 아직 식품이나 의약품의 재료로 충분히 이용되고 있지 않으며, 그 이유중 하나는 노빌레틴과 탄제레틴을 고함량으로 함유하는 추출물을 경제적으로 얻을 수 있는 추출법의 개량이 부족했기 때문이다.In particular, nobiletin and tangeretin have been reported to be present in a large amount in the fruit juice but in the juice residue. Despite this possibility of the citrus juice residue, it has not yet been fully utilized as a food or medicine material, One of the reasons is the lack of an improved extraction method that economically obtains extracts containing a high content of Novartin and Benzaretin.
대한민국 공개특허 제10-2013-0034319호(진피, 당귀 및 계피의 혼합 생약 추출물을 유효성분으로 함유하는 비만 및 고지혈증의 예방 및 치료용 조성물)는 진피(Citrus unshiu), 당귀(Angelicae gigantis radix) 및 계피(Cinnamomi cortex)의 혼합 생약 추출물을 유효성분으로 함유하는 비만증의 예방 및 치료용 약학조성물에 관한 것인데, 선행기술에서 추출법은 진귤의 과피를 물, 메탄올, 에탄올 또는 이들의 혼합용매로 열수추출할 뿐이다. 이렇게 감귤류에서 노빌레틴과 탄제레틴 함유 추출물을 제조하는 종래의 방법은 추출 효율이 낮고 장시간이 소요되거나 비용이 많이 들고 에너지의 소비가 높아 산업적으로 적용하기에는 여러 가지 문제점을 안고 있다. 이에, 본 발명자들은 노빌레틴과 탄제레틴 함량이 높은 추출물을 추출하는 새로운 방법과 그 추출물의 용도를 제공하고자 한다.
Korean Patent Laid-Open No. 10-2013-0034319 (a composition for preventing and treating obesity and hyperlipidemia containing an herbal extract of dandelion, cinnamon and cinnamon as an active ingredient) comprises at least one selected from the group consisting of Citrus unshiu, Angelica gigantis radix, The present invention relates to a pharmaceutical composition for the prevention and treatment of obesity, which comprises a mixed herbal medicine extract of Cinnamomi cortex as an active ingredient. In the prior art, the extraction method comprises the steps of extracting the skin of the orange with hot water, methanol, ethanol or a mixed solvent thereof Only. Thus, the conventional methods for preparing the extracts containing nobiletin and tamsuletin in citrus have various problems in industrial application due to low extraction efficiency, long time, high cost and high energy consumption. Accordingly, the present inventors intend to provide a novel method for extracting nobiletin and a high-content extract of retinol, and the use of the extract.
본 발명의 목적은 부작용이 없는 천연물 소재인 감귤류에서 노빌레틴 또는 탄제레틴 함량이 높은 추출물을 종래 추출방법에 비하여 간단하고 비용이 절감되며 대량 추출이 가능한 새로운 방법을 제공함에 있다.It is an object of the present invention to provide a novel method for extracting a high content of nobiletin or a marine retin in citrus fruits, which is a natural material without side effects, in comparison with the conventional extraction method.
또한 본 발명의 목적은 노빌레틴 또는 탄제레틴 함량이 높은 감귤류 추출물을 유효성분으로 함유하는 기억력 증진, 치매 예방, 항암, 항염증, 아토피개선, 항비만, 지질대사 질병 개선, 치주염 개선, 골다공증을 포함한 골대사성 질환 개선 및 지방간 개선 효과가 있는 조성물을 제공함에 있다.
It is also an object of the present invention to provide a composition containing citrus extract having a high content of novelletin or enzymaticretin as an active ingredient for improving memory, preventing dementia, anticancer, antiinflammation, atopic improvement, anti-obesity, improving lipid metabolism disease, A metabolic disease improvement and a fatty liver improvement effect.
상기 목적을 달성하기 위하여, 본 발명은 (1) 감귤류의 과육 또는 과피를 염기성용액으로 세척하고 회수하는 단계; (2) 상기 회수물을 알콜 수용액으로 추출하여 추출물을 획득하는 단계; (3) 상기 추출물을 여과 후 농축하여 농축물을 획득하는 단계; 및 (4) 상기 농축물을 침전시키고 건조시켜 최종 산물을 얻는 단계를 포함하는 노빌레틴(Nobiletin) 또는 탄제레틴(Tangeretin) 함유 감귤류 추출물의 제조 방법을 제공한다.In order to accomplish the above object, the present invention provides a method for producing citrus fruits, comprising the steps of: (1) washing and recovering flesh or peel of citrus fruits with a basic solution; (2) extracting the recovered product with an aqueous alcohol solution to obtain an extract; (3) filtering and then concentrating the extract to obtain a concentrate; And (4) precipitating the concentrate and drying to obtain a final product. The present invention also provides a method for producing a citrus extract containing Nobiletin or Tangeretin.
상기 (1)단계 이전에 감귤류의 과육 또는 과피를 세절하고 세척하여 회수한 후 건조시키는 사전 처리 단계를 포함하는 것을 특징으로 한다.And a pretreatment step of finely pulverizing and washing the citrus flesh or skin before the step (1), and collecting and drying the citrus fruits.
상기 감귤류는 시쿠와사(Citrus depressa), 타치바나(C.tachibana), 코우지(C.leiocarpa), 기리 귤(C.tardiva), 지미 강(C.succosa), 키시 우(C.kinokuni), 코베니미캉(C.erythrosa), 치츄우카이망다링(C.deliciosa), 킹(C.nobilis), 본관(C.retuculata), 당시-탄지에린(C.tangerina), 하나 유모(C.hanaya), 코우 라이 타치바나(C.nippokoreana), 진귤(C.sunki hort. ex Tanaka) 및 한라봉(C.hybrid Shiranuhi)으로 구성된 군으로부터 선택된 하나 이상의 감귤인 것을 특징으로 한다.The citrus fruits include citrus depressa, C. tachibana, C. leiocarpa, C. tardiva, C. succosa, C. kinokuni, C.erythrosa, C.deliciosa, C. nobilis, C.retuculata, C. tangerina, C.hanaya, And at least one citrus fruit selected from the group consisting of C. nippokoreana, C.sunki hort. Ex Tanaka and C. hybrid Shiranuhi.
상기 염기성용액은 수산화나트륨, 중탄산나트륨, 수산화칼슘, 수산화칼륨, 수산화마그네슘 및 암모니아 수용액으로 이루어진 군에서 선택된 하나 이상의 염기성 물질을 포함하는 히드록시드(OH) 화합물을 증류수에 0.01 내지 5 중량%의 농도로 용해한 것을 특징으로 한다.The basic solution is prepared by adding a hydroxide (OH) compound containing at least one basic substance selected from the group consisting of sodium hydroxide, sodium bicarbonate, calcium hydroxide, potassium hydroxide, magnesium hydroxide and aqueous ammonia to distilled water at a concentration of 0.01 to 5% .
상기 (1)단계에서 상기 염기성용액을 실온에서 20시간 이상 처리하는 것을 특징으로 한다.In the step (1), the basic solution is treated at room temperature for 20 hours or more.
