Megastigmane Glucosides Research Articles

Terpenic and Phenolic Glycosides from Leaves of Breynia officinalis Hemsl.

AbstractFor Abstract see ChemInform Abstract in Full Text.

Staphylionosides A-K: Megastigmane Glucosides from the Leaves of Staphylea bumalda DC.

Chemical investigation of leaves of Staphylea bumalda DC., collected in the suburbs of Hiroshima City, afforded 11 new megastigmane glucosides, named staphylionosides A-K (3-13), along with two known megastigmane glucosides (1, 2). The relative structures were elucidated from spectroscopic evidence, and the absolute structures of the aglycones were determined by means of the combination of beta-D-glucosylation-induced shift-trends and the modified Mosher's method.

New Megastigmane Glucosides from Excoecaria cochinchinensis LOUR. var. cochinchinensis

Two new megastigmane glucosides, called excoecariosides A and B were isolated from the leaves of a medicinal Vietnamese plant, Excoecaria cochinchinensis LOUR. var. cochinchinensis (Euphorbiaceae) together with seven known compounds. Their structures were elucidated by spectroscopic analyses and chemical reactions including the modified Mosher's method.

A Monoterpene Glucoside and Three Megastigmane Glycosides from Juniperus communis var. depressa

A new monoterpene glucoside (1) and three new natural megastigmane glycosides (2-4) were isolated along with a known megastigmane glucoside (5) from twigs with leaves of Juniperus communis var. depressa (Cupressaceae) collected in Oregon, U.S.A., and their structures were determined on the basis of spectral and chemical evidence. In addition, the antibacterial activities of the isolated components against Helicobacter pylori were also investigated.

Megastigmane and Phenolic Components from Laurus nobilis L. Leaves and Their Inhibitory Effects on Nitric Oxide Production

Laurus nobilis L. leaves are widely used in cooking and in folk medicine. Five new megastigmane glucosides (2-4, 7, and 9) named laurosides A-E and a new phenolic glucoside 12 were isolated from the methanolic extract of L. nobilis L. leaves, along with 10 known components: megastigmane (5), megastigmane glucosides (1, 6, 8, 10, and 11), aromatic compounds (13 and 14), and flavonoids (15 and 16). The structures and relative stereochemistry have been elucidated by one- and two-dimensional nuclear magnetic resonance experiments ((1)H and (13)C NMR, DEPT, correlation spectroscopy, heteronuclear multiple quantum correlation, heteronuclear multiple bond correlation, and nuclear Overhauser enhancement spectroscopy) and by chemical derivatization. The effect of isolated compounds on nitric oxide production in lipopolysaccharide-activated murine macrophages were examined.

Lasianthionosides A—C, Megastigmane Glucosides from Leaves of Lasianthus fordii

AbstractFor Abstract see ChemInform Abstract in Full Text.

Terpenic and phenolic glycosides from leaves of Breynia officinalis HEMSL.

From the leaves of Breynia officinalis, collected on Okinawa Island, six terpenic glucosides and six phenolic glycosides were isolated. Two of the terpenic glucosides were found to be known, and they were identified as turpinionoside B and betulalbuside A. The structures of the remaining terpenic glucosides were elucidated to be megastigmane glucosides, named breyniaionosides A-D, using spectroscopic analyses. The absolute structure of breyniaionoside D was determined using the modifed Mosher's method. The absolute structure of the known compound betulalbuside A was determined for the first time in this study. Six phenolic glycosides were found to be arbutin and its derivatives. Two known compounds were found to be robustaside A and eximine. New compounds were named isorobustaside A, and breyniosides A and B, and their structures were elucidated from spectroscopic evidence.

Lasianthionosides A–C, megastigmane glucosides from leaves of Lasianthus fordii

From the leaves of Lasianthus fordii, three megastigmane glucosides, lasianthionosides A, B and C, were isolated together with the known iridoid glucoside, asperuloside, deacetylasperuloside and methyl deacetyl-asperulosidate, and a megastigmane glucoside, citroside A. The structures have been elucidated based on spectroscopic analyses and/or X-ray crystallographic analysis.

Glochidionionosides A‐D: Megastigmane Glucosides from Leaves of Glochidion zeylanicum (Gaertn.) A. Juss.

