Iridoids—XXIII

Bianco, Armandodoriano; Guiso, Marcella; Iavarone, Carlo; Passacantilli, Pietro; Trogolo, Corrado

doi:10.1016/0040-4020(77)80032-x

Cited by 38 publications

(91 citation statements)

References 9 publications

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“…This plant was utilized for dyeing since it contains anthraquinone dyes (Usai, 2004). Other compounds such as pentacyclic triterpenes (Pukl & Umek, 1992), iridoid glucosides (Bianco, Guiso, Iavarone, Passacantilli, & Trogolo, 1978), and α-tocopherol (Cerrati, Mallet, Ucciani, Gamisans, & Gruber, 1992), have also been isolated from the leaves of R. peregrina.…”

Section: Introductionmentioning

confidence: 97%

Identification and quantification of anthocyanins in the berries of Pistacia lentiscus L., Phillyrea latifolia L. and Rubia peregrina L.

Longo

Scardino

Vasapollo

2007

Innovative Food Science & Emerging Technologies

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Section: Introductionmentioning

confidence: 97%

Identification and quantification of anthocyanins in the berries of Pistacia lentiscus L., Phillyrea latifolia L. and Rubia peregrina L.

Longo

Scardino

Vasapollo

2007

Innovative Food Science & Emerging Technologies

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“…This paper describes the structural elucidation and identification of two new iridoid glycosides (1, 2), isolated along with six known (3-8) and three artifact (9-11) iridoids from this plant. The known iridoid glycosides were identified as monotropein methyl ester (ϭgalioside, 3), [3][4][5] gardenoside (4), [4][5][6] deacetylasperulosidic acid methyl ester (5), [7][8][9] scandoside methyl ester (6), 9-11) geniposide (7) 6,12) and ixoroside (8), 13) respectively, by direct comparison with authentic samples and/or by comparison of various spectral and chemical data with those reported in the literature. Inouye et al reported the following biosynthetic sequences: 7→5→3 and 7→6→4, that is, 7 was a biosynthetic precursor of both 3 and 4.…”

mentioning

confidence: 99%

Studies on the Constituents of Gardenia Species. III. New Iridoid Glycosides from the Leaves of Gardenia jasminoides cv. fortuneana HARA

Machida

Takehara

Kobayashi

et al. 2003

CHEMICAL & PHARMACEUTICAL BULLETIN

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We have reported the isolation of 13 new terpenoids from Gardeniae Fructus [the fruit of Gardenia jasminoides ELLIS (Rubiaceae)], known as the Shan-zhi-zi (in Chinese) herbal drug, and it has been used for its antiphlogistic, diuretic, and cholagogue effects. 1,2) In the course of further studies on the constituents of Gardenia species, we have now examined the iridoid constituents from the leaves of G. jasminoides cv. fortuneana HARA. This plant does not bear medicinal fruit, and there is no report, so far as we know, on the constituents of this plant. This paper describes the structural elucidation and identification of two new iridoid glycosides (1, 2), isolated along with six known (3-8) and three artifact (9-11) iridoids from this plant. The known iridoid glycosides were identified as monotropein methyl ester (ϭgalioside, 3), [3][4][5] gardenoside (4), [4][5][6] deacetylasperulosidic acid methyl ester (5), [7][8][9] scandoside methyl ester (6), 9-11) geniposide (7) 6,12) and ixoroside (8), 13) respectively, by direct comparison with authentic samples and/or by comparison of various spectral and chemical data with those reported in the literature. Inouye et al. reported the following biosynthetic sequences: 7→5→3 and 7→6→4, that is, 7 was a biosynthetic precursor of both 3 and 4.14) To our knowledge, this is the first example of co-occurrence of 3 and 4 in Gardenia species.Compound 1 was obtained as an amorphous powder, [a] D Ϫ43.4°(MeOH). The molecular formula of 1, C 17 H 24 O 11 , was confirmed by high-resolution (HR)-FAB-MS. In the 1 Hand 13 C-NMR spectra of 1, signal patterns were similar to those of 6-deoxycatalpol, which also has a 7, 8-epoxide, 15) . From the above data, the structure of 1 was elucidated as shown in the chart and termed 7b,8b-epoxy-8a-dihydrogeniposide. Compound 1 was isolated from a natural source for the first time, although a partially acetylated derivative of 1 has been synthesized from 7.11) To our knowledge, this is the first report of an iridoid glycoside containing a 7,8-epoxide function from Gardenia species.Compound 2 .07 (1H, m)] in 2 was evidently coupled with H-9 (d H 2.72), which appeared as a double double doublet. The NOE difference experiment showed that irradiation at H-9 resulted in NOE enhancements at H-5 and H-8 (d H 3.07). There was also NOE enhancement between H-1 and H-10 B . Consequently, compound 2 was revealed to be the epimer at C-8 of apodantheroside, 16) and the structure of 2 was determined to be 8-epiapodantheroside.Compound 9 was obtained as an amorphous powder, [a] D Ϫ114.1°(MeOH). The molecular formula of 9, C 18 H 26 O 11 , was confirmed by HR-FAB-MS. The 1 H-and 13 C-NMR spectra of 9, exhibited signal patterns very similar to those of 3, except for the presence of signals due to a methoxyl group [d H 3.27 (3H, s), d C 51.8]. The 13 C-NMR signal at C-8 of 9 was shifted by ϩ6.3 ppm (d C 92.4) in comparison with that of 3, suggesting that the methoxyl group is located at the 8- Aoba-ku, Sendai, Miyagi 981-8558, Japan. Received May 21, 2003; acc...

