KR970069973A - A new sesquiterpene ester compound - Google Patents

A new sesquiterpene ester compound Download PDF

Info

Publication number
KR970069973A
KR970069973A KR1019960009782A KR19960009782A KR970069973A KR 970069973 A KR970069973 A KR 970069973A KR 1019960009782 A KR1019960009782 A KR 1019960009782A KR 19960009782 A KR19960009782 A KR 19960009782A KR 970069973 A KR970069973 A KR 970069973A
Authority
KR
South Korea
Prior art keywords
ester compound
formula
compound
pharmaceutical composition
iii
Prior art date
Application number
KR1019960009782A
Other languages
Korean (ko)
Other versions
KR100191901B1 (en
Inventor
이정준
김영호
김세은
홍영수
Original Assignee
김은영
한국과학기술연구원
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 김은영, 한국과학기술연구원 filed Critical 김은영
Priority to KR1019960009782A priority Critical patent/KR100191901B1/en
Publication of KR970069973A publication Critical patent/KR970069973A/en
Application granted granted Critical
Publication of KR100191901B1 publication Critical patent/KR100191901B1/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
    • C07D493/08—Bridged systems

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

본 발명은 노박덩굴 추출물 및 이로부터 얻은 하기 구조식(Ⅰ), (Ⅱ), (Ⅲ)의 새로운 세스퀴테르펜 에스테르 화합물에 관한 것이다.The present invention relates to Novak Vine extract and novel sesquiterpene ester compounds of the following structural formulas (I), (II) and (III) obtained therefrom.

본 발명은 구조식 (Ⅰ), (Ⅱ), (Ⅲ)의 새로운 세스퀴테르펜 에스테르 화합물을 노박덩굴(Celastrus orbiculatus)의 뿌리로부터 분리·정제하는 방법에 관한 것이다. 또한 본 발명은 세스퀘테르펜 에스테르 화합물 및 이의 유도체를 유효 성분으로 하는 약학적 조성물을 다제내성(multi-drug resistance) 조절제로서 사용하는 용도에 관한 것이다.The present invention relates to a method for separating and purifying a new sesquiterpene ester compound of the structural formulas (I), (II) and (III) from the roots of Celastrus orbiculatus. The present invention also relates to the use of a pharmaceutical composition comprising a cesium quaterpene ester compound and a derivative thereof as an active ingredient as a multi-drug resistance modulator.

Description

새로운 세스퀘테르펜 에스테르 화합물New SES quaterpene ester compounds

본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음Since this is a trivial issue, I did not include the contents of the text.

제1도는 본 발명의 구조식(Ⅰ)의 화합물의 자외선 흡수 스펙트럼을 나타낸다. 제2도는 본 발명의 구조식(Ⅰ)의 화합물의 수소 핵자기 공명 스펙트럼을 나타낸다. 제3도는 본 발명의 구조식(Ⅰ)의 화합물의 탄소 핵자기 공명 스펙트럼을 나타낸다. 제4도는 본 발명의 구조식(Ⅱ)의 화합물의 수소 핵자기 공명 스펙트럼을 나타낸다. 제5도는 본 발명의 구조식(Ⅱ)의 화합물의 탄소 핵자기 공명의 스펙트럼을 나타낸다. 제6도는 본 발명의 구조식(Ⅲ)의 화합물의 수소 핵자기 공명 스펙트럼을 나타낸다. 제7도는 본 발명의 구조식(Ⅲ)의 화합물의 탄소 핵자기 공명 스펙트럼을 타나탠다. 제8도는 항암제인 아드리아미이신 처리시 본발명의 구조식(Ⅲ)의 화합물의 다제내성 극복 활성을 나타낸다. 제9도는 항암제인 빈브라스틴 처리시 본발명의 구조식(Ⅲ)의 화합물의 다제내성 극복 활성을 나타낸다. 제10도는 항암제인 탁솔 처리시 본 발명의 구조식(Ⅲ)의 화합물의 다제내성 극복 활성을 나타낸다.Figure 1 shows the ultraviolet absorption spectrum of the compound of formula (I) of the present invention. 2 shows the hydrogen nuclear magnetic resonance spectrum of the compound of formula (I) of the present invention. Figure 3 shows the carbon nuclear magnetic resonance spectrum of the compound of formula (I) of the present invention. 4 shows the hydrogen nuclear magnetic resonance spectrum of the compound of formula (II) of the present invention. 5 shows the spectrum of the carbon nuclear magnetic resonance of the compound of formula (II) of the present invention. 6 shows the hydrogen nuclear magnetic resonance spectrum of the compound of formula (III) of the present invention. FIG. 7 shows the carbon nuclear magnetic resonance spectrum of the compound of formula (III) of the present invention. FIG. 8 shows the multidrug resistance-overcoming activity of the compound of formula (III) of the present invention upon treatment with the anticancer drug adriamycin. FIG. 9 shows the multidrug resistance-overcoming activity of the compound of formula (III) of the present invention when treated with the anticancer drug binblastine. FIG. 10 shows the multidrug resistance-overcoming activity of the compound of formula (III) of the present invention when treated with Taxol, an anticancer agent.

