1,10-Secoguaianolides from Artemisia austro-yunnanensis and Their Anti-Inflammatory Effects

Abstract

Seven 1,10-secoguaianolides 1–7, including a new one (compound 1), were isolated from Artemisia austro-yunnanensis and identified by HRESIMS and other spectroscopic methods. Their anti-inflammatory effects were evaluated by the model of LPS-induced RAW264.7 cells in vitro. Bioassay results showed that six of them (1–4, 6 and 7), with the exception of 5, produce some cytotoxicity on RAW264.7 cells at its high dosage, can significantly decrease the release of NO, TNF-α, IL-1β, IL-6 and PGE2 in a dose dependent manner, and down-regulate the expression of proteins iNOS and COX-2. The mechanism study indicated they regulated the NF-κB dependent transcriptional activity through decreasing the phosphorylation of NF-κB. Further, the relationship between their structures and cytokines to anti-inflammatory were studied by PCA and discussed.

Interleukin-8 Release Inhibitors Generated by Fermentation of Artemisia princeps Pampanini Herb Extract With Lactobacillus plantarum SN13T

“…A previous report has shown that guaiane-type SQL have a wide range of pharmacological activities including anticancer, anti-inflammatory, antioxidant, and antibacterial effects (Liu et al, 2018). Artemisinin, which is a well-known antimalarial drug, is also classified into SQL and is in clinical trials as an anti-cancer drug (Ghantous et al, 2010).…”

“…Thus, SQL is important as a lead compound for drug discovery. Seco-tanapartholide C belongs to 1,10-seco-guaianolides which show anti-inflammatory effects due to the inhibition of the NF-κB signaling pathway (Makiyi et al, 2009;Liu et al, 2018). Joshi-Barve et al (2007) have reported that IL-8 expression is mediated by NF-κB in the in vitro NASH cell model.…”

Cytotoxic Sesquiterpenoids from Ammoides atlantica Aerial Parts

“…The remaining isolated compounds were characterized as the sesquiterpenes epi -tanaphilin ( 8 ), 26 seco -tanapartholide B ( 9 ), 27 9α-acetoxyartecanin ( 10 ), 15 apressin ( 11 ), 28 3α-chloro-9α-acetoxy-4β,10α-dihydroxy-1β,2β-epoxy-5α,7αH-guai-11(13)-en-12,6α-olide ( 12 ), 15 and 1β,3β-dihydroxy-13-acetoxy-eudesma-4(15),7(11)-dien-12,6α-olide ( 13 ) 24 and the polymethylated flavonoids gossypetin 3,7,3′-trimethyl ether ( 14 ) 29 and tanetin ( 15 ), 30 by NMR and MS analysis and comparison of their data with those reported in the literature. Furthermore, the relative stereoassigment of seco -tanapartholide B ( 9 ) as 4 S* ,5 R* ,6 R* ,7 R* (2.12 and 0.17 for 13 C and 1 H MAE values, respectively) was suggested.…”

Sesquiterpenes from Myrrh and Their ICAM-1 Inhibitory Activity In Vitro

“…In the literature, other seco-guaianolides were previously described mostly in the genus Tanacetum and Artemisia . The majority of these compounds belong to the 1,10-seco-type [ 24 , 25 , 27 , 28 , 29 ], but also 4,5-seco-molecules do occur [ 26 , 30 ] whereas a 8,9 C-C cleavage has only once been reported for Curcuma wenyujin [ 31 ]. Thus, describing a peroxide in myrrh for the first time, we suggest the name myrrhanoperoxide.…”