Sesquiterpenoids from the Aerial Parts of Inula japonica

Abstract

Fourteen sesquiterpenoids with an eudesmane C-atom skeleton, including four new ones, (1b,5a,7b,8b,11b)-5-hydroperoxy-1-hydroxyeudesm-4(15)-eno-12,8-lactone (1), (1b,5a,7b,8b)-8-(acetyloxy)-5-hydroperoxy-1-hydroxycostic acid methyl ester (12), and a mixture of (1b,3b,4b,7b,8b)-1,3-dihydroxyeudesma-5,11(13)-dieno-12,8-lactone (7) and (1b,3b,4b,7b,8b,11b)-1,3-dihydroxyeudesm-5-eno-12,8-lactone (8), were isolated from the aerial parts of Inula japonica (Asteraceae). Their structures were determined by extensive spectroscopic methods, and those of 7 and 12 confirmed by means of single-crystal X-ray diffraction analysis.

DNA Topoisomerase Inhibitory Activity of Constituents from the Flowers of <i>Inula japonica</i>

“…Two new (1, 2) and twelve known compounds (3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14) were isolated by various chromatographic separations from the EtOAc extract of the flowers of I. japonica (Fig. 1) (Fig.…”

“…Structures of 3-14 were identified by comparison of 1 H-and C 13 -NMR, FAB-MS spectral data and optical rotation values with those previously reported to be budlein B (3), 23) 6β-hydroxytomentosin (4), 24) 6-deacetoxybritanin (5), 25) 4-epipulchellin (6), 26) britanin (7), 27) tomentosin (8), 28) (+)-dihydroquercetin (9), 29) (−)-syringaresinol (10), 30) quercetagetin 3,4′-dimethy ether (11), 31) luteolin (12), 32) britanin G (13) 33) and inuchinenolide C (14) 34) (see the Supplementary materials). These compounds (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14) were tested for inhibitory activities of DNA topoisomerases I and II (Fig. 5, Table 1).…”

“…1) Some terpenes [2][3][4][5][6][7] and flavonoids 8,9) have previously been isolated from this medicinal plant and have been reported to possess diverse biological activities, such as anti-diabetes, 10) antihypolipidemia, 11) hepatoprotective, 12) anti-inflammatory 7) and anti-tumor 1,2,13) effects. We have been isolating compounds that inhibited topoisomerases I and II from the source of medicinal plants.…”

IVSE, isolated from Inula japonica,suppresses LPS-induced NO production via NF-κB and MAPK inactivation in RAW264.7 cells

“…I. japonica has been used in traditional Chinese medicine for the treatment of cough, digestive disorders, and bronchitis [6]. We previously reported the inhibition of allergic reaction [20], attenuation of inflammatory response [4], and anti-asthmatic effect on murine model of asthma [26], by the flower extracts of I. japonica.…”

Semisynthesis, an Anti-Inflammatory Effect of Derivatives of 1β-Hydroxy Alantolactone from Inula britannica

“…1β-Hydroxy alantolactone ( 1 , a 6/6-fused bicyclic system, Figure 2 ), mainly isolated from the Inula genus ( Inula britannica , Inula japonica and Inula helenium ) plants [ 1 , 15 , 16 ], have shown anticancer and anti-inflammatory effects [ 1 , 17 ]. α-methylene-γ-butyrolactone has been considered as its active moiety.…”