Claims (13)

세스퀘테르펜 에스테르 화합물을 유효 성분으로 하느 다제내성 조절제.A multidrug resistance modifier which uses a scequaterpene ester compound as an active ingredient. 구조식(Ⅰ)의 신규한 세스퀘테르펜 에스테르 화합물.A novel scequaterpene ester compound of formula (I). 구조식(Ⅱ)의 신규한 세스퀘테르펜 에스테르 화합물.A novel scequaterpene ester compound of formula (II). 구조식(Ⅲ)의 신규한 세스퀘테르펜 에스테르 화합물.A novel cesium quaterpene ester compound of formula (III). 노박덩굴 및 그의 뿌리로부터 저급 알코올 또는 몰로 추출하여 추출액을 정제하여 얻어지는 것을 특징으로 하는 다제내성을 조절제용 노박덩굴 추출물.Wherein the extract is obtained by extracting from an olive leaf and its roots with a lower alcohol or mol, and purifying the extract. 노박덩굴 및 그의 뿌리로부터 저급 알코올 또는 몰로 추출하고 이를 농축하여 얻어지는 것을 특징으로 하는 노박덩굴 추출물의 제조방법.Wherein the extract is obtained by extracting from an olive leaf and its roots with a lower alcohol or mol, and concentrating the same. 제6항에 있어서, 상기 과정에 더하여 다이클로로메탄과 물로 분획하고 다이클로로메틴과 메탄올을 용매로 사용하여 실리카겔 컬럼 크로마트그래피를 수행하는 것을 특징으로 하는 노박덩굴 추출물의 제조방법.7. The method according to claim 6, wherein in addition to the above process, fractionation with dichloromethane and water and silica gel column chromatography are performed using dichloromethane and methanol as a solvent. 제7항에 있어서, 상기 과정에 더하여 메탄올을 용매로 다시 역상 크로마토그래피 또는 고속액체 크로마토그래피 등을 통하여 구조식(Ⅰ), (Ⅱ) ,(Ⅲ)의 화합물을 정제하는 것을 특징으로 하는 제조방법.The process according to claim 7, wherein the compound of formula (I), (II) or (III) is further purified by reversed phase chromatography or high performance liquid chromatography using methanol as a solvent. 세스퀴테르펜 에스테르 화합물 및 그의 유도체를 유효 성분으로하여 이에 약제학적으로 허용가능한 물질이 첨가된 것을 특징으로 하는 다제내성 조절제용 약학적 조성물.A pharmaceutical composition for a multidrug resistance modulating agent comprising a sesquiterpene ester compound and a derivative thereof as an active ingredient and a pharmaceutically acceptable substance added thereto. 제9항에 있어서, 세스퀴테르펜 에스테르 화합물은 구조식(Ⅰ)의 화합물인 것을 특징으로 하는 약학적 조성물.10. The pharmaceutical composition according to claim 9, wherein the sesquiterpene ester compound is a compound of formula (I). 제9항에 있어서, 세스퀴태르펜 에스테르 화합물은 구조식(Ⅱ)의 화합물인 것을 특징으로 하는 약학적 조성물.10. The pharmaceutical composition according to claim 9, wherein the sesquiathiene ester compound is a compound of formula (II). 제9항에 있어서, 세스퀴태르펜 에스테르 화합물은 구조식(Ⅲ)의 화합물인 것을 특징으로 하는 약학적 조성물.The pharmaceutical composition according to claim 9, wherein the sesquiathiene ester compound is a compound of formula (III). 제9항의 약학적 조성물을 유효 성분으로 하는 것을 특징으로 하는 항암 치료 보조제.An adjuvant for chemotherapeutic treatment, which comprises the pharmaceutical composition of claim 9 as an active ingredient. ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.※ Note: It is disclosed by the contents of the first application.
KR1019960009782A 1996-04-01 1996-04-01 Novel sesquiterpene ester compound KR100191901B1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
KR1019960009782A KR100191901B1 (en) 1996-04-01 1996-04-01 Novel sesquiterpene ester compound