상기 (1)단계에서 상기 염기성용액을 50 내지 80℃에서 2시간 이내로 처리하는 것을 특징으로 한다.In the step (1), the basic solution is treated at 50 to 80 캜 for 2 hours or less.
상기 (2)단계에서 상기 알콜 수용액은 50 내지 100% 에탄올 수용액이며, 알콜 수용액으로 추출하는 온도는 실온이며, 알콜 수용액으로 추출하는 시간은 24시간 이상인 것을 특징으로 한다.In the step (2), the alcohol aqueous solution is a 50-100% ethanol aqueous solution, the temperature for extracting with an alcohol aqueous solution is room temperature, and the time for extracting with an aqueous alcohol solution is 24 hours or more.
상기 (3)단계에서 상기 농축 과정은 여과된 추출물을 실온에서 15 내지 20분 동안 정치하여 농축하는 것을 특징으로 한다.In the step (3), the filtered extract is allowed to stand at room temperature for 15 to 20 minutes and then concentrated.
상기 (4)단계에서 상기 침전 과정은 농축물에 증류수 또는 20% 에탄올 수용액을 가한 후 정치하는 것이고, 원심분리하여 침전물을 획득한 후 건조시키는 것을 특징으로 한다.In the step (4), the precipitation is performed by adding distilled water or 20% ethanol aqueous solution to the concentrate, and then centrifuging the precipitate to obtain a precipitate, followed by drying.
본 발명은 상기 제조방법에 의해 추출된 노빌레틴(Nobiletin) 또는 탄제레틴(Tangeretin) 함유 감귤류 추출물을 제공한다.The present invention provides a citrus extract containing Nobiletin or Tangeretin extracted by the above-described method.
또한, 본 발명은 상기 노빌레틴(Nobiletin) 또는 탄제레틴(Tangeretin) 함유 감귤류 추출물을 유효 성분으로 함유하는 학습능력 향상 또는 기억력 증진용 약학적 조성물을 제공한다.In addition, the present invention provides a pharmaceutical composition for improving learning ability or memory effect containing the above-mentioned citrus extract containing Nobiletin or Tangeretin as an active ingredient.
또한, 본 발명은 상기 노빌레틴(Nobiletin) 또는 탄제레틴(Tangeretin) 함유 감귤류 추출물을 유효 성분으로 함유하는 노년기 노망, 치매 예방 또는 치료제용 약학적 조성물을 제공한다.In addition, the present invention provides a pharmaceutical composition for preventing or treating dementia of old age, containing citrus extract containing nobiletin or tangeretin as an active ingredient.
또한, 본 발명은 상기 노빌레틴(Nobiletin) 또는 탄제레틴(Tangeretin) 함유 감귤류 추출물을 유효 성분으로 함유하는 항암용 약학적 조성물을 제공한다.The present invention also provides a pharmaceutical composition for anticancer therapy comprising the above-mentioned citrus extract containing Nobiletin or Tangeretin as an active ingredient.
또한, 본 발명은 상기 노빌레틴(Nobiletin) 또는 탄제레틴(Tangeretin) 함유 감귤류 추출물을 유효 성분으로 함유하는 항염증, 아토피개선용 및 피부가려움증 개선용 약학적 조성물을 제공한다.The present invention also provides a pharmaceutical composition for improving antiinflammation, atopic eczema and skin itching, which comprises, as an active ingredient, a citrus extract containing Nobiletin or Tangeretin.
또한, 본 발명은 상기 노빌레틴(Nobiletin) 또는 탄제레틴(Tangeretin) 함유 감귤류 추출물을 유효 성분으로 함유하는 항비만 및 체중조절용 약학적 조성물을 제공한다.The present invention also provides a pharmaceutical composition for controlling anti-obesity and body weight, which contains the above-mentioned citrus extract containing Nobiletin or Tangeretin as an active ingredient.
또한, 본 발명은 상기 노빌레틴(Nobiletin) 또는 탄제레틴(Tangeretin) 함유 감귤류 추출물을 유효 성분으로 함유하는 치주염 개선용 약학적 조성물을 제공한다.In addition, the present invention provides a pharmaceutical composition for improving periodontal disease, which contains the above-mentioned citrus extract containing Nobiletin or Tangeretin as an active ingredient.
또한, 본 발명은 상기 노빌레틴(Nobiletin) 또는 탄제레틴(Tangeretin) 함유 감귤류 추출물을 유효 성분으로 함유하는 골다공증을 포함한 골대사성 질환 개선용 약학적 조성물을 제공한다.In addition, the present invention provides a pharmaceutical composition for improving bone metabolic diseases including osteoporosis, which contains, as an active ingredient, citrus extract containing nobiletin or tangeretin.
또한, 본 발명은 상기 노빌레틴(Nobiletin) 또는 탄제레틴(Tangeretin) 함유 감귤류 추출물을 유효 성분으로 함유하는 지질대사 관련 질병 개선용 약학적 조성물을 제공한다.The present invention also provides a pharmaceutical composition for improving a lipid metabolism-related disease, which comprises the above-mentioned citrus extract containing Nobiletin or Tangeretin as an active ingredient.
또한, 본 발명은 상기 노빌레틴(Nobiletin) 또는 탄제레틴(Tangeretin) 함유 감귤류 추출물을 유효 성분으로 함유하는 비알콜성 지방간 개선 및 알콜성 지방간 개선용 약학적 조성물을 제공한다.The present invention also provides a pharmaceutical composition for the improvement of non-alcoholic fatty liver and the improvement of alcoholic fatty liver comprising the above-mentioned citrus extract containing nobiletin or tangeretin as an active ingredient.
또한, 본 발명은 상기 노빌레틴(Nobiletin) 또는 탄제레틴(Tangeretin) 함유 감귤류 추출물을 유효 성분으로 함유하는 건강기능식품을 제공한다.
In addition, the present invention provides a health functional food containing the above-mentioned citrus extract containing Nobiletin or Tangeretin as an active ingredient.
상기와 같은 본 발명에 따르면, 감귤류의 과육 또는 과피를 염기성용액으로 세척하고 회수한 후 알콜 수용액으로 추출함으로써 종래 추출방법에 비하여 간단한 방법으로 노빌레틴 또는 탄제레틴 함량이 높은 감귤류 추출물을 추출함과 동시에 비용을 절감하는 효과가 있다.According to the present invention, citrus fruit or peel of citrus fruits is washed with a basic solution and recovered, and then extracted with an aqueous alcohol solution to extract a citrus extract having a high content of nobiletin or tamoxifen It is effective to reduce the cost.
또한 본 발명은 노빌레틴 또는 탄제레틴 함량이 높은 감귤류 추출물을 유효성분으로 함유하여 기억력 증진, 치매 예방, 항암, 항염증, 아토피개선, 항비만, 지질대사 질병 개선, 치주염 개선, 골다공증을 포함한 골대사성 질환 개선 및 지방간 개선 효과가 있는 조성물을 제공하는 효과가 있다.
