Thirty-seven flavonoids from flowers ofArnica longifolia

Skibiński, A; Merfort, Irmgard; Willuhn, G.

doi:10.1016/s0031-9422(00)89581-3

Cited by 8 publications

(3 citation statements)

References 12 publications

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“…The study by Merfort (1994) also included O-methylated flavonols (6-methoxykaempferol and 6-methoxyquercetin). This richness in flavonoid expression is also seen in A. longifolia from which Skibinski et al (1994) reported no less than 19 aglycones and 18 glycosides. 0-Glycosylation is common involving both glucosides and glucuronides of common flavonoids as well as of O-methylated flavonoids.…”

Section: Flavonoids Of Heliantheae Slmentioning

confidence: 61%

Flavonoids of the Sunflower Family (Asteraceae)

Bohm

Stuessy

2001

120

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This work is subject to copyright. All rights are reserved, whether the whole or part of the material is concerned, specifically those of translation, reprinting, re-use of illustrations, broadcasting, reproduction by photocopying machines or similar means, and storage in data banks. This book is dedicated to:Arthur Cronquist Outstanding plant systematist and major contributor to understanding taxonomic relationships within Asteraceae and Ralph E. Alston (1925Alston ( -1967) Visionary natural products chemist and geneticist who pioneered the use of chemical data in studies of plant systematics and evolution PrefaceCertainly many of the readers of this book will remember the early developments of chemosystematics in the late 1950s. We ourselves remember the excitement of these new data bearing on plant interrelationships. The hopes were high, the techniques were rapidly evolving, the quantities of data were large, and young workers were eagerly enthusiastic. Some even went so far as to predict that chemical data would soon replace morphological information as the basis for plant classification. These overly zealous predictions did not materialize, of course, as the history of plant systematics has amply shown during the past two centuries. If there is any distinct characteristic of systematics it is synthesis, as Lincoln Constance (1964) called it, the "unending synthesis." New tools generate new data and provide insights on additional dimensions of plant relationships. This will never change-we will continue to discover new tools and new data in the years ahead, and they will continue to be incorporated into the predictive general reference system of classification.The earlier efforts in chemosystematics focused on secondary plant products: alkaloids, betacyanins, carbohydrates, cyanogenic glycosides, glucosinolates, lipids, terpenoids, and especialiy flavonoids. The latter were particularly well suited for chemosystematic investigation for several reasons: ease of isolation and characterization, small amounts of plant material needed for analysis, stability of compounds especially through routine preparation of herbarium specimens, and low cost to obtain useful information. As a result of these considerable advantages, literally thousands of studies on use of flavonoids in plant systematics have been published. Although now with the present zest for macromolecular data from DNA restriction sites and sequences, there are fewer workers and laboratories dedicated to flavonoid chemosystematic studies; twenty years ago they were the new currency of exciting data in plant systematics.Because of many workers historically interested in the sunflower family, Asteraceae (or Compositae), in part due to its large size (approximately 23,000 species;Bremer, 1994), and because hundreds of flavonoid compounds were discovered in this family, many chemosystematic investigations have been completed on various taxa. Many studies came from the laboratories of R. A. Alston, B. L. Turner, and T. J. Mabry in the Department of Botany ...

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Section: Flavonoids Of Heliantheae Slmentioning

confidence: 61%

Flavonoids of the Sunflower Family (Asteraceae)

Bohm

Stuessy

2001

120

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“…Compounds 1-6, bearing a cyclopropane moiety, belong to a novel skeletal class that was first reported in 2004, when 7 and several analogues were found to be chemokine receptor 5 (CCR5) inhibitors. 12 The structures of the other known compounds isolated in the present study were identified by physical and spectroscopic measurements ([R] D , 1 H NMR, 13 C NMR, DEPT, 2D-NMR, and MS) and by comparing the data obtained with published values, as daucosterol, 13 ursolic acid, 14 2R-hydroxyursolic acid (maslinic acid), 14 5,3′-dihydroxy-3,7,4′trimethoxyflavone (ayanin), 15 3,5,3′-trihydroxy-7,4′-dimethoxyflavone (ombuin), 16 and 5,6,3′-trihydroxy-3,7,4′-trimethoxyflavone (8). 17 The development of cancer involves a wide spectrum of changes at the molecular level, which include, but are not limited to, sustained activation of proteasome and nuclear factor κB (NF-κB), as well as resistance to apoptosis.…”

