Biarylheptanoids and other constituents from wood of Alnus japonica

New Diarylheptanoids from Alnus japonica and Their Antioxidative Activity

“…Compounds 1 and 2 having a 3,4-dihydroxyphenyl and a 4-hydroxyphenyl moieties showed moderate activity, but 8 having two 4-hydroxyphenyl moieties and 14 having no free catechol structure showed no activity. Hirusutanonol glucoside (6) showed weak activity. These results indicated that the catechol structure was important for the potent anti-oxidative effect of biarrylheptanoids from A. japonica and the type of sugar moiety at C-5 was important for the activity.…”

“…Compounds isolated from Alnus plants include numerous diarylheptanoids along with triterpenoids. [6][7][8][9][10] Many kinds of diarylheptanoids have also been isolated from Zingiberaceae [11][12][13] and Betulaceae plants, including some which showed inhibitiory activity toward cyclooxygenase-2, 14) and antiemetic activity. 15) Curcumin, one of the best known diarylheptanoids, has various biological properties including anticancer, 16) antiinflammatory 17) and antioxidative activities.…”

Anti-inflammatory activities, triterpenoids, and diarylheptanoids ofAlnus acuminatassp.arguta

“…The isolated compounds are as follows: taraxeryl acetate (1) (Matsunaga et al, 1988), 14-taraxeren-3-one (2) (Valente et al, 2004), 3β-acetoxy-olean-12-ene-28-al (3) (Kim et al, 2004;Chen et al, 2006), 3β-hydroxy-14-taraxerene (4) (Zou et al, 2006;Jutiviboonsuk et al, 2007), 3β-hydroxy-lup-20(29)-ene (5) (Uddin & Ur-Rahman, 1994;Ragasa et al, 2005), 3β-hydroxy-lup-20(29)-ene-28-al (6) (Pohjala et al, 2009), 3β,28-dihydroxy-lup-20(29)ene (7) (Pohjala et al, 2009), β-sitosterol (8), β-sitosteryl glycoside (9) (Della Greca et al, 1991), (−) -centrolobol (10) (Craveiro 1970;Nagai et al, 1986;Alegrio et al, 1989;Park et al, 2010), 1,7-bis(4-hydroxyphenyl)-4-hepten-3-one (11) (Nomura et al, 1981;Fuchino et al, 1996), 1,7-di-(3′,4′-dihydroxyphenyl)-4-hepten-3-one (12) (Kuroyanagi et al, 2005), hirsutanonol (13) (Ohta et al, 1984), and hirsutanonol 5-O-β-d-glucopyranoside (14) (Ohta et al, 1984).…”

“…Triterpenoids 1, 7, and sterol 9 have been previously isolated from other species of the genus Alnus (Harborne, 1985;Duke, 1992;Máñez et al, 1997;Huguet et al, 2000;Chen et al, 2006), as well as diarylheptanoids 11-14 (Nomura et al, 1981;Chen et al, 2000;Park et al, 2010;Tung et al, 2010). Akihisa et al (2006) demonstrated that (−)-centrolobol (10) possesses marked anti-inflammatory activity against TPA-induced inflammation in mice and antitumor-promoting effect in two-stage carcinogenesis initiated by 7,12-dimethylbenz[a]anthracene.…”

Quantitative Analysis and Validation of Hirsutenone and Muricarpone B from Fermented Alnus sibirica

“…1 It was reported that Alnus species contain many phenolic constituents (concluding diarylheptanoids, 5 flavonoids, 6,7 and tannins [8][9][10][11] ) and triterpenoids [12][13] and it exhibits a variety of bioactivities including anti-oxidant activity, antiinflammation, 14 cytotoxicity, 15 and anti-adipogenic activity.…”