The present invention also relates to a pharmaceutical composition comprising a nobiletin or a citrus extract having a high content of a resorcinol as an active ingredient and containing an effective amount of at least one compound selected from the group consisting of bone metabolism including osteoporosis, There is an effect of providing a composition having a disease improving effect and a fatty liver improving effect.
도 1은 노빌레틴 또는 탄제레틴 함량이 높은 감귤류 추출물의 제조공정.
도 2는 NaOH를 처리한 경우와 처리하지 않은 경우의 PMF 함량 비교.
도 3은 60℃에서 다양한 농도의 NaOH를 처리한 경우의 PMF 함량 비교.
도 4은 실온에서 다양한 농도의 NaOH를 처리한 경우의 PMF 함량 비교.
도 5는 NaOH 처리 시간을 다양하게 한 경우의 PMF 함량 비교.
도 6는 NaOH 처리 온도를 변화시킨 경우의 PMF 함량 비교.
도 7은 에탄올 수용액의 농도를 변화시킨 경우의 추출 PMF 함량 비교.
도 8은 침전 형성 시 에탄올 농도를 변화시킨 경우의 PMF 함량 비교.
도 9는 감귤류 추출물 제조방법의 세부조건을 변경하여 처리하고 침전시킨 후 침전물을 회수하기 전의 모습.BRIEF DESCRIPTION OF THE DRAWINGS FIG. 1 is a process for preparing citrus extract having a high content of nobiletin or a margarine.
Figure 2 compares the PMF content with and without NaOH treatment.
Figure 3 compares the PMF content when treated with various concentrations of NaOH at 60 < 0 > C.
Figure 4 compares the PMF content of NaOH treated at various concentrations at room temperature.
Figure 5 compares the PMF content when the NaOH treatment time is varied.
6 compares the PMF content when the NaOH treatment temperature is varied.
7 compares the extracted PMF content when the concentration of the aqueous ethanol solution is changed.
Figure 8 compares the PMF content when ethanol concentration is varied during precipitation formation.
FIG. 9 is a view showing a state before the precipitate is recovered after the treatment of the detailed conditions of the method for producing citrus extract and the precipitation.
이하, 본 발명을 상세히 설명한다.Hereinafter, the present invention will be described in detail.
본 발명은 (1) 감귤류의 과육 또는 과피를 염기성용액으로 세척하고 회수하는 단계; (2) 상기 회수물을 알콜 수용액으로 추출하여 추출물을 획득하는 단계; (3) 상기 추출물을 여과 후 농축하여 농축물을 획득하는 단계; 및 (4) 상기 농축물을 침전시키고 건조시켜 최종 산물을 얻는 단계를 포함하는 노빌레틴(Nobiletin) 또는 탄제레틴(Tangeretin) 함유 감귤류 추출물의 제조 방법을 제공한다.(1) washing and recovering flesh or peel of citrus with a basic solution; (2) extracting the recovered product with an aqueous alcohol solution to obtain an extract; (3) filtering and then concentrating the extract to obtain a concentrate; And (4) precipitating the concentrate and drying to obtain a final product. The present invention also provides a method for producing a citrus extract containing Nobiletin or Tangeretin.
상기 (1)단계 이전에 감귤류의 과육 또는 과피를 세절하고 세척하여 회수한 후 건조시키는 사전 처리 단계를 더 포함하여 대량생산의 경우 필요한 추출과정의 효율화를 꾀할 수 있다.The method of the present invention may further include a pretreatment step of finely pulverizing and washing citrus fruits or peels prior to the step (1), followed by drying and recovering the citrus fruits.
상기 감귤류는 시쿠와사(Citrus depressa), 타치바나(C.tachibana), 코우지(C.leiocarpa), 기리 귤(C.tardiva), 지미 강(C.succosa), 키시 우(C.kinokuni), 코베니미캉(C.erythrosa), 치츄우카이망다링(C.deliciosa), 킹(C.nobilis), 본관(C.retuculata), 당시-탄지에린(C.tangerina), 하나 유모(C.hanaya), 코우 라이 타치바나(C.nippokoreana), 진귤(C.sunki hort. ex Tanaka) 및 한라봉(C.hybrid Shiranuhi)등이 있다. 이 중에서 진귤(C.sunki hort. ex Tanaka)은 제주에서 자생하는 토종귤의 하나이며 한라봉(C.hybrid Shiranuhi)은 제주에서 생산하는 고급 품종의 감귤로서 한라봉을 이용한 과자, 음료 등을 생산할 때 잔여물의 효과적인 재활용이 필요한 품종이다.The citrus fruits include citrus depressa, C. tachibana, C. leiocarpa, C. tardiva, C. succosa, C. kinokuni, C.erythrosa, C.deliciosa, C. nobilis, C.retuculata, C. tangerina, C.hanaya, C. nippokoreana, C.sunki hort. Ex Tanaka, and C. hybrid Shiranuhi. Among them, C.sunki hort. Ex Tanaka is one of the native mandarin oranges native to Jeju. C. hybrid Shiranuhi is a high-grade citrus fruit produced in Jeju. It is a kind of water that needs effective recycling.
상기 염기성용액은 수산화나트륨, 중탄산나트륨, 수산화칼슘, 수산화칼륨, 수산화마그네슘 및 암모니아 수용액으로 이루어진 군에서 선택된 하나 이상의 염기성 물질을 포함하는 히드록시드(OH) 화합물을 이용할 수 있고, 이를 증류수에 0.01 내지 5 중량%, 바람직하게는 1%의 농도로 용해한 것이 최적의 효과를 나타낸다.The basic solution may be a hydroxide (OH) compound containing at least one basic substance selected from the group consisting of sodium hydroxide, sodium bicarbonate, calcium hydroxide, potassium hydroxide, magnesium hydroxide and aqueous ammonia, %, Preferably 1% by weight of the composition.
상기 (1)단계에서 상기 염기성용액을 실온에서 20시간 이상 처리하는 것이 60℃에서 1시간 처리하는 것과 함께 최적의 효과를 나타낸다.In the step (1), treatment of the basic solution at room temperature for 20 hours or more is most effective when treated at 60 ° C for 1 hour.
상기 (1)단계에서 상기 염기성용액을 50 내지 80℃, 바람직하게는 60℃에서 2시간 이내로 처리하는 것이 최적의 효과를 나타낸다.In the step (1), the basic solution is treated at 50 to 80 ° C, preferably at 60 ° C for 2 hours or less.
상기 (2)단계에서 상기 알콜 수용액은 50 내지 100% 에탄올 수용액이며, 알콜 수용액으로 추출하는 온도는 실온이며, 알콜 수용액으로 추출하는 시간은 24시간 이상 처리하는 것이 최적의 효과를 나타낸다.In step (2), the alcohol aqueous solution is 50 to 100% ethanol aqueous solution, the temperature for extracting with alcohol aqueous solution is room temperature, and the extraction time for alcohol aqueous solution is more than 24 hours.
