An unusual caffeic acid derived bicyclic [2.2.2] octane lignan and other constituents from Cordia rufescens

Vale, Ademir Evangelista do; David, Jorge; Santos, Edlene O. dos; David, Juceni P.; Silva, Lidercia C. R. C. e; Bahia, Marcus Vinicius; Brandão, Hugo Neves

doi:10.1016/j.phytochem.2011.09.019

Cited by 11 publications

(11 citation statements)

References 22 publications

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“…Monoterpenes Cordinol (85) C. latifolia [77] Leaves 2.6. Steroids b-Sitosterol C. cylindrostachya [75] C. myxa [112] C. obliqua [80,118,119] C. platythyrsa [121] C. rothii [83,84,93,121,122] C. rufescens [123] C. trichotoma [109] C. exaltata [92] C. salicifolia [124] Leaves Seed Root Stem bark, seed -Fruit, Leaves Stem wood Leaves Leaves b-Sitosterol 3-glucoside C. obliqua [80] Seed…”

Section: Abietane Diterpenesmentioning

confidence: 99%

“…exaltata [92] Bark Rufescenolide B (127) C. americana [97] Bark Rufescenolide C (128) C. americana [97] Bark Rufescenolide D (129) C. americana [97] Bark Yunnaneic acid I (130) C. americana [97] Bark Yunnaneic acid J (131) C. americana [97] Bark [61] Root bark Cordicilin (134) C. latifolia [77] Leaves Latifolicinin A (135) C. latifolia [98] Fruit Latifolicinin B (136) C. latifolia [98] Fruit Latifolicinin C (137) C. latifolia [98] Fruit Latifolicinin D (138) C. latifolia [98] Fruit 2.11. Phenolics 2-Hydroxy-3-(4-hydroxy-3-methoxyphenyl)-2-Me propionamide C. macleodii [128] Leaves and flower Methyl caffeate C. rufescens [123] Stem Methyl rosmarinate (139) C. dichotoma [101] C. rufescens [123] Leaves Stem Magnesium lithospermate (140) C. spinescens [135] Leaves Calcium rosmarinate (141) C. spinescens [135] Leaves Magnesium rosmarinate (142) C. spinescens [135] Leaves…”

Section: Abietane Diterpenesmentioning

confidence: 99%

“…Ferulic acid C. macleodii [128] Leaves and Flower Caffeic acid and C. macleodii [128] Leaves and Flower Chlorogenic acids C. macleodii [128] Leaves and Flower Rosmarinic acid (143) C. americana [99] C. dentate [100] C. dichotoma [101] C. latifolia [77] C. verbenacea [102] Leaves Flower Leaves Fruit Leaves 4-Methoxy-protocatechuic acid C. rufescens [123] Stem p-Hydroxybenzoic acid C. macleodii [128] Leaves and Flower p-Hydroxyphenyl lactic acid (144) C. macleodii [128] Leaves and Flower (2R)-(4-Hydroxyphenyl)lactic acid (145) C. rothii [93] Leaves (E)-7-(3,4-Dihydroxyphenyl)-7-propenoic acid (146) C. exaltata [92] Stem bark Methyl 2-hydroxy-3-(4 0 -hydroxy)-phenyl propionate (147) C. rothii [93] Leaves m-Methoxy-p-hydroxybenzaldehyde (148) C. exaltata [92] Stem bark Polyphenols Benzofuran III (149) C. goetzei [103] Stem bark Benzofuran IV (150) C. goetzei [103] Stem bark Cordigone (151) C. goetzei [103] Stem bark Cordigol (152) C. goetzei [103] Stem bark 2.12. Essential oil a-Pinene C. curassavica [211] C. cylindrostachya [136] C. verbenacea [137,138] Leaves Twigs and Leaves Flower, Leaves a-Humulene C. globosa [51] C. verbenacea [106,139] Leaves a-Cadinol C. trichotoma [62] Wood a-Muurolol C. trichotoma [62] Wood 6a-Hydroxygermacra-1(10) 4-diene C. chacoensis [140] b-Caryophyllene C. boissieri …”

Section: Phenolic Acidsmentioning

confidence: 99%

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Traditional uses, phytochemistry and pharmacology of the medicinal species of the genus Cordia (Boraginaceae)

Oza

Kulkarni

2017

Journal of Pharmacy and Pharmacology

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Objectives Cordia (family Boraginaceae) is a genus of deciduous flowering trees or shrubs comprising more than 300 species distributed widely in the tropical regions. The aim of this review was to provide exhaustive scientific information on traditional uses, phytochemistry and pharmacological activities of the 36 important species with medicinal value from the genus Cordia, to divulge prospects for further research on its therapeutic potential. Key findings Leaves, fruit, bark and seed of a majority of the species were found to possess abundant ethnomedicinal value, but leaves were found to be used most frequently to treat many ailments such as respiratory disorders, stomach pain, wound, inflammation, myalgia, cough, dysentery and diarrhoea. The phytochemical investigation of 36 species resulted in isolation of 293 chemical constituents from various chemical classes. The crude extracts, fractions, essential oils and pure compounds isolated from various Cordia species were reported to have a varied range of pharmacological activities. Summary Many of the traditional uses of the genus Cordia were supported by the results obtained from pharmacological studies performed using various extracts or pure compounds. More attention should be given to the biological evaluation using pure phytochemicals and to identify the mechanism of actions and exploring this genus for new drug discovery.