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“…The phytochemical analysis of the EtOH extract of O. luteus allowed the isolation and the identification of a total of 13 iridoid compounds, namely melampyroside ( 1 ), bartsioside ( 2 ), aucubin ( 3 ), 6‐ O ‐glucosylaucubin ( 4 ), aucubigenin‐1‐ O ‐ β ‐cellobioside ( 5 ), agnuside ( 6 ), shanzhiside methyl ester ( 7 ), mussaenoside ( 8 ), 8‐ epi ‐loganin ( 9 ), 8‐ epi ‐loganic acid ( 10 ), adoxosidic acid ( 11 ), monotropein ( 12 ), and 6,7‐dihydromonotropein ( 13 ), together with two seco ‐iridoids, methyl oleoside ( 14 ) and methyl glucooleoside ( 15 ) ( Fig. ).…”

Section: Resultsmentioning

confidence: 99%

Chemical Traits of Hemiparasitism in Odontites luteus

Venditti

Frezza

Foddai

et al. 2017

Chemistry & Biodiversity

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The study of the monoterpene glycosides content of Odontites luteus has shown the presence of a total of fifteen iridoid glucosides. The presence of compounds 1 - 5 and 7 - 10 is perfectly on-line with both the biogenetic pathway for iridoids biosynthesis in Lamiales and the current botanical classification of the species. On the other side, the presence of compounds like agnuside (6), adoxosidic acid (11), monotropein (12), 6,7-dihydromonotropein (13), methyl oleoside (14) and methyl glucooleoside (15) is of high interest because, first of all, they have never been reported before in Lamiales. In second instance, the majority of the last compounds are formally derived from a different biogenetic pathway which involves deoxyloganic acid/loganin and led to the formation of decarboxylated iridoid showing the 8β-configuration. Furthermore, a second abnormality was found during our study and this regards compounds 14 and 15 which are seco-iriodids and thus not typical for this family. The presence of these unusual compounds, biogenetically not related to species belonging to Lamiales, is a clear evidence of the metabolites transfer from the hosts. In fact, the collection area is also populated by species belonging to Oleaceae and Ericaceae which could be the possible hosts since the biosynthesis of seco-iridoids and or iridoids related to deoxyloganic acid/loganin pathway, with the 8β-configuration, is well documented in these species.

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Iridoids—XXIII

Cited by 38 publications

References 9 publications

Identification and quantification of anthocyanins in the berries of Pistacia lentiscus L., Phillyrea latifolia L. and Rubia peregrina L.

Identification and quantification of anthocyanins in the berries of Pistacia lentiscus L., Phillyrea latifolia L. and Rubia peregrina L.

Studies on the Constituents of Gardenia Species. III. New Iridoid Glycosides from the Leaves of Gardenia jasminoides cv. fortuneana HARA

Chemical Traits of Hemiparasitism in Odontites luteus

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