상기 (3)단계에서 상기 농축 과정은 여과된 추출물을 실온에서 15 내지 20분 동안 정치하여 농축하는 것이 최적의 효과를 나타낸다.In the step (3), the filtered extract is concentrated at 15 to 20 minutes at room temperature.
상기 (4)단계에서 상기 침전 과정은 농축물에 증류수 또는 20% 에탄올 수용액을 가한 후 정치하는 것이고, 원심분리하여 침전물을 획득한 후 건조시키는 것이 최적의 효과를 나타낸다.In the step (4), the precipitation is performed by adding distilled water or 20% ethanol aqueous solution to the concentrate, and then centrifuging the precipitate to obtain a precipitate and drying it.
본 발명은 상기 제조방법에 의해 추출된 노빌레틴(Nobiletin) 또는 탄제레틴(Tangeretin) 함유 감귤류 추출물을 제공한다.The present invention provides a citrus extract containing Nobiletin or Tangeretin extracted by the above-described method.
또한, 본 발명은 상기 노빌레틴(Nobiletin) 또는 탄제레틴(Tangeretin) 함유 감귤류 추출물을 유효 성분으로 함유하므로 학습능력 향상 또는 기억력 증진용 약학적 조성물을 제공한다.In addition, the present invention provides a pharmaceutical composition for improving learning ability or memory ability by containing citrus extract containing nobiletin or tangeretin as an active ingredient.
또한, 본 발명은 상기 노빌레틴(Nobiletin) 또는 탄제레틴(Tangeretin) 함유 감귤류 추출물을 유효 성분으로 함유하므로 노년기 노망, 치매 예방 또는 치료제용 약학적 조성물을 제공한다.The present invention also provides a pharmaceutical composition for preventing or treating dementia of the elderly, comprising a nobiletin or a citrus extract containing tangeretin as an active ingredient.
또한, 본 발명은 상기 노빌레틴(Nobiletin) 또는 탄제레틴(Tangeretin) 함유 감귤류 추출물을 유효 성분으로 함유하므로 항암용 약학적 조성물을 제공한다.The present invention also provides a pharmaceutical composition for anticancer therapy comprising the above-mentioned citrus extract containing Nobiletin or Tangeretin as an active ingredient.
또한, 본 발명은 상기 노빌레틴(Nobiletin) 또는 탄제레틴(Tangeretin) 함유 감귤류 추출물을 유효 성분으로 함유하므로 항염증, 아토피개선용 및 피부가려움증 약학적 조성물을 제공한다.In addition, the present invention provides a pharmaceutical composition containing anti-inflammatory, atopic amelioration, and skin itching pharmaceutical compositions containing the above-mentioned citrus extract containing nobiletin or tangeretin as an active ingredient.
또한, 본 발명은 상기 노빌레틴(Nobiletin) 또는 탄제레틴(Tangeretin) 함유 감귤류 추출물을 유효 성분으로 함유하므로 항비만 및 체중조절용 약학적 조성물을 제공한다.The present invention also provides a pharmaceutical composition for controlling anti-obesity and body weight, comprising the above-mentioned citrus extract containing Nobiletin or Tangeretin as an active ingredient.
또한, 본 발명은 상기 노빌레틴(Nobiletin) 또는 탄제레틴(Tangeretin) 함유 감귤류 추출물을 유효 성분으로 함유하므로 지질대사 관련 질병 개선용 약학적 조성물을 제공한다.In addition, the present invention provides a pharmaceutical composition for improving lipid metabolism-related diseases by containing the above-mentioned citrus extract containing Nobiletin or Tangeretin as an active ingredient.
또한, 본 발명은 상기 노빌레틴(Nobiletin) 또는 탄제레틴(Tangeretin) 함유 감귤류 추출물을 유효 성분으로 함유하므로 비알콜성 지방간 개선 및 알콜성 지방간 개선용 약학적 조성물을 제공한다.The present invention also provides a pharmaceutical composition for the improvement of non-alcoholic fatty liver and the improvement of alcoholic fatty liver by containing the above-mentioned citrus extract containing nobiletin or Tangeretin as an active ingredient.
또한, 본 발명은 상기 노빌레틴(Nobiletin) 또는 탄제레틴(Tangeretin) 함유 감귤류 추출물을 유효 성분으로 함유하므로 치주염 개선용 약학적 조성물을 제공한다.In addition, the present invention provides a pharmaceutical composition for improving periodontal disease, containing the above-mentioned citrus extract containing Nobiletin or Tangeretin as an active ingredient.
또한, 본 발명은 상기 노빌레틴(Nobiletin) 또는 탄제레틴(Tangeretin) 함유 감귤류 추출물을 유효 성분으로 함유하므로 골다공증을 포함한 골대사성 질환 개선용 약학적 조성물을 제공한다.Also, the present invention provides a pharmaceutical composition for improving bone metabolic diseases including osteoporosis, comprising the above-mentioned citrus extract containing nobiletin or tangeretin as an active ingredient.
본 발명에서 약학적 조성물에 대해 사용 가능한 담체, 부형제 또는 희석제로는 락토오스, 덱스트로오스, 수크로오스, 솔비톨, 만니톨, 자일리톨, 에리스리톨, 말리톨, 전분, 아카시아 고무, 알지네이트, 젤라틴, 칼슘 포스페이트, 칼슘 실리케이트, 셀룰로오스, 메틸셀룰로오스, 미정질 셀룰로오스, 폴리비닐 피롤리돈, 물, 메틸히드록시벤조에이트, 프로필히드록시벤조에이트, 탈크, 마그네슘 스테아레이트 또는 광물유 등을 들 수 있다.Examples of the carrier, excipient or diluent which can be used for the pharmaceutical composition in the present invention include lactose, dextrose, sucrose, sorbitol, mannitol, xylitol, erythritol, maltitol, starch, acacia rubber, alginate, gelatin, calcium phosphate, calcium silicate , Cellulose, methylcellulose, microcrystalline cellulose, polyvinylpyrrolidone, water, methylhydroxybenzoate, propylhydroxybenzoate, talc, magnesium stearate or mineral oil.
상기 약학 조성물은 산제, 과립제, 정제, 캡슐제, 현탁액, 유제, 시럽제, 액제, 에어로졸, 엑스제, 주사제, 경피 투여제 또는 좌제 형태로 제조될 수 있다.The pharmaceutical composition may be in the form of powders, granules, tablets, capsules, suspensions, emulsions, syrups, solutions, aerosols, excipients, injections, transdermal drugs or suppositories.
