Chemical Constituents from the Aerial Parts of Agastache rugosa and Their Inhibitory Activities on Prostaglandin E₂ Production in Lipopolysaccharide-Treated RAW 264.7 Macrophages

Abstract

A new flavone glucoside, acacetin-7-O-(3″-O-acetyl-6″-O-malonyl)-β-d-glucopyranoside (1), two new phenolic glucosides, (3R,7R)-tuberonic acid-12-O-[6′-O-(E)-feruloyl]-β-d-glucopyranoside (14) and salicylic acid-2-O-[6′-O-(E)-feruloyl]-β-d-glucopyranoside (15), and two new phenylpropanoid glucosides, chavicol-1-O-(6′-O-methylmalonyl)-β-d-glucopyranoside (17) and chavicol-1-O-(6′-O-acetyl)-β-d-glucopyranoside­(18), as well as 26 known compounds, 2–13, 16, and 19–31, were isolated from the aerial parts of Agastache rugose. The structures of the new compounds were established by spectroscopic/spectrometric methods such as HRESIMS, NMR, and ECD. The anti-inflammatory effect of the isolated compounds was evaluated by measuring their inhibitory activities on prostaglandin E2 (PGE2) in lipopolysaccharide (LPS)-treated RAW 264.7 macrophages. New compounds 1, 15, 17, and 18 inhibited LPS-induced PGE2 production with IC50 values of 16.8 ± 0.8, 33.9 ± 4.8, 14.3 ± 2.1, and 48.8 ± 4.4 μM, respectively. Compounds 5, 7, 9−11, 13, 19, 20, 22, and 27–30 showed potent inhibitory activities with IC50 values of 1.7–8.4 μM.

Pharmacological Effects of Agastache rugosa against Gastritis Using a Network Pharmacology Approach

“…Rosmarinic acid and five acacetin derivates were detected in 70% ethanolic extract of A. rugosa by using HPLC (Figure 2), and 14 flavonoids, including acacetin, diosmetin, and luteolin, were isolated in our laboratory previously [9]. The compounds identified in A. rugosa in this study are similar to those identified in previous studies and those deposited in ingredient databases.…”

“…The chemical components in A. rugosa were searched for using public databases in TM-MC: A database of medicinal materials and chemical compounds in Northeast Asian traditional medicine (http: //informatics.kiom.re.kr/compound/, updated 3 December 2018) and Korean Traditional Knowledge Portal (http://www.koreantk.com/ktkp2014/, updated 14 December 2019) [24]. Information of chemical components isolated previously from A. rugosa in our laboratory was also used for the study [9]. Through the above process, a total of 99 components derived from A. rugosa were identified (Supplementary Table S1).…”

Water Extract of Agastache rugosa Prevents Ovariectomy-Induced Bone Loss by Inhibiting Osteoclastogenesis

“…To clarify the biological properties of WEAR and the mechanisms underlying its benefits, we next investigated the phytochemical profile of WEAR. A. rugosa has been reported to contain essential oils and several types of compounds, such as phenylpropanoids, lignans, flavonoids, and terpenoids [ 7 , 8 ]. The typical UV (at 280 nm) base peak chromatograms and the extracted ion chromatogram for each WEAR analyte are shown in Figure 4 .…”

“…Seventeen reference standards with more than 98% were used to identify the phytochemicals in WEAR. Chlorogenic acid and neochlorogenic acid were purchased from ChemFace (Wuhan, China), and rosmarinic acid, citrusin C, nepetoidin B, diosmetin-7- O-β - d -glucopyranoside, tilianin, isoagastachoside, acacetin, apigetrin, phlorizin, luteolin, diosmetin, apigenin, acacetin-7- O -(6″- O -malonyl)-β- d -glucopyranoside, acacetin-7- O -(3″- O -acetyl)-β- d -glucopyranoside, and acacetin-7- O -(2″- O -acetyl-6″- O -malonyl)-β- d -glucopyranoside were isolated from A. rugosa as previously described [ 7 ]. The Dionex UltiMate 3000 system equipped with a Thermo Q-Exactive mass spectrometer (Thermo Fisher Scientific, San Jose, CA, USA) was used as in previously described methods [ 16 ].…”

“…Water extract of A. rugosa has traditionally been used to treat several symptoms, including vomiting, fever, headaches, diarrhea, and halitosis. Chemical studies have shown that the chemical composition of A. rugosa mainly includes flavonoids, terpenoids, and essential oils [ 7 , 8 ]. Previous studies reported that extracts of A. rugosa have various bioactivities, including anti-HIV integration, anti-inflammatory, anti-tumor, anti-fungal, anti-oxidant, and anti-atherogenic properties [ 9 , 10 ].…”