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Section: Abietane Diterpenesmentioning

confidence: 99%

Section: Abietane Diterpenesmentioning

confidence: 99%

Section: Phenolic Acidsmentioning

confidence: 99%

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Traditional uses, phytochemistry and pharmacology of the medicinal species of the genus Cordia (Boraginaceae)

Oza

Kulkarni

2017

Journal of Pharmacy and Pharmacology

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“…Cordia rufescens, commonly known as "old-growth" or "pigeon-bellied", is a small shrub in northeastern Brazil and, like other species of the Cordia genus, is used in folk medicine as an abortifacient, anti-inflammatory agent and in the treatment of dysmenorrhea and dyspesia 2 . Previous chemical studies of C. rufescens A.DC identified the presence of saponins, glycosylated steroids, lignan arylnaphthalene and polyphenols 3,4 . The objective of the present study is to isolate, purify, characterize and identify/ determine fixed chemical constituents of the aerial parts of Cordia rufescens A.DC.…”

Section: Introductionmentioning

confidence: 99%

Phytochemical research of <em>Cordia rufescens</em> A.DC

Trigueiro

Silva

Lins

et al. 2018

Proceedings of MOL2NET 2018, International Conference on Multidisciplinary Sciences, 4th Edition

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Cordia rufescens A. DC, a small shrub in northeastern Brazil is popularly referred to as "old-growth" or "pigeon-claw". This plant is used in folk medicine as abortive, antiinflammatory agent and in the treatment of dysmenorrhea and dyspesia (VALE et al., 2012). Thus, the need for a greater chemical and pharmacological knowledge of Cordia rufescens A.DC species was observed, necessitating a more in-depth study of the isolation and characterization of new compounds. The plant material (leaves) was collected in 2002 in the municipality of Cruz do Espírito Santo-PB and identified by Profa. Dr. Maria de Fátima Agra. The material was then oven dried with circulating air at an average temperature of 45 ° C, ground in a mechanical mill and subjected to steeping with 95% EtOH. The crude ethanolic extract (106.10 g) was dissolved in a methanol: water (7: 3 v / v) solution and partitioned with the following solvents: hexane, dichloromethane and ethyl acetate. An aliquot of the dichloromethane phase (7 g) was subjected to the chromatographic column (CC), using as a stationary phase silica gel, and as mobile phase hexane, ethyl acetate and methanol, with elution systems in increasing polarity order, obtaining 34 fractions. All fractions were submitted to analytical thin layer chromatography (ADCC) and analyzed and assembled according to their retention factors (Rfs) and after visualization in ultraviolet light. Fractions 2, 3 and 5 presented different retention factors and therefore were submitted to liquid chromatography of high efficiency in analytical scale, where fraction 5 was chosen to obtain a better resolution of the chromatogram in front of the others, being then submitted to the purification by HPLC on a semi-preparative scale that resulted in the identified substances 4-hydroxy-benzaldeído and ethyl 4-hydroxy-3,5-dimethoxycinnamate, reported for the first time in the species under study.

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“…All these facts led to the proposal of structure 1. A compound with a similar lactone core in which C-9 is a methyl ester, rufescenolide, was recently isolated from Cordia rufescens [8], and for that reason compound 1 was named rufescenolide B. The relative configuration of 1 was determined by the correlations observed in a phase-sensitive NOESY experiment (l " Fig.…”

mentioning

confidence: 99%

Antioxidant Neolignans from Cordia americana

et al. 2013

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Five new neolignans with a bicyclo[2.2.2]octene framework were isolated from an ethanolic extract of the bark of Cordia americana. The structures and relative configurations of the compounds were elucidated by a combination of spectroscopic methods. All the isolated compounds showed good antioxidant activities in the DPPH radical scavenging (0.5-100 µg/mL) and Ferric-reducing antioxidant power (FRAP, 1-100 µg/mL) assays. One of the compounds displayed mild fungistatic activity at 0.1 µmol/spot against Fusarium virguliforme while, at the same time, all compounds were inactive against several strains of Gram (+) and Gram (-) bacteria at all assayed concentrations (10-1,000 µg/mL).

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An unusual caffeic acid derived bicyclic [2.2.2] octane lignan and other constituents from Cordia rufescens

Cited by 11 publications

References 22 publications

Traditional uses, phytochemistry and pharmacology of the medicinal species of the genus Cordia (Boraginaceae)

Traditional uses, phytochemistry and pharmacology of the medicinal species of the genus Cordia (Boraginaceae)

Phytochemical research of <em>Cordia rufescens</em> A.DC

Antioxidant Neolignans from Cordia americana

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