Iridoid glucosides from Phlomis tuberosa L. and Phlomis herba-ventis L

A new iridoid glucoside, 5-desoxysesamoside, was isolated from Phlomis tuberosa L. (Lamiaceae) together with three known iridoid glucosides sesamoside, shanziside methyl ester and lamalbid. Lamiide was found in P. herba-ventis ssp. pungens in high concentrations.     

Lignan and megastigmane glycosides from Sauropus androgynus

A lignan diglycoside, (-)-isolariciresinol 3alpha-O-beta-apiofuranosyl-(1-->2)-O-beta-glucopyranoside, and a megastigmane glucoside, sauroposide, were isolated from the aerial part of Sauropus androgynus together with (+)-isolariciresinol 3alpha-O-beta-glucopyranoside, (-)-isolariciresinol 3alpha-O-beta-glucopyranoside, (+)-syringaresinol di-O-beta-glucopyranoside, guanosine and corchoionoside C. The structural elucidations were bases on analyses of physical and spectroscopic data.     

Iridoid glycosides from Penstemon confertus

Three ester iridoids of the valeriana type have been isolated from dried leaves of Penstemon confertus. Their structures were elucidated by ¹H     

Iridoid glycosides from Gmelina arborea

Three iridoid glycosides 6-O-(3'-O-benzoyl)-alpha-l-rhamnopyranosylcatalpol (1a), 6-O-(3'-O-trans-cinnamoyl)-alpha-l-rhamnopyranosylcatalpol (2a) and 6-O-(3'-O-cis-cinnamoyl)-alpha-l-rhamnopyranosylcatalpol (3a) were isolated from aerial parts of Gmelina arborea and structures were elucidated by spectral analysis. Additionally a known iridoid 6-O-(3', 4'-O-dibenzoyl)-alpha-l-rhamnopyranosylcatalpol (4) was also isolated and identified.     

Iridoid glycosides from Lonicera quinquelocularis

A new iridoid glycoside 6'-O-beta-apiofuranosylsweroside was isolated from the ethanolic extract of the roots of Lonicera quinquelocularis along with the known compounds loganin and sweroside.     

Iridoid glycosides from Gmelina philippensis

Six new iridoids, 6-O-alpha-L-(2"-O-, 3"-O-, 4"-O-tribenzoyl)rhamnopyranosylcatalpol, 6-O-alpha-L-(2"-O-, 3"-O-dibenzoyl, 4"-O-cis-p-coumaroyl)rhamnopyranosylcatalpol, 6-O-alpha-L-(2"-O-, 3"-O-dibenzoyl, 4"-O-trans-p-coumaroyl)rhamnopyranosylcatalpol, 6-O-alpha-L-(2"-O-benzoyl, 3"-O-trans-p-coumaroyl)rhamnopyranosylcatalpol, 6-O-alpha-L-(2"-O-, 3"-O-dibenzoyl)rhamnopyranosylcatalpol, and gmephiloside as well as five known monoacyl and diacyl rhamnopyranosylcatalpol derivatives were isolated from the aerial parts of Gmelina philippensis. Their structures were established by spectroscopic means. Additionally, the known iridoids catalpol, geniposidic acid, gardoside, and 8-epi-loganic acid were identified and quantified by GC and GC-MS. The taxonomic significance of rhamnopyranosylcatalpol derivatives and iridoid acids as chemical characters is discussed.     

Iridoid glycosides from Penstemon richardsonii

Five ester iridoids of the valeriana type have been isolated from dried leaves of Penstemon richardsonii. The structures have been elucidated by FAB MS ¹H NMR and ¹³C NMR spectroscopy and by enzymatic cleavage of the glycosidic linkages. Besides the known iridoids penstemide penstemide-aglucone 8-epi-valerosidatum and serrulatoside a new iridoid penstebioside (penst of an iridoid aglycone attached to cellobiose.     

Iridoid and bisiridoid glycosides from Globularia cordifolia

From the methanolic extract of the underground parts of Globularia cordifolia, a new iridoid glycoside, 5-hydroxydavisioside (1) and a new bisiridoid glycoside, globuloside C (2) were isolated along with six known iridoid glycosides, aucubin, melampyroside, monomelittoside, globularifolin, alpinoside and asperuloside. The structures of the isolates were established by 1D and 2D NMR spectroscopy in combination with IR, UV and MS analyses.     