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Eudesmane and megastigmane glucosides from Laggera alata

Four eudesmane glucosides, alatosides A–D ( 1– 4), and one megastigmane glucoside, alatoside E ( 5), were isolated from the BuOH fraction of Laggera alata along with six known compounds. Structures of the new compounds were elucidated by a combination of chemical and spectroscopic methods. Alatosides A–E were characterized as: 1α- O-(β- d-glucopyranosyloxyl)-7- epi-eudesma-11-en-2β,4α-diol ( 1), 2β- O-(β- d-glucopyranosyloxyl)-eudesma-4α-hydroxyl-11(13)-en-12-oic-acid ( 2), 5β- O-(β- d-glucopyranosyloxyl)-eudesma-4(15),11(13)-dien-12-oic-acid ( 3), 5α- O-(β- d-glucopyranosyloxyl)-eudesma-3,11(13)-dien-12-oic acid ( 4) and 3β- O-(β- d-glucopyranosyloxyl)-megastigma-9-one ( 5), respectively. Based on the chemical characteristics of eudesmane derivatives isolated from the Laggera genus, it was suggested that there are probably two different biogenetic pathways for these secondary metabolites in this genus.

Lignan and megastigmane glycosides from Sauropus androgynus

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

Stereochemistry of megastigmane glucosides from Glochidion zeylanicum and Alangium premnifolium

From Glochidion zeylanicum, two megastigmane glucosides, 3- and 9- O-β- d-glucopyranosides of (3 S,5 R,6 R,7 E,9 S)-megastigman-7-ene-3,5,6,9-tetrol ( 1 and 2, respectively), were isolated. Their structures were different from those of kiwiionoside ( 3) and actinidioionoside ( 4), isolated from Actinidia chinensis and Actinidia polygama, respectively, in the stereochemistry at the 9-positions. Alangionosides E ( 5) and O ( 6), isolated from the leaves of Alangium premnifolium, are also megastigmane glucosides, and the latter is closely related to 1 and actinidioionoside ( 4). However, the absolute configurations of the 9-position remained to be determined. They were analyzed to be R by means of a modified Mosher's method. Alangionoside E ( 5) is identical with corchoionoside A in all aspects. The name of corchoionoside A must be retained thereafter.

Iridoid Glucosides from Veronica hederifolia.

AbstractFor Abstract see ChemInform Abstract in Full Text.

Glochidionionosides A-D: megastigmane glucosides from leaves of Glochidion zeylanicum (Gaertn.) A. Juss.

Five megastigmane glucosides were isolated from the leaves of Glochidion zeylanicum. One of them was a known compound, blumenol C O-beta-D-glucopyranoside (1), and the structures of the four new compounds, glochidionionosides A-D (2-5), were mainly elucidated by spectroscopic methods, including a modified Mosher's method. The absolute configurations of the six-membered ring of glochidionionoside D (5) were deduced by beta-D-glucopyranosylation-induced shift trends in the (13)C-NMR spectra and confirmed by X-ray analysis as its p-bromobenzoate (5b), and the axis chirality of C-7 was determined to be R.

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.

Megastigmane and iridoid glucosides from Clerodendrum inerme

From the aerial parts of Clerodendrum inerme, two megastigmane glucosides (sammangaosides A and B) and a iridoid glucoside (sammangaoside C) were isolated together with 15 known compounds. The structural elucidations were based on analyses of physical and spectroscopic data.

Alkaloidal, Megastigmane and Lignan Glucosides fromAntidesma membranaceum (Euphorbiaceae)

