Iridoids from Viburnum betulifolium

Two iridoid glycosides have been isolated from Viburnum betulifolium. Viburnalloside, the major leaf glycoside, is composed of an iridoid aglucone acylated at C-1 with isovaleric acid and with a di-O-acetyl-β-D-allopyranosyl moiety attached through a glycosidic bond to C-11. Decapetaloside (10-hydroxyiridodial glucoside) has been isolated from the bark. The structure and absolute configuration of viburnalloside have been established by spectroscopic means, and those of decapetaloside by chemical correlation with adoxoside.     

The bitter iridoids from Viburnum urceolatum

Four new bitter iridoid glucosides, including three bis-iridoids, were isolated from Viburnum urceolatum and their structures elucidated. They are composed of loganin or deoxyloganin as the aglucone esterified with either aromatic glucoside or with glucose in the 4-position.     

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.     

Iridoid glucosides in Avicennia marina

2′-Cinnamoyl-mussaenoside, 10-O-(5-phenyl-2,4-pentadienoyl)-geniposide, 7-O-(5-phenyl-2,4-pentadienoyl)-8-epiloganin, and the known iridoids geniposide and mussaenoside have been isolated from a methylated extract of the leaves of Avicennia marina. Evidence is presented that the iridoids occur as the free acids in the plant. The taxonomic significance of these findings is discussed.     

A spiro-bis-γ-lactone glucoside from viburnum dilatatum

A new spiro-bis-γ-lactone glucoside was isolated from the leaves of Viburnum dilatatum and its structure was elucidated on the basis of spectral and chemical evidence.     

Chrysoeriol derivatives and other constituents from Glandularia selloi

Glandularia selloi (Verbenaceae) presents phenylethanoids, iridoids and flavone glycosides as the main constituents. Two novel chrysoeriol derivatives, selloiside A (1) and selloiside B (2) were isolated from the methanolic extract of the aerial parts. Both flavones are acylated disaccharides. Two known compounds, verbascoside (3) and 6β-hydroxy-ipolamiide (4), were isolated from the methanolic extract of the roots. The structures were elucidated using 1D, 2D NMR and MS. Acylflavones have taxonomic significance since they occur mainly is species from the order Lamiales, specifically from the family Lamiaceae, closely related to Verbenaceae. The compounds 1 – 4 and the methanolic extract were investigated for antichemotactic activity.     

Iridoid glucosides from Pedicularis

Pedicularis palustris contains the iridoid glucosides aucubin and gardoside methyl ester, and five hydroxy derivatives of 8-epi-deoxyloganin, together with boschnaloside and three hydroxy derivatives of boschnaloside. From P. silvatica, plantarenaloside, 8-epiloganin and euphroside have been isolated. Euphroside is also present in P. lapponica, in addition to aucubin and mussaenoside. Chemical evidence for the structure of euphroside is presented. Pedicularioside is shown to be identical with penstemoside, and the former name is thus redundant.     

Two acylated flavanone glycosides from Nierembergia hippomanica

Two new acylated flavanone glycosides have been isolated from Nierembergia hippomanica and identified by spectral data as pinocembrin 7-O-β-(3?-O-acetyl)neohesperidoside and pinocembrin 7-O-β-(6″-O-acetyl)neohesperidoside.     

Iridoid glucosides from Campsis chinensis

Two new iridoid glucosides, 5-hydroxycampenoside and cachineside I, were isolated together with tecomoside from leaves of Campsis chinensis and their structures were elucidated. The absolute stereochemistry of 5-hydroxycampenoside has been established by X-ray analysis, and the structural correlation between 5-hydroxy-campenoside and tecomoside has been determined by spectral and chemical experiments.     

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     

Iridoid aglycones from Deutzia scabra

Scabrogenin and deutziogenin, the stable aglycones of known iridoid glucosides scabroside and deutzioside, have been isolated from Deutzia scabra. Their structures and mutarotational equilibria were investigated by detailed analysis of ¹H NMR and ¹³C NMR data.     

