Identification of a New Aromatic Geranyl Derivative in the Resinous Exudate of Heliotropium Filifolium (Boraginaceae)

Urzúa, Alejandro; Modak, Brenda; Torres, René

doi:10.4067/s0366-16442001000200011

Cited by 12 publications

(25 citation statements)

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“…In our study, we observed that tricetin demonstrated maximum DPPH scavenging activity because it has three hydroxyl groups in the B-ring of its structure. All the isolated flavonoids showed antioxidant activity because they have one to three hydroxyl groups in the B-ring of their structure (Urzúa et al 2001). It has also been proven that a higher number of hydroxyl groups exhibited stronger antioxidant activity but lack of them reduced the ability to scavenge free radicals (Moreira et al 2007).…”

Section: Discussionmentioning

confidence: 99%

Flavonoids from Heliotropium subulatum exudate and their evaluation for antioxidant, antineoplastic and cytotoxic activities II

2016

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The flavonoids are the largest group of phenolic compounds isolated from a wide range of higher plants. These compounds work as antimicrobials, anti-insect agents and protect plants from other types of biotic and abiotic stresses. Various researchers have suggested that flavonoids possessed antioxidant, antineoplastic and cytotoxic activities. The main objective of this study was to test dichloromethane fraction of resinous exudate of Heliotropium subulatum for their antioxidant, antineoplastic and cytotoxic activities, as well as to search new antioxidant and antineoplastic agents for pharmaceutical formulations. Five flavonoids were isolated from resinous exudate of this plant species and screened for their in vitro and in vivo antioxidant models (DPPH radical scavenging, reducing power, superoxide anion scavenging, metal chelating scavenging systems, catalase and lipid peroxidation), antineoplastic (Sarcoma 180), and cytotoxic (Chinese hamster V79 cells) activities. Tricetin demonstrated maximum antioxidant activity against both in vitro and in vivo experimental systems while galangin exhibited maximum inhibition (78.35%) at a dose of 10 lg/kg/day against Sarcoma 180. Similarly, it was found that galangin also showed highest activity (21.1 ± 0.15%) at a concentration of 70 lg/ml to Chinese hamster V79 cells. The observed results suggest that tricetin has a potential to scavenge free radicals in both in vitro and in vivo models while the galangin could be considered as antitumor and cytotoxic agent.

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Section: Discussionmentioning

confidence: 99%

Flavonoids from Heliotropium subulatum exudate and their evaluation for antioxidant, antineoplastic and cytotoxic activities II

2016

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“…The results showed that resin and their main component filifolinol inhibited the viral development at 10 µg/mL in 36% and 27% respectively. The other compounds did not show effect 25 .…”

Section: Percentaje Of Inhibitionmentioning

confidence: 93%

“…These compounds were purified from the resinous exudate of H. filifolium (Miers) Reiche (ST-2214 SSUC) as has been described 24,25 . The hemisynthetic compound, filifolinoic acid 3 ( Figure 1) was obtained by hydrolysis from compound 1 [24][25][26] . Fungitoxicity of H. filifolium extract and of the purified compounds was assessed using the radial growth test on malt-yeast extract agar 14 .…”

Section: Methodsmentioning

confidence: 99%

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In Vitro Sensitivity of Botrytis Cinérea to Resinous Exudates of Heliotropium Filifoliumand Geranyl Derivatives Compounds

Mendoza

Modak

Torres

et al. 2008

J. Chil. Chem. Soc.

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The activity of the extract of Heliotropium filifolium, of the natural compounds obtained from its resinous exudates, filifolinol and filifolinyl senecionate, and of the synthetic derivative of filifolinol, filifolinoic acid, on the mycelial growth of the phytopathogenic fungus Botrytis cinerea was analyzed in liquid and solid media. The extract of H. filifolium, filifolinol, and filifolinoic acid reduced mycelial growth of this fungus. The effect of these compounds was dose-dependant. The compound filifolinyl senecionate was inactive in all the tested conditions. The extract of H. filifolium and filifolinol retarded the germination of conidia of the fungus.

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“…The epicuticular components of these species are characterized by the presence of flavonoids and, in some cases, aromatic geranyl derivatives. Flavonoids and aromatic geranyl derivatives have been reported in: Heliotropium filifolium 2,3,4 , H. huascoense 5,6 , H. glutinosum 7 , H. taltalense 8 and H. sclerocarpum 9 and only flavonoids were found in: H. sinuatum 10,11 , H. chenopodiaceum 12 and H. megalantum 5 . We previously reported that Heliotropium stenophyllum Hook et Arn.,contains a mixture of : 2-geranyl-4-hydroxyphenyl acetate and the flavonoids: 5,7-dihydroxyflavanone (pinocembrin) (1) ( Figure 1); 5,7-dihydroxy-3-methoxyflavone (3-O-methylgalangin) (2) ( Figure 1); 5,7,4'-trihydroxyflavanone (naringenin); 5,4'-dihydroxy-7-methoxyflavanone (sakuranetin); 3,5,7-trhihydroxyflavanone (galangin); 3,7,4'-trihydroxy-5,3'-dimethoxyflavone (5,3'-di-O-methylquercetin); 4'-acetoxy-5-hydroxy-7-methoxyflavanone (4'-O-acetylsakuranetin) and 5,3',4'-trihydroxy-7-methoxyflavanone (7-O-methyleriodictyol), in which pinocembrin (1) and 3-O-methylgalangin (2) accounted for around 80% of the mixture of surface components and the other flavonoids and 2-geranyl-4-hydroxyphenyl acetate were only found in minute amounts 13,14 .…”

Section: Introductionmentioning

confidence: 99%

Seasonal Variation of the Flavonoids Pinocembrin and 3-O-Methylgalangin, in the Surface Component Mixture (Resinous Exudates and Waxy Coating) of Heliotropium Stenophyllum

Modak

Torres

Urzúa

2011

J. Chil. Chem. Soc.

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In this report we study the seasonal variation of the flavonoids pinocembrin and 3-O-methylgalangin in the surface component mixture (resinous exudate and waxy coating) of Heliotropium stenophyllum. The quantitative analysis of the flavonoids was performed using high-performance liquid chromatography of samples collected monthly over a whole year. The results showed an increase in the spring and summer yield of surface components and a decrease during the winter. Although the sum of pinocembrin and 3-O-methylgalangin did not follow a pattern related with hydric stress, UV radiation or high temperature during the year, a relationship between pinocembrin and 3-O-methylgalangin was found. On average during the months of September to August, excluding March, the amount of pinocembrin decreased wile the amount of 3-O-methylgalangin increased. The results suggest that the above compounds may play different ecophysiological functions during plant development and are consistent with the biosynthetic relationship between the two compounds.

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Identification of a New Aromatic Geranyl Derivative in the Resinous Exudate of Heliotropium Filifolium (Boraginaceae)

Cited by 12 publications

References 0 publications

Flavonoids from Heliotropium subulatum exudate and their evaluation for antioxidant, antineoplastic and cytotoxic activities II

Flavonoids from Heliotropium subulatum exudate and their evaluation for antioxidant, antineoplastic and cytotoxic activities II

In Vitro Sensitivity of Botrytis Cinérea to Resinous Exudates of Heliotropium Filifoliumand Geranyl Derivatives Compounds

Seasonal Variation of the Flavonoids Pinocembrin and 3-O-Methylgalangin, in the Surface Component Mixture (Resinous Exudates and Waxy Coating) of Heliotropium Stenophyllum

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