Artematrovirenins A–P, guaiane-type sesquiterpenoids with cytotoxicities against two hepatoma cell lines from Artemisia atrovirens

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

“…Artemisia, one of the dominant genus within Asteraceae family, contains nearly 380 species globally with 186 species being dispersed in China [9]. Many Artemisia plants, such as A. annua, A. argyi, A. capillaris, and A. scoparia, have been recorded for the treatment of malaria, inflammation, hepatitis, cancer in the traditional Chinese medicine system [9][10][11][12].…”

“…Artemisia, one of the dominant genus within Asteraceae family, contains nearly 380 species globally with 186 species being dispersed in China [9]. Many Artemisia plants, such as A. annua, A. argyi, A. capillaris, and A. scoparia, have been recorded for the treatment of malaria, inflammation, hepatitis, cancer in the traditional Chinese medicine system [9][10][11][12]. Phytochemical investigation revealed that Artemisia genus are rich in sesquiterpenoids with antimalarial, antiinflammatory, antitumor, cytotoxic, antibacterial, and antihelminthic activities [13].…”

“…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.…”

New Guaiane-Type Sesquiterpenoids Biscogniauxiaols A–G with Anti-Fungal and Anti-Inflammatory Activities from the Endophytic Fungus Biscogniauxia Petrensis

“…Guaiane-type sesquiterpenoids are typical bicyclic sesquiterpenes possessing a [5/7] fused ring skeleton, and [5/7/5], [5/6/5], [5/7/6], [5/5/7] tricyclic chemical scaffolds, [5/5/5/6], [5/5/6/5] tetracyclic systems and [5/5/6/5/5] pentacyclic system were afforded via oxidation and cyclization reactions [3][4][5]. These compounds usually exhibit potent bioactivities, including anti-fungal, anti-inflammatory, anticancer and multidrug resistance (MDR) reversal activities [6][7][8][9]. However, plants are the main source of guaiane-type sesquiterpenoids, such as Daphne genkwa, Pogostemon cablin, Xylopia vielana, Stellera chamaejasme, Artemisia zhongdianensis, Curcuma wenyujin [10][11][12][13][14][15], and there are few reports in microorganisms, which restricts the development and utilization of such active substances.…”

Design and synthesis of guaianolide‐germacranolide heterodimers as novel anticancer agents against hepatocellular carcinoma

“…However, the discovery and application of disesquiterpenoids were seriously restricted by their low content in plants and difficulty in total synthesis. Over the past years, our research group had discovered a series of sesquiterpenoid dimers from Artemisia eriopoda (He et al, 2023), Artemisia atrovirens (Su et al, 2020; Su et al, 2021; Su et al, 2021), Artemisia zhongdianensis (Dong et al, 2022), Artemisia dubia (Gao et al, 2022), and found that the guaianolide dimers lavandiolide H and artematrolides A, J, and K exhibited cytotoxicity equal to or superior to that of sorafenib against HepG2, SMMC‐7721, and Huh7 cell lines with IC 50 values from 3.8 to 9.6 μM by inducing G2/M cell cycle arrest and cell apoptosis. The semisynthesis of lavandiolides H, I, and K and artematrolide D from naturally abundant guaianolide arglabin via a biomimetic Diels−Alder reaction had been developed (Li et al, 2021).…”