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Molecules 2013, 18(6), 7309-7322; doi:10.3390/molecules18067309
Article

Monoterpenoid Indole Alkaloids from Alstonia rupestris with Cytotoxic, Anti-Inflammatory and Antifungal Activities

1,†, 2,† and 3,*
1 Department of Pharmacy, No. 455 Hospital of People's Liberation Army, Shanghai 200052, China 2 Department of Pharmacology, School of Pharmacy, Second Military Medical University, Shanghai 200433, China 3 Department of Pharmacy, No. 202 Hospital of People's Liberation Army, Shenyang 110003, Liaoning, China These authors contributed equally to this work.
* Author to whom correspondence should be addressed.
Received: 22 April 2013 / Revised: 3 June 2013 / Accepted: 9 June 2013 / Published: 21 June 2013
(This article belongs to the Section Metabolites)
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Abstract

Phytochemical investigation of the 70% EtOH extract of the leaves of Alstonia scholaris afforded seven new monoterpenoid indole alkaloids: scholarisins I-VII (1-7), and three known compounds: (3R,5S,7R,15R,16R,19E)-scholarisine F (8), 3-epi-dihydro- corymine (9), and (E)-16-formyl-5α-methoxystrictamine (10). Structural elucidation of all the compounds was accomplished by spectral methods such as 1D- and 2D-NMR, IR, UV, and HRESIMS. The isolated compounds were tested in vitro for cytotoxicity against seven tumor cell lines, anti-inflammatory activities against Cox-1 and Cox-2, and antifungal potential against five species of fungi. Compounds 1, 6, and 10 exhibited significant cytotoxicities against all the tested tumor cell lines with IC50 values of less than 30 μM and selective inhibition of Cox-2 comparable with the standard drug NS-398 (>90%). Additionally, 1, 2, 3 and 8 showed antifungal activity against two fungal strains (G. pulicaris and C. nicotianae).
Keywords: Alstonia rupestris; Apocynaceae; monoterpenoid indole alkaloids; cytotoxicity; anti-inflammatory; antifungal Alstonia rupestris; Apocynaceae; monoterpenoid indole alkaloids; cytotoxicity; anti-inflammatory; antifungal
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Wang, W.; Cheng, M.-H.; Wang, X.-H. Monoterpenoid Indole Alkaloids from Alstonia rupestris with Cytotoxic, Anti-Inflammatory and Antifungal Activities. Molecules 2013, 18, 7309-7322.

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