5,7-Bisdeoxycynanchoside, an iridoid glucoside from Macfadyena cynanchoides

Adriani, Claudio; Iavarone, Carlo; Trogolo, Corrado

doi:10.1016/0031-9422(82)80054-x

Cited by 16 publications

(29 citation statements)

References 2 publications

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“…5a), and two or three bond correlations observed in the HMBC (Fig. 5a) spectrum supported the carbon framework to be as shown as 2 and the 13 C NMR spectrum was indeed very similar to that published for bisdeoxycynanchoside (Adriani et al, 1982). The PSNOESY experiment showed that the hydroxy groups at the 5-and 8-positions are both on the b-face (Fig.…”

Section: Resultssupporting

confidence: 68%

Chlorine-containing iridoid and iridoid glucoside, and other glucosides from leaves of Myoporum bontioides

et al. 2008

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Section: Resultssupporting

confidence: 68%

Chlorine-containing iridoid and iridoid glucoside, and other glucosides from leaves of Myoporum bontioides

et al. 2008

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“…Iridoids in Bignonieae proved to be mainly C-4 carboxylated, the only exception being Macfadyena cynanchoides with decarboxylated iridoids (Poser et al, 2000). In addition leaf extracts of M.cynanchoides contain the iridoids macfadienoside (Bianco, et al, 1974) cynanchoside (Bonini, et al 1981), and 5, 7-bisdeoxycynanchoside (Adriani et al, 1982). Root extracts of M.unguis-cati were found to contain lapachol; quinovic acid; 3-(O-fucosyl) alcohol; β-amyrin and β-sitosterol (Joshi et al, 1985).…”

Section: Introductionmentioning

confidence: 99%

Flavonoids, anti-inflammatory activity and cytotoxicity of <i>Macfadyena unguis-cati</i> l.

Aboutabl¹,

Hashem²,

Sleem³

et al. 2008

Afr. J. Trad. Compl. Alt. Med.

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Ethyl acetate and ethanol extracts of unflowering aerial part of Macfadyena unguis-cati L.(Fam. Bignoniaceae) were found to be rich in phenolic compounds. From ethyl acetate extract,six flavonoids were identified, 8, methoxy, acacetin, 7-O glucoside; 6, methoxy apigenin 7-O glucoside; 4`-O methyl scutellarin, 6-O apiosyl galactoside; acacetin, 7-O glucosyl, 8-C rhamnosyl, 3-O-α arabinofuranoside; 4`-methyl, 6-methoxy kaempferol, 7-O, 8-C diglucoside and vicenin II were isolated, while 6, methoxy, acacetin 7-O glucoside; and quercitrin were isolated from ethanol extract. These compounds were characterized and identified by their physicochemical and spectral data. The crude ethanol extract exhibited significant anti-inflammatory activity (80.47%) and moderate cytotoxic activity against lung cell line.

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“…Pentacosanol (C25 alcohol) was a deterrent against Plutella xylostella larvae [11] and triacontanol (C30 alcohol) exhibited antifeedant activity against S. litura with an ED 50 of 5.42 µg/cm 2 [2,12]. Although many iridoid glycoside compounds have been isolated from D. cynanchoides [13,14] and iridoid glycosides have been reported as deterring consumption by generalist insect herbivores [15], we did not find iridoids to be among the most active antifeedant compounds. Compound 1 did show strong antifeedant activity, suggesting that D. cynanchoides mostly relies on 1 for its defense against herbivores.…”

Section: Choice Assay Against S Frugiperda and E Paenulatamentioning

confidence: 60%

Insecticidal Properties of a Highly Potent Wax Isolated from Dolichandra cynanchoides Cham

2016

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Bioassay-guided fractionation of an ethanolic extract of the aerial parts of Dolichandra cynanchoides Cham. (Bignoniaceae) led to the isolation of a natural wax with anti-insect activity against Spodoptera frugiperda (Noctuidae) and Epilachna paenulata (Coleptera). The compound was identified spectroscopically as an ester of a C27 fatty acid and a C25 alcohol, pentacosyl heptacosanoate (1). The effective doses of 1 for 50% feeding inhibition (ED 50 ) of S. frugiperda and E. paenulata were 0.82 and 8.53 µg/cm 2 , respectively, in a choice test, while azadirachtin showed ED 50 of 0.10 and 0.59 µg/cm 2 , respectively. In a no-choice test, both insects refused to feed on leaves treated with 1 at doses of 0.1 µg/cm 2 or greater inhibiting larval growth and dramatically reducing survival. The lethal doses 50 (LD 50 ) of 1 were 0.39 and 0.68 µg/cm 2 for S. frugiperda and E. paenulata, respectively. These results indicate that 1 has potential for development as botanical insecticides. Similar esters might be obtainable in large quantities as many edible crops produce wax esters that are discarded during food processing. Research on these materials could lead to the detection of similar waxes with insecticidal activity.

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5,7-Bisdeoxycynanchoside, an iridoid glucoside from Macfadyena cynanchoides

Cited by 16 publications

References 2 publications

Chlorine-containing iridoid and iridoid glucoside, and other glucosides from leaves of Myoporum bontioides

Chlorine-containing iridoid and iridoid glucoside, and other glucosides from leaves of Myoporum bontioides

Flavonoids, anti-inflammatory activity and cytotoxicity of <i>Macfadyena unguis-cati</i> l.

Insecticidal Properties of a Highly Potent Wax Isolated from Dolichandra cynanchoides Cham

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