On the chemical constituents of Dipsacus asper

Bioassay-guided fractionation of 95% EtOH extract from the roots of Dipsacus asper lead to the isolation of some phenolic acids (caffeic acid, 2,6-dihydroxycinnamic acid, vanillic acid, 2'-O-caffeoyl-D-glucopyranoside ester, and caffeoylquinic acid) as the major active components, and five new iridoid glucoside dimers (1-5) and one new iridoid glucoside monomer (6), other known iridoid glycosides loganin, cantleyoside, triplostoside A, lisianthioside, 6'-O-beta-D-apiofuranosyl sweroside, as well as triterpenoids oleanic acid and akebiasaponin D. The structures of new compounds 1-6 were determined as dipsanosides C (1), D (2), E (3), F (4), G (5), and 3'-O-beta-D-glucopyranosyl sweroside (6) by spectroscopic, including 1D and 2D NMR techniques, and chemical methods.     

New Iridoid Glycosides from Lamium eriocephalum subsp. eriocephalum

Two new iridoid glycosides, eriobioside ( 1 ) and lamerioside ( 2 ), were isolated from the aerial parts of Lamium eriocephalum subsp. eriocephalum, along with the two known compounds lamiide ( 3 ) and ipolamiide ( 4 ). Their structures were elucidated by spectroscopic methods (UV, 1D‐ and 2D‐NMR) and by mass spectrometry (HR‐ESI‐MS).     

An iridoid glucoside dimer and a non-glycosidic iridoid from the leaves of Lasianthus wallichii

A new iridoid glucoside dimer (1) and a non-glycosidic iridoid (2) was isolated together with the known compounds, asperuloside (3), paederoside (4), daphylloside (5), citroside A (6) and benzyl 6-O-alpha-L-rhamnopyranosyl-beta-D-glucopyranoside (7), from the leaves of Lasianthus wallichii. The structures of the new compounds were elucidated by spectroscopic and chemical evidence.     

Allobetonicoside and 6-O-Acetylmioporoside: Two new iridoid glycosides from Betonica officinalis L.

A new allose-containing iridoid diglycoside, allobetonicoside ( 1 ), and a new acyl iridoid glucoside, 6-O-acetylmioporoside ( 2 ) have been isolated from the aerial parts of Betonica officinalis L. in addition to two known iridoid glucosides, acetylharpagide ( 3 ) and reptoside ( 4 ). Their structures have been determined by spectroscopic methods as well as by means of chemical evidence.     

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.     

A 9-hydroxyiridoid isolated from Junellia seriphioides (Verbenaceae)

[structure: see text] An unusual iridoid glucoside, namely 9-hydroxy-8-epihastatoside (1), was isolated from Junellia seriphioides (Verbenaceae), together with the known compounds auroside (2), pulchelloside I (3), and 8-epihastatoside (4) as well as verbascoside.     

New Bisabolane-Type Sesquiterpenes from the Aerial Parts of Lippia dulcis

Two new bisabolane-type sesquiterpenes, lippidulcine A (3) and epilippidulcine A (4), have been isolated from the aerial parts of Lippia dulcis TREV. along with five known flavonoids, cirsimaritin (5), salvigenin (6), eupatorin (7), 5-hydroxy-6,7,3',4'-tetramethoxyflavone (8) and 5,3'-dihydroxy-6,7,4',5'-tetramethoxyflavone (9), three known phenylethanoid glycosides, decaffeoylverbascoside (10), acteoside (11) and isoacteoside (12), and two known iridoid glucosides, 8-epiloganin (13) and lamiide (14). Their chemical structures have been determined on the basis of spectroscopic data. Among them, 5, 7, and 9 exhibited almost the same activity as that of alpha-tocopherol, and 10-12 were identified as stronger antioxidants than alpha-tocopherol using the ferric thiocyanate method.     

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.     

