np9b00631_si_001.pdf (2.02 MB)
Structurally Modified Cyclopenta[b]benzofuran Analogues Isolated from Aglaia perviridis
journal contribution
posted on 2019-10-17, 12:05 authored by Garima Agarwal, James R. Wilson, Steven J. Kurina, Gerardo D. Anaya-Eugenio, Tran N. Ninh, Joanna E. Burdette, Djaja D. Soejarto, Xiaolin Cheng, Esperanza J. Carcache de Blanco, L. Harinantenaina Rakotondraibe, A. Douglas KinghornFour 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 IC50 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.
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2.3 μ MStructurally Modified Cyclopentaprostate cancer cell linecompoundHTPCIC 50 valuesUV2 D NMRAglaia perviridisECD spectroscopic dataepisilvestrolcancer cell line cytotoxicitypotently cytotoxic chloroform subfractiondioxanyl ring-containing rocaglate analoguesbenzofuranIRchiral-phase HPLC columnHRESIMS
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