제제화할 경우에는 보통 사용하는 충진제, 증량제, 결합제, 습윤제, 붕해제, 계면활성제 등의 희석제 또는 부형제를 사용하여 조제된다. 경구투여를 위한 고형 제제에는 정제, 환제, 산제, 과립제, 캡슐제 등이 포함되며, 이러한 고형제제는 상기 화합물은 적어도 하나 이상의 부형제, 예를 들면, 전분 칼슘카보네이트, 수크로오스 또는 락토오스, 젤라틴 등을 섞어 조제한다. 또한, 단순한 부형제 이외에 마그네슘 스테아레이트, 탈크 같은 윤활제들도 사용된다. 경구를 위한 액상 제제로는 현탁제, 내용액제, 유제, 시럽제 등이 해당되는데 흔히 사용되는 단순희석제인 물, 리퀴드 파라핀 이외에 여러 가지 부형제, 예를 들면, 습윤제, 감미제, 방향제, 보존제 등이 포함될 수 있다. 비경구 투여를 위한 제제에는 멸균된 수용액, 비수성용제, 현탁제, 유제, 동결건조 제제, 좌제가 포함된다. 비수성용제, 현탁제로는 프로필렌글리콜, 폴리에틸렌글리콜, 올리브 오일과 같은 식물성 기름, 에틸올레이트와 같은 주사 가능한 에스테르 등이 사용될 수 있다. In the case of formulation, a diluent or excipient such as a filler, an extender, a binder, a wetting agent, a disintegrant, or a surfactant is usually used. Solid formulations for oral administration include tablets, pills, powders, granules, capsules and the like, which are prepared by mixing at least one excipient, for example, starch calcium carbonate, sucrose or lactose, Prepare. In addition to simple excipients, lubricants such as magnesium stearate and talc may also be used. Examples of liquid formulations for oral use include suspensions, solutions, emulsions, and syrups. In addition to water and liquid paraffin, which are commonly used simple diluents, various excipients such as wetting agents, sweetening agents, have. Formulations for parenteral administration include sterilized aqueous solutions, non-aqueous solutions, suspensions, emulsions, freeze-dried preparations, and suppositories. Examples of the suspending agent include propylene glycol, polyethylene glycol, vegetable oil such as olive oil, injectable ester such as ethyl oleate, and the like.
또한, 본 발명은 상기 노빌레틴(Nobiletin) 또는 탄제레틴(Tangeretin) 함유 감귤류 추출물을 유효 성분으로 함유하는 건강기능식품을 제공한다.The present invention also provides a health functional food containing the above-mentioned citrus extract containing Nobiletin or Tangeretin as an active ingredient.
상기 건강기능식품은 산제, 과립제, 정제, 캡슐제, 현탁액, 유제, 시럽제, 액제, 에어로졸, 엑스제, 차, 젤리 또는 음료 형태로 제조될 수 있다. 더욱 구체적으로, 드링크제, 육류, 소세지, 빵, 비스켓, 떡, 쵸코렛, 캔디류, 스넥류, 과자류, 피자, 라면, 기타 면류, 껌류, 아이스크림류를 포함한 낙농제품, 각종 스프, 음료수, 알콜 음료 및 비타민 복합제 등이 있으며, 통상적인 의미에서의 건강 식품을 모두 포함한다.The health functional food may be prepared in the form of powders, granules, tablets, capsules, suspensions, emulsions, syrups, solutions, aerosols, extracts, tea, jellies or drinks. More specifically, dairy products such as drink, meat, sausage, bread, biscuit, rice cake, chocolate, candy, snack, confectionery, pizza, ramen, other noodles, gums and ice cream, various soups, beverages, alcoholic beverages and vitamins And includes all health foods in a conventional sense.
본 발명에 따른 노빌레틴(Nobiletin) 또는 탄제레틴(Tangeretin) 함유 감귤류 추출물을 식품에 그대로 첨가하거나 다른 식품 또는 식품 성분과 함께 사용될 수 있고, 통상적인 방법에 따라 적절하게 사용될 수 있다. 유효성분의 혼합양은 그의 사용 목적(예방 또는 개선)에 따라 적합하게 결정될 수 있다. 일반적으로, 건강 식품 중의 상기 추출물의 양은 전체 식품 중량의 0.01 내지 15 중량%로 가할 수 있으며, 건강 음료 조성물은 100 ㎖를 기준으로 0.02 내지 5 g, 바람직하게는 0.3 내지 1 g의 비율로 가할 수 있다. 그러나, 건강 및 위생을 목적으로 하거나 건강 조절을 목적으로 하는 장기간의 섭취의 경우에 첨가되는 양은 상기 범위 이하일 수 있으며, 안전성 면에서 아무런 문제가 없기 때문에 유효성분은 상기 범위 이상의 양으로도 사용될 수 있다.The citrus extract containing Nobiletin or Tangeretin according to the present invention can be added directly to the food or can be used together with other food or food ingredients and can be suitably used according to conventional methods. The amount of the active ingredient to be mixed can be suitably determined according to the purpose of use (prevention or improvement). Generally, the amount of the extract in the health food may be 0.01 to 15% by weight of the total food, and the health beverage composition may be added in a proportion of 0.02 to 5 g, preferably 0.3 to 1 g, based on 100 ml have. However, the amount added in the case of long-term intake intended for health and hygiene purposes or for the purpose of controlling health may be less than the above range, and since there is no problem in terms of safety, the active ingredient may be used in an amount exceeding the above range .
본 발명에 따른 건강 음료 조성물은 필수성분으로서 상기 지시된 비율로 상기 추출물을 함유하는 외에는 다른 성분에는 특별한 제한이 없으며 통상의 음료와 같이 여러 가지 향미제 또는 천연 탄수화물 등을 추가성분으로서 함유할 수 있다.The health beverage composition according to the present invention is not particularly limited as long as it contains the above-mentioned extract at the indicated ratio as an essential ingredient, and may contain various flavors or natural carbohydrates as an additional ingredient such as ordinary beverages .
본 발명에 의한 기능성 화장품은 유연 화장수, 수렴 화장수, 영양 화장수, 영양 크림, 마사지 크림, 에센스, 팩, 파운데이션, 립스틱 또는 파우더 파운데이션 등으로 제형화될 수 있으나, 이에 한정되는 것은 아니다. 각 제형의 기능성 화장품에 있어서, 상기 감귤류 추출물 이외에 다른 성분들은 기타 화장료의 제형 또는 사용 목적에 따라 당업자가 어려움 없이 적의 선정하여 배합할 수 있다.The functional cosmetic composition according to the present invention may be formulated into a flexible lotion, a convergent lotion, a nutritional lotion, a nutritional cream, a massage cream, an essence, a pack, a foundation, a lipstick or a powder foundation. In functional cosmetic formulations of the respective formulations, other ingredients other than the citrus extracts may be appropriately selected and mixed by those skilled in the art depending on the formulation or purpose of use of other cosmetics.
이하, 실시예를 통하여 본 발명을 더욱 상세히 설명하고자 한다. 이들 실시예는 오로지 본 발명을 예시하기 위한 것으로서, 본 발명의 범위가 이들 실시예에 의해 제한되는 것으로 해석되지 않는 것은 당업계에서 통상의 지식을 가진 자에게 있어서 자명할 것이다.Hereinafter, the present invention will be described in more detail with reference to Examples. It is to be understood by those skilled in the art that these embodiments are merely illustrative of the present invention and that the scope of the present invention is not construed as being limited by these embodiments.
실시예. 감귤류 추출물의 제조Examples. Preparation of Citrus Extracts
본 발명의 실시예에서는 감귤류의 과육 또는 과피를 세절하고 세척하여 회수한 후 건조시키는 사전 처리를 하여 추출원료를 준비하였다.In the example of the present invention, citrus fruit or peel was cut, washed, recovered, and dried to prepare raw materials for extraction.
