4 research outputs found
Caeruleanone A, a Rotenoid with a New Arrangement of the DâRing from the Fruits of <i>Millettia caerulea</i>
Caeruleanone A (<b>1</b>), a novel rotenoid with an unprecedented
arrangement of the D-ring, was isolated with another two new analogues,
caeruleanones B (<b>2</b>) and C (<b>3</b>), together
with 11 known rotenoids from the fruits of <i>Millettia caerulea</i>. The structures of the new compounds were determined by spectroscopic
data analysis, with that of <b>1</b> being confirmed by single-crystal
X-ray diffraction. Compounds <b>2</b> and <b>3</b> displayed
potent mitochondrial transmembrane potential inhibitory and quinone
reductase induction activities
Bioactive Flavaglines and Other Constituents Isolated from <i>Aglaia perviridis</i>
Eight new compounds, including two cyclopentaÂ[<i>b</i>]Âbenzopyran derivatives (<b>1</b>, <b>2</b>), two cyclopentaÂ[<i>b</i>]Âbenzofuran derivatives (<b>3</b>, <b>4</b>), three cycloartane triterpenoids (<b>5</b>â<b>7</b>), and an apocarotenoid (<b>8</b>), together with 16 known
compounds, were isolated from the chloroform-soluble partitions of
separate methanol extracts of a combination of the fruits, leaves,
and twigs and of the roots of <i>Aglaia perviridis</i> collected
in Vietnam. Isolation work was monitored using human colon cancer
cells (HT-29) and facilitated with an LC/MS dereplication procedure.
The structures of the new compounds (<b>1</b>â<b>8</b>) were determined on the basis of spectroscopic data interpretation.
The Mosher ester method was employed to determine the absolute configurations
of <b>5</b>â<b>7</b>, and the absolute configuration
of the 9,10-diol unit of compound <b>8</b> was established by
a dimolybdenum tetraacetate [Mo<sub>2</sub>(AcO)<sub>4</sub>] induced
circular dichroism procedure. Seven known rocaglate derivatives (<b>9</b>â<b>15</b>) exhibited significant cytotoxicity
against the HT-29 cell line, with rocaglaol (<b>9</b>) being
the most potent (ED<sub>50</sub> 0.0007 ΞM). The new compounds <b>2</b>â<b>4</b> were also active against this cell
line, with ED<sub>50</sub> values ranging from 0.46 to 4.7 ΞM.
The cytotoxic compounds were evaluated against a normal colon cell
line, CCD-112CoN. In addition, the new compound perviridicin B (<b>2</b>), three known rocaglate derivatives (<b>9</b>,<b> 11</b>, <b>12</b>), and a known sesquiterpene, 2-oxaisodauc-5-en-12-al
(<b>17</b>), showed significant NF-ΚB (p65) inhibitory
activity in an ELISA assay
Sphenostylisins AâK: Bioactive Modified Isoflavonoid Constituents of the Root Bark of Sphenostylis marginata ssp. erecta
Sphenostylisins
AâC (<b>1</b>â<b>3</b>), three complex dimeric
compounds representing two novel carbon
skeletons, along with an additional eight new compounds, sphenostylisins
DâK (<b>4</b>â<b>11</b>), were isolated
from the active chloroform-soluble extract of the root bark of Sphenostylis marginata ssp. erecta using a bioactivity-guided isolation approach. The structures were
elucidated by means of detailed spectroscopic analysis, including
NMR and HRESIMS analysis, and tandem MS fragmentation was utilized
to further support the structures of <b>1</b>â<b>3</b>. The absolute configuration of sphenostylisin C (<b>3</b>)
was established by electronic circular dichroism analysis. Plausible
biogenetic relationships between the modified isoflavonoids <b>1</b>â<b>11</b> are proposed, and a cyclization reaction
of <b>9</b> was conducted to support one of the biogenetic proposals
made. All of these pure isolates were evaluated against a panel of
in vitro bioassays, and among the results obtained, sphenostylisin
A (<b>1</b>) was found to be a very potent NF-ΚB inhibitor
(IC<sub>50</sub> = 6 nM)