Isobyakangelicin Angelate; A Novel Furanocoumarin from<i>Peucedanum palustre</i>

Vuorela, Heikki; Erdelmeier, C. A. J.; Nyiredy, Sz.; Dallenbach-Tölke, K.; Anklin, Clemens; Hiltunen, R.; Sticher, Otto

doi:10.1055/s-2006-962542

Cited by 15 publications

(6 citation statements)

References 8 publications

(10 reference statements)

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“…For all the identified coumarins, a prominent protonated molecule ([ M +H] + ) was observed ( Table ). For oxypeucedanin hydrate , isobyakangelicin angelate , oxypeucedanin , and ostruthol , this is in accordance with published reports.…”

Section: Resultssupporting

confidence: 93%

“…It grows in moist inland environments, e.g ., on river banks or in moist forests . The plant contains a complex mixture of coumarin‐structured compounds, i.e ., simple coumarins, and linear and angular furano‐ and hydroxyisopropylfuranocoumarins as well as volatile oil . Coumarins are known to have several roles in the plant, especially in the defense against insects and plant pathogens, e.g ., , but they may also act as attractants to certain insect species .…”

Section: Introductionmentioning

confidence: 99%

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Profiling of Coumarins in Peucedanum palustre (L.) Moench Populations Growing in Finland

Yrjönen

Eeva

Kauppila

et al. 2016

Chemistry & Biodiversity

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The coumarin composition of Peucedanum palustre (L.) Moench populations growing in Finland was investigated. A total of 132 flowering P. palustre specimens from 43 locations in southern and central Finland were collected, divided into root, stem, leaf, and umbel samples, and analyzed by HPLC. HPLC coupled to high-resolution mass spectrometry was used to aid the identification of coumarins. A total of 13 coumarin-structured compounds were quantitatively analyzed from the samples. The coumarin profile of root samples was found to differ from the aerial plant parts. The main coumarins in roots were oxypeucedanin and columbianadin. In aerial parts, peulustrin isomers were the most abundant coumarin components. Umbels and leaves also contained a considerable amount of umbelliprenin, which was only found in traces in roots. Based on hierarchical cluster analysis of the coumarin profiles, some populations shared common characteristics. The most distinct property connecting certain populations was their high peulustrin content. Another notable common property between some populations was the high umbelliprenin content in aerial plant parts. Some populations were clustered together due to their low overall coumarin content.

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Section: Resultssupporting

confidence: 93%

Section: Introductionmentioning

confidence: 99%

Profiling of Coumarins in Peucedanum palustre (L.) Moench Populations Growing in Finland

Yrjönen

Eeva

Kauppila

et al. 2016

Chemistry & Biodiversity

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“…Columbianadin was isolated from the roots of P. palustre as described by Vuorela et al. (1) and the purity was 100 % when tested by TLC and HPLC. Both columbianadin and verapamil were dissolved in a vehicle containing polyethylene glycol 400 and ethanol (1: 2).…”

Section: Methodsmentioning

confidence: 99%

“…Columbianadin is a furanocoumarin isolated from Peucedanum palustre (L.) Moench (1). Columbianadin relaxes the contractions of aortic smooth muscle preparations when depolarized with high concentrations of K (2).…”

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confidence: 99%

The Furanocoumarin Columbianadin Inhibits Depolarization Induced Ca²⁺Uptake in Rat Pituitary GH₃Cells

Törnquist

Vuorela²

1990

Planta Med

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The 1H-NMR spectrum of 4 (Table 1) indicated a pentamethoxy derivative. The splitting of the aromatic proton signals clearly showed that the additional methoxy group was at C-7. The broadening of the signals in the spectra of 2-4 obviously is due to a hindered rotation of the 4,9'-bond. Compound 2 (4-[3-hydroxy-1,2-dimethoxy-9-xanthonylj-1 ,3-dihydroxy-4-methoxy-xanthone) we have named mazatlan one, Materials and Methods Instruments IR: Beckmann JR 4230; MS: Varian MAT 711, 70eV; 1H and 13C-NMR spectra: BrukerWM 400. The roots of Polygala nitida T.S. Brandegee, collected in the Huasteca Tamaulipeca, May, 1987, voucher No. 3643, deposited in Department of Botany, ITESM, were dried and extracted as described (3). A portion (1 g) of the reddish extract (27 g) was separated by HPLC (