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confidence: 99%

Bioactive 5,6-Dihydro-α-pyrone Derivatives from Hyptis brevipes

et al. 2009

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Six new 5,6-dihydro-α-pyrone derivatives (1-6), namely, brevipolides A-F, together with seven known compounds, including a 5,6-dihydro-α-pyrone derivative (7), three flavonoids, a steroid glycoside, and two triterpenoids, were isolated from the entire plant of Hyptis brevipes. Compounds 1-7 were assigned with the absolute configuration, 5R, 6S, 7S, and 9S, as elucidated by analysis of data obtained from their CD spectra and by Mosher ester reactions. Compounds 2, 6, and 7 exhibited ED 50 values of 6.1, 6.7 and 3.6 μM against MCF-7 cells, and compounds 1, 2, 6, and 8 (the known 5,6,3′-trihydroxy-3,7,4′-trimethoxyflavone) gave ED 50 values of 5.8, 6.1 7.5, and 3.6 μM against HT-29 cells, respectively. However, no significant cytotoxicity was found against Lu1 cells for any of the compounds isolated. When these compounds were subjected to evaluation in a panel of mechanism-based in vitro assays, compound 7 were found to be active in an enzyme-based ELISA NF-κB assay, with an ED 50 value of 15.3 μM. In a mitochondrial transmembrane potential assay, compounds 3, 7, and 8 showed ED 50 values of 8.5, 75, and 310 nM, respectively. However, no potent activity was found in a proteasome inhibition assay for any of the isolated compounds.The genus Hyptis (Lamiaceae) is composed of approximately 350-400 species in the form of small herbs to large bushes, which are distributed in the tropics and warmer temperate regions all over the world. Previous studies on the constituents of species of the genus Hyptis have revealed diterpenoids, 1,2 flavonoids, 3,4 lignans, 4,5 and α-pyrone derivatives. 6,7 Hyptis brevipes Piot. originated from tropical America but is now widely distributed in other tropical regions of the world as an alien invasive species. Biological studies on crude extracts of this plant have shown inhibitory activities against bacterial and fungal growth, as well as DNA intercalation activity. 8,9 There has been no previous report on the phytochemical evaluation of this plant to date.* To whom correspondence should be addressed. Tel: .edu. † Division of Medicinal Chemistry and Pharmacognosy, The Ohio State University. ‡ University of Illinois at Chicago. § Division of Pharmacy Practice and Administration, The Ohio State University. ⊥ Research Center for Indonesian Medicinal Plants, Tawangmangu, Indonesia. || Indonesian Institute of Science, Tangerang, Indonesia. ∇ Present address: College of Pharmacy, University of Hawaii-Hilo, Hilo, Hawaii 96720. Supporting Information Available: 1 H and 13 C NMR spectra of compounds 1 -6, DEPT and 2D NMR spectra including 1 H-1 H COSY, HSQC, HMBC, and NOESY of compound 1, as well as 1 H NMR spectra of R-and S-TPMA esters of compound 3. This material is available free-of-charge via the Internet at http://pubs.acs.org. As part of a collaborative, multi-disciplinary approach to the discovery of new naturally occurring anticancer drugs, 10,11 the entire plant of H. brevipes was selected for further investigation, following initial cytotoxicity screening using the MCF-7 human b...

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“…Most of the reports about the Arnica genus regard the chemistry, systematics (Willuhn et al, 1995), and identification of several biologically active chemical compounds such as helenalin, an anti-inflammatory sesquiterpene lactone (Malarz et al, 1993;Paßreiter et al, 1995;Lyß et al, 1997;Merfort et al, 1997), caffeoylquinic acids from flowers of A. montana and A. chamissonis (Merfort, 1992), flavonoid glycosides in A. longifolia subgenus chamissonis (Skibinski et al, 1994), and guaianolide glucosides from flowers of A. mollis (Merfort et al, 1996). Micropropagation protocols for A. montana described earlier were based on the use of cytokinin -auxin combinations (Zǎpârţan, 1996a).…”

Section: Resultsmentioning

confidence: 99%

Clonal propagation of Arnica montana L., a medicinal plant

Butiuc-Keul

Deliu

2001

In Vitro Cell.Dev.Biol.-Plant

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Micropropagation of Arnica montana L. using Murashige and Skoog (MS) medium supplemented with N 6 -[2-isopentenyl]adenine (2iP), zeatin and a-naphthaleneacetic acid (NAA) in different concentrations does not ensure the formation of a high number of regenerated plants; a maximum of 3.2 neoplantlets per explant were obtained. After 4 wk of culture on medium with zeatin (4.5 mM ) and NAA (5.3 mM ), plants were 3.06 cm in length. The following step was to improve the clonal propagation of this species. Micropropagation of Arnica montana L., initiated from nodal segments using semisolid media (4 g l 21 agar), was obtained. Explants were inoculated on MS medium supplemented with NAA (5.3 mM ), 2iP (5.0 mM ), maize extract (1.0 ml l 21 ), phloroglucinol (0.6 mM ) or adenine sulfate (0.2 mM ). Only 3 wk after the inoculation, plant multiplication as well as induction of roots were obtained, the optimal variant being that containing NAA (5.3 mM ), 2iP (5.0 mM ) and maize extract (1.0 ml l 21 ). Six weeks after the inoculation plants were transferred to Perlite, with 80% plant survival being obtained. By isoesterase pattern we concluded that we have obtained the clonal propagation of Arnica montana, because the pattern of several individuals belonging to different clones was the same. Only one region with esterase activity that is present in all individuals has been identified.

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Thirty-seven flavonoids from flowers ofArnica longifolia

Cited by 8 publications

References 12 publications

Flavonoids of the Sunflower Family (Asteraceae)

Flavonoids of the Sunflower Family (Asteraceae)

Bioactive 5,6-Dihydro-α-pyrone Derivatives from Hyptis brevipes

Clonal propagation of Arnica montana L., a medicinal plant

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