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.     

Platanionosides D-J: megastigmane glycosides from the leaves of Alangium platanifolium (Sieb. et Zucc.) Harms var. platanifolium Sieb. et Zucc

From the leaves of Alangium paltanifolium var. platanifolium, collected in Fukuoka Prefecture, twelve further megastigmane glycosides were isolated. Seven of them, named platanionosides D-J (1-7), were found to be new compounds. Their structures were elucidated from spectroscopic evidence and their absolute structures were determined from beta-D-glucosylation-induced shift trends of 13C-NMR and by application of a modified Mosher's method.     

Megastigmane Glycosides from Polygala hongkongensis Hemsl

Two new megastigmane glycosides,7Z-roseoside,and 7Z-trifostigmanoside Ⅰ,as well as,four known compounds,trifostigmanoside Ⅱ,epimedin C,3',7-dihydroxy-4'-methoxyisoflavone-7-D-glucopyranoside,and formenonetin,were isolated from Polygala hongkongensis Hemsl.The structures of the isolated compounds were established on the basis of UV,IR,NMR,and MS spectral data.Megastigmane glycosides(1-3)were isolated from the family Polygalaceae for the first time.     

Bioactive constituents from Chinese natural medicines. XXII. Absolute structures of new megastigmane glycosides, sedumosides E1, E2, E3, F1, F2, and G, from Sedum sarmentosum (Crassulaceae)

Six new megastigmane glycosides, sedumosides E1, E2, E3, F1, F2, and G, were isolated from the whole plant of Sedum sarmentosum (Crassulaceae). The structures of new constituents including the absolute configuration were elucidated on the basis of chemical and physicochemical evidence.     

Two labdane diterpene and megastigmane glycosides from Aquilegia hybrida

Two new labdane diterpene glycosides, named aquosides A and B, and a new megastigmane glycoside, named aquoside C, have been isolated from the air-dried aerial parts of Aquilegia hybrida together with three known compounds comprising a phenolic glycoside and two flavone C-glycosides. Their structures were determined on the basis of spectroscopic data and chemical evidence.     

Bioactive constituents from Chinese natural medicines. XXIII. Absolute structures of new megastigmane glycosides, sedumosides A(4), A(5), A(6), H, and I, and hepatoprotective megastigmanes from Sedum sarmentosum

The methanol-eluted fraction of the hot water extract from the whole plant of Sedum sarmentosum (Crassulaceae) was found to show hepatoprotective effect on D-galactosamine-induced cytotoxicity in primary cultured mouse hepatocytes. From the active fraction, five new megastigmane glycosides, sedumosides A(4), A(5), A(6), H, and I, were isolated together with 22 megastigmane constituents. Their absolute stereostructures were elucidated on the basis of chemical and physicochemical evidence. Among them, sedumoside F(1) (IC(50)=47 microM), (3S,5R,6S,9R)-megastigmane-3,9-diol (61 microM), and myrsinionosides A (52 microM) and D (62 microM) were found to show the strong hepatoprotective activity.     

Absolute structures of new megastigmane glycosides, foliasalaciosides E(1), E(2), E(3), F, G, H, and I from the leaves of Salacia chinensis

Following the investigation of foliasalaciosides A(1), A(2), B(1), B(2), C, and D, seven new megastigmane glycosides named foliasalaciosides E(1)-I (1-7), together with four known constituents, were isolated from the leaves of Salacia chinensis LINN. collected in Thailand. The absolute stereostructures of the new compounds were characterized on the basis of chemical and physicochemical evidence, including the application of the modified Mosher's method.     

Two New Diterpenoid Glucosides from Clerodendrathus spicatus

Two new diterpenoid glucosides, clerodendranthusides B and C ( 1 and 2 , resp.), together with 16 known compounds, comprising four lignans, five miscellaneous phenylpropanoids, two flavonoids, one sesquiterpenoid glycoside, two triterpenoid glycosides, one megastigmane, as well as one anthraquinone, were isolated from the 50% EtOH extract of the whole plants of Clerodendrathus spicatus. Their structures were elucidated by chemical and spectroscopic methods.     

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.     

