13C and1H NMR spectroscopy as a tool in the configurational analysis of iridoid glucosides

Damtoft, Søren; Rosendal, Søren; Jensen,; Nielsen, Bent

doi:10.1016/0031-9422(81)85275-2

Cited by 202 publications

(128 citation statements)

References 28 publications

Supporting

Mentioning

116

Contrasting

Unclassified

Order By: Relevance

“…9 According to the data in the literature, the chemical shift of C-9 at a relatively high field (δ 48.1) indicated that the glucosyl moiety at C-8 was α-oriented and the methyl group at C-8 was β-oriented.…”

Section: H-mentioning

confidence: 99%

Three New Iridoid Glucosides from the Roots of Patrinia scabra

Di¹,

Li²,

Zu³

et al. 2011

Bulletin of the Korean Chemical Society

View full text Add to dashboard Cite

To probe the chemical constituents of Patrinia scabra, we undertook the phytochemical investigation on its roots, which led to the isolation and elucidation of three new iridoid glucosides, scabroside A-C (1-3), along with three known iridoids, jatamanin J (4), isopatriscabroside I (5) and loganic acid (6) from the aqueous fraction of the ethanolic extract of the roots. The structures and relative configurations of the three new compounds were elucidated by spectroscopic methods including IR, UV, MS, 1D and 2D NMR experiments. Compound 3 was an unusual iridoid with an oxygen bridge connecting C-3 and C-8.

show abstract

Section: H-mentioning

confidence: 99%

Three New Iridoid Glucosides from the Roots of Patrinia scabra

Di¹,

Li²,

Zu³

et al. 2011

Bulletin of the Korean Chemical Society

View full text Add to dashboard Cite

show abstract

“…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

View full text Add to dashboard Cite

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...

show abstract

“…[11][12][13][14][15][16] The antifungal activity of compounds 1, 2, 6-10 against Cladosporium cladosporioides and C. sphaerospermum was evaluated by direct bioautography on a TLC plate. 17,18 Only compound 1 exhibited moderate activity (MIC of 100 μg), when compared with the standard nystatin (1.0 μg).…”

Section: Resultsmentioning

confidence: 99%

A new antifungal phenolic glycoside derivative, iridoids and lignans from Alibertia sessilis (vell.) k. schum. (Rubiaceae)

Silva¹,

Bolzani²,

Young³

et al. 2007

J. Braz. Chem. Soc.

View full text Add to dashboard Cite

Um novo derivado fenólico glucosilado antifúngico, 3,4,5-trimetoxifenil-1-O-β-D-(5-Osiringoila)-apiofuranosil-(1→6)-β-D-glicopiranosideo (1), juntamente com quatro iridóides conhecidos, ácido geniposídico (2), geniposídeo (3), 6α-hidroxigeniposideo (4) e 6β-hidroxigeniposideo (5); duas lignanas, ( (7); e dois ácidos fenólicos, ácidos clorogênico (8) e salicílico (9) e D-manitol (10), foram isolados do extrato etanólico dos galhos de Alibertia sessilis. As estruturas de 1 e dos compostos conhecidos foram determinadas por análise espectroscópica. Todos os compostos isolados foram avaliados quanto à atividade antifúngica frente aos dois fungos fitopatogênicos Cladosporium cladosporioides e C. sphaerospermum por bioautografia direta. (1), together with four known iridoids, geniposidic acid (2), geniposide (3), 6α-hydroxygeniposide (4) and 6β-hydroxygeniposide (5); two lignans, (+)-lyoniresinol-3α-O-β-D-glucopyranoside (6), (-)-lyoniresinol-3α-O-β-D-glucopyranoside (7); and two phenolic acids, chlorogenic (8) and salicylic acids (9) and D-manitol (10), were isolated from the ethanolic extract of the stems of Alibertia sessilis. Structures of 1 and of the known compounds were determined by spectroscopic analysis. All compounds isolated were evaluated for their antifungal activities against two phytopathogenic fungi strains Cladosporium cladosporioides and C. sphaerospermum by direct bioautography. A new antifungal phenolic glycoside, 3,4,5-trimethoxyphenyl-1-O-β-D-(5-O-syringoyl)-apiofuranosyl-(1→6)-β-D-glucopyranoside

show abstract

13C and1H NMR spectroscopy as a tool in the configurational analysis of iridoid glucosides

Cited by 202 publications

References 28 publications

Three New Iridoid Glucosides from the Roots of Patrinia scabra

Three New Iridoid Glucosides from the Roots of Patrinia scabra

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

A new antifungal phenolic glycoside derivative, iridoids and lignans from Alibertia sessilis (vell.) k. schum. (Rubiaceae)

Contact Info

Product

Resources

About