Two novel alkaloidal glucosides derived from the recently discovered antidesmone (1), together with four known megastigmane and three lignan glucosides, two of which had not previously been described, were isolated from 1-butanol extracts of Antidesma membranaceum (Euphorbiaceae). The structural elucidation of (17RS)-17-(β-D-glucopyranosyloxy)antidesmone (2) and (17RS)-8-deoxo-17-(β-D-glucopyranosyloxy)antidesmone (3) is based on 1H, 13C, COSY, NOESY, HMQC and HMBC NMR spectra, together with LC/ESI-CIDMS and CD data. Determination of the absolute configuration at C-17 was accomplished by comparison with 1H NMR spectroscopic data for alk-2-yl β-D-glucopyranosides, an approach that also proved useful for the megastigmane glucosides blumenyl C β-D-glucopyranoside (4), 3-oxo-α-ionyl β-D-glucopyranoside (5), blumenyl B β-D-glucopyranoside (6) and blumenyl A β-D-glucopyranoside (7). The lignan glucosides lyoniresin-4-yl β-D-glucopyranoside (8), 4′-O-methyllyoniresin-4-yl β-D-glucopyranoside (9) and secoisolariciresin-4-yl β-D-glucopyranoside (10), featuring an unusual glucosylation position, were investigated with the aid of 1H and 2D NMR, CD and MS data.

Iridoid and megastigmane glycosides from Phlomis aurea

From the leaves of Phlomis aurea, two new iridoids of unique structures named 3-epiphlomurin ( 1 ) and phlomurin ( 2 ), a new megastigmane glucoside phlomuroside ( 3 ) and a new benzyl alcohol glycoside having the structure benzyl alcohol- O-β-xylopyranosyl-(1→2)-β-glucopyranoside ( 4 ) have been isolated together with four known iridoids auroside, lamiide, 8-epiloganin and ipolamiide, two known phenolic glycosides acteoside (verbascoside) and syringin, one known phenylethanoid glycoside 2-phenylethyl- O-β-xylopyranosyl-(1→2)-β-glucopyranoside, one known lignan liriodendrin and three known flavonoids chrysoeriol-7- O-β-glucopyranoside, acacetin-7- O-β-glucopyranoside and luteolin-7- O-β-glucopyranoside. The structures of the isolated compounds were verified by means of mass spectrometry (MS) and nuclear magnetic resonance (NMR) spectral analyses.

ChemInform Abstract: Megastigmane, Benzyl and Phenethyl Alcohol Glycosides, and 4,4′-Dimethoxy-β-truxinic Acid Catalpol Diester from the Leaves of Premna subscandens MERR.

Extensive isolation work on the n-BuOH-soluble fraction obtained from the leaves of Premna subscandens, collected on Ishigaki island, Okinawa, afforded six compounds. Two were identified as megastigmane glucosides, 7-(3,5-dihydroxy-1,1,5-trimethylcyclohexylidene)-9-methylprop++ +-8-enyl 9-O-beta-D-glucopyranoside and 3-hydroxy-5,6-epoxy-beta-ionol 9-O-beta-D-glucopyranoside. The structures of the remaining four new compounds were elucidated to be a 2'-O-beta-D-apiofuranosyl derivative of 3-hydroxy-5,6-epoxy-beta-ionol 9-O-beta-D-glucopyranoside, named premnaionoside, benzyl alcohol beta-D-(2'-O-beta-D-xylopyranosyl)glucopyranoside, phenethyl alcohol beta-D-(2'-O-beta-D-glucopyranosyl)glucopyranoside, and 4,4'-dimethoxy-beta-truxinic acid catalpol diester by spectroscopic analyses.

Megastigmane, benzyl and phenethyl alcohol glycosides, and 4,4'-dimethoxy-beta-truxinic acid catalpol diester from the leaves of Premna subscandens MERR.

Extensive isolation work on the n-BuOH-soluble fraction obtained from the leaves of Premna subscandens, collected on Ishigaki island, Okinawa, afforded six compounds. Two were identified as megastigmane glucosides, 7-(3,5-dihydroxy-1,1,5-trimethylcyclohexylidene)-9-methylprop++ +-8-enyl 9-O-beta-D-glucopyranoside and 3-hydroxy-5,6-epoxy-beta-ionol 9-O-beta-D-glucopyranoside. The structures of the remaining four new compounds were elucidated to be a 2'-O-beta-D-apiofuranosyl derivative of 3-hydroxy-5,6-epoxy-beta-ionol 9-O-beta-D-glucopyranoside, named premnaionoside, benzyl alcohol beta-D-(2'-O-beta-D-xylopyranosyl)glucopyranoside, phenethyl alcohol beta-D-(2'-O-beta-D-glucopyranosyl)glucopyranoside, and 4,4'-dimethoxy-beta-truxinic acid catalpol diester by spectroscopic analyses.