준비한 감귤류 과피(실험에서는 진귤박) 20g에 200 내지 400ml의 1% NaOH 수용액을 처리하고 실온에서 20시간 이상 정치하여 감귤류 과피의 조직을 약화시킨다. 이후 여과하여 회수한 후 증류수로 세척한 후, 50 내지 100 % 에탄올 수용액에 실온에서 24 시간 이상 동안 추출하였다. 이러한 결과는 (도 9)와 같은 모습을 보인다. 이후, 불용성 성분을 여과하고 여과된 추출물을 실온에서 정치하여 농축한 후 증류수를 첨가하고 침전물을 3000rpm에서 3분간 원심분리하여 분리하였다. 원심분리한 침전물을 여과한 후, 다시 여과한 농축물에 증류수 또는 20% 에탄올 수용액을 가한 후 정치하며 이후 원심분리하여 침전물을 획득한 후 건조시켜 최종 감귤류 추출물을 획득한다.20 g of prepared citrus peel (in the experiment, citrus oranges) is treated with 200 to 400 ml of a 1% NaOH aqueous solution and allowed to stand at room temperature for 20 hours or more to weaken the texture of the citrus peel. Then, it was collected by filtration, washed with distilled water, and then extracted in 50 to 100% aqueous ethanol solution at room temperature for 24 hours or more. These results are the same as in Fig. Then, the insoluble component was filtered, and the filtered extract was concentrated at room temperature, distilled water was added, and the precipitate was separated by centrifugation at 3000 rpm for 3 minutes. After centrifugation, the precipitate is filtered, and then the distilled water or 20% ethanol aqueous solution is added to the filtrate. The precipitate is collected by centrifugation and dried to obtain the final citrus extract.
이러한 추출물 제조 과정의 확립을 위해 하기와 같은 실험을 진행하였다.The following experiment was conducted to establish the process of producing such an extract.
실험예 1. 추출조건별 PMF 함량 측정Experimental Example 1. Measurement of PMF content by extraction condition
위와 같은 방법으로 추출된 조건별 감귤류 추출물에 포함된 노빌레틴 및 탄제레틴 함량 분석을 위해 고속액체크로마토그래피(HPLC)를 이용하여 분석하였다.The content of Novartin and carboletin contained in the citrus extracts extracted by the above method was analyzed by high performance liquid chromatography (HPLC).
검출기는 UV를 이용하여 파장인 215 nm를 선택하여 분석하였고, 고속액체크로마토그래피에 사용되는 이동상은 각각 메탄올, 증류수로 분석하였으며 이동상의 조건은 70% (v/v)메탄올로 분석하였다. 분석시간은 60분으로 하였다. 노빌레틴 및 탄제레틴의 함량은 표준시약을 이용하여 검량선 작성후 계산하였다. 이때 사용된 표준시약은 Wako사의 표준시약을 사용하였다. 검량선 작성에 이용한 표준시약의 농도는 0.01, 0.05, 0.1, 0.5, 1, 5 mg/ml로 하여 검량선을 작성하고, 이 검량선을 이용해 노빌레틴과 탄제레틴의 함량을 분석하였다. 함량계산을 위해 각 추출물의 농도를 10 mg/ml로 일정하게 하여 고속액체크로마토그래피분석을 한 후 그 결과값을 가지고 함량을 계산하였다. 노빌레틴과 탄제레틴의 함량은 전체 추출물의 중량을 분모로 하고 검량선을 이용해 계산한 각 물질의 중량을 분자로 하여 계산되었다. PMF의 함량은 % 단위로 계산된 노빌레틴 및 탄제레틴의 함량 수치를 합하여 계산하였다.Detectors were analyzed by UV with wavelength of 215 nm. The mobile phases used in high performance liquid chromatography were analyzed with methanol and distilled water. The mobile phase conditions were analyzed with 70% (v / v) methanol. The analysis time was 60 minutes. The contents of novilectin and ergotretin were calculated after preparing a calibration curve using standard reagents. The standard reagent used was Wako's standard reagent. The concentrations of standard reagent used in the calibration curve were 0.01, 0.05, 0.1, 0.5, 1, and 5 mg / ml, and the concentrations of nobiletin and tamsuletin were analyzed using this calibration curve. In order to calculate the content, the concentration of each extract was fixed at 10 mg / ml and analyzed by high performance liquid chromatography. The content of Novartin and Triglyretin was calculated by using the weight of each extract as a denominator and the weight of each substance as a numerator using a calibration curve. The content of PMF was calculated by adding the contents of the contents of novirretin and ergotretin calculated in%.
실험결과.Experiment result.
(1) NaOH를 처리한 경우와 처리하지 않은 경우의 PMF 함량 비교 결과.(1) Comparison of PMF content with and without NaOH.
상기 실시예에 의한 추출과정에서 NaOH를 처리한 경우와 처리하지 않은 경우의 PMF 함량을 비교한 결과는 (도 2)에 나타내었다.The results of comparing the PMF content in the case of treatment with NaOH and in the case of not treatment in the extraction process according to the above example are shown in FIG.
그 결과, 1%의 NaOH를 처리한 후에 100% 에탄올 수용액으로 추출한 경우에는 최종 추출물에서 노빌레틴과 탄제레틴을 포함한 PMF 함량이 50% 이상이었지만, 1% NaOH 대신 60℃의 열수를 처리한 경우에는 PMF 함량이 20% 미만이었으며, 1% NaOH 용액의 사전 처리 없이 100% 에탄올과 50% 에탄올만으로 추출한 경우 20%를 약간 넘는 정도에 그쳤다. 따라서 PMF 함량을 높이기 위해서는 NaOH를 처리하여 감귤류 세포 표면의 조직을 약화시키는 과정이 필수적이고 효율적이라는 것을 비교하여 알 수 있다.As a result, when 1% NaOH was treated and 100% ethanol aqueous solution was used, the final extract had a content of PMF including nobiletin and resercinol of 50% or more. However, when treated with hot water at 60 ° C instead of 1% NaOH The PMF content was less than 20% and only slightly more than 20% when extracted with 100% ethanol and 50% ethanol without pretreatment of 1% NaOH solution. Therefore, in order to increase the PMF content, it is understood that the process of weakening the tissue of the citrus cell surface by treating with NaOH is essential and efficient.
(2) 다양한 농도의 NaOH를 처리한 경우의 PMF 함량 비교 결과.(2) Comparison of PMF contents in the case of treatment with various concentrations of NaOH.
상기 실시예에 의한 추출과정에서 60℃에서 NaOH의 농도를 0.5%, 1%, 2%로 변경하여 PMF 함량을 비교한 결과는 (도 3)에 나타내었고, 실온에서 NaOH의 농도를 0.01%, 0.1%, 1%, 5%로 변경하여 PMF 함량을 비교한 결과는 (도 4)에 나타내었다.The results of comparing the PMF contents by changing the concentration of NaOH to 0.5%, 1% and 2% at 60 ° C. in the extraction process according to the above Example are shown in FIG. 3, and the concentration of NaOH at 0.01% 0.1%, 1%, and 5%, and the results of comparing PMF contents are shown in FIG.
