Iridoid glucosides from Viburnum sargenti

The phytochemical study of aerial parts of Viburnum sargenti Koehne, a species spontaneous in Mongolia and Northern China, led to the isolation of three iridoid glucosides of Valeriana-type: the novel 7,10,2'-triacetylsuspensolide F, 1, and the known viburtinoside IV and V. In addition, (+)-epicatechin was also isolated.     

Iridoid glucosides from Allamanda neriifolia

<正>A new iridoid glucoside,allamanoid(1),was isolated from the aerial parts of Allamanda neriifolia,together with three known glucosides,plumieride,protoplumericin,and nicotiflorin.Their structures were elucidated by 1D and 2D spectroscopic analyses, hydrolysis,and comparison with literature data.     

Iridoid glucosides from Veronica hederifolia

A new iridoid glucoside, urphoside A, and six known iridoid glucosides, pikuroside, aucubin, veronicoside, catalposide, amphicoside, and verminoside, were isolated from Veronica hederifolia together with a known megastigmane glucoside, 3-hydroxy-5,6-epoxy-beta-ionol-9-O-beta-D-glucopyranoside, and a hexitol, dulcitol. The structures of the isolated compounds were established by the extensive 1D- and 2D-NMR spectroscopy.     

Iridoid glucosides from Wendlandia tinctoria roots

Four new iridoid glucosides, 5-dehydro-8-epi-adoxosidic acid, 5-dehydro-8-epi-mussaenoside, 10-O-dihydroferuloyldeacetyldaphylloside, and wendoside, together with one known iridoid glucoside, 8-epi-mussaenoside, beta-D-glucose, D-mannitol and beta-sitosterol have been isolated from the roots of Wendlandia tinctoria. On the basis of chemical and spectral analyses, the structures of new iridoid glucosides have been elucidated.     

Iridoid glucosides from Lamium garganicum flowers

In the flowers of Lamium garganicum L. a single iridoid is present, as main glycosidic component, the 8-acetyl-shanzhiside methyl ester, 1. The structure of 1 was established by spectroscopic studies and chemical evidence.     

Iridoid glucosides from Wendlandia tinctoria roots

A new iridoid glucoside, 8-O-(E)-caffeoylmussaenosidic acid (1), together with ixoside (2), was isolated from the roots of Wendlandia tinctoria. The structure of the new compound was established on the basis of detailed spectroscopic (2D NMR) and chemical analysis.     

Iridoid glucosides from the fruit of Genipa americana

Four new iridoid glucosides, called genamesides A-D, have been isolated from the fruit of Genipa americana L. (Rubiaceae), along with four known iridoid glucosides, geniposidic acid, geniposide, gardenoside and genipin-gentiobioside. Their chemical structures were determined on the basis of spectroscopic data.     

Iridoid glucosides from the aerial parts of Globularia alypum L. (Globulariaceae)

From the hydromethanolic extract of the aerial parts of Globularia alypum grown in Morocco, a new chlorinated iridoid glucoside, globularioside has been isolated beside 5 known iridoid glycosides, globularin, globularicisin, globularidin, globularinin and globularimin. This is the first report of a chlorinated iridoid in G. alypum and in the Globulareaceae. Unlike all other known 7-chlorinated iridoid glucosides where the chlorine atom exhibits an alpha configuration, globularioside incorporate the chlorine atom as a 7beta substituent. The structures of the isolated compounds were established on the basis of ESI-MS, MS-MS, 1D and 2D NMR spectral analysis.     

Iridoids from Viburnum cylindricum

Two new iridoids, methyl (+)‐rel‐(1R,3S,4R,5R,8R,9R)‐1,3,4,5,8,9‐hexahydro‐8‐hydroxy‐3‐methoxy‐2H‐1a,2‐dioxacyclopent[cd]indene‐4‐carboxylate ( 1 ) and methyl (+)‐rel‐(1R,3S,4S,5R,8R,9R)‐1,3,4,5,8,9‐hexahydro‐8‐hydroxy‐3‐methoxy‐2H‐1a,2‐dioxacyclopent[cd]indene‐4‐carboxylate ( 2 ), were isolated from Viburnum cylindricum along with 14 known compounds. Their structures were determined by spectroscopic analyses. This type of iridoids bearing a MeO group at C(3) was discovered for the first time.     

