Anti-HIV Macrocyclic Daphnane Orthoesters with an Unusual Macrocyclic Ring from <i>Edgeworthia chrysantha</i>

Edgeworthianins A–E (1–5) were isolated from Edgeworthia chrysantha as a class of macrocyclic daphnane orthoesters with an unusual macrocyclic ring formed from a C14 aliphatic chain. Their structures were elucidated by extensive physicochemical and spectroscopic analyses. Compounds 2, 4, and 5 exhibited potent anti-HIV activity against HIV-1 infection of MT4 cells with EC50 values of 29.3, 8.4, and 2.9 nM, respectively. These compounds broaden the findings of the structure–activity relationship of macrocyclic daphnane orthoesters for further anti-HIV drug development

Cytotoxic activity of two natural sesquiterpene lactones, isobutyroylplenolin and arnicolide D, on human colon cancer cell line HT-29

<div><p>In this study, we found that two sesquiterpene lactones, isobutyroylplenolin and arnicolide D, from <i>Centipeda minima</i> L. (Compositae) exerted stronger cytotoxic activity than cisplatin on the human colon carcinoma HT-29 cell line. Furthermore, the cytotoxicity of these two compounds on normal cells was weaker than that of cisplatin. Treatment with isobutyroylplenolin and arnicolide D increased the levels of intracellular reactive oxygen species and decreased the levels of nuclear factor-κB protein, resulting in cell cycle arrest in G1 phase and apoptosis. We also discuss the difference in structure and activity between these two compounds.</p></div

Isolation, Structural Elucidation, and Liquid Chromatography–Mass Spectrometry Analysis of Steroidal Glycosides from Polygonatum odoratum

The rhizomes of Polygonatum odoratum represent a traditional Chinese medicine and functional food. A phytochemical investigation resulted in the isolation of eight steroidal glycosides (<b>1</b>–<b>8</b>), including two new compounds, polygonatumosides F (<b>1</b>) and G (<b>2</b>). The structures were elucidated by spectroscopic data and chemical reactions. Compound <b>7</b> showed antiproliferation activity against human hepatocellular carcinoma cell line HepG2 (IC₅₀ of 3.2 μM). The chemical profile and contents of steroidal glycosides of P. odoratum rhizomes collected at different dates and geographical locations were also investigated, indicating that the rational harvest of P. odoratum in spring and autumn is preferable to obtain higher levels of steroidal glycosides. Compounds <b>1</b> and <b>7</b> showed the highest contents in all P. odoratum samples and have potential to serve as chemotaxonomic and chemical markers for quality control of this important plant material. 14-Hydroxylation may be a key step for the biosynthesis of compounds <b>1</b>–<b>7</b>

Phellilane L, Sesquiterpene Metabolite of <i>Phellinus linteus</i>: Isolation, Structure Elucidation, and Asymmetric Total Synthesis

A new cyclopropane-containing sesquiterpenoid, phellilane L (<b>1</b>), was isolated from the medicinal mushroom <i>Phellinus linteus</i> (“Meshimakobu” in Japanese), a member of the Hymenochaetaceae family and a well-known fungus that is widely used in East Asia. The planar structure of <b>1</b> was determined on the basis of spectroscopic analysis. The authors achieved the first total synthesis of <b>1</b>. Our protecting group-free synthesis features a highly stereoselective one-pot synthesis involving an intermolecular alkylation/cyclization/lactonization strategy for construction of the key cyclopropane-γ-lactone intermediate. Additionally, our synthesis determined the absolute configuration of phellilane L (<b>1</b>)

Isolation, Structure Determination, and Anti-HIV Evaluation of Tigliane-Type Diterpenes and Biflavonoid from <i>Stellera chamaejasme</i>

Five novel tigliane-type diterpenes, stelleracins A–E (<b>3</b>–<b>7</b>), a novel flavanone dimer, chamaeflavone A (<b>8</b>), and six known compounds were isolated from the roots of <i>Stellera chamaejasme</i>. Their structures were elucidated by extensive spectroscopic analyses. The isolated compounds were evaluated for anti-HIV activity in MT4 cells. New compounds <b>3</b>–<b>5</b> showed potent anti-HIV activity (EC₉₀ 0.00056–0.0068 μM) and relatively low or no cytotoxicity (IC₅₀ 4.4–17.2 μM). These new compounds represent promising new leads for development into anti-AIDS clinical trial candidates

Isolation, Structure Determination, and Anti-HIV Evaluation of Tigliane-Type Diterpenes and Biflavonoid from <i>Stellera chamaejasme</i>

Five novel tigliane-type diterpenes, stelleracins A–E (<b>3</b>–<b>7</b>), a novel flavanone dimer, chamaeflavone A (<b>8</b>), and six known compounds were isolated from the roots of <i>Stellera chamaejasme</i>. Their structures were elucidated by extensive spectroscopic analyses. The isolated compounds were evaluated for anti-HIV activity in MT4 cells. New compounds <b>3</b>–<b>5</b> showed potent anti-HIV activity (EC₉₀ 0.00056–0.0068 μM) and relatively low or no cytotoxicity (IC₅₀ 4.4–17.2 μM). These new compounds represent promising new leads for development into anti-AIDS clinical trial candidates