Artatrovirenols A and B: Two Cagelike Sesquiterpenoids from Artemisia atrovirens

Abstract

Artatrovirenols A and B (1 and 2), two novel cagelike sesquiterpenoids, possess a unique 5/5/6/5/5-pentacyclic and a 5/5/6/5-tetracyclic system with an unprecedented tetracyclo[5.3.1.1. 4,11 0 1,5 ]dodecane scaffold from Artemisia atrovirens. The structures of compounds 1 and 2 including their absolute stereochemistry were elucidated through extensive spectroscopic analyses, X-ray crystallography, and quantum chemical calculations. Plausible biosynthetic pathways for the new isolates were proposed from the naturally occurring arglabin (3) via the key intramolecular Diels−Alder cycloaddition. Compound 1 showed cytotoxicity against three human hepatoma cell lines (HepG2, SMMC-7721, and Huh7) with half maximal inhibitory concentration values of 123.8, 44.0, and 142.6 μΜ, respectively.

Artemyrianosins A–J, cytotoxic germacrane-type sesquiterpene lactones from Artemisia myriantha

“…Our ongoing efforts to investigate bioactive sesquiterpenoids from the Artemisia plants, bioassay-guided isolation of A. atrovirens let to 26 guaiane dimers ([4 + 2] Diels-Alder cyclization) [18,19], six rotundane-guaiane dimers ([4 + 2] Diels-Alder cyclization or containing a methylene-bridge) [19,20], two guaiane-rotundane-guaiane trimers (containing a methylene-bridge) [20], two novel cagelike sesquiterpenoids (formed by intramolecular Diels-Alder cycloaddition) [21], and 16 undescribed guaiane sesquiterpenoids [9]. Among them, four guaianeguaiane dimers (lavandiolide H and artematrolides A, J, and K) possessed significant cytotoxicity against HepG2, SMMC-7721, and Huh7 cell lines with IC 50 values Fig.…”

Artemongolides A–F, undescribed sesquiterpenoid dimers from Artemisia mongolica and their antihepatic fibrosis activities

“…9,10 SDs are a characteristic group of components in Artemisia species. To date, 172 natural SDs have been reported from the genus Artemisia, 2,7,[11][12][13][14][15][16][17][18] of which only 13 seco-guaianolide dimers were found. 7,[16][17][18] However, farnesane-guaiane type dimers had never been obtained.…”

“…In our previous investigation on A. atrovirens, A. dubia, and A. zhongdianensis, we identified 73 novel SDs involving 67 guaianolide dimers, six rotundane-guaiane dimers and two guaiane-rotundane-guaiane trimers with a methylene-bridge, and two novel cage-like sesquiterpenoids via intramolecular Diels-Alder cycloaddition. 2,[10][11][12][13][14] Lavandiolide H showed sig-nificant antihepatoma activity with IC 50 values of 3.8 μM (HepG2), 4.6 μM (SMMC-7721), and 4.5 μM (Huh7). Further mechanism studies showed that lavandiolide H dose-dependently inhibited cell migration and invasion, and induced G2/M cell cycle arrest and cell apoptosis in HepG2 cells.…”

Enantioselective Total Synthesis of (−)-Artatrovirenol A

“…It has been recommended by the World Health Organization (WHO) as a frontline therapy for all cases of malaria. In 2020, Chen and co-workers isolated artatrovirenols A ( 3 ) and B ( 4 ) from Artemisia atrovirens . Compound 3 exhibits cytotoxicity against human hepatoma cell lines (HepG2, SMMC-7721, and Huh7), and its potential for preparing antihepatoma drug was patented .…”