Open AccessStructurally Modified Cyclopenta[b]benzofuran Analogues Isolated from Aglaia perviridis
Author(s) -
Garima Agarwal,
James R. Wilson,
Steven J. Kurina,
Gerardo D. Anaya-Eugenio,
Tran Ngoc Ninh,
Joanna E. Burdette,
Djaja D. Soejarto,
Xiaolin Cheng,
Esperanza Carcache de Blanco,
L. Harinantenaina Rakotondraibe,
A. Douglas Kinghorn
Publication year - 2019
Publication title -
journal of natural products
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.976
H-Index - 139
eISSN - 1520-6025
pISSN - 0163-3864
DOI - 10.1021/acs.jnatprod.9b00631
Subject(s) - stereochemistry , benzofuran , chemistry , cytotoxicity , caprifoliaceae , biology , in vitro , biochemistry , botany
Four new cyclopenta[ b ]benzofuran derivatives based on an unprecedented carbon skeleton ( 1 - 4 ), with a dihydrofuran ring fused to dioxanyl and aryl rings, along with a new structural analogue ( 5 ) of 5‴-episilvestrol (episilvestrol, 7 ), were isolated from an aqueous extract of a large-scale re-collection of the roots of Aglaia perviridis collected in Vietnam. Compound 5 demonstrated mutarotation in solution due to the presence of a hydroxy group at C-2‴, leading to the isolation of a racemic mixture, despite being purified on a chiral-phase HPLC column. Silvestrol ( 6 ) and episilvestrol ( 7 ) were isolated from the most potently cytotoxic chloroform subfraction of the roots. All new structures were elucidated using 1D and 2D NMR, HRESIMS, IR, UV, and ECD spectroscopic data. Of the five newly isolated compounds, only compound 5 exhibited cytotoxic activity against a human colon cancer (HT-29) and human prostate cancer cell line (PC-3), with IC 50 values of 2.3 μM in both cases. The isolated compounds ( 1 - 5 ) double the number of dioxanyl ring-containing rocaglate analogues reported to date from Aglaia species and present additional information on the structural requirements for cancer cell line cytotoxicity within this compound class.