Phenolic Compounds from Viburnum cylindricum

Three novel quinic acid esters, i.e., neochlorogenic acid methyl ester ( 1 ), cryptochlorogenic acid methyl ester ( 2 ), and chlorogenic acid methyl ester ( 3 ), were isolated from Viburnum cylindricum. Their structures were determined by spectroscopic analysis.     

Iridoid glycosides from Globularia davisiana

From the ethanolic extract of the aerial parts of Globularia davisiana, a new iridoid glycoside, davisioside (1), was isolated. Davisioside (1) comprises a rare iridoid aglycone structure with a saturated double bond between C-3 and C-4. Nine known iridoid glycosides, asperuloside (2), alpinoside (3), geniposide (4), globularin (5), globularicisin (6), 10-O-benzoylcatalpol (7), lytanthosalin (8), melampyroside (9), agnuside (10), and three known phenylethanoid glycosides, verbascoside, isoacteoside and leucosceptoside A were also isolated and characterized. The structures of the isolates were established by spectroscopic methods (one-dimensional (1D)- and two-dimensional (2D)-NMR, MS).     

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.     

Iridoid esters from Patrinia saniculaefolia

Two new iridoids, named patridoid I (1) and patridoid II (2), were isolated from the whole plant of Patrinia saniculaefolia (Valerianaceae), together with the known one, nardostachin (3). The structures of compounds 1 and 2 were established on the basis of spectroscopic methods, including two dimensional (2D NMR) and high resolution fast atom bombardment mass spectrometry (HR-FAB-MS).     

Iridoid Glycosides from Hedyotis corymbosa

Three new iridoid glycosides, hedycorysides A–C ( 1 – 3 , resp.), were isolated from the whole plant of Hedyotis corymbosa (Linn .) Lam ., along with four known compounds. Their structures were elucidated by extensive 1D‐ and 2D‐NMR analysis, as well as by HR‐ESI‐MS experiments. The three new compounds are the first benzoylated geniposide derivatives from Hedyotis.     

Vibsane-type diterpenes from Taiwanese Viburnum odoratissimum

Two new eleven-membered and three new seven-membered vibsane-type diterpenes, named vibsanin L (1) and 14-hydroxyvibsanin F (2), and vibsanin I (3), 14R*,15-epoxyvibsanin C (4) and 14S*,15-epoxyvibsanin C (5) respectively, have been isolated from Viburnum odoratissimum collected in Taiwan. Their structures have been elucidated by spectroscopic analyses and comparison of Nuclear magnetic resonance method (NMR) data with those of the previously reported vibsane-type diterpenes. High performance liquid chromatography (HPLC) analyses indicated that the methanol extract of V. odoratissimum collected in Taiwan contained no neovibsanines, characteristic chemicals occurring in V. awabuki.     

Triterpenoids and diterpenoids from Viburnum chingii

Two new oleanane triterpenoids (1-2) and one new vibsane-type diterpenoid (3), together with 7 known compounds (4-10), were isolated from the leaves of Viburnum chingii. The structures of compounds 1-3 were elucidated by means of spectroscopic methods including extensive 1D- and 2D-NMR technique. Cytotoxicity of compounds 1-10 were tested against HL-60, SMMC-7721, A-549, SK-BR-3, and PANC-1 cell lines. Compound 3 showed significant cytotoxicity against HL-60, SK-BR-3, and PANC-1 cell lines.     

Iridoid Glycosides from Gardenia jasminoides Ellis

Three new iridoid glycosides, 4″‐O‐[(E)‐p‐coumaroyl]gentiobiosylgenipin ( 1 ), 6′‐O‐[(E)‐caffeoyl]deacetylasperulosidic acid methyl ester ( 2 ), and 6′‐O‐[(E)‐sinapoyl]gardoside ( 3 ), together with seven analogues, 4 – 10 , were isolated from the BuOH extract of the fruits of Gardenia jasminoides Ellis . Their structures were determined by means of spectroscopic analyses, including HR‐ESI‐MS, IR, and ¹H‐ and ¹³C‐NMR, and 2D experiments (COSY, HSQC, and HMBC), and comparison with known related compounds.