Three New Cytotoxic Monoterpenoid Bisindole Alkaloids from Tabernaemontana bufalina

Si-Yuan Zhou; Ting-Lan Zhou; Guofu Qiu; Xiajuan Huan; Ze-Hong Miao; Sheng-Ping Yang; Shugeng Cao; Fengkai Fan; You-Sheng Cai

doi:10.1055/a-0608-4988

Planta Medica, Table of Contents

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

¹Institute of TCM and Natural Products, School of Pharmaceutical Sciences, Wuhan University, Wuhan, P. R. China

,

Ting-Lan Zhou

¹Institute of TCM and Natural Products, School of Pharmaceutical Sciences, Wuhan University, Wuhan, P. R. China

,

Guofu Qiu

¹Institute of TCM and Natural Products, School of Pharmaceutical Sciences, Wuhan University, Wuhan, P. R. China

,

Xiajuan Huan

²State Key Laboratory of Drug Research Institute of Materia Medica Chinese Academy of Sciences, Shanghai, P. R. China

,

Ze-Hong Miao

²State Key Laboratory of Drug Research Institute of Materia Medica Chinese Academy of Sciences, Shanghai, P. R. China

,

Sheng-Ping Yang

¹Institute of TCM and Natural Products, School of Pharmaceutical Sciences, Wuhan University, Wuhan, P. R. China

,

Shugeng Cao

³Department of Pharmaceutical Sciences, Daniel K. Inouye College of Pharmacy, University of Hawaii at Hilo, Hilo, USA

,

Fengkai Fan

⁴Hubei 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

¹Institute of TCM and Natural Products, School of Pharmaceutical Sciences, Wuhan University, Wuhan, P. R. China

³Department of Pharmaceutical Sciences, Daniel K. Inouye College of Pharmacy, University of Hawaii at Hilo, Hilo, USA

› Author Affiliations

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

Full Text

References

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