Specioside: A New Iridoid Glycoside From Catalpa speciosa

El-Naggar, Sha'aban F.; Doskotch, Raymond W.

doi:10.1021/np50010a015

Cited by 49 publications

(26 citation statements)

References 4 publications

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“…In 13 C-NMR spectra of 3-8, 10, and 11, fifteen signals for catalpol were detected with similar chemical shift values (Table I. (3), amphicoside (6), catalposide (7), and verproside (10) by comparison of spectral data with published data in the literatures (El-Naggar and Beal, 1980;Sticher and Afifi-Yazar, 1979;Iwagawa et al, 1990;Gao et al, 2003;El-Naggar and Doskotch, 1980;Afifi-Yazar and Sticher, 1980). Phenylpropanoid moieties for compounds 4, 5, 8, and 11 were identified from their spectral data as isoferuloyl, trans-p-coumaroyl, cis-pcoumaroyl, and caffeoyl groups, respectively.…”

Section: Resultssupporting

confidence: 54%

Antioxidative iridoid glycosides and phenolic compounds from Veronica peregrina

et al. 2009

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Eight iridoid glycosides and four phenolic compounds were isolated from the EtOAc soluble fraction of Veronica peregrina MeOH extract as the radical scavengers for antioxidant activity. The compounds were identified as protocatechuic acid (1), luteolin (2), veronicoside (3), minecoside (4), specioside (5), amphicoside (6), catalposide (7), 6-O-cis-p-coumaroyl catalpol (8), p-hydroxy benzoic acid methyl ester (9), verproside (10), verminoside (11), and chrysoeriol 7-glucuronide (12) by spectroscopic analysis. All compounds except for 1 and 2 were isolated for the first time from this plant. The antioxidant activity was evaluated by the ORAC(Oxygen Radical Absorbance Capacity) assay, which measures scavenging activity against peroxy radicals induced by 2,2'-azobis (2-methoxypropion-amidine) dihydrochloride, and the ORAC value is expressed as relative trolox equivalent. Compounds 2, 4, 5, 6, 8, and 12 exhibited potent antioxidant activity, and compounds 1, 11 had similar activity with trolox, whereas the other compounds showed weaker activity than trolox.

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Section: Resultssupporting

confidence: 54%

Antioxidative iridoid glycosides and phenolic compounds from Veronica peregrina

et al. 2009

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“…The LC was coupled to a LCT of a TOF MS (Micromass, Manchester, UK) operated in the positive electrospray ion mode using 5-leucineenkephalin as lock mass. The known compounds isolated were identified by their NMR data: mannitol (21), (Bock and Pedersen, 1983); and iridoids (1-4, 6, 11) (Rønsted et al, 2000); erinoside (5) (Taskova et al, 2005); sinuatol (10; 6-O-rhamnopyranosylaucubin) ; verproside (12) (Afifi-Yazar and Sticher, 1980); specioside (13) (El-Naggar, and Doskotch, 1980); verminoside (14) and minecoside (15) (Sticher and Afifi-Yazar, 1979); 6-O-rhamnopyranosylcatalpol (16) (Helfrich and Rimpler;1999); scrophularioside (19) ; persicoside (22) (Harput et al, 2002); epiaucubin (Bianco et al, 1983);…”

Section: Generalmentioning

confidence: 99%

Unusual iridoid glycosides in Veronica sects. Hebe and Labiatoides

Jensen

Gotfredsen

Grayer

2008

Biochemical Systematics and Ecology

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In a chemosystematic investigation of three Southern hemisphere species of Veronica, derwentiana is unique, since 6-O-esters of aucubin rather than of catalpol dominate, however, the acyl groups are the same as those present in catalpol esters found in some other Veronica sections. V. catarractae also contains one of the catalpol esters characteristic of Veronica, but in addition three 6-O-rhamnopyranosyl substituted iridoid glycosides, one of which is 6-O-rhamnopyranosylcatalpol. Esters of the latter compound are previously only known from the more derived species in recent phylogenetic trees of sect. Hebe to which V. catarractae now also belongs, but as a more basal member.

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“…Evidence from other studies has suggested that iridoid glycosides might be important in feeding preferences of L.dispar. For example, El-Nagger & Doskotch (1980) isolated two iridoid glycosides, specioside and catalposide, from leaves of Catalpa speciosa Warder (Bignoniaceae), and suggested that t k s e compounds were responsible for an earlier finding ) that extracts of Cspeciosa were deterrent to gypsy moth larvae. Four other iridoid glycosides, aucubin, catalpol, loganin and asperuloside, significantly reduced growth of gypsy moth larvae when incorporated into artificial diets at levels of 0.2% , suggesting that iridoid glycosides reduced diet suitability.…”

Section: Introductionmentioning

confidence: 99%

Iridoid glycosides and insect feeding preferences: gypsy moths (Lymantria dispar, Lymantriidae) and buckeyes (Junonia coenia, Nymphalidae)

Bowers

Puttick

1989

Ecological Entomology

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ABSTRAm. 1. The effect of increasing concentrations of an iridoid glycoside; catalposide, was tested on a generalist and an adapted specialist lepidopteran, using artificial diets.2. Two strains of the gypsy moth, Lymantria dispar (L.) (Lymantriidae), were tested. Larvae of a wild strain showed. a negative dose-dependent response to increasing concentrations of catalposide (up to 7.2% dry weight), while a laboratory strain showed no such pattern. Choice tests using the laboratory strain showed that these larvae often preferred diets relatively low in catalposide over those with higher concentrations.3. In contrast, larvae of the iridoid glycoside specialist, the buckeye, Junonia coenia Hiibner (Nymphalidae), showed a positive dose-dependent response and grew better on diets with higher doses of catalposide. 4. We tested whether the improved growth of J.coenia at higher concentrations of catalposide may have been due to extra glucose yielded by hydrolysis of catalposide. Larvae were fed increasing doses of glucose equivalent to the amount potentially obtained by hydrolysing the quantities of catalposide used in the previous experiment. However, added glucose did not effect growth, suggesting that increased growth at higher catalposide concentrations was due to increased feeding rates.

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Specioside: A New Iridoid Glycoside From Catalpa speciosa

Cited by 49 publications

References 4 publications

Antioxidative iridoid glycosides and phenolic compounds from Veronica peregrina

Antioxidative iridoid glycosides and phenolic compounds from Veronica peregrina

Unusual iridoid glycosides in Veronica sects. Hebe and Labiatoides

Iridoid glycosides and insect feeding preferences: gypsy moths (Lymantria dispar, Lymantriidae) and buckeyes (Junonia coenia, Nymphalidae)

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