Lignans fromArnicaspecies† ‡

Abstract

From four Arnica species (A. angustifolia Vahl ssp. attenuata (Greene) Maguire, A. lonchophylla Greene ssp. lonchophylla Maguire (flowerheads), A. chamissonis Less. ssp. foliosa (Nutt.) Maguire, A. montana L. (roots and rhizomes)) a total of twelve lignans of the furofuran-, dibenzylbutyrolactone- and dibenzylbutyrolactol-type were isolated. No report on lignans as constituents of Arnica species exists so far. Besides the known pinoresinol, epipinoresinol, phillygenin, matairesinol, nortrachelogenin and nortracheloside, six dibenzylbutyrolactol derivatives with different stereochemistry and substitution at C-9 were isolated and their structures elucidated by NMR spectroscopic and mass spectral analysis.

Sesquiterpenoids and Lignans from the Roots of <i>Syringa pinnatifolia</i>

“…All the above data suggested 1 was a sesquiterpenoid. Comparison of the 13 C-NMR data of 1 with those of the known compound (3R,4aS,8aR)-3,4,4a,8a-tetrahydro-6-hydroxy-5,8a-dimethyl-3-(1-methylethenyl)-1,7-naphthalenedione 10) displayed that most of the 13 C-NMR signals of the two compounds were almost same, except the signals at δ C 54.4 (C-8a), 32.0 (C-8), 27.1 (C-12) and 10.8 (C-13) in 1 had a few differences from the signals of δ C 49.7, 29.3, 24.4, 13.9 in the compared compound, suggesting that C-8a, C-8, C-12 and C-13 did not have the same chemical environment as the compared compound. The H correlation spectroscopy (COSY) cross-peaks of H-8a (δ H 2.66)/H-8 (δ H 3.01), H-3 (δ H 1.60)/H-2 (δ H 2.29) and H-4 (δ H 2.21), and the heteronuclear multiple bond connectivity (HMBC) correlations from H-12 (δ H 1.36) to C-8a (δ C 54.4), C-4a (δ C 42.9), C-4 (δ C 42.1) and C-5 (δ C 129.6), indicated that a methyl (C-12) was connected to C-4a.…”

“…[11][12][13][14][15] Oxidant stress plays an important role in the pathogenesis of many cardiovascular diseases (CVDs), and the use of antioxidant supplements is very benefit to the prevention of coronary artery diseases. 16) Due to the bioactivity of S. pinnatifolia related to the cardiovascular system, all the lignans isolated from this plant in our present studies were tested for their anti-oxidant activity.…”

Evaluation of the chemical composition of essential oils with respect to the maturity of flower heads of Arnica montana L. and Arnica chamissonis Less. cultivated for industry

“…This is an attractive plant species for the pharmaceutical industry, as it contains numerous pharmacologically active substances and is characterised by similarity of pharmacological effects to A. montana (Willuhn et al, 1983;Leven and Willuhn, 1987;Nichterlein, 1995). Moreover, A. chamissonis is a good source of bioactive compounds (Leven and Willuhn, 1987;Merfort and Wendisch, 1987;Roki et al, 2001;Schmidt et al, 2006;Gawlik-Dziki et al, 2009), a valuable source of herbal raw material and a pharmaceutical substitute for the endangered mountain arnica (Willuhn, 1998;Cassell et al, 1999;Sugier and Gawlik-Dziki, 2009;Gawlik-Dziki et al, 2011). A. chamissonis extracts exhibit potent antiinflammatory and antiradical activity and possesses high antioxidant abilities that might be helpful in preventing or slowing the progress of free radical-dependent diseases (Cassell et al, 1999;Gawlik-Dziki et al, 2009).…”

Influence of carbon sources on growth and GC-MS basedmetabolite profiling of Arnica montana L. hairy roots

“…Its pharmacological value is due to the presence of sesquiterpene lactones, flavonoids, essential oils, and other active compounds in various parts of the plant. The roots contain essential oils, phenolic acids, oligosaccharides, lignans, etc (Willuhn, 1972a(Willuhn, , 1972bRossetti et al, 1984;Schmidt et al, 2006;Pljevljaušić et al, 2012). The chemical composition of hairy roots of A. montana obtained by genetic transformation of plant tissue with Agrobacterium rhizogenes is less studied.…”