Veronicosid,ein neues Iridoidglucosid aus Veronica officinalisL.(Scrophulariaceae)

Veronicoside, a new iridoid glucoside from Veronica officinalis L. (Scrophulariaceae) A new iridoid glucoside, Veronicoside ( 1 ) has been isolated from Veronica officinalis L. The structure of 1 has been determined by chromatographic and spectroscopic analysis as 6-benzoylcatalpol.     

New Iridoid Glucosides and a Lignan Diglucoside from Globularia alypumL

The four new iridoid glucosides globularicisin (2) , globularidin (5) , globularimin (9) , and globularinin (13) , the lignan diglucoside liriodendrin (18) , and syringin (20) have been isolated from Globularia alypum L. along with the previously reported glucosides globularin (1) and catalpol (4) . Compound 2 is the first report of any cinnamoyl iridoid with a cis-configuration at the acyl double bond. Compound 5 is another novel iridoid which lacks the characteristic C(3), C(4) double bond in the aglucone part. Compounds 9 and 13 are diastereomeric and contain highly oxygenated aglucone structures. The isolation of liriodendrin, from Globularia alypum is the first demonstration of the occurrence of a lignan in the family Globulariaceae. The structures have been elucidated by ¹ H - and ¹³ C-NMR . spectroscopy as well as by chemical transformations. Taxonomical significance of the cooccurrence of iridoid and lignan glycosides as well as the antileukemic potentiality of the latter are also appraised.     

Minecosid und Verminosid,zwei neue Iridoidglucoside aus Veronica officinalisL. (Scrophulariaceae)

Minecoside and verminoside, two new iridoid glucosides from Veronica officinalis L. (Scrophulariaceae) Two new esters of catalpol, minecoside ( 1 ) and verminoside ( 3 ), have been isolated from Veronica officinalis L. The structures of 1 and 3 have been determined on the basis of the spectral data as 6-isoferuloylcatalpol and 6-caffeeoylcatalpol, respectively.     

Two New Iridoid Esters from the Root and Rhizome of Valeriana jatamansi Jones

Two new iridoid esters, named valerjatadoids A and B ( 1 and 2 , resp.), together with three known iridoid esters, jatamanin O ( 3 ), jatamanvaltrate P ( 4 ), and jatamanvaltrate Q ( 5 ), have been isolated from the root and rhizome of Valeriana jatamansi Jones . The structures of the two new compounds were elucidated by spectroscopic analyses, including 2D‐NMR techniques.     

Iridoide aus Verbascum nigrum L. 182. Mitteilung über organische Naturstoffe

Iridoids from Verbascum nigrum L. Two new iridoid glycosides, nigroside 1 ( ? 6-O-(3-O-einnamoyl-α-L-rhamno-pyranosyl)aucubin (2) , and nigroside 2 (?6-O-(2-O-cinnamoyl-α-L-rhamnopy-ranosyl)aucubin (3) , and the known compound laterioside (1) have been isolated from extracts of the stems of Verbascum nigrum L., and their structures established primarily on the basis of NMR. spectroscopy. Harpagoside (4) , a known iridoid glucoside, was also isolated from the roots of this plant.     

Iridoid-glycoside isolation and purification from Premna fulva leaves

Premna fulva Craib, rich in iridoid glycosides, is widely used to treat periarthritis, osteoproliferation, pain, and other diseases. However, no studies have reported effective purification methods for obtaining iridoid glycosides as active materials. This paper describes an efficient strategy for separating iridoid glycosides from Premna fulva leaves using high-speed counter-current chromatography and preparative high-performance liquid chromatography. A two-phase solvent system, ethyl acetate/n-butanol/water (7.5:2.5:10, v/v), was selected for high-speed counter-current chromatography separation. The proposed method effectively separated and purified four iridoid glycosides and four lignans, including three new iridoid glycosides ( 4–6 ) and five known compounds ( 1–3, 7, 8 ), from Premna fulva leaves, indicating that high-speed counter-current chromatography combined with prep-HPLC can efficiently isolate catalpol derivatives from the genus Premna. Additionally, the in vitro anti-inflammatory activities of all isolated compounds were analyzed using lipopolysaccharide-stimulated RAW 264.7 cells, and the results indicated that six compounds ( 1 and 3–7 ) exhibited potential anti-inflammatory activities.     

