KR960031583A - Novel C_22 Fatty Acid Lactone Derivatives and Extraction Methods thereof - Google Patents

Novel C_22 Fatty Acid Lactone Derivatives and Extraction Methods thereof Download PDF

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Publication number
KR960031583A
KR960031583A KR1019950002621A KR19950002621A KR960031583A KR 960031583 A KR960031583 A KR 960031583A KR 1019950002621 A KR1019950002621 A KR 1019950002621A KR 19950002621 A KR19950002621 A KR 19950002621A KR 960031583 A KR960031583 A KR 960031583A
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South Korea
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fatty acid
fraction
derivatives
acid lactones
extraction
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KR1019950002621A
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Korean (ko)
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KR0137687B1 (en
Inventor
신종헌
서영완
노정래
복성해
권병목
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송원오
한국해양연구소
김은영
한국과학기술연구원
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D313/00—Heterocyclic compounds containing rings of more than six members having one oxygen atom as the only ring hetero atom
    • C07D313/16—Eight-membered rings
    • C07D313/18—Eight-membered rings not condensed with other rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K35/00—Medicinal preparations containing materials or reaction products thereof with undetermined constitution
    • A61K35/56—Materials from animals other than mammals
    • A61K35/614—Cnidaria, e.g. sea anemones, corals, coral animals or jellyfish
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D15/00—Separating processes involving the treatment of liquids with solid sorbents; Apparatus therefor
    • B01D15/08—Selective adsorption, e.g. chromatography
    • B01D15/26—Selective adsorption, e.g. chromatography characterised by the separation mechanism

Abstract

본 발명은 항암효과를 갖는 신규의 지방산락톤(fatty acid lactones) 유도체 및 그 추출방법에 관한 것으로, 본 발명에 의한 지방산락톤 유도체는, 아래의 구조식(I) 및 (Ⅱ)와 같이 이루어져 있고, 강장동물, 특히 히드라(hydroid) 솔란데리아 세쿤다(Solanderia secunda)로부터 유기용매로 용출하여 크로마토그래피 방법에 의해 분리추출하며, 파내실 단백질 전이효소(farnesyl protein transferase)의 작용을 저해하여 Ras 유전자의 파내실화를 방지하는 기능을 함으로써 항암작용을 하는 것으로 밝혀진 것이다.The present invention relates to a novel fatty acid lactone derivative having an anticancer effect and a method for extracting the same, wherein the fatty acid lactone derivative according to the present invention comprises the following structural formulas (I) and (II) Elution with organic solvents from animals, in particular the hydroid Solanderia secunda, separated by chromatographic methods, and the inhibition of the farnesyl protein transferase to inhibit the Ras gene It has been found to act as an anticancer agent by preventing internalization.

Description

신규의 C22지방산락톤 유도체 및 그 추출방법New C22 fatty acid lactone derivatives and extraction methods thereof

본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음Since this is an open matter, no full text was included.

제1도는 본 발명에 의한 지방산락톤 유도체(솔란데락톤 C)의 구조식,1 is a structural formula of a fatty acid lactone derivative (soladerlactone C) according to the present invention,

제2도는 본 발명에 의한 다른 지방산락톤 유도체(솔란데락톤 G)의 구조식,2 is a structural formula of another fatty acid lactone derivative (soladerlactone G) according to the present invention,

제3도 (가)는 솔란데락톤 C의 수소 NMR 스펙트럼, (나)는 솔란데락톤의 C의 탄소 NMR 스펙트럼, (다)는 솔란데락톤의 C의 수소 COSY NMR 스펙트럼,Figure 3 (a) is the hydrogen NMR spectrum of solanderactone C, (b) is the carbon NMR spectrum of solanderactone C, (c) is the hydrogen COSY NMR spectrum of solanderactone C,

제4도 (가)는 솔란데락톤 G의 수고 NMR 스펙트럼, (나)는 솔란데락톤 G의 탄소 NMR 스펙트럼, (다)는 솔란데락톤 G의 수소 COSY NMR 스펙트럼이다.Fig. 4 (A) shows the NMR spectrum of solanderactone G, (B) the carbon NMR spectrum of solanderactone G, and (C) the hydrogen COSY NMR spectrum of solanderactone G.