New iridoid glucosides from the aerial parts of Verbena brasiliensis

Two new iridoid glucosides, verbenabraside A (1) and verbenabraside B (2), were isolated from the aerial parts of Verbena brasiliensis VELL., along with six known iridoid glucosides, gelsemiol 3-O-beta-D-glucoside (3), verbraside (4), 9-hydroxysemperoside (5), griselinoside (6), aralidioside (7), and 6alpha-hydroxyforsythide dimethyl ester (8), three known phenylethanoid glycosides, 2-phenylethyl O-beta-D-xylopyranosyl-(1-->2)-beta-D-glucopyranoside (9), acteoside (10), and leucosceptoside A (11), two known lignan glucosides, dihydroxymethyl-bis(3,5-dimethoxy-4-hydroxyphenyl) tetrahydrofuran-9 (or 9')-O-beta-glucopyranoside (12) and (+)-lyoniresinol 3alpha-O-beta-D-glucopyranoside (13), a known methyl salicylate glucoside, methyl 2-O-beta-D-glucopyranosylbenzoate (14), and two known sterols, beta-sitosterol 3-O-beta-D-glucopyranoside (15) and beta-sitosterol (16). Their chemical structures were determined on the basis of spectroscopic data. Compound 1 exhibited stronger scavenging effect on the stable free radical 1,1-diphenyl-2-picrylhydrazyl than that of alpha-tocopherol.     

New Iridoid and Secoiridoid Glucosides from the Roots of Gentiana manshurica

One new iridoid glucoside, 4″‐O‐β‐D ‐glucosyl‐6′‐O‐(4‐O‐β‐D ‐glucosylcaffeoyl)linearoside ( 1 ), and two new secoiridoid glucosides, 6′‐O‐acetylsweroside ( 2 ) and 6′‐O‐acetyl‐3′‐O‐[3‐(β‐D ‐glucopyranosyloxy)‐2‐hydroxybenzoyl]sweroside ( 3 ), were isolated from the dried roots of Gentiana manshurica (Gentianaceae), together with 11 known ones, including one iridoid glucoside, five secoiridoid glucosides, and five triterpenes. The structures of the new compounds were determined on the basis of detailed spectroscopic analyses and acidic hydrolysis.     

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.     

DNA damaging activities of methanol extract of Ajuga postii and iridoid glucoside reptoside

An iridoid glucoside reptoside (1) has been isolated as a DNA damaging active agent by bioassay-guided fractionation of the methanol extract of Ajuga postii. Furthermore, from the acetone extract of A. postii two known triterpenic compounds ursolic acid, alpha-amyrin and two steroidal compounds (24S)-24-ethylcholesta-5,25-dien-3beta-ol and beta-sitosterol were isolated. Their structures were elucidated based on 1D and 2D NMR techniques and mass data.     

Two novel tetrairidoid glucosides from Dipsacus asper

[reaction: see text] Two new iridoid glucoside tetramers, dipsanosides A (1) and B (2), the first-reported iridoid tetramers with four glucosides, were isolated from Dipsacus asper. Their structures were determined by analysis of 1D and 2D NMR data as well as by comparison with model compounds. Their cytotoxicities were tested, but neither of them showed obvious activity.     

Two new iridoid glycosides from the Tibetan folk medicine Swertia franchetiana

Two new iridoid glycosides designated as senburiside III (2) and senburiside IV (3), together with one known iridoid glycoside senburiside I (1) and three known secoiridoid glucosides swertiamarin (4), gentiopicroside (5) and sweroside (6), were isolated from the whole plant of Swertia franchetiana. The structures of the two new compounds were elucidated by spectroscopic methods.     

Synthesis of monoterpene alkaloid derivatives from the iridoid glucoside geniposide

Nine novel monoterpene alkaloid derivatives (3(a)-(c), 4(a)-(c), 5(a)-(c)) were prepared as a reaction of genipin 2 with L-amino acid methyl hydrochlorides utilized the reaction of reductive amination. Genipin was obtained by beta-glucosidase, catalyzed hydrolysis of the iridoid glucoside geniposide 1. The chemical structures were confirmed by 1D-, 2D-NMR and MS.     

A New Bis-iridoid Glucoside from Mussaenda incana

Mussaenda incana Wall (Rubiaceae), an endemic medium sized tree of semi-forest regions of North Eastern States of India, is used in traditional medicine as detergent to ulcers and treatment of white leprosy1. Earlier we reported some terpenoids and iridoi…     

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.     

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.     

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.     

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.