Caeruleanone A, a Rotenoid with a New Arrangement of the D‑Ring 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 cyclopenta­[<i>b</i>]­benzopyran derivatives (<b>1</b>, <b>2</b>), two cyclopenta­[<i>b</i>]­benzofuran derivatives (<b>3</b>, <b>4</b>), three cycloartane triterpenoids (<b>5</b>–<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>–<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>–<b>7</b>, and the absolute configuration of the 9,10-diol unit of compound <b>8</b> was established by a dimolybdenum tetraacetate [Mo₂(AcO)₄] induced circular dichroism procedure. Seven known rocaglate derivatives (<b>9</b>–<b>15</b>) exhibited significant cytotoxicity against the HT-29 cell line, with rocaglaol (<b>9</b>) being the most potent (ED₅₀ 0.0007 μM). The new compounds <b>2</b>–<b>4</b> were also active against this cell line, with ED₅₀ values ranging from 0.46 to 4.7 μM. 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 A–K: Bioactive Modified Isoflavonoid Constituents of the Root Bark of Sphenostylis marginata ssp. erecta

Sphenostylisins A–C (<b>1</b>–<b>3</b>), three complex dimeric compounds representing two novel carbon skeletons, along with an additional eight new compounds, sphenostylisins D–K (<b>4</b>–<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>–<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>–<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 (IC₅₀ = 6 nM)