Flavonoids from Distemonanthus benthamianus Baillon. Methoxylated flavones and inter-relationships of benthamianin, a [2]benzopyrano[4,3-b][1]benzopyran

Malan, Elfranco; Roux, David G.

doi:10.1039/p19790002696

Cited by 36 publications

(12 citation statements)

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“…Further purification over Sephadex LH-20 using as MeOH/CH 2 Cl 2 /n-hexane (1 : 1 : 1) eluent yielded 1.2 g of ayanin as an amorphous solid, which was purified by crystallization from acetone/MeOH. Identification of ayanin was made by comparison of its m. p., 1 H-and 13 C-NMR spectra with previously published data [6], [7].…”

Section: Extraction and Isolationmentioning

confidence: 99%

“…1 H-and 13 C-NMR spectra were recorded on Bruker WP 200 SY (200.13 MHz) and Bruker 400 DRX (400 MHz) instruments using DMSO-d 6 and TMS as internal standards. Sephadex LH-20 (Fluka, 25 ± 100 mm) and silica gel 60 (Merck, 230 ± 400 mesh) were used for column chromatography; precoated silica gel plates (Merck, Kieselgel 60 F254, 0.25 mm) were used for TLC analysis.…”

Section: Extraction and Isolationmentioning

confidence: 99%

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Inhibitory Effect of N(G)-Nitro-L-arginine Methyl Ester on the Anti-Adrenergic Response Elicited by Ayanin in the Pithed Rat

Guerrero

Puebla²,

Martín³

et al. 2002

Planta med

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In this study we evaluated the anti-adrenergic response elicited by ayanin, a flavonoid compound isolated from Croton schiedeanus Schlecht, in the pithed rat, and the inhibitory effect of NO synthase inhibitor N(G)-nitro-L-arginine methyl ester (L-NAME), and its acute toxicity profile in mice. In pithed rats ayanin (5 - 50 mg/kg i. v.) caused a dose-dependent decrease in the pressor and chronotropic responses induced by intravenous noradrenaline administration (0.25 microg/kg). This anti-adrenergic response was completely abolished by prior treatment with L-NAME (10 mg/kg i.v ) and the inhibitory effect of L-NAME was reversed after intravenous administration of L-arginine (100 mg/kg, i. v.). No lethal or major toxic effects were observed in mice receiving i. p. administration of ayanin up to a dose of 500 mg/kg. Our findings confirm that ayanin exerts protective cardiovascular effects against the increase in blood pressure and heart rate mainly through a mechanism that depends on the NO/cyclic guanosine monophosphate (cGMP) pathway without acute toxic effects. These results suggest that extracts of Croton schiedeanus, the native south American plant from which ayanin was isolated, might be beneficial in cardiovascular disease.

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Section: Extraction and Isolationmentioning

confidence: 99%

Section: Extraction and Isolationmentioning

confidence: 99%

Inhibitory Effect of N(G)-Nitro-L-arginine Methyl Ester on the Anti-Adrenergic Response Elicited by Ayanin in the Pithed Rat

Guerrero

Puebla²,

Martín³

et al. 2002

Planta med

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“…The structural similarity of betuletol 3-methyl ether and 5,3'-dihydroxy-3,7,4'-trimethoxyflavone (4) obtained as the major product prompted us to prepare derivatives. Thus, typical acetylation gave acetyl derivatives 3'-acetoxy-5-hydroxy-3,7,4'-trimethoxyflavone (4a) [17] and 5,3'-diacetoxy-3,7,4'-trimethoxyflavone (4b) [18]. The methylation of 4 with CH 2 N 2 yielded 5-hydroxy-3,7,3',4'-tetramethoxyflavone (4c) [19], and the acetylation of the latter gave 5-acetoxy-3,7,3',4'-tetramethoxyflavone (4d) [19].…”

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confidence: 99%

Secondary Metabolites from Two Species of Pulicaria and Their Cytotoxic Activity

Triana

López

Pérez

et al. 2011

Chemistry & Biodiversity

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Two new compounds, the sesquiterpene (1E,5E)-8β-acetoxy-4α-hydroxy-7βH-germacra-1(10),5-dien-14-oic acid (2), and a nor-sesquiterpene, (5E)-8β-acetoxy-4α-hydroxy-7βH-germacr-5-en-10-one (3), were isolated from Pulicaria canariensis ssp. lanata, along with ten known compounds, including the flavonoid 5,3'-dihydroxy-3,7,4'-trimethoxyflavone (4). From Pulicaria burchardii, we isolated seven known compounds; the physical and spectroscopic data of the triterpenoid 3β-hydroxytaraxaster-20-en-30-al (1) are reported. The structures of compounds 1-3 were determined on the basis of HR-MS, and 1D- and 2D-NMR studies. The structure of 2 was corroborated by X-ray crystal diffraction. Cell viability experiments revealed that the semisynthetic flavonoid 4b was the most cytotoxic compound against human leukemia cells, and the cytotoxicity was caused by induction of apoptosis, as determined by microscopy of nuclear changes.

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“…In this paper we report the isolation and structure elucidation of six other clerodanes, two of them (1, 4) being new compounds. In addition, two known flavonoids, ayanin 6,7) and quercetin-3,7-dimethyl ether 8) were also obtained from this fraction. Structural elucidation was achieved by spectroscopic experiments and by comparison with other closely related compounds.…”

mentioning

confidence: 99%

“…The known compounds 2, 3, 5, 6 were determined to be (Ϫ)-12,16-dihydroxy-cis-cleroda-3,13-dien-15-oic acid-15,16-olide (2), 9) floridolide A (3), 10,11) haplopappic acid (5), 12) and (ϩ)-15-hydroxy-cis-cleroda-3,13-dien-18-oic-acid (6) 11) by comparison of physical data with literature values and from spectroscopic evidence. Compound 1 was isolated as colourless gum.…”

mentioning

confidence: 99%

New cis-Clerodane Diterpenoids from Croton schiedeanus

Puebla

Correa

Guerrero

et al. 2005

CHEMICAL & PHARMACEUTICAL BULLETIN

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Flavonoids from Distemonanthus benthamianus Baillon. Methoxylated flavones and inter-relationships of benthamianin, a [2]benzopyrano[4,3-b][1]benzopyran

Cited by 36 publications

References 1 publication

Inhibitory Effect of N(G)-Nitro-L-arginine Methyl Ester on the Anti-Adrenergic Response Elicited by Ayanin in the Pithed Rat

Inhibitory Effect of N(G)-Nitro-L-arginine Methyl Ester on the Anti-Adrenergic Response Elicited by Ayanin in the Pithed Rat

Secondary Metabolites from Two Species of Pulicaria and Their Cytotoxic Activity

New cis-Clerodane Diterpenoids from Croton schiedeanus

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