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Planta Med 2019; 85(08): 648-656
DOI: 10.1055/a-0879-4721
Biological and Pharmacological Activity
Original Papers
Georg Thieme Verlag KG Stuttgart · New York

Effects of Enantiomerically Pure β-Carboline Alkaloids from Picrasma quassioides on Human Hepatoma Cells

Wen-Yu Zhao
1   School of Traditional Chinese Materia Medica, Key Laboratory of Computational Chemistry-Based Natural Antitumor Drug Research & Development, Liaoning Province, Shenyang Pharmaceutical University, Shenyang, Peopleʼs Republic of China
,
Jing-Jie Chen
1   School of Traditional Chinese Materia Medica, Key Laboratory of Computational Chemistry-Based Natural Antitumor Drug Research & Development, Liaoning Province, Shenyang Pharmaceutical University, Shenyang, Peopleʼs Republic of China
,
Chun-Xin Zou
1   School of Traditional Chinese Materia Medica, Key Laboratory of Computational Chemistry-Based Natural Antitumor Drug Research & Development, Liaoning Province, Shenyang Pharmaceutical University, Shenyang, Peopleʼs Republic of China
,
Wei-Yu Zhou
1   School of Traditional Chinese Materia Medica, Key Laboratory of Computational Chemistry-Based Natural Antitumor Drug Research & Development, Liaoning Province, Shenyang Pharmaceutical University, Shenyang, Peopleʼs Republic of China
,
Guo-Dong Yao
1   School of Traditional Chinese Materia Medica, Key Laboratory of Computational Chemistry-Based Natural Antitumor Drug Research & Development, Liaoning Province, Shenyang Pharmaceutical University, Shenyang, Peopleʼs Republic of China
,
Xiao-Bo Wang
2   Chinese Peopleʼs Liberation Army 210 Hospital, Dalian, Peopleʼs Republic of China
,
Bin Lin
3   School of Pharmaceutical Engineering, Shenyang Pharmaceutical University, Shenyang, Peopleʼs Republic of China
,
Xiao-Xiao Huang
1   School of Traditional Chinese Materia Medica, Key Laboratory of Computational Chemistry-Based Natural Antitumor Drug Research & Development, Liaoning Province, Shenyang Pharmaceutical University, Shenyang, Peopleʼs Republic of China
2   Chinese Peopleʼs Liberation Army 210 Hospital, Dalian, Peopleʼs Republic of China
,
Shao-Jiang Song
1   School of Traditional Chinese Materia Medica, Key Laboratory of Computational Chemistry-Based Natural Antitumor Drug Research & Development, Liaoning Province, Shenyang Pharmaceutical University, Shenyang, Peopleʼs Republic of China
› Author Affiliations
Further Information

Publication History

received 20 November 2018
revised 04 March 2019

accepted 14 March 2019

Publication Date:
11 April 2019 (online)

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Abstract

Four pairs of β-carboline enantiomers (1a/1b–4a/4b), 2 β-carboline derivatives (5 – 6) with a single enantiomeric configuration, together with 2 known achiral congeners (7 – 8) were isolated from the stems of Picrasma quassioides. Their structures were elucidated on the basis of extensive spectroscopic analyses and quantum mechanical calculations. Compound 5 possesses a 4,5-seco β-carboline framework and represents the first example of this type of β-carboline alkaloids from nature. A possible biosynthetic pathway is proposed to generate the racemate 4 and the enantiomerically pure compounds 5 and 6. All isolates were screened for their cytotoxicity against hepatocellular carcinoma Hep3B and HepG2 cells, which revealed that enantiomeric compounds 4a and 4b had distinctive effects in HepG2 cells. Further investigation showed that 4b could induce apoptosis in HepG2 cells.

Key words

Picrasma quassioides - Simaroubaceae - β-carboline alkaloids - biosynthesis - cytotoxicity - enantioselectivity

Supporting Information

    NMR, HRESIMS, and UV spectra of compounds 1 – 6 (Figs. 1S–38S) and further detailed experimental information (Tables 1S–6S, Figs. 39S–48S) are available as Supporting Information.

  • Supporting Information
 

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