Iridoid and phenolic glycosides from Wulfenia carinthiaca

Two new phenylpropanoid glycosides (2'-O-acetylplantamajoside and 2'-O, 6"-O-diacetylplantamajoside), a new iridoid glycoside (10-O-(cinnamoyl)-6'-O-(desacetylalpinosidyl)-catalpol), the two known iridoid glycosides globularin and isoscrophularioside, and the known phenylpropanoid glycoside platamajoside were isolated from the methanolic extract of the underground parts of Wulfenia carinthiaca. Structure elucidations were based on high-resolution mass spectrometry and extensive 1-D and 2-D NMR spectroscopy.     

Iridoid and phenolic glycosides from Morinda coreia

From the leaves and branches of Morinda coreia, six compounds [yopaaosides A-C, 10-O-acetylmonotropein, 6-O-acetylscandoside and 3,4,5-trimethoxyphenyl 1-O-beta-apiofuranosyl (1"-->6')-beta-glucopyranoside] have been isolated together with five known compounds. Structural elucidations were based on analyses of physical and spectroscopic data.     

Iridoid and phenylethanoid glycosides from Heterophragma sulfureum

An unusual iridoid diglycoside (specioside 6′-O-α-d-galactopyranoside) and a new phenylethanoid triglycoside (heterophragmoside) were isolated from the leaves and branches of Heterophragma sulfureum together with specioside, verminoside, 6-trans-feruloylcatapol, stereospermoside, (−)-lyoniresinol 3α-O-β-d-glucopyranoside, (+)-lyoniresinol 3α-O-β-d-glucopyranoside, (−)-5′-methoxyisolariciresinol 3α-O-β-d-glucopyranoside, (+)-5′-methoxyisolariciresinol 3α-O-β-d-glucopyranoside, and dehydroconiferyl 4-O-β-d-glucopyranoside. The structural elucidations were based on analyses of chemical and spectroscopic data.     

Iridoid glycosides and cucurbitacin glycoside from Neopicrorhiza scrophulariiflora

Three iridoid glycosides, picrorosides A (1), B (2) and C (3), and a cucurbitacin glycoside, scrophoside A (4), were isolated from the rhizomes of Neopicrorhiza scrophulariiflora (Scrophulariaceae), along with two known iridoid glycosides, picrosides I (5) and II (6), and three known cucurbitacin glycosides (7-9). Their structures were elucidated on the basis of both chemical and spectroscopic data.     

Iridoid glycosides from Galium verum

From the aerial parts of Galium verum in flower, asperuloside and V₁ iridoid were isolated. From the mother liquor obtained on recrystallizatio     

Phenylethanoid glycosides from Phlomis integrifolia Hub.-Mor

Two new phenylethanoid glycosides integrifoliosides A (2) and B (3), along with a known phenylethanoid glycoside alyssonoside (1) and a flavone glucoside chrysoeriol-7-O-beta-D-glucopyranoside (4) were isolated from the aerial parts of Phlomis integrifolia. The structures of the new compounds were identified as 3,4-dihydroxy-beta-phenylethoxy-O-beta-D-apiofuranosyl-(1 --> 4)-alpha-L-rhamnopyranosyl-(1 --> 3)-4-O-feruloyl-beta-D-glucopyranoside (2) and 3-hydroxy-4-methoxy-beta-phenylethoxy-O-beta-D-apiofuranosyl-(1 --> 4)-alpha-L-rhamnopyranosyl-(1 --> 3)-4-O-feruloyl-beta-D-glucopyranoside (3), on the basis of spectroscopic (UV, IR, 1D- and 2D-NMR, and HR-FABMS) methods.     

Flavonol glycosides of Phlomis spectabilis

Four flavonol glucosides, one new, have been isolated from a methanolic extract of Phlomis spectabilis. Their structures were established as the 3-glucosides and 3-(6″-(E)-p-coumaroyl)glucosides of kaempferol and of kaempferol 7,4′-dimethyl ether.     

Iridoid glycosides and glycosidic constituents from Eriophyton wallichii Benth

C₉-iridoid glycosides, wallichiisides A–C (1–3), and four dimers, wallichiisides D–G (4–7), together with 13 known glycosidic compounds, were isolated from whole plants of Eriophyton wallichii Benth. Their structures were elucidated by spectroscopic methods and comparison with literature values. Four of these compounds showed moderate DPPH free radical scavenging activity.