Ladroside (= 6′-Caffeoyl-mussaenoside), a New Iridoid Glucoside from Veronica officinalis L. (Scrophulariaceae) and the elucidation of the absolute configuration at C(8) of mussaenoside

A new iridoid glucoside, named ladroside, together with mussaenoside (1) [2], has been isolated from Veronica officinalis L . The structure of ladroside (4) and the identity of mussaenoside have been established by spectral analysis. Additionally, the absolute configuration at C(8) carrying the tertiary hydroxyl group has been established by chemical evidence.     

Euphroside,A New Iridoid Glucoside from Euphrasia salisburgensis HOPPE

Five iridoid glucosides have been isolated from the whole plant of Euphrasia salisburgensis. The structure of the new compound, named euphroside, and the identity of the others have been established by chemical transformations and spectral data.     

A new iridoid diglycoside from Sambucus ebulus L

Abstract

The phytochemical examination of the polar constituents of Sambucus ebulus L. leaves led to the identification of patrinoside (1) and of a new diglycoside iridoid, patrinoside-aglycone-11-O-[β-D-glucopyranosyl-(1→6)-2′-deoxy-β-D-glucopyranoside] (trivially named as sambuloside) (2). Both of these structures have been assigned by spectroscopic means (NMR and MS).     

Iridoid Glycosides and Phenolic Compounds from the Flowers of Vitex agnus‐castus

A new and rare type of iridoid glycoside, agnusoside ( 1 ), a new caffeoylquinic acid derivative, castusic acid ( 2 ), and a new sugar ester, 1,2‐di‐(4‐hydroxybenzoyl)‐β‐glucopyranose ( 3 ), along with ten known compounds belonging to iridoid glycosides (agnuside, trans‐eurostoside), caffeoylquinic acid derivatives (chlorogenic acid and isochlorogenic acid A), flavonoids (isoorientin, isovitexin, kaempferol 3‐O‐sophoroside, luteolin 6‐C‐(2′′‐O‐trans‐caffeoyl)glucopyranoside, and simple phenolic acids (4‐hydroxybenzoic acid, 3,4‐dihydroxybenzoic acid), chemical classes were isolated from the flowers of Vitex agnus‐castus. The structures of the isolates were established by extensive 1D‐ and 2D‐NMR spectroscopic analysis as well as HR‐ESI‐MS. Agnusoside ( 1 ) represents an unusual type of iridoid glycoside with its 6‐keto C(4) nonsubstituted aglycone.     

Verproside,a New Iridoid Glucoside from Veronica officinalis L. (Scrophulariaceae)

A new iridoid glucoside, verproside (2) , has been isolated from Veronica officinalis L. and its structure has been established to be 6-O-protocatechuoylcatalpol.     

Globularifolin,A New Acyl Iridoid Glucoside from Globularia cordifolia

Six iridoid glucosides have been isolated from Globularia cordifolia by the combination of open column - and high performance liquid chromatography. The structure of the new compound, named globularifolin, and the identity of the others have been established by chemical transformations and spectral evidence of the compounds and their derivatives.     

A new iridoid diglucoside from Harpagophytum procumbens

A new iridoid diglucoside has been isolated from an aqueous extract of Harpagophytum procumbens secondary roots, together with six known compounds. Its structure has been assigned as 6′-O-glucopyranosyl-8-O-trans-coumaroylharpagide by spectroscopic means.     

Iridoid and Aryl Glucosides from Globularia nudicaulis and Globularia nana

The iridoid and aryl glycosidic constituents of Globularia nudicaulis L. and G. nana LAM . are reported. The structure determination of lytanthosalin (10-O-(E)-cinnamoylaucubin), a new acylated iridoid glucoside, isolated from the latter species, is described.     

