• 한국응용과학기술학회지
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• 제28권2호
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• pp.196-202
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• 2011

Coumarin derivatives were shown to possess valuable pharmacological properties such as anticancer/anti carcinogenic, anti-inflammatory, anti helicobacter, anti genotoxic, neuroprotective and dietary effect. In this study, novel coumarin derivatives structurally related to 7-geranyloxycoumarin were effectively synthesised in good yields by $Cs_2CO_3$/acetonitrile in mild condition. The synthesis of geranyloxycoumarin derivatives in weak base($Na_2CO_3$, $K_2CO_3$, $Cs_2CO_3$ etc)/$CH_3CN$ at room temperature obtained in good yield. On the other hand, the reaction of geranyloxycoumarin formation in strong base(NaOH, KOH, CsOH etc)/$CH_3CN$ at reflux condition obtained in low yield.

• 한국응용과학기술학회지
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• 제29권4호
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• pp.610-617
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• 2012

탱자에는 여러 종류의 monoterpenes, limonoids, flavonoids과 coumarins 등의 구성성분으로 이루어져 있다. 탱자의 구성 성분중에 7-제라닐옥시쿠마린는 7개의 탄소로 구성된 제라닐옥시기의 곁사슬을 가진 물질이다. 그리고 7-제라닐옥시쿠마린은 여러 약리적인 효과들을 나타낸다고 알려져 있다. 본 연구에서는 탱자의 구성성분인 7-제라닐옥시쿠마린과 이들의 다양한 유도체를 합성하였다. 그리고 항염증에 대한 항염증 효능을 알아보기 위하여 염증을 유발하는 일산화질소 억제 cytokine을 측정한 결과는 6-제라닐옥시쿠마린의 성분이 사이토카인인 인터루킨-6가 $1{\mu}M$농도에서 68.9% 를, $10{\mu}M$에서 72.6% 의 저해효과를 나타냈다.

• Archives of Pharmacal Research
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• 제8권3호
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• pp.187-190
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• 1985

A cytotoxic coumarin against L1210 cell was isolated from the unripe fruit of Poncirus trifoliata ($ED_{5}$) = 10.2 $\mu$ g/ml. Its structure was identified as aurapten, 7-geranyloxycoumarin. Hydrolysis of the substance gave umbelliferone and geraniol. Only geraniol showed the cytotoxic activity ($ED_{53}$ = 6.5 $\mu$g/ml) while umbelliferone and its methyl or allyl derivatives were not active.

• 한국식품과학회지
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• 제21권6호
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• pp.749-754
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• 1989

탱자(Poncirus trifoliata)의 향기성분을 분석하기 위해 gas co-distillation 방법으로 정유를 추출한 후 GC/retention index(RI)와 GC/MS를 이용해 multi-dimensional analysis를 행하였다. Gas co-distillation 방법으로 탱자의 향도 그대로 지니며 기기분석에 적합한 정유를 얻을 수 있었다. 향기성분의 확인작업에는 GC/RI와 GC/MS를 상보적으로 사용한 multi-dimensional analysis가 효과적이었으며 GC/RI로만 확인할 경우 극성이 다른 두 가지 column을 사용해서 신뢰도를 높일 수 있었다. 탱자에 다량 함유되어 있는 향기성분들은 limonene, myrcene, ${\beta}-caryophllene,\;trans-{\beta}-ocimene,\;{\beta}-pinene$, 3-thujene, 7-geranyloxycoumarin 등으로 밝혀졌으며 확인된 30개의 성분 중 cis-3-hexenyl acetate, n-hexyl acetate, 2-methyl acetophenone, elixene 그리고 elemicine 등은 이제까지 감귤류에서는 발견되지 않았던 새로운 성분들이다.

• 생약학회지
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• 제17권2호
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• pp.168-177
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• 1986

Bioassay-directed isolation has yielded some cytotoxic substances against L1210 cell from the Korean traditional medicine. These include 5,2'-dihydroxy-6,7,8,6'-teramethoxyflavone $(IV,\;scutellaria\;root,\;ED_{50}\;=\;1.7\;{mu}g/ml)$, 7-geranyloxycoumarin $(XXXII,\;poncirus\;fruit,\;10.2\;{mu}g/ml) $and panaxydol $(I,\;white\;ginseng,\;0.03\;{mu}g/ml)$. IV, XXXII and their derivatives were synthesized in the purpose of in vivo tests and for observation of structure-activity relations. Among the flavone derivatives, 5,2',6'-trihydroxy-6,7,8-trimethoxy flavone (XVIII), 5-hydroxy-6,7,8-trimethoxy-6'-benzyloxyflavone (XVII) and 5,8-dihydroxy-6,7-dimethoxyflavone (X) showed the cytotoxicity which has no correlation to the flavone structures. Of the coumarins synthesized, 7,8-dihydroxycoumarin (XXVI), 6-7-dihydroxycoumarin (XXIX) and 6-hydroxy-5,7-dimethoxycoumarin (XXXI) showed considerable activities. Acetylated XXXI has moderate activity $(ED_{50}=17.2\;{mu}g/ml)$. Monobydroxycoumarins or their methyl and allyl ether were inactive. IV inhibits the growth of the solid form of S-180 by 70% at 40 mg/kg and shows T/C of 166% on the ascitic S-180 at 40 mg/kg. It strongly inhibits the activity of the membrane bounded ATPase from L1210 cell. The most cytotoxic fraction of the antitumor materials studied is the one from the trichosanthes root showing $ED_{50}=0. 0003\;{mu}g/ml$ against L1210 cell. This fraction, obtained from ethyl acetate extract, showed T/C of 130 and 135%, on ICR mice bearing S-180 and $BDF_1$ mice bearing L1210 at 10 mg/kg and 7.5 mg/kg, respectively.