Claims (9)

하기 구조식(I)을 갖는 C22지방산락톤(fatty acid lactones) 유도체.C 22 fatty acid lactones derivatives having the structure (I). 하기 구조식(Ⅱ)을 갖는 C22지방산락톤(fatty acid lactones) 유도체.C 22 fatty acid lactones derivatives having the structure (II). 해양으로부터 강장동물을 채집하여 추출원료를 준비하는 단계; 이 추출원료를 용액에 넣어 용액을 만들고 그 용액을 여과, 증류하여 조추출물을 분리하는 단계; 상기 조추출물을 크로마토그래피에 의해 더욱 분리 정제하는 단계를 포함하여 이루어지는 C22지방산락톤(fatty acid lactones) 유도체의 추출방법.Collecting tonic animals from the ocean to prepare an extract; Putting the extract raw material into a solution to form a solution, and filtering and distilling the solution to separate the crude extract; Extracting the C 22 fatty acid lactone derivatives comprising the step of further separating and purifying the crude extract by chromatography. 제3항에 있어서, 상기 강장동물은 히드라(hydroid) 솔란데리아 세쿤다(Solanderia secunda)인 것을 특징으로 하는 C22지방산락톤(fatty acid lactones) 유도체의 추출방법.The method of claim 3, wherein the extraction of the tonic animals Hydra (hydroid) solran to Syrian Secunda C 22 fatty acid lactone (fatty acid lactones) derivative, characterized in that (Solanderia secunda). 제3항에 있어서, 상기 용매는 디클로로메탄인 것을 특징으로 하는 C22지방산락톤(fatty acid lactones) 유도체의 추출방법.The method of extracting C 22 fatty acid lactones derivatives according to claim 3, wherein the solvent is dichloromethane. 제3항에 있어서, 상기 조추출물의 크로마토그래피에 의한 분리 정체 단계는, 진공 실리카 플래시 크로마토그래피(vacuum silica flash chromatography)를 이용하고, 용리액은 100% 헥산(hexane)으로부터 에틸아세테이트(ethylacetate)를 5%씩 증가시켜 100% 에틸아세테이트에 이르기까지의 헥산과 에틸아세테이트의 혼합액을 사용하여, 상기 조추출물을 여러개의 분획으로 분리한 후, 이 분획들을 C18역산 반-분취 HPLC 컬럼(C18reversed phase semi-preprative HPLC column)상에서 다시 크로마토그래피하여 분리 추출하는 과정으로 이루어지는 것을 특징으로 하는 C22지방산락톤(fatty acid lactones) 유도체의 추출방법.The method of claim 3, wherein the separation and stabilization of the crude extract by chromatography is performed using vacuum silica flash chromatography, and the eluent is 5% ethylacetate from 100% hexane. The crude extract was separated into several fractions using a mixture of hexane and ethyl acetate in increments of up to 100% ethyl acetate, and then these fractions were separated by a C 18 reverse acid preparative HPLC column (C 18 reversed phase). A method for extracting C 22 fatty acid lactones derivatives, which comprises the step of chromatographic extraction on a semi-preprative HPLC column again. 제6항에 있어서, 상기 분획은 16개로 하고, 이 분획중 분획 14, 분획 15 및 분획 16을 용리유체로 물/아세트니트릴(1:1)의 혼합용매를 사용하여 크로마토그래피하는 것을 특징으로 하는 C22지방산락톤(fatty acid lactones) 유도체의 추출방법.The method according to claim 6, wherein the fraction is 16, and fraction 14, fraction 15 and fraction 16 of the fraction are chromatographed using a mixed solvent of water / acetonitrile (1: 1) as an eluting fluid. Extraction method of C 22 fatty acid lactones derivatives. 제6항에 있어서, 상기 분획은 16개로 하고, 이 분획중 분획 12, 분획 13 및 분획 14을 용리유체로 42% 물/아세트니트릴 혼합용액을 사용하여 크로마토그래피하는 것을 특징으로 하는 C22지방산락톤(fatty acid lactones) 유도체의 추출방법.The C 22 fatty acid lactone according to claim 6, wherein the fraction is 16, and fraction 12, fraction 13 and fraction 14 of the fraction are chromatographed using a 42% water / acetonitrile mixed solution as an eluting fluid. Extraction of Fatty Acid Lactones 제1항 또는 제2항에 기재된 C22지방산락톤(fatty acid lactones) 유도체를 유효성분으로 함유하는 항암제.An anticancer agent comprising the C 22 fatty acid lactones derivative according to claim 1 as an active ingredient. ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.※ Note: The disclosure is based on the initial application.
KR1019950002621A 1995-02-13 1995-02-13 Novel fatty acid lactone derivatives and extracting method thereof KR0137687B1 (en)

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