Flavonoids from Haplophyllum pedicellatum, H. robustum AND H. glabrinum

Haplophyllum pedicellatum, H. robustum and H. glabrinum all yielded the known compound gossypetin 8,3′-dimethyl ether 3-rutinoside. In addition the first two species afforded isorhamnetin and its 3-rutinoside. A new glycoside, gossypetin 8,3′-dimethyl ether 3-glucoside was obtained from H. pedicellatum together with the 3-malonylrutinoside, 3-malonylglucoside and 3-galactoside of isorhamnetin plus kaempferol 3-malonylglucoside. H. robustum yielded isorhamnetin 7-glucoside and 3-glucoside and quercetin 3-galactoside, while H. glabrinum was found to contain gossypetin 8-methyl ether 3-malonylrutinoside in addition to kaempferol and isorhamnetin 3-glucoside.     

Iridoid Derivatives with Cytotoxic Activity from Pedicularis uliginosa Bunge

Three new iridoids, rel‐(4aR,7S,7aS)‐7‐hydroxy‐7‐methyl‐1,4a,5,6,7,7a‐hexahydrocyclopenta[c]pyran‐4‐carbaldehyde ( 1 ), 1‐methoxy‐7‐methyl‐1,3,5,6‐tetrahydrocyclopenta[c]pyran‐4‐carbaldehyde ( 2 ), and rel‐(1R,4S,4aS,7R,7aR)‐7‐methylhexahydro‐1,4‐(epoxymethano)cyclopenta[c]pyran‐3(1H)‐one ( 3 ), together with seven known analogues, were isolated from the 95 % EtOH extract of the whole plants of Pedicularis uliginosa Bunge . Their structures were elucidated via extensive NMR spectroscopy and mass spectral data. In terms of inhibitory effects on human tumor cells, compounds 1 , 2 , 6 , 7 , and 8 exhibited better inhibitory activities against ACHN cells than the positive control (vinblastine).     

Structure and properties of the acylated anthocyanins from Vitis species

The acylated anthocyanins of Ives grapes have been isolated using column chromatography on polyamide and polyvinylpyrrolidone. Controlled hydrolysis with Dowex 50W-X8 ion exchange resin, KOH. peroxide oxidation and speciroscopic characterization revealed their tructure as the 3-(6-O-p-coumarylglucoside)-5-glucosides of cyanidin, peonidin, delphinidin, petunidin, and malvidin and the 3-(6-O-p-coumary lglucoside)s of delphinidin, petunidin and malvidin. On cellulose TLCs in the five solvent systems used, no clear-cut separation of these pigments could be obtained without their preliminary separation on polyamide and polyvinylpyrrolidone columns.     

Secoiridoid glucosides from Lonicera periclymenum

The stems of Lonicera periclymenum have been investigated for secoiridoid glycosides. In addition to two well-known glucosides, secologanin and morroniside, two rare secoiridoids, secoxyloganin and secologanoside, have been isolated and characterized by chemical and spectroscopic means. Secologanoside has been isolated for the first time as a genuine, non-derivatized compound.     

Iridoid glucosides from Utricularia australis and Pinguicula vulgaris (lentibulariaceae)

Utricularia australis contained 6-deoxycatalpol, a new iridoid glucoside, besides aucubin, gardoside and mussaenosidic acid. From Pinguicula vulgaris was isolated catalpol, globularin and 10-(Z)-cinnamoyl-catalpol, the latter being a new compound. Thus, the iridoids found in Lentibulariaceae belong to structural types which are common in Scrophulariaceae and related families.     

Triterpenoid sapogenins from leaves of Pittosporum undulatum

Three triterpenoid sapogenins were obtained on enzymatic hydrolysis of a saponin fraction from the leaves of Pittosporum undulatum. On the basis of