그 결과, 60℃에서는 NaOH의 농도를 0.5%로 처리한 경우 PMF 함량이 가장 높았으나, 실온에서는 NaOH의 농도를 1%로 처리한 경우의 PMF 함량이 가장 높았다. 그런데 고온을 적용하여 처리하는 경우는 대량생산을 위해서는 추가 설비가 필요하다. 결국 NaOH와 같은 염기성인 히드록시드(OH) 화합물을 증류수에 0.01 내지 5 중량%의 농도, 바람직하게는 1 중량%의 농도로 처리하는 것이 최적의 효과를 나타낸다.As a result, PMF content was the highest when NaOH concentration was 0.5% at 60 ℃, but PMF content was the highest when NaOH concentration was 1% at room temperature. However, when applying high temperature treatment, additional equipment is needed for mass production. As a result, it is most effective to treat a basic hydroxide (OH) compound such as NaOH at a concentration of 0.01 to 5% by weight, preferably 1% by weight, in distilled water.
(3) NaOH 처리시간을 다양하게 한 경우의 PMF 함량 비교 결과.(3) Comparison of PMF contents when the NaOH treatment time was varied.
상기 실시예에 의한 추출과정에서 NaOH를 처리하는 시간을 다르게 하여 PMF 함량을 비교한 결과는 (도 5)에 나타내었다.The results of comparing the PMF contents by varying the time for treating NaOH in the extraction process according to the above embodiment are shown in FIG.
그 결과, 실온에서 1% NaOH 농도에서 24시간 이상 처리하면, 60℃ 1% NaOH 농도에서 1시간 처리한 경우와 유사하며, 60℃ 1% NaOH 농도에서는 시간을 늘릴수록 오히려 수율이 떨어진다는 것을 알 수 있다. 고온에서 NaOH 처리시 NaOH 농도가 1%인 경우에는 1시간 처리로 충분하며, 실온인 경우에는 20시간 이상 처리하는 것이 높은 수율을 얻을 수 있어서 최적의 효과를 나타낸다. As a result, it was found that the treatment at 1% NaOH concentration at room temperature for 24 hours or more was similar to the treatment at 1% NaOH concentration at 60 ° C for 1 hour, and that at 60 °
(4) NaOH 처리 중 온도를 변화시킨 경우의 PMF 함량 비교 결과.(4) Comparison of PMF content in the case of changing the temperature during NaOH treatment.
상기 실시예에 의한 추출과정에서 NaOH를 처리하는 온도를 다르게 하여 PMF 함량을 비교한 결과는 (도 6)에 나타내었다.The results of comparing the PMF content by varying the temperature for treating NaOH in the extraction process according to the above embodiment are shown in FIG.
그 결과, 온도가 50 내지 80℃에서 모두 20% 이상의 PMF 함량 결과를 보여주었지만, 가장 높은 수율을 나타낸 것은 70℃로 처리한 경우였다. 온도를 높이는 것은 비용이 추가로 들게 되므로 50 내지 80℃에서 2시간 이내, 바람직하게는 60℃에서 1시간 처리하는 것이 최적의 효과를 나타낸다. As a result, although the PMF content was 20% or more at 50 to 80 ° C, the highest yield was obtained at 70 ° C. Since increasing the temperature increases the cost, it is most preferable to treat at 50 to 80 ° C for 2 hours, preferably at 60 ° C for 1 hour.
(5) 에탄올 수용액의 에탄올 농도를 변화시킨 경우의 추출 수율 비교 결과.(5) Comparison of extraction yields when the ethanol concentration of the ethanol aqueous solution was changed.
상기 실시예에 의한 추출과정에서 (2)단계의 에탄올 추출과정의 에탄올 수용액의 농도를 다르게 하여 PMF 함량을 비교한 결과는 (도 7)에 나타내었다.The results of the comparison of the PMF contents by varying the concentration of the ethanol aqueous solution in the ethanol extraction process of the step (2) in the extraction process according to the above example are shown in FIG.
그 결과, 에탄올 농도가 80%일 때 가장 높은 수율을 보였고 50%일 때도 유용한 PMF 함량을 나타냈다. 대량생산 시 에탄올의 재사용을 고려한다면 에탄올 농도가 높은 것이 유리하므로, 50 내지 100% 에탄올 수용액을 사용하되 바람직하게는 100% 에탄올을 처리하는 것이 최적의 효과를 나타낸다.As a result, the highest yield was obtained when the ethanol concentration was 80%, and the useful PMF content was 50%. Considering the re-use of ethanol at the time of mass production, it is advantageous to have a high ethanol concentration. Therefore, it is most effective to use 50 to 100% ethanol aqueous solution, preferably 100% ethanol.
(6) 침전 형성 시 에탄올 비율을 변화시킨 경우의 PMF 함량 비교 결과.(6) The results of PMF content comparison with ethanol ratio during precipitation.
상기 실시예에 의한 추출과정에서 (4)단계의 에탄올 침전과정의 증류수와 에탄올의 비율을 다르게 하여 PMF 함량을 비교한 결과는 (도 8)에 나타내었다. 구체적 진귤원료와 침전물 총량 수치는 아래 (표 1)과 같다.The results of comparing the PMF contents by different ratios of distilled water to ethanol in the ethanol precipitation process of step (4) in the extraction process according to the above example are shown in FIG. 8. The total amount of the raw material and the total amount of the precipitate is shown in Table 1 below.
그 결과, 50% 에탄올 비율인 경우 침전물의 중량이 적고 침전물 중에서 PMF 함량도 10%대에 불과하였으나, 20% 에탄올을 이용하여 침전물을 형성시킨 경우에는 침전물도 많이 형성되고 침전물 중에서 PMF 함량이 60% 가까운 양호한 수치를 보였다. 증류수로 침전시킨 경우에는 침전물 중 PMF의 함량은 60%에 가까웠으나 진귤 원료에서 침전물 형성하는 중량이 (표 1)과 같이 적었다. 따라서 침전 과정에서는 농축물에 증류수 또는 20% 에탄올 수용액을 가한 후 정치하는 것이 효과적이다.As a result, in case of 50% ethanol ratio, the weight of the precipitate was small and the PMF content in the precipitate was only about 10%, but when the precipitate was formed using 20% ethanol, many precipitates were formed and the PMF content in the precipitate was 60% Good close figures were shown. When precipitated with distilled water, the content of PMF in the precipitate was close to 60%, but the weight of precipitate formation in the citrus raw material was as shown in Table 1. Therefore, it is effective to add distilled water or 20% ethanol aqueous solution to the concentrate in the precipitation process.
