Artemlavanins A and B from Artemisia lavandulaefolia and Their Cytotoxicity Against Hepatic Stellate Cell Line LX2

Abstract

Two new sesquiterpenoids, artemlavanins A ( 1 ) and B ( 3 ), together with fifteen known compounds ( 2 and 4−17 ) were isolated from the EtOH extract of Artemisia lavandulaefolia . The structures of new compounds were elucidated by extensive spectroscopic analyses (HRESIMS, 1D and 2D NMR) and ECD calculations. Compound 1 was a sesquiterpenoid lactone possessing a rearranged eudesmane skeleton; compounds 2–5 , 6–8 , 9 and 10–12 belonged to the eudesmane, guaiane, oppositane and farnesane sesquiterpenoids, respectively; compounds 13–17 were the phenyl derivatives with a 4-hydroxyacetophenone moiety. Twelve compounds ( 1–3 , 5–7 , 10–12 , 14 , 15 and 17 ) displayed cytotoxicity against hepatic stellate cell line LX2 (HSC-LX2) with IC 50 values ranging from 35.1 to 370.3 μ M. Compounds 2 , 7 , 10–12 and 17 exhibited the stronger cytotoxicity than silybin (IC 50 , 169.6 μ M) with IC 50 values of 82.1, 35.1, 95.0, 83.8, 81.6 and 90.1 μ M. Compound 7 as the most active one showed significant inhibition on the deposition of human collagen type I (Col I), human hyaluronic acid (HA) and human laminin (HL) with IC 50 values of 10.7, 24.5 and 13.3 μ M. Graphic Abstract Electronic supplementary material The online version of this article (10.1007/s13659-020-00254-0) contains supplementary material, which is available to authorized users.

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

“…The cytotoxicity assay of compounds was conducted by referring to our previous papers. [30][31][32] Please see the ESI. †…”

“…The Col I, HA and HL secretion assay of compound 1 was performed with reference to our previous papers. [30][31][32] Please see the ESI. †…”

Biomimetic Synthesis of Lavandiolides H, I, and K and Artematrolide F via Diels–Alder Reaction

“…In particular, artematrolides A, J, and K and lavandiolide H showed cytotoxicity equal to or superior to that of sorafenib with IC 50 values ranging from 3.8 to 9.6 μM. Importantly, lavandiolide H could inhibit cell migration and invasion and induce G2/M cell cycle arrest and cell apoptosis in HepG2 cells. , Artematrolide A also exhibited significant inhibitory activity on HeLa S3 and SiHa cell lines via the ROS/ERK/mTOR pathway and a metabolic shift . Simultaneously, Ye et al reported the isolation of lavandiolides A–L from Artemisia lavandulifolia and suggested that lavandiolides A, C, G, and I showed potent inhibitory effects on NO production in LPS-stimulated macrophages with IC 50 values of 0.61, 1.64, 1.89, and 1.40 μM, respectively .…”

“…In our search for antiheptoma sesquiterpenoids from Artemisia species, , 25 guaianolide dimers, artematrolides A–R, lavandiolides A–C, H, and J, and artematrodimers A and B were isolated from Artemisia atrovirens . Biological assessment indicated these compounds possessed obvious cytotoxicity against HepG2, SMMC-7721, and Huh7 cell lines.…”

Design and synthesis of ludartin derivatives as potential anticancer agents against hepatocellular carcinoma

“…The synthesis of lavandiolides H, I, and K and artematrolide F via a biomimetic Diels−Alder reaction was accomplished in our laboratory [ 19 ]. Ludartin, a 6,12-guaianolide isolated from A. lavandulaefolia [ 20 ], exhibited moderate cytotoxicity against HepG2 and Huh7 cell lines with IC 50 values of 32.7 and 34.3 μM, respectively. Ludartin was first isolated from A. carruthii [ 21 ], which was also found in Stevia yaconensi [ 22 ] and other Artemisia species [ 23 – 25 ].…”