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
KR1019960009782A KR100191901B1 (en) 1996-04-01 1996-04-01 Novel sesquiterpene ester compound

Publications (2)

Publication Number Publication Date
KR970069973A true KR970069973A (en) 1997-11-07
KR100191901B1 KR100191901B1 (en) 1999-06-15

Family

ID=19454824

Family Applications (1)

Application Number Title Priority Date Filing Date
KR1019960009782A KR100191901B1 (en) 1996-04-01 1996-04-01 Novel sesquiterpene ester compound

Country Status (1)

Country Link
KR (1) KR100191901B1 (en)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103109810B (en) * 2011-11-16 2014-08-06 中国科学院海洋研究所 Rotifer killing medicine, and preparation method and application thereof
CN103041015B (en) * 2012-12-29 2014-09-10 南宁多灵生物科技有限公司 Medicine for treatment of hepatitis
CN103073529B (en) * 2013-01-03 2015-09-30 西北农林科技大学 2-ketone type-β-dihydroagarofuran sesquiterpenoids its preparation method and application in Siberian cocklebur seven
CN104341376B (en) * 2014-09-03 2017-03-15 中国医学科学院药用植物研究所海南分所 A kind of new sequiterpene quinones and its preparation method and application in arrowleaf abelmoschus root
CN105713009B (en) * 2014-12-03 2017-12-26 天津中医药大学 Calamus alcoholic lactone compound and preparation method and application

Also Published As

Publication number Publication date
KR100191901B1 (en) 1999-06-15

Similar Documents

Publication Publication Date Title
Gaoni et al. Isolation and structure of. DELTA.+-tetrahydrocannabinol and other neutral cannabinoids from hashish
AU687039B2 (en) Method for purifying taxoids
EP0578723B1 (en) PROCESS FOR PURIFICATION OF HMG-CoA REDUCTASE INHIBITORS
AU728188B2 (en) A process for the simultaneous production of artemisnin and essential oil from the plant artemisia annua
KR970069973A (en) A new sesquiterpene ester compound
RU97117177A (en) SUBSTANCES EXTRACTED FROM DICTYOTALES, METHOD FOR PRODUCING THEM AND COMPOSITIONS CONTAINING THEM
Damtoft et al. Tomentoside and 7-hydroxytomentoside, two iridoid glucosides from Paulownia tomentosa
US5900367A (en) Method for purifying taxol from taxus biomass
Ogura et al. Efficient 1, 2-Asymmetric Induction in Radical Reactions: Stereoselective Radical Addition to 3-Hydroxy-1-(methylthio)-1-(p-tolylsulfonyl)-1-alkenes
CN1326343A (en) Agent for lowering prolactin
KR930004471A (en) Antibiotic GE 2270 Factor C₂ａ
Hoffmann et al. Cytotoxic and tumor inhibitory agent from Polygala macradenia gray (Polygalaceae): 4′‐demethyldeoxypodophyllotoxin
Inada et al. Three putrescine bisamides from the leaves of Aglaia grandis
JPH01294657A (en) Novel amide compound and production thereof
KR970061261A (en) Hypoglycemic agent composition containing Hwanggi extract and method for preparing Hwanggi extract
JP2579255B2 (en) Angiotensin converting enzyme activity inhibitor from Tochu leaf extract
Karalai et al. Medicinal plants of euphorbiaceae occurring and utilized in thailand. V. Skin irritants of the daphnane and tigliane type in latex of Excoecaria bicolor and the uterotonic activity of the leaves of the tree
KR960022497A (en) Isolation and Purification of Lignans from Ginkgo Leaf Extract
Hwang et al. Development of quantitative extraction method of amygdalin without enzymatic hydrolysis from tōnin (Persicae semen) by high performance liquid chromatography
JPS58150584A (en) Kuwanon compound
San Feliciano et al. Artegallin, a sesquiterpene lactone from Artemisia Caerulescens subsp. gallica
KR970009802A (en) Method of preparing a pharmaceutical extract from the preparation and a pharmaceutical composition for the prevention and treatment of liver disease containing the extract
JPS58150538A (en) Kuwanon compound
KR960040361A (en) Novel antifungal substances, methods for purification thereof and antifungal compositions comprising the same
JPS5692283A (en) Novel biscatechin derivative

Legal Events

Date Code Title Description
A201 Request for examination
E902 Notification of reason for refusal
E701 Decision to grant or registration of patent right
GRNT Written decision to grant
FPAY Annual fee payment

Payment date: 20021210

Year of fee payment: 5

LAPS Lapse due to unpaid annual fee