이상의 실시예를 통해 제조한 감귤류 추출물에는 노빌레틴과 탄제레틴이 포함되어 있음이 확인되었으므로, 발명의 배경이 되는 기술에서 기술한 대로 노빌레틴과 탄제레틴에 대해 보고된 약리작용인 항암, 항염증, 면역조절, 신경보호, 기억력손상 회복 효과 작용(Li, R. W. et al), 간기능 개선 효과(Satomi Onoue et al.), 항비만 효과(Young-Sil Lee et al.), 치주염 질환 개선 효과(Tsukasa Tominari et al.), 골다공증을 포함한 골대사성 질환 개선 효과(Suguru Harada et al.), 가려움증 개선 효과(Se-Eun Jang et al.), 지질대사 이상 개선 효과(Yuguang Lin et al.)를 갖는다. 이러한 감귤 추출물을 유효성분으로 함유하는 약학적 조성물, 건강기능식품, 기능성 화장품으로 이용될 수 있다.It was confirmed that the citrus extract prepared through the above examples contains nobiletin and cerzetine. Therefore, as described in the background of the present invention, it has been found that the anti-cancer, anti-inflammatory, anti- (Li, RW et al), liver function improvement effect (Satomi Onoue et al.), Anti-obesity effect (Young-Sil Lee et al.), Improvement effect of periodontal disease Tominari et al., Suguru Harada et al., Se-Eun Jang et al., And Yuguang Lin et al., Both of which have improved osteoporosis including osteoporosis. It can be used as a pharmaceutical composition containing the citrus extract as an active ingredient, a health functional food, and a functional cosmetic.
이상, 본 발명내용의 특정한 부분을 상세히 기술하였는바, 당업계의 통상의 지식을 가진 자에게 있어서, 이러한 구체적인 기술은 단지 바람직한 실시태양일 뿐이며, 이에 의해 본 발명의 범위가 제한되는 것이 아닌 점은 명백할 것이다. 따라서 본 발명의 실질적인 범위는 첨부된 청구항들과 그것들의 등가물에 의해 정의된다고 할 것이다.Having described specific portions of the present invention in detail, it will be apparent to those skilled in the art that this specific description is only a preferred embodiment and that the scope of the present invention is not limited thereby. It will be obvious. Accordingly, the actual scope of the present invention will be defined by the appended claims and their equivalents.
Claims (6)
상기 염기성용액은 수산화나트륨, 중탄산나트륨, 수산화칼슘, 수산화칼륨, 수산화마그네슘 및 암모니아 수용액으로 이루어진 군에서 선택된 하나 이상의 염기성 물질을 포함하는 히드록시드(OH) 화합물을 증류수에 0.01 내지 2 %(w/v)의 농도로 용해한 것임을 특징으로 하는 단계;
(2) 상기 회수물을 알콜 수용액으로 추출하여 추출물을 획득하는 단계;
(3) 상기 추출물을 여과 후 농축하여 농축물을 획득하는 단계; 및
(4) 상기 농축물을 침전시키고 건조시켜 최종 산물을 얻는 단계;를 포함하는 노빌레틴(Nobiletin) 또는 탄제레틴(Tangeretin) 함유 추출물의 제조 방법.
(1) treating a basic solution of flesh or peel of citrus fruits at 50 to 80 DEG C for 0.01 to 2 hours and recovering,
Wherein the basic solution is added to a distilled water in an amount of 0.01 to 2% (w / v), in a distilled water, a hydroxide (OH) compound comprising at least one basic substance selected from the group consisting of sodium hydroxide, sodium bicarbonate, calcium hydroxide, potassium hydroxide, magnesium hydroxide, ) ≪ / RTI >;
(2) extracting the recovered product with an aqueous alcohol solution to obtain an extract;
(3) filtering and then concentrating the extract to obtain a concentrate; And
(4) precipitating the concentrate and drying to obtain a final product. ≪ Desc / Clms Page number 19 >
상기 (1)단계 이전에,
감귤류의 과육 또는 과피를 세절하고 세척한 후 건조시키는 사전 처리 단계;를 포함하는 것을 특징으로 하는 노빌레틴(Nobiletin) 또는 탄제레틴(Tangeretin) 함유 추출물의 제조 방법.
The method according to claim 1,
Prior to step (1) above,
A method for producing Nobiletin or Tangeretin-containing extract, which comprises pulping citrus flesh or rind and washing and drying.
상기 감귤류는 시쿠와사(Citrus depressa), 타치바나(C.tachibana), 코우지(C.leiocarpa), 기리 귤(C.tardiva), 지미 강(C.succosa), 키시 우(C.kinokuni), 코베니미캉(C.erythrosa), 치츄우카이망다링(C.deliciosa), 킹(C.nobilis), 본관(C.retuculata), 당시-탄지에린(C.tangerina), 하나 유모(C.hanaya), 코우 라이 타치바나(C.nippokoreana), 진귤(C.sunki hort. ex Tanaka) 및 한라봉(C.hybrid Shiranuhi)으로 구성된 군으로부터 선택된 하나 이상의 감귤인 것을 특징으로 하는 노빌레틴(Nobiletin) 또는 탄제레틴(Tangeretin) 함유 추출물의 제조 방법.
The method according to claim 1,
The citrus fruits include citrus depressa, C. tachibana, C. leiocarpa, C. tardiva, C. succosa, C. kinokuni, C.erythrosa, C.deliciosa, C. nobilis, C.retuculata, C. tangerina, C.hanaya, Nobiletin or Tangeretin which is characterized by at least one citrus fruit selected from the group consisting of C. nippokoreana, C.sunki hort. Ex Tanaka and C. hybrid Shiranuhi. ). ≪ / RTI >
상기 (2)단계에서,
상기 알콜 수용액으로 추출하는 온도는 실온이며, 상기 알콜 수용액으로 추출하는 시간은 24시간 이상인 것을 특징으로 하는 노빌레틴(Nobiletin) 또는 탄제레틴(Tangeretin) 함유 추출물의 제조 방법.
The method according to claim 1,
In the step (2)
Wherein the temperature for extraction with the alcohol aqueous solution is room temperature and the time for extraction with the aqueous alcohol solution is 24 hours or more.
상기 (3)단계에서,
상기 농축 과정은 여과된 추출물을 실온에서 15 내지 20분 동안 정치하여 농축하는 것을 특징으로 하는 노빌레틴(Nobiletin) 또는 탄제레틴(Tangeretin) 함유 추출물의 제조 방법.
The method according to claim 1,
In the step (3)
Wherein the concentrated extract is concentrated by allowing the filtered extract to stand at room temperature for 15 to 20 minutes and then concentrating the extracted extract with Nobiletin or Tangeretin.
상기 (4)단계에서,
상기 침전 과정은 농축물에 증류수 또는 에탄올 수용액을 가한 후 정치하는 것이고, 원심분리하여 침전물을 획득한 후 건조시키는 것을 특징으로 하는 노빌레틴(Nobiletin) 또는 탄제레틴(Tangeretin) 함유 추출물의 제조 방법.The method according to claim 1,
In the step (4)
Wherein the precipitation step is performed by adding distilled water or an aqueous ethanol solution to the concentrate and then allowing the concentrate to stand to obtain a precipitate by centrifugation and then drying the precipitate.
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