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“…In addition, the UV spectra of peaks 10 and 19 exhibited the typical absorption of coumarins. From the protonated molecules and fragment ion at 187, their structures were proposed as libanoridin and columbianadin [1,36,37]. The rest (peaks 1, 12, 16 and 17) were proposed as ferulic acid, 3 0 (R)-?-hamaudol, 3 0 -O-acetylhamaudol and osthol by comparing UV and MS spectral data with that of relevant literature reports [8,29].…”

Section: Lc-dad-esi-ms Analyses Of the Sample Solutionmentioning

confidence: 99%

Simultaneous Qualitative Analysis of Coumarins in the Rhizome of Angelica polymorpha Maxim. by LC–DAD–ESI–MS

Liu

Yu²,

et al. 2011

Chromatographia

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A novel method has been developed for simultaneous qualitative analysis of coumarins in the rhizome of Angelica polymorpha Maxim. with the use of high-performance liquid chromatography (LC)-photodiode array detection (DAD)-electrospray ionization (ESI)-tandem mass spectrometry (MS). LC analysis was performed on an Agilent Eclipse XDB-C 18 analytical column with a gradient solvent system of water and methanol, ultraviolet (UV) absorption detection was at 300 nm and peak UV spectrum and (?) ESI-MS data were acquired by DAD and a quadrupole mass spectrometer, respectively. Eight peaks were identified as linear furocoumarins including aviprin, isopimpinellin, bergapten, isooxypeucedanin, gosferol, imperatorin, phellopterin and isoimperatorin by comparing their retention time, UV, and MS spectra with that of the authentic standards, and the analysis of UV spectra and ESI-MS data of the standards gave the characteristics of UV absorption and ESI-MS fragmentation. On the basis of the above characteristics, the possible structures of four other linear furocoumarins were deduced in LC. The other chemical structures were proposed as three angular furocoumarins, a simple coumarin, two chromones, and a cinnamic acid by comparing their UV and MS data with that of literature reports. Accordingly, the method we established can simply and accurately identify the key chemical constituents in the rhizome of A. polymorpha.

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Isobyakangelicin Angelate; A Novel Furanocoumarin fromPeucedanum palustre

Cited by 15 publications

References 8 publications

Profiling of Coumarins in Peucedanum palustre (L.) Moench Populations Growing in Finland

Profiling of Coumarins in Peucedanum palustre (L.) Moench Populations Growing in Finland

The Furanocoumarin Columbianadin Inhibits Depolarization Induced Ca²⁺Uptake in Rat Pituitary GH₃Cells

Simultaneous Qualitative Analysis of Coumarins in the Rhizome of Angelica polymorpha Maxim. by LC–DAD–ESI–MS

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Isobyakangelicin Angelate; A Novel Furanocoumarin fromPeucedanum palustre

Cited by 15 publications

References 8 publications

Profiling of Coumarins in Peucedanum palustre (L.) Moench Populations Growing in Finland

Profiling of Coumarins in Peucedanum palustre (L.) Moench Populations Growing in Finland

The Furanocoumarin Columbianadin Inhibits Depolarization Induced Ca2+Uptake in Rat Pituitary GH3Cells

Simultaneous Qualitative Analysis of Coumarins in the Rhizome of Angelica polymorpha Maxim. by LC–DAD–ESI–MS

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The Furanocoumarin Columbianadin Inhibits Depolarization Induced Ca²⁺Uptake in Rat Pituitary GH₃Cells