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Planta Med 2018; 84(15): 1127-1133
DOI: 10.1055/a-0608-4988
Natural Product Chemistry and Analytical Studies
Original Papers
Georg Thieme Verlag KG Stuttgart · New York

Three New Cytotoxic Monoterpenoid Bisindole Alkaloids from Tabernaemontana bufalina

Si-Yuan Zhou
1   Institute of TCM and Natural Products, School of Pharmaceutical Sciences, Wuhan University, Wuhan, P. R. China
,
Ting-Lan Zhou
1   Institute of TCM and Natural Products, School of Pharmaceutical Sciences, Wuhan University, Wuhan, P. R. China
,
Guofu Qiu
1   Institute of TCM and Natural Products, School of Pharmaceutical Sciences, Wuhan University, Wuhan, P. R. China
,
Xiajuan Huan
2   State Key Laboratory of Drug Research Institute of Materia Medica Chinese Academy of Sciences, Shanghai, P. R. China
,
Ze-Hong Miao
2   State Key Laboratory of Drug Research Institute of Materia Medica Chinese Academy of Sciences, Shanghai, P. R. China
,
Sheng-Ping Yang
1   Institute of TCM and Natural Products, School of Pharmaceutical Sciences, Wuhan University, Wuhan, P. R. China
,
Shugeng Cao
3   Department of Pharmaceutical Sciences, Daniel K. Inouye College of Pharmacy, University of Hawaii at Hilo, Hilo, USA
,
Fengkai Fan
4   Hubei Key Laboratory of Purification and Application of Plant Anti-Cancer Ingredients, College of Chemistry and Life Science, Hubei University of Education, Wuhan, P. R. China
,
You-Sheng Cai
1   Institute of TCM and Natural Products, School of Pharmaceutical Sciences, Wuhan University, Wuhan, P. R. China
3   Department of Pharmaceutical Sciences, Daniel K. Inouye College of Pharmacy, University of Hawaii at Hilo, Hilo, USA
› Author Affiliations
Further Information

Publication History

received 11 February 2018
revised 30 March 2018

accepted 09 April 2018

Publication Date:
24 April 2018 (online)

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Abstract

Three new bisindole alkaloids, 3′-(2-oxopropyl)-19,20-dihydrotabernamine (1), 3′-(2-oxopropyl)-ervahanine B (2), 19,20-dihydrovobparicine (3), and 20 known compounds were isolated from the aerial parts of Tabernaemontana bufalina. The structures of these alkaloids were elucidated using spectroscopic methods. The absolute configurations of 1–3 were determined by the circular dichroic exciton chirality method. Compounds 1–23 were screened for their cytotoxicity against two human cancer cell lines, A-549 and MCF-7. Ten compounds (1–3, 10, 14, 16, 17, 19, 22, and 23) exhibited inhibitory effects against the two human cancer cells with IC50 values of 1.19 ~ 6.13 µM.

Key words

Tabernaemontana bufalina - Apocynaceae - monoterpenoid indole alkaloids - cytotoxicity

Supporting Information

    1H and 13C NMR, 1H-1H COSY, HSQC, HMBC, ROESY, and high-resolution MS spectra of compounds 1–3, and 1H and 13C NMR of tabernaecorymbosine A (19) are available as Supporting Information.

  • Supporting Information
 

  • References

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