Phenylpropanoid and iridoid glycosides from Pedicularis striata.

A new phenylpropanoid glycoside, pedicularioside A, and five known glycosides, acteoside, isoacteoside, decaffeoylacteoside, echinacoside and 8-acetylharpagide, were isolated from whole plants of Pedicularis striata. On the basis of spectral and chemical evidence, pedicularioside A was shown to be 1'-O-beta-D-(3,4-dihydroxy-beta-phenyl)-ethyl-4'-O-caffeoyl-beta-D -apiosyl-(1----3')-alpha-L-rhamnosyl-(1----6')-glucopyranosi de.     

Phenylpropanoid and iridoid glycosides from Pedicularis spicata.

One new phenylpropanoid glycoside, pedicularioside H, and five known glycosides, gardoside methyl ester, shanzhiside methyl ester, 5-deoxypulchelloside I, verbascoside and pedicularioside A, were isolated from whole plants of Pedicularis spicata. On the basis of the spectral data, chemical evidence and comparison with authentic samples, pedicularioside H was determined to be 1'-O-beta-D-(3-methoxy-4-hydroxy-beta-phenyl)-ethyl-4'-O-feruloyl- beta-D- apiosyl(1----3')-alpha-L-rhamnosyl-(1----6')-glucopyranoside .     

Phenylpropanoid glycosides from Marrubium alysson.

From the aerial parts of Marrubium alysson a new phenylpropanoid glycoside, alyssonoside, and five known glycosides, verbascoside (= acteoside), leucosceptoside A, martynoside, forsythoside B and leucosceptoside B were isolated. On the basis of spectral data, the structure of the new compound was elucidated as beta-(3,4-dihydroxyphenyl)ethyl-O-[alpha-L-rhamnopyranosyl-(1-->3)]-O- [beta-D-apiopyranosyl-(1-->6)]-4-O-feruloyl-beta-D-glucopyra noside.     

Phenylpropanoid glycosides from Smilax glabra

Five phenylpropanoid esters of sucrose glycosides, trivially named smiglasides A-E, were isolated from the rhizomes of Smilax glabra. Their structures were elucidated on the basis of spectroscopic studies.     

Sesquiterpenoids and iridoid glycosides from Valeriana fauriei.

A new guaiane sesquiterpenoid glycoside together with known sesquiterpenoids and iridoid glycosides have been isolated from the rhizomes and roots of Valeriana fauriei. The 13C NMR assignments of the isolated compounds are presented.     

Phenylpropanoid glycosides from Scrophularia ningpoensis

Three phenylpropanoid glycosides named ningposides A (3-O-acetyl-2-O-feruloyl-alpha-L-rhamnopyranose), B (4-O-acetyl-2-O-feruloyl-alpha-L-rhamnopyranose) and C (3-O-acetyl-2-O-p-hydroxycinnamoyl-alpha-L-rhamnopyranose) along with the known compounds sibirioside A, cistanoside D, angoroside C, acteoside, decaffeoylacteoside and cistanoside F were obtained from the roots of Scrophularia ningpoensis.     

Phenylpropanoid glycosides isolated from Scrophularia scopolii

A new phenylpropanoid glycoside, angoroside A, and a known glycoside, acteoside, were isolated from the roots of Scrophularia scopolii var. scopolii. On the basis of chemical and spectral evidence, angoroside A was shown to be 3,4-dihydroxy-β-phenylethoxy-O-α-l-arabinopyranosyl-(1 → 6)-α-l-rhamnopyranosyl-(1 → 3)-4-O-caffeoyl-β-d-glucopyranoside.     

Tetrahydroisoquinoline-monoterpene and iridoid glycosides from Alangium lamarckii

From the water soluble fraction of the dried fruits of Alangium lamrckii, four tetrahydroisoquinoline-monoterpene glycosides, 6-O-methyl-N-deacetylisoipecosidic acid, 7-O-methyl-N-deacetylisoipecosidic acid, 6,7-di-O-methyl-N-deacetylisoipecosidic acid and 6"-O-alpha-D-glucopyranosyl-6-O-methyl-N-deacetylisoipecosidic acid, and an iridoid glycoside, 6'-O-alpha-D-glucopyranosylloganic acid, were isolated, together with six known compounds. The structures of the previously unknown compounds were determined by spectroscopic and chemical means. The significance of these glucosides in the biogenesis of Alangium alkaloids is discussed; 6-O-methyl-N-deacetylisoipecosidic acid was also chemically converted into 10-O-demethylprotoemetine and dihydroisoalangine.     

Phenolic and iridoid glycosides from Strychnos axillaris

Five phenolic glycosides 1-5 and an iridoid glucoside 6 were isolated, together with 22 known compounds, from the dried barks and woods of Strychnosaxillaris. Their structures were determined by application of spectroscopic (NMR, MS) and chemical methodologies.     

Two iridoid glycosides from Campsidium valdivianum

Besides stansioside and plantarenaloside, the aerial parts of Campsidium valdivianum contain two new iridoid diglucosides, stansiosigenin 1-O-β-gentiobioside and plantarenalosigenin 1-O-β-gentiobioside.     

