Minor Prenylated Flavonoids from the Twigs of Macarangaadenantha and Their Cytotoxic Activity.

Da-Song Yang,Wei-Bing Peng,Xiao-Li Li,Wei-Lie Xiao,Shuang-Mei Wang,Yong-Ping Yang,Ke-Chun Liu

doi:10.1007/s13659-015-0059-1

Abstract

Three new minor prenylated flavonoids, named macadenanthins A–C (1–3), together with three known ones (4–6), were isolated from the twigs of Macaranga adenantha. Their structures were elucidated on the basis of extensive spectroscopic analysis including NMR, UV and MS. The prenyl moieties in compounds 1–3 were further modified by cyclization and hydroxylation. The new compounds were tested for their cytotoxicity against four cancer cell lines (MCF-7, Hep G2, Hela and P388) and showed IC50 values in the range of 13.76–22.27 μM.Electronic supplementary materialThe online version of this article (doi:10.1007/s13659-015-0059-1) contains supplementary material, which is available to authorized users.

Highlights

Prenylated flavonoids are attracting great attention from the scientific community due to their structural uniqueness andDa-Song Yang and Shuang-Mei Wang authors contributed to this work.Electronic supplementary material The online version of this article contains supplementary material, which is available to authorized users.W.-B
The new compounds were tested for their cytotoxicity against four cancer cell lines (MCF7, Hep G2, human cervical carcinoma (Hela) and P388) and showed IC50 values in the range of 13.76–22.27 lM
As part of our program to discover new anticancer prenylated aromatic products from the genus Macaranga [6–8], a phytochemical investigation on this plant led to the isolation and characterization of three minor new prenylated flavonoids, named macadenanthins A–C (1–3), along with three known ones, including glyasperin A (4) [9], broussoflavonol F (5) [10], and macarangin (6) [11]

Summary

Introduction

Electronic supplementary material The online version of this article (doi:10.1007/s13659-015-0059-1) contains supplementary material, which is available to authorized users. Macaranga adenantha Gagnep (Euphorbiaceae) is an arbor distributed in the tropical rainforests, previous studies showed that it contained triterpenoids, steroids and phenolic compounds [3–5]. As part of our program to discover new anticancer prenylated aromatic products from the genus Macaranga [6–8], a phytochemical investigation on this plant led to the isolation and characterization of three minor new prenylated flavonoids, named macadenanthins A–C (1–3), along with three known ones, including glyasperin A (4) [9], broussoflavonol F (5) [10], and macarangin (6) [11]. The new compounds 1–3 were evaluated for their cytotoxicity against a small panel of cancer cell lines. Described are the isolation, structure elucidation and cytotoxicity of these compounds (Fig. 1)

Results and Discussion

General Experimental Procedures

Extraction and Isolation

Cytotoxicity Bioassays