• Archives of Pharmacal Research
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• 제23권6호
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• pp.589-591
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• 2000

Six benzo[c]phenanthridine alkaloids, corynoline (1), acetylcorynoline (2), corynoloxine (3), luguine (4), 6-oxocorynoline (5), and 12-hydroxycorynoloxine (6) were isolated from the aerial parts of Corydalis incisa, and 6 was isolated for the first time from nature. The structure was elucidated by NMR techniques.

• 대한약학회:학술대회논문집
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• 대한약학회 2003년도 Proceedings of the Convention of the Pharmaceutical Society of Korea Vol.2-2
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• pp.65.1-65.1
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• 2003

Natural benzo[c]phenanthridine and protoberberine alkaloids which have been attractive to synthetic organic chemists and biochemists over the last 2 decades since such compounds have shown interesting biological properties such as antitumor, antiviral and antimicrobacterial activities. For the systematic research on these alkaloids, several total syntheses of these alkaloids have been reported. However, the bulk of reported benzo[c]phenanthridine synthetic studies to date have involved multistep sequences for assembly of the target molecules as well as lack of generality for synthesizing substituted molecules. (omitted)

• KSBB Journal
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• 제24권2호
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• pp.195-200
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• 2009

본 연구에서는 Eschscholtzia californica의 이차 대사산물인 benzo[c]phenanthridine alkaloids의 생산량을 향상시키기 위해 주요 영양성분인 질소원 농도를 조절하여 배지의 조성을 최적화하였다. 그 결과, 질산과 암모늄 이온의 초기 농도 비율은 세포 성장과 alkaloids 생산량 증대에 중요한 영향을 미치는 인자로서 작용함을 볼 수 있었다. 총 질소 농도를 standard MS배지의 총 질소원 농도와 동일하게 유지하고 (60 mM), 농도 비율 다양하게 조절했을 때, 세포 성장과 alkaloids 생산량은 질산과 암모늄 이온을 각각 단독으로 이용할 때 보다 효율적으로 증대함을 볼 수 있었다. 최대 성장 (9.84 g DCW/L)과 alkaloids 생산량 (60.72 mg/L)은 50 : 10의 비율에서 나타났으며, 농도 비율의 감소는 세포 성장을 억제하고 alkaloids 생산량을 감소시켰다. 또한, 질산과 암모늄 이온이 세포 성장과 alkaloids 생산량에 미치는 영향력을 보다 명확히 확인하기 위해 질산 이온과 암모늄 이온 농도를 각각 조절한 결과, 암모늄 이온이 증가할수록 alkaloids 생산량은 비슷하나, 세포 성장은 감소하였으며, 또한, 질산 이온의 농도를 증가시킬수록 세포 성장은 비슷한 값을 나타내었지만, alkaloids 생산량은 다양한 차이를 나타내었다. 본 실험에서 세포성장과 alkaloids 생산량에 적합한 농도는 50 : 25 (mol/mol) 비율에서 나타났으며, 본 실험을 통해 Eschscholtzia californica의 현탁 세포배양에서 질소원 농도의 조절을 통한 외부 환경조절은 세포 성장과 alkaloids 향상에 매우 효과적이며, 소량의 암모늄 이온의 첨가 시 질산 이온 농도조절은 세포 성장을 억제하지 않으면서 alkaloids 생산량을 유도하는데 적합한 이온임을 확인하였다.

• Archives of Pharmacal Research
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• 제19권4호
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• pp.321-325
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• 1996

Aiming at the development of anticancer agents by modification of phenolic benzo[c]phenanthridine alkaloid, additional hydroxyl group was put on C10 position of fagaridine (1) by a biomimetic synthetic procedure to afford 10-hydroxyfagaridine (12). All of the synthetic intermediates were also screened in vitro antitumor activities against five different cell lines as well as 12. Among them the representative cytotoxic results are shown as follows; P-quinone (11) $[ED_50;(A549=0.22; {\mu}g/ml)$, $(HCT;15=0.21 {\mu}g/ml)$, fagaridine (1) $(HCT;15=0.41 {\mu}g/ml)$, olefin (6) $(HCT; 15=0.06 {\mu}g/ml)$, acetal (7) $(SKMEL-2=0.07 {\mu}g/ml)$, dihydrofagaridne (10) $(A549=0.38 {\mu}g/ml)$, 10-hydroxyfagaridine (12) $(A 549=0.45{\mu}g/mi)$. From these observation three main remarks can be drawn; (i) the iminium part of benzo[c]phenanthridine is not essential for showing acitvities, (ii) the additional hydroxyl group did not contribute to enhance the cytotoxicity, (iii) the 3-arylisoquinolin-1(2H)-one derivatives were found to display significant in vitro antitumor activity.

• 대한약학회:학술대회논문집
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• 대한약학회 2001년도 Proceedings of International Convention of the Pharmaceutical Society of Korea
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• pp.232.2-232.2
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• 2001

• Archives of Pharmacal Research
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• 제19권3호
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• pp.240-242
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• 1996

We have reported the convenient biomimetic methodology for the synthesis of all kinds of substituent pattern benzo[c]phenanthridine alkaloids (Hanaoka et al., 1990; Hanaoka et al., 1991). Regioselective demethylation of C-8 position on oxyfagaridine (5), an intermediate for the synthesis of Fagaridine (4), would afford the precursor for the synthesis of Isofagaridine because the strong hydrogen bonding between amide and hydroxyl group of C-7 position probably resists to be reacted with week base and electrophiles. Thus, a selective alkylation of dihydroxy compound supposed to be possible and be lead to the target compound, Isofagaridine.

• Bulletin of the Korean Chemical Society
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• 제27권12호
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• pp.2093-2096
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• 2006

• 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.

• 대한약학회:학술대회논문집
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• 대한약학회 2002년도 Proceedings of the Convention of the Pharmaceutical Society of Korea Vol.2
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• pp.348.2-348.2
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• 2002

The significant antitumor activities of 3-arylisoquinolines promoted us to explore the structure-activity relationship of these compounds. A series of 3-Arylisoquinoline derivatives, which related to Benzo［c］ phenanthridine alkaloids. were evaluated for antitumor cytotoxicity against human lung tumor cell (A 549). We tried to study structure-activity relationship (SAR) of 3-Arylisoquinolines using the comparative molecular field analysis (CoMFA) method. (omitted)

• 대한약학회:학술대회논문집
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• 대한약학회 2002년도 Proceedings of the Convention of the Pharmaceutical Society of Korea Vol.2
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• pp.355.2-355.2
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• 2002

Benzo［c］ phenanthridine alkaloids occurring in the Fumariaceae, Papaveraceae, and Rutaceae. posses numerous pharmacological activities, such as antitumor. antimicrobal and antifungal activities. Thus, they have attracted much interests of chemists and as the result, several total syntheses of these heterocycle structure were accomplished. Among that, procedures which involve 3-arylisoquinoline intermediates are useful methods and these synthons could be also applied to the preparation of other alkaloids. (omitted)