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SUPPLEMENTARY MATERIAL One New Alkaloid from Chelidonium majus L. Wen-Juan Zhang a , Chun-Xue You a , Cheng-Fang Wang a,b, *, Li Fan b , Ying Wang a , Yang Su c , Zhi-Wei Deng d , and Shu-Shan Du a, * a State Key Laboratory of Earth Surface Processes and Resource Ecology, Beijing Normal University, No.19 Xinjiekouwai Street, Haidian District, Beijing 100875, China; b China CDC Key Laboratory of Radiological Protection and Nuclear Emergency, National Institute for Radiological Protection, Chinese Center for Disease Control and Prevention, Xicheng District, Beijing 100088, China; c College of Clinical Medicine Science, Tibet University, No. 36 Jiangsu Road, Lhasa 850000, Tibet Autonomous Region, China; d Analytic and Testing Center, Beijing Normal University, No.19 Xinjiekouwai Street, Haidian District, Beijing 100875, China. * Corresponding authors. E-mail address: [email protected] (S.S. Du); [email protected] (C.F. Wang). One new alkaloid, together with ten known compounds were isolated from the aerial parts of Chelidonium majus L. by repeated sillica gel column chromatography. Their chemical structures were elucidated on the basic of physicochemical and spectroscopic data. Among them, 6-acetonyldihydrochelerythrine (4), 6- acetonyldihydrosanguinarine (5), 6-ketenesanguinarine (6), demethylchelerythrine (7) and demethylsanguinarine (11) were isolated for the first time from this plant. Compound 6 was identified as a new compound. These compounds were screened for cytotoxicity against human non-small lung carcinoma (H1299), breast cancer (MCF-7) and liver cancer (SMMC- 7721). Within the series of cytotoxic tests, compounds

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Page 1: TF_Template_Word_Windows_2010€¦  · Web viewWen-Juan Zhanga, Chun-Xue Youa, Cheng-Fang Wanga,b,*, Li Fanb, Ying Wanga, Yang Suc, Zhi-Wei Dengd, and Shu-Shan Dua,* a. State Key

SUPPLEMENTARY MATERIAL

One New Alkaloid from Chelidonium majus L.

Wen-Juan Zhanga, Chun-Xue Youa, Cheng-Fang Wanga,b,*, Li Fanb, Ying Wanga, Yang Suc, Zhi-Wei

Dengd, and Shu-Shan Dua,*

aState Key Laboratory of Earth Surface Processes and Resource Ecology, Beijing Normal University,

No.19 Xinjiekouwai Street, Haidian District, Beijing 100875, China;bChina CDC Key Laboratory of Radiological Protection and Nuclear Emergency, National Institute for

Radiological Protection, Chinese Center for Disease Control and Prevention, Xicheng District, Beijing

100088, China; cCollege of Clinical Medicine Science, Tibet University, No. 36 Jiangsu Road, Lhasa 850000, Tibet

Autonomous Region, China; dAnalytic and Testing Center, Beijing Normal University, No.19 Xinjiekouwai Street, Haidian

District, Beijing 100875, China.

* Corresponding authors. E-mail address: [email protected] (S.S. Du);

[email protected] (C.F. Wang).

One new alkaloid, together with ten known compounds were isolated from the

aerial parts of Chelidonium majus L. by repeated sillica gel column

chromatography. Their chemical structures were elucidated on the basic of

physicochemical and spectroscopic data. Among them, 6-

acetonyldihydrochelerythrine (4), 6-acetonyldihydrosanguinarine (5), 6-

ketenesanguinarine (6), demethylchelerythrine (7) and demethylsanguinarine (11)

were isolated for the first time from this plant. Compound 6 was identified as a

new compound. These compounds were screened for cytotoxicity against human

non-small lung carcinoma (H1299), breast cancer (MCF-7) and liver cancer

(SMMC-7721). Within the series of cytotoxic tests, compounds 9 and 10

displayed potent cytotoxic activity against H1299, MCF-7 and SMMC-7721,

with the IC50 values of 8.16 to 35.25 μg/mL.

Keywords: 6-ketenesanguinarine; Chelidonium majus L.; cytotoxic activity

Page 2: TF_Template_Word_Windows_2010€¦  · Web viewWen-Juan Zhanga, Chun-Xue Youa, Cheng-Fang Wanga,b,*, Li Fanb, Ying Wanga, Yang Suc, Zhi-Wei Dengd, and Shu-Shan Dua,* a. State Key

Figure S1. H–H COSY and Key HMBC correlations for compound 6.

Figure S2. The 1H-NMR spectrum of compound 6 (DMSO-d6).

Page 3: TF_Template_Word_Windows_2010€¦  · Web viewWen-Juan Zhanga, Chun-Xue Youa, Cheng-Fang Wanga,b,*, Li Fanb, Ying Wanga, Yang Suc, Zhi-Wei Dengd, and Shu-Shan Dua,* a. State Key

Figure S3. The 13C-NMR spectrum of compound 6 (DMSO-d6).

Figure S4. The H-H COSY spectrum of compound 6 (DMSO-d6).

Page 4: TF_Template_Word_Windows_2010€¦  · Web viewWen-Juan Zhanga, Chun-Xue Youa, Cheng-Fang Wanga,b,*, Li Fanb, Ying Wanga, Yang Suc, Zhi-Wei Dengd, and Shu-Shan Dua,* a. State Key

Figure S5. The HSQC spectrum of compound 6 (DMSO-d6).

Figure S6. The HMBC spectrum of compound 6 (DMSO-d6).

Page 5: TF_Template_Word_Windows_2010€¦  · Web viewWen-Juan Zhanga, Chun-Xue Youa, Cheng-Fang Wanga,b,*, Li Fanb, Ying Wanga, Yang Suc, Zhi-Wei Dengd, and Shu-Shan Dua,* a. State Key

Figure S7. The HR-ESI-MS spectrum of compound 6.