4'-deoxy iridoid glycosides from Centranthus longiflorus

The new iridoid glycosides, 4'-deoxykanokoside A and 4'-deoxykanokoside C, were isolated from the methanolic root extract of Centranthus longiflorus ssp. longiflorus. They were accompanied by the three known iridoid glycosides, kanokoside A, kanokoside C and valerosidatum, and two known phenylpropanoid glycosides, coniferin and isoconiferinoside. The structures were elucidated mainly by spectroscopic methods. The presence of 4-deoxy glucose as a part of plant glycosides is rather unusual. Cytotoxic effects of the isolated compounds were also investigated.     

New tetraacetylated iridoid glycosides from Sambucus ebulus L. leaves

Two new minor “Valeriana type” iridoid glycosides (1) and (2) along with 3 known flavonol glycosides [quercetin-3-O-β-glucopyranosyl-7-O-α-rhamnopyranoside (3), quercetin-3-O-β-glucopyranoside (4) and isorhamnetin-3-O-β-glucopyranoside (5)] were isolated from Sambucus ebulus L. leaves. Their structures were unambiguously elucidated by means of 1D- and 2D-NMR, and UPLC-TOF MS. Compound 2 is a rare representative of iridoid diglycosides, containing uncommon ribohexo-3-ulopyranosyl sugar moiety.     

Phenylpropanoid glycosides from the roots of Jasminum giraldii

As part of our ongoing research in medicinal herbs of Qinba Mountains in China, the plant Jasminum giraldii was chemically investigated. Four new phenylpropanoid glycosides, 9-O-(E-cinnamoyl)-coniferin (1), 6′-O-(E-cinnamoyl)-coniferin (2), 6′-O-(E-cinnamoyl)-syringin (3) and 2′-O-(E-cinnamoyl)-syringin (4), together with two known phenylpropanoid glucosides, coniferin (5) and ethylsyringin (6) were obtained from the roots of Jasminum girialdii. The structures of these compounds have been characterized according to spectral evidences and named on basis of their biosynthetic pathway. In addition, in vitro cytotoxic activities of these compounds were evaluated, however, none of these compounds showed cytotoxicity.     

Phenylpropanoid glycosides of Gnidia polycephala

Two phenylpropanoid glucosides, 2-O-beta-D-glucosyloxy-4-methoxybenzenepropanoic acid and its methyl ester, together with syringin and adicardin were isolated from the stem of Gnidia polycephala and characterized by physical and spectroscopic data.     

Ionone,iridoid and phenylethanoid glycosides from Ajuga salicifolia

From the aerial parts of Ajuga salicifolia (L.) Schreber, a new ionone glycoside (3beta-hydroxy-7,8-dihydro-4-oxo-beta-ionol-9-O-beta-D-glucopyranoside) was isolated, along with the known compounds, corchoionoside C, 8-O-acetylmioporoside, ajugol, harpagide, 8-O-acetylharpagide, lavandulifolioside and leonosides A and B. This is the first report of the occurrence of ionone glycosides and 8-O-acetylmioporoside in Ajuga species. Ajugol, lavandulifolioside, leonoside A and B were isolated for the first time from Ajuga salicifolia. The structures were elucidated by means of 1D-, 2D-NMR spectroscopy, and HR-MALDI mass spectrometry.     

Lignan, phenolic and iridoid glycosides from Stereospermum cylindricum

A lignan glycoside [(+)-cycloolivil 4'-O-beta-d-glucopyranoside], a phenolic glycoside [3,4-dimethoxyphenyl 1-O-beta-d-xylopyranosyl-(1-->6)-beta-d-glucopyranoside] and a iridoid glycoside (stereospermoside) were isolated from the leaves and branches of Stereospermum cylindricum, together with (+)-cycloolivil, (+)-cycloolivil 6-O-beta-d-glucopyranoside, (-)-olivil, (-)-olivil 4-O-beta-d-glucopyranoside, (-)-olivil 4'-O-beta-d-glucopyranoside, vanilloloside, decaffeoyl-verbascoside, isoverbascoside, 3,4,5-trimethoxyphenyl 1-O-beta-d-xylopyranosyl-(1-->6)-beta-d-glucopyranoside, ajugol, verminoside, and specioside. The structure elucidations were based on spectroscopic evidence.     

Anti-inflammatory iridoid glycosides from fruits of Cornus officinalis

Three undescribed iridoid glycosides, cyc(7β-O-6′)-morroniside (1), 6′-methyl succinate-7β-O-methylmorroniside (2), and 7β-O-methyl phenyllactate morroniside (3) were isolated from 50% ethanol extract of Cornus officinalis fruits. The structures of the isolated compounds were determined by HRESIMS, ¹D NMR, ²D NMR, UV and IR spectroscopic methods. Compounds 1-3 exhibited moderate anti-inflammatory activities in vivo in a CuSO₄-induced zebrafish inflammation model (when evaluated at 50 μM).     

Three iridoid glycosides from Viburnum furcatum

Three new bitter iridoid glycosides having an 8,10,11-oxygen substituted iridoid skeleton with an isovaleryl moiety at C-1, have been isolated from the ether and ethyl acetate soluble fractions of the leaves of Viburnum furcatum. Two of them had a glucose moiety at C-11 of the iridoid skeleton and a p-coumaroyl group linked to C-6 of the sugar, and they were found to be geometrical isomers about the double bond of the p-coumaroyl2 moiety. The third one was characterized as a alloside of the same aglycone.