A New Megastigmane Glucoside and Three New Flavonoid Glycosides from Spiraea prunifolia var. simpliciflora

A new megastigmane glucoside, simplicifloranoside ( 1 ), and three new flavonol glycosides, prunifolianosides A–C ( 2 – 4 , resp.), were isolated from the aerial parts of Spiraea prunifolia var. simpliciflora. In addition, fifteen known compounds, including five phenolic acids, three lignans, four flavonoids, one eugenol glycoside, and two alkyl‐primeverosides, were also identified. Their structures were elucidated on the basis of detailed spectroscopic analyses and acid hydrolysis.     

Two New Megastigmane Glycosides and a New Iridoid Glycoside from Gelsemium elegans

Two new megastigmane glycosides, eleganosides A and B ( 1 and 3 , resp.), and one new iridoid glycoside, gouwenoside A ( 4 ), together with two known compounds, foliasalacioside B₁ ( 2 ) and loganin ( 5 ), were isolated from the aerial parts of Gelsemium elegans (Gardn. et Champ.) Benth. (Loganiaceae). Their structures were elucidated by spectroscopic methods including 1D‐ and 2D‐NMR techniques. The absolute configuration of 1 was determined by CD spectroscopy.     

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.     

Two new megastigmanes from the leaves of Cucumis sativus

Two new megastigmane, cucumegastigmanes I (1) and II (2), together with a known megastigmane, (+)-dehydrovomifoliol (3), and five other known compounds were isolated from the leaves of Cucumis sativus. The structures of the new compounds were elucidated from spectroscopic analysis and their absolute stereochemistries were determined in detail using the chemical conversion and a modified Mosher's method.     

Three new flavonoid glycosides, byzantionoside B 6'-O-sulfate and xyloglucoside of (Z)-hex-3-en-1-ol from Ruellia patula

Three new flavonoid glycosides, demethoxycentaureidin 7-O-β-D-galacturonopyranoside, pectolinarigenin 7-O-α-L-rhamnopyranosyl-(1?→4″)-β-D-glucopyranoside and 7-O-α-L-rhamnopyranosyl-(1?→4″)-β-D-glucuronopyranoside, a new megastigmane glucoside, byzantionoside B 6'-O-sulfate, and a new (Z)-hex-3-en-1-ol O-β-D-xylopyranosyl-(1″→2')-β-D-glucopyranoside, were isolated from leaves of Ruellia patula JACQ., together with 12 known compounds, β-sitosterol glucoside, vanilloside, bioside (decaffeoyl verbascoside), acteoside (verbascoside), syringin, benzyl alcohol O-β-D-xylopyranosyl-(1″→2')-β-D-glucopyranoside, cistanoside E, roseoside, phenethyl alcohol O-β-D-xylopyranosyl-(1″→2')-β-D-glucopyranoside, (+)-lyoniresinol 3α-O-β-D-glucopyranoside, isoacteoside and 3,4,5-trimethoxyphenol O-α-L-rhamnopyranosyl-(1″→6')-β-D-glucopyranoside. Their structures were elucidated by means of spectroscopic analyses.     

New megastigmane glycoside and aromadendrane derivative from the aerial part of Piper elongatum

A new megastigmane glycoside, called pipeloside A, and a new aromadendrane type sesquiterpenoid, pipelol A, were isolated from the MeOH extract of the aerial part of Piper elongatum VAHL. along with a known megastigmane glycoside, byzantionoside B. The structures of these compounds were elucidated on the basis of spectroscopic data and chemical evidence.     

New megastigmane and tetraketide from the leaves of Euscaphis japonica

New megastigmane (1) and tetraketide (2) were isolated from the leaves of Euscaphis japonica and the structures were elucidated by means of spectroscopic and chemical evidence.     

Cis-aconitic anhydride ethyl ester and phenolic compounds from the seeds of Alisma orientale

From the seeds of Alisma orientale, cis-aconitic anhydride ethyl ester and cis-2,4,5-trihydroxycinnamic acid were isolated, together with nine known phenolic compounds and a megastigmane sesquiterpene. All compounds are reported for the first time from Alisma species.     

New Approach to the Synthesis of the Natural Product Aripuanin

Abstract

Aripuanin is a megastigmane that exists in the leaves of Ficus aripuanensis C.C. Berg (Moraceae). The present study describes a new approach to the total synthesis of this natural product starting from the readily available β-ionone. The proposed synthetic route provided racemic aripuanin in moderate yields (~31%). This route can be applied to the synthesis of other natural products bearing the megastigmane moiety, as well as to the enantioselective synthesis of aripuanin derivatives.     

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.     

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.