• Archives of Pharmacal Research
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• 제20권5호
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• pp.476-479
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• 1997

Three types of dihydroberberine derivatives such as spirobenzylisoquinoline, benzindenoazepine and cyclopropanated quinolizine species were synthesized from dihydroberberine for the investigation on their anti-tumor activity. Among them, cyclopropanated quinolizine species were more effective than spirobenzylisoquinoline and benzindenoazepine against P-388 and L-1210 leukemia cell.

• 약학회지
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• 제36권3호
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• pp.250-254
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• 1992

Benzo[C]phenanthidine alkaloids were found to exhibit considerably strong antileukemic activies. These alkaloids have been shown to be biosynthesized from the corresponding alkaloids throung an oxidative $C_6-N$ bond cleavage followed by recyclization between $C_6\;and\;C_{13}$ position of the protoberberine. Recently we have achieved the biomimetic transformation of protoberberine alkaloid, berberine into benzo[C]phenanthridine alkaloid, chelerythrine.

• 한국의류학회지
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• 제33권6호
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• pp.980-989
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• 2009

본 연구는 황벽으로부터 추출하는 염료를 가스 크로마토그라피 질량분석기로 분석할 때 berberine 색소를 가장 효과적으로 검출할 수 있도록 추출방법을 표준화하고 적절한 GC-MS 분석방법을 찾는데 목적을 둔다. 항온진탕기와 가열판을 이용한 다양한 추출법을 적용하였으며 GC 컬럼내 온도조작과 MSD 스캔범위에 따라 5종류의 GC-MS 분석방법의 유효성을 검사하였다. Berberine 표준색소와 추출염료 내 berberine 화합물의 유무는 r.t. 15.0분에서 dihydroberberine의 검출로 확인하였다. 가열판 추출이 항온진탕기 추출보다 더 효과적으로 나타났으며 이는 추출 전 실온에서 사전침지를 한 경우와 하지 않은 경우 모두 동일하였다. 물을 이용한 추출은 berberine 검출에 적합하지 않은 것으로 확인되었다. 본 연구에서 도입한 다섯가지 GC-MS 방법 중 berberine 검출에 가장 효과적인 방법은 Method 4였으며 그 조건은, GC 컬럼내초기온도를 $50^{\circ}C$로 하고 $23^{\circ}C$/분 비율로 온도를 올려 $210^{\circ}C$에 달하면 다시 $30^{\circ}C$/분 비율로 온도를 올려 최종온도 $305^{\circ}C$에 도달했을 때 14분간 온도를 그대로 유지하여 전체 분리시간을 24.12분으로 하며 질량 분석기의 스캔 범위는 $35\sim400$m/z로 하는 것이다.

• 한국의류학회지
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• 제33권12호
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• pp.2002-2010
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• 2009

본 연구는 가스크로마토그라피 질량분석기(GC-MS)를 이용하여 황벽의 주 염료성분인 berberine의 퇴화 거동을 조사하는데 목적을 두며 궁극적으로는 심하게 퇴색된 출토직물의 염료성분을 판정하기 위해 각 천연염료별 퇴화물 자료를 수집하고자 한다. Berberine chloride 0.1% 수용액을 $100^{\circ}C$ 오븐법과 $H_2O_2/UV/O_2$법을 이용해 최고 408시간까지 퇴화시키고 GC-MS를 이용해 시료를 분석하였다. 연구결과 오븐 퇴화에 의해 dihydroberberine, 2-pteridinamine, 6,7-dimethyl-N-[(trimethylsilyl)oxy]-, and 8-methoxy-11-[3-methylbutyl]-11H-indolo[3,2-c]-quinoline, 5-oxide의 3개 화합물이 주로 검출되었으며 이들은 berberine 염료의 초기 퇴화 과정에서 나타나는 화합물로 판정되었다. 반면 $H_2O_2/UV/O_2$법으로 퇴화시킨 시료에서는 isobenzofuran-1,3-dione,4,5-dimethoxy-, 9H-fluorene,3,6-bis(2-hydroxyethyl)-, 1,3-dioxolo[4,5-g]isoquinolin-5(6H)-one,7,8-dihydro-, and 3-tert-butyl-4-hydroxyanisole의 4개 화합물이 퇴화 시작과 더불어 새로 생산되었는데 이들은 berberine 염료가 극심한 퇴화 조건에 놓이게 될 때 검출될 수 있는 화합물로 판정되었다. $H_2O_2/UV/O_2$법은 매우 강한 산화작용으로 염료를 퇴화시키는 방법임을 감안할 때 $H_2O_2/UV/O_2$법으로 생성된 화합물은 심하게 퇴색된 출토직물 중 berberine 염료가 사용된 직물을 확인하는데 사용될 수 있을 것으로 사료된다.

• 한국의류학회지
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• 제34권6호
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• pp.1042-1052
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• 2010

The Degradation of amur cork tree extract is investigated by GC-MS after treating the dye with three thermal degradation systems of, room temperature (RT), $4^{\circ}C$ refrigeration (LT), $100^{\circ}C$ oven (OV), and $H_2O_2$/UV/$O_2$ (PER) degradation system for 0-24 days. It was found that PER degradation system represented the highest intensity of degradation treatment followed by OV treatment among the four degradation parameters. The possible fingerprint products of amur cork tree dye, that yielded 68% (or higher) reliability in the NIST spectral match, were isobenzofuran-1,3-dione,4,5-dimethoxy- (8.37 min, PER only), 1,3-dioxolo[4,5-g]isoquinolin-5(6H)-one,7,8-dihydro (9.41 min, PER only), canthine-6-one (10.24 min, RT, LT, OV only), and dihydroberberine (15.05 min, RT, LT, OV, PER) in the order of higher to lower possibility of detection. Unknown products 7 (13.43 min) and 8 (16.35 min) are two other possible fingerprint products of amur cork tree dye that require future identification.

• 분석과학
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• 제30권6호
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• pp.379-389
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• 2017

In this study, we set up an analytical method that can be used for rapid and accurate determination of representative isoquinoline alkaloids in medicinal plants using UPLC-ESI-Q-TOF MS (ultra pressure liquid chromatography-electrospray ionization-quadrupole-time-of-flight mass spectrometry). The compounds were eluted on a C18 column with 0.1 % formic acid and acetonitrile, and separated with good resolution within 13 min. Each of the separated components was characterized by precursor ions (generated by ESI-Q-TOF) and fragment ions (produced by collision-induced dissociation, CID), which were used as a reliable database. We also performed method validation: analytes showed excellent linearity ($R^2$, 0.9971-0.9996), LOD (5-25 ng/mL), LOQ (17-82 ng/mL), accuracy (91.6-97.4 %) as well as intra- and inter-day precisions (RSD, 1.8-3.2 %). In the analysis of Chelidonium majus L., magnoflorine, coptisine, sanguinarine, berberine and palmatine were detected by matching retention times and characteristic fragment ion patterns of reference standards. We also confirmed that, among the quantified components, coptisine was present in the highest quantity. Furthermore, alkaloid profiling was carried out by analyzing the fragment ion patterns corresponding to peaks of unknown components. In this manner, protopine, chelidonine, stylopine, dihydroberberine, canadine, and nitidine were tentatively identified. We also proposed the molecular structure of the fragment ions that appear in the mass spectrum. Therefore, we concluded that our suggested method for the determination of major isoquinoline alkaloids by UPLC-Q-TOF can be useful not only for quality control, but also for rapid and accurate investigation of phytochemical constituents of medicinal plants.