• 한국응용약물학회:학술대회논문집
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• 한국응용약물학회 2000년도 춘계학술대회
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• pp.10-14
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• 2000

The cycloooxygenase enzymes catalyze the oxidative conversion of arachidonic acid into prostag1andin H$_2$Which mediates both benificial and pathological effects. The COX-1 is constitutively expressed in most tissues and in blood platelets wherease the expression of COX-2 isoform is induced in response to inflmmatory stimuli such as cyctokynes. Thus the identification of a novel COX-2 selective inhibitor should offer excellent antiinflammatory activity with minimal side effects such as gastrointestinal toxicity. Recently, a group of structurally unique and biologically active pimarane diterpenoids has been isolated from indigenous Korean medicinal plants. These new diterpenoids turned out to be potential analgesic and antiinflammatory agent due to their potent inhibitory activities of prostaglandin synthesis. We have also found that the inhibition of PGE$_2$synthesis is attributed to the potent COX inhibition by pimarane diterpenoid in arachidonic acid cascade. In conjunction with development of new analgesic and nonsteroidal antiinflammatory agent, a series of works on these diterpenoids have been extensively carried out in our laboratories. These efforts involve the structure-activity relationship of pimaradienoic acid, molecular modelings and COX inibitory activities as well as actiinflammatory effects of its structural analogues. In addition, the total syntheses of the new natural pimarane diterpenoids, their stereoisomers and other structural variants were intensively investigated.

• 약학회지
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• 제33권4호
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• pp.226-228
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• 1989

In connection with the synthesis of the biologically active pimarane diterpenoids, some synthetic routes to the quaternary carbon unit were examined. Especially, Claisen rearrangement of allyl acetates prepared from acetol provided ${\gamma}-hydroxy$ acid containing vinyl substituent as the desired unit.

• Archives of Pharmacal Research
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• 제27권5호
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• pp.467-470
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• 2004

Comparative molecular field analysis and comparative molecular similarity indices analysis were performed on twenty five analogues of pimarane COX-2 inhibitor to optimize their cyclooxygenase-2 (COX-2) selective anti-inflammatory activities.

• 한국작물학회지
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• 제50권2호
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• pp.147-150
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• 2005

ent-Kaurane- and ent-pimarane-type diterpenoids were isolated from the methanol extract of Siegesbeckia pubescens by column chromatography. Their structures were elucidated as ent-16$\alpha$H,17-hydroxy-kau­ran-19-oic acid (1), ent-4,17-dihydroxy-16$\alpha$-methyl-kau­ran-19-oic acid (2), ent-16$\beta$,17-dihydroxy-kauran-19-oic acid (3), kirenol (4) and ent-16$\beta$,17,18-trihydroxy-kauran­19-oic acid (5) by spectral analysis. The cytotoxicity of these compounds in Caki cells was assayed by a cell counting kit. Only one group treated with kirenol (4), an entpimarane-type diterpenoid, showed the inhibition of the cell growth in Caki cells.

• 생약학회지
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• 제43권4호
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• pp.286-290
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• 2012

Many diterpenoids from Siegesbeckia species (Compositae) and their anti-inflammatory actions have been examined. In this research, high-performance liquid chromatography-ultraviolet spectrophotometer (HPLC-UV) method was used to compare the quantitative level of kirenol (ent-pimarane-type diterpenoid) in the aerial parts of Korean S. glabrescens and S. pubescens and the Chinese Siegesbeckiae Herba. Fingerprints of the two HPLC chromatograms of Korean S. glabrescens and S. pubescens were similar, but considerably different from Chinese Siegesbeckiae Herba. The content of kirenol in S. pubescens ($16.51{\pm}0.10$ mg/ml dry weight as mean${\pm}$RSD) was higher than S. glabrescens ($13.48{\pm}0.12$ mg/g dry weight). These values were considerably higher than the Chinese Siegesbeckiae Herba ($1.55{\pm}0.74$ mg/g dry weight). Thin layer chromatography (TLC) analysis demonstrated the containing of kirenol in the three plant materials, but the presence of siegeskaurolic acid (entkaurane-type diterpenoid) only in the Chinese Siegesbeckiae Herba.

• 헤리티지:역사와 과학
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• 제54권4호
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• pp.78-89
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• 2021

유기잔존물 분석(organic residues analysis)은 동식물의 종에 따라 물질을 구성하고 있는 주요 성분이 다르다는 특성을 이용하여 유기물 시료의 종류를 밝혀내는 분석 방법이다. 본 연구에서는 의정부 신곡동 유적에서 출토된 조선시대 회묘 내 목관 부착 유기잔존물과 현대 재료에 대한 과학적 분석을 적용하여 유기잔존물의 주성분을 확인하고 유기물의 용도를 추정하여 과거 생활 모습을 밝힐 수 있는 자료를 확보하고자 하였다. 목관 부착 유기물과 현대 재료는 적외선 분광 분석(FT-IR)과 기체 크로마토그래피-질량 분석(GC-MS)을 수행하였다. 목관 내부에 부착된 유기물의 FT-IR 분석 결과 식물성 천연 수지 물질로 확인되었다. 또한 천연 수지의 특성 인자를 확인하기 위해 GC-MS 분석 결과 디하이드로아비트산(dehydroabietic acid), 피마릭산(pimaric acid) 등 아비탄(abietane)과 피마란(pimarane)의 디터페노이드(diterpenoid) 화합물과 포화·불포화지방산 성분이 함께 검출되었다. 디터페노이드 화합물은 주로 소나무과 수지에서 나타나는 성분이다. 소나무과 수지에서 기인하는 송진은 문헌에 접착제 재료로 사용된 기록이 있으며, 유기물 시료가 목관 이음새 부분에 잔존하고 있었던 점을 고려한다면 목관에 부착되어 있던 유기물은 소나무과 수지로 만들어진 접착 물질로 추정된다. 또한 디터페노이드 화합물과 함께 검출된 지방산은 식물성 기름에서 유래된 성분으로, 문헌의 기록처럼 송진과 기름을 혼합하여 만든 것으로 추정할 수 있다. 본 연구를 통해 고고자료에 남아 있는 유기물이 매장 환경에서도 그 특성이 남아 있는 것을 확인할 수 있었고, 당시 사용되었던 천연 수지의 종류와 용도를 밝힘으로써 과거 생활 모습 복원에 중요한 정보를 확보하였다는 점에서 큰 의미가 있다고 본다.