New Glycosidic Constituents of Abutilon pakistanicum

Pakisides A and B ( 1 and 2 , resp.), new catalpol‐type iridoid glycosides, and a new glycoside, 3 , of scutellarein have been isolated from the AcOEt‐soluble fraction of the whole plant of Abutilon pakistanicum, along with buddlejoside and lapachol. The structures of new compounds were elucidated by spectroscopic techniques including ¹H‐and ¹³C‐NMR (DEPT), and 2D‐NMR experiments.     

Iridoid Glucosides from Eremostachys moluccelloides Bunge

From the aerial parts of Eremostachys moluccelloides Bunge , a new iridoid glucoside, lamalbidic acid ( 7 ), was isolated as its choline salt 7a together with six known iridoid glucosides, 5‐deoxysesamoside ( 1 ), 6β‐hydroxy‐7‐epiloganin ( 2 ), lamalbide ( 3 ), shanzhiside methyl ester ( 4 ), sesamoside ( 5 ), and 5‐deoxypulchelloside I ( 6 ). The structures of 7a and 7 (obtained from 7a ) were elucidated by spectroscopic (UV, IR, 1D‐ and 2D‐NMR, and ESI‐MS) methods.     

Monoterpenoid glucoindole alkaloids and iridoids from Pterocephalus pinardii

A new secondary metabolite, pterocephaline, along with the known cantleyoside, 7α‐morroniside, 3β,5α‐tetrahydrodesoxycordifoline lactam, 5S‐5‐carboxyvincoside, sweroside, and loganin have been isolated from the aerial parts of P. pinardii (Dipsacaceae). Moreover, cantleyoside‐methyl‐hemiacetal and cantleyoside‐dimethyl‐acetal were obtained as seco‐iridoid artifacts. The structures were elucidated by extensive spectroscopic methods including 1D‐(¹H, ¹³C and TOCSY) and 2D‐NMR (DQF‐COSY, HSQC and HMBC). Monoterpenoid glucoindole alkaloids were encountered for the first time in Dipsacaceae family. Copyright © 2010 John Wiley & Sons, Ltd.     

Galiridosid,ein Iridoidglucosid aus Galeopsis tetrahit L. (Labiatae)

From fresh leaves of Galeopsis tetrahit L. (Labiatae) a compound observed earlier only by paper chromatography and known as ‘Tetrahit-Pseudoindican’ or ‘Gal. tetr. 47’ has been isolated, and its constitution (II) as a new iridoid glucoside has been established. The name of galiridoside is proposed for this compound. Acetylation of galiridoside gave the tetraacetyl-derivative III. Catalytic reduction of II by Pd/C gave dihydrogaliridoside (IV). Basic hydrolysis of II with Ba(OH)₂ gave desepoxydihydroxy-galiridoside (VI). Reduction of galiridoside by lithium and ammonia yielded among other compounds a small amount of dideoxy-aucubin (XI), isolated as its tetraacetate XII. The NMR. spectra of galiridoside and its derivatives support the proposed structure and configuration.     

A new iridoid glucoside from <Emphasis Type="Italic">Lamiophlomis rotata</Emphasis>

A new iridoid glucoside and seven known compounds were isolated from the herb of Lamiophlomis rotata (Benth.) Kudo, which is a Tibetan folk medicine. The structure of the new iridoid glucoside was elucidated by spectroscopic methods. The others were lamiophlomiol A, shanzhigenin methyl ester, loganin, 8-O-acetyl-shanzhiside methyl ester, schismoside, phlomiol, and 7,8-dehydropenstemoside. Published in Khimiya Prirodnykh Soedinenii, No. 3, pp. 306–307, May–June, 2009.     

Iridoid Glycosides from Lamiophlomis rotata

The seven new iridoid diglycosides 1 – 7 , together with eleven known iridoid and phenylpropanoid glycosides, were isolated from the 50% EtOH extract of the roots of Lamiophlomis rotata. Their structures were elucidated by chemical and spectroscopic methods.