Di-O-acyl derivatives of shikimic acid from Senecio nebrodensis

Barrero, Alejandro F.; Sánchez, Juan Francisco López; E.J.Alvarez-Manzaneda, R.; R., R. Alvarez-Manzaneda

doi:10.1016/0031-9422(88)80300-5

Cited by 8 publications

(2 citation statements)

References 7 publications

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“…A number of active compounds have been characterized from these plants: Eremophilanes (Zdero et al, 1989), sesquiterpenoids (Bohlmann and Ziesche, 1981), diterpenoids (Cheng et al, 1993), triterpenoids (Ruicker et al, 1999), pyrrolizidines (Bohlmann et al, 1986) and shikimic acid derivatives (Barrero et al, 1988) exhibiting a range of bioactivities including antimicrobial (Perez et al, 1999), cytotoxic (Loizzo et al, 2007), molluscidal (Grace and Khattab, 1998), gastroprotective (Hariprasath et al, 2012) and antibacterial (El-Shazly et al, 2002) properties.…”

Section: Introductionmentioning

confidence: 99%

In vitro propagation of Senecio candicans DC and comparative antioxidant properties of aqueous extracts of the in vivo plant and in vitro-derived callus

Lakshmanan

Raman

Pandian

et al. 2015

South African Journal of Botany

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a b s t r a c tSenecio candicans DC is an endemic sub-shrubby climber and the hot water extract of this plant is being used traditionally for the treatment of gastric ulcer. The first objective of the present study was to design a standardized protocol for in vitro regeneration of S. candicans from leaf explants and compare the antioxidant activities of aqueous extracts of in vitro calluses and in vivo leaves by three different methods. Callus was initiated on Murashige and Skoog's (MS) basal media supplemented with various concentrations (0.5 mg L −1 to 2.0 mg L −1 ) and combinations of auxins and cytokinins under dark incubation for 2 weeks. The percentage of callus induction (PCI) and the fresh weights were recorded after 28 days of culture. The fresh weights were again recorded after 4 weeks of sub-culture to determine the relative fresh weight growth (RFWG). The highest PCI of 87% and RFWG of 3.245 were obtained on an MS medium supplemented with 6-benzyl amino purine (BA) 2 mg L −1 and indole-3-acetic acid (IAA) 2 mg L −1 . The callus obtained after 28 days of culture were inoculated on MS medium supplemented with different growth regulators. The maximum average shoot length (4.28 ± 0.27 cm) and maximum percentage of shoot induction (81%) was observed on MS medium supplemented with BA (2.0 mg L −1 ) + IAA (1.0 mg L −1 ). The maximum root induction percentage (90%) from shoots was observed on half strength MS medium fortified with 3.0 mg L −1 α-naphthalene acetic acid (NAA) alone. The antioxidant activity of in vivo leaf was significantly high compared to the in vitro callus in all the three antioxidant assays. A linear correlation between antioxidant activity and the total phenolic content was observed. The current protocol for in vitro regeneration would pave the way for further research on the isolation of bioactive compounds including antioxidants by cell suspension culture.

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Section: Introductionmentioning

confidence: 99%

In vitro propagation of Senecio candicans DC and comparative antioxidant properties of aqueous extracts of the in vivo plant and in vitro-derived callus

Lakshmanan

Raman

Pandian

et al. 2015

South African Journal of Botany

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“…However, acylation of methyl shikimate ( 2 ) did not display regioselectivity with any of the enzymes tested. To our knowledge, regioselective enzymatic acylation of shikimic acid derivatives has not been described, although saturated and unsaturated esters (among them, cynnamoyl esters) of quinic and shikimic acids were shown to be plant metabolites, some of them with a broad spectrum of biological activities. In our research program directed toward the syntheses of quinic and shikimic acid derivatives, we describe here the regioselective enzymatic acylation of methyl shikimate and the influence of several parameters such as enzyme, solvent, temperature, and acyl chain length on the rate and regioselectivity.…”

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Regioselective Enzymatic Acylation of Methyl Shikimate. Influence of Acyl Chain Length and Solvent Polarity on Enzyme Specificity

et al. 2002

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Candida antarctica lipase A (CAL-A) selectively catalyzes the acylation at the secondary C-4 hydroxyl group of methyl shikimate (2), which possesses three secondary hydroxyl groups, the C-3 allylic one being chemically more reactive. The effect both of the acyl group of the acylating agents and of the solvent polarity has been studied. The selectivity of CAL-A is almost complete with acyl donors that possess short chains. However, when acyl donors have longer chains, better results are obtained by C. antarctica lipase B (CAL-B).

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Analysis of the essential oil of Senecio vernalis Waldst. & Kit. from Iran

Nori‐Shargh

Raftari

Deyhimi

2008

Flavour & Fragrance J

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The volatile constituents of the aerial parts of Senecio vernalis growing wild in Iran have been characterized by GC-FID and GC-MS. The oil was found to contain 13 components. Altogether, 10 compounds were identified from the aerial parts of this plant, collected during its flowering stage. The oil was rich in spathulenol (37.1%), 1,8-cineol (19.0%), m-cymene (16.6%). The other major constituents were isobicyclogermacrenal (15.2%) and α α α α α-phellandrene (3.4%).

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Di-O-acyl derivatives of shikimic acid from Senecio nebrodensis

Cited by 8 publications

References 7 publications

In vitro propagation of Senecio candicans DC and comparative antioxidant properties of aqueous extracts of the in vivo plant and in vitro-derived callus

In vitro propagation of Senecio candicans DC and comparative antioxidant properties of aqueous extracts of the in vivo plant and in vitro-derived callus

Regioselective Enzymatic Acylation of Methyl Shikimate. Influence of Acyl Chain Length and Solvent Polarity on Enzyme Specificity

Analysis of the essential oil of Senecio vernalis Waldst. & Kit. from Iran

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