Chemical Constituents of the Leaves of Campanula takesimana (Korean Bellflower) and Their Inhibitory Effects on LPS-induced PGE2 Production

Abstract

Campanula takesimana Nakai (Campanulaceae; Korean bellflower) is one of the endemic herbs of Korea. The plant has been used as traditional medicines for treating asthma, tonsillitis, and sore throat in Korea. A hot water extract of the leaves of C. takesimana exhibited a significant inhibitory effect on lipopolysaccharide (LPS)-stimulated prostaglandin E2 (PGE2) production. Repetitive chromatographic separation of the hot water extract led to the isolation of three new neolignan glucosides, campanulalignans A–C (1–3), with 15 known compounds (4–18). The structures of new compounds 1–3 were elucidated by analyzing nuclear magnetic resonance (NMR) spectroscopic data, along with high resolution quadrupole time of flight mass (HR-Q-TOF-MS) spectrometric data. Among the isolates, simplidin (7), 5-hydroxyconiferaldehyde (11), icariside F2 (12), benzyl-α-l-arabinopyranosyl-(1″→6′)-β-d-glucopyranoside (13), and kaempferol 3-O-β-d-apiosyl (1→2)-β-d-glucopyranoside (15) were isolated from the Campanulaceae family for the first time. The isolates (1, 2, and 4–18) were assessed for their anti-inflammatory effects on LPS-stimulated PGE2 production on RAW 264.7 cells. 7R,8S-Dihydrodehydrodiconiferyl alcohol (5), 3′,4-O-dimethylcedrusin 9-O-β-glucopyranoside (6), pinoresinol di-O-β-d-glucoside (8), ferulic acid (10), 5-hydroxyconiferaldehyde (11), and quercetin (18) showed significant inhibitory effects on LPS-stimulated PGE2 production.

Protective effects on ovalbumin‐induced mouse asthma models and qualitative and quantitative analysis of multiple compounds in Gerberae Piloselloidis Herba

“…The data of fragment ions was consistent with references previously reported [24]; therefore, peak 40 was preliminarily inferred to be apigenin 7-rutinoside reported in the family Asteraceae [25]. Based on the retention times and fragmentation pathways of authentic substances, peaks 35 [28]. Because of giving the same ions and molecular formula, compounds 12 and 14 should be isomers.…”

“…Peak 6 (4.01 min) gave [M‐H+HCOOH] – ion at m/z 337.11386 and the same fragment ions (179.05540) as peak 5 in negative ion mode, suggesting that peak 6 also was a polar compound containing sugar moieties. On the basis of quasi‐molecular ions [M‐H] – , [M+COOH] − and [M+NH 4 ] + at m/z 401.14499, 447.15051, and 420.18626, as well as fragment ions at m/z 269.10104 [M‐H‐C 5 H 8 O 4 ] – corresponded to the loss of C 5 H 8 O 4 (132 Da) from [M‐H] – , 161.04439 [M‐H‐C 5 H 8 O 4 ‐C 7 H 8 O] – coming from loss of C 5 H 8 O 4 (132 Da), and C 7 H 8 O (a phenethyl moiety) from [M‐H] – , and 295.10202 [M+H‐C 7 H 8 O] + , 259.08032 [M+H‐C 7 H 8 O‐2H 2 O] + , 133.04939 [M+H‐C 7 H 8 O‐Glc] + , and 115.03907 [M+H‐C 7 H 8 O‐Glc‐H 2 O] + derived from the loss of C 7 H 8 O, Glc and H 2 O, the peak 25 was tentatively identified as icariside F2 [35]. Similarly, compound 30 producing quasi‐molecular ions at m/z 741.26074 ([M‐H] – ), 787.26593 ([M+COOH] − ), 743.27344 ([M+H] + ), and 760.30121 ([M+NH 4 ] + ) at 12.25 min, gave birth to product ions corresponded to loss of Glc, CH 3 , and H 2 O from [M‐H] – or [M+H] + , including 579.20691 ([M‐H‐Glc] – ), 417.15503 ([M‐H‐2Glc] – ), 402.13159 ([M‐H‐2Glc‐CH 3 ] – ), 419.16916 ([M+H‐2Glc] + ), and 401.15887 ([M+H‐2Glc‐H 2 O] + ).…”

Chemical Characterization of Flowers and Leaf Extracts Obtained from Turnera subulata and Their Immunomodulatory Effect on LPS-Activated RAW 264.7 Macrophages

“…When overexpressed, these proinflammatory mediators can lead to cell and tissue damage, resulting in various physiological disorders related to inflammation [ 55 , 56 ]. Therefore, compounds that inhibit the production of proinflammatory mediators such as PGE-2 and NO can be candidates as anti-inflammatory drugs [ 57 ].…”

Anti-Inflammatory Effect of Liverwort (Marchantia polymorpha L.) and Racomitrium Moss (Racomitrium canescens (Hedw.) Brid.) Growing in Korea

“…In positive mode ionization, the mass data show a similar fragmentation profile with m/z at 543, 527, and 381, which is correlated to pinoresinol-di- O - β -D-glucopyranoside ( Figure 11 ) [ 40 ]. Pinoresinol-di- O - β -D-glucopyranoside exhibited remarkable inhibitory activity against the production of PGE 2 in LPS-induced RAW264.7 cells [ 41 ]. In methanol extract of liverwort, peak 9 shows m/z at 439, 331, and 226; this compound could be identified as marchantin G [ 42 ].…”