Minor Phenolic Constituents of Grevillea robusta and Hakea saligna

Varma, Manju; Varma, Rajender S.; Parthasarathy, M. R.

doi:10.1515/znc-1980-3-428

Cited by 8 publications

(10 citation statements)

References 4 publications

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+ )-Lyoniresinol {!] and ( -Hyoniresinol [ent-1] (the former being more abundant), (+ )-lyoniresinol 2a-0-3-D-glucopyranoside [3], lyoniside [4], and a new metabolite, namely (-Hyoniresinol 2a-0-fl-D-xylopyranoside [ent-4]1, have been isolated from Quercus petraea heartwood. Their structures were deduced from chemical and spectral data.

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confidence: 99%

“…sessiflora D.C. = Quercus sessilis Ehur.) (Fagaceae), which led to the isolation and structural determination of five disyringyl lignans having an aryl-tetralin skeleton, namely (+)and (-)lyoniresinol (the former, 1, prevailing in the mixture) (2)(3)(4)(5)(6), (+)-lyoniresinol 2a--ß-D-glucoside [31 (7), lyoniside [4] (5, [8][9][10][11], and (-)-lyoniresinol 2a-0-ß-D-xyloside \ent-4]1. The last compound had not been reported so far.…”

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confidence: 99%

“…The first compound isolated from the aqueous extract (see Experimental) appeared to be (+)-lyoniresinol 2&-0-ß-glucopyranoside [3] on the basis of its acid hydrolysis, giving rise to enantiomerically pure (+)-lyoniresinol [1] and Dglucose. Structure 3 was confirmed by comparison of its 'Hand 13C-nmr spectra with those reported by Miyamura et al (7).…”

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confidence: 99%

“…To our knowledge, no glycoside of (-Hyoniresinol has been reported so far, the only known natural occurrence of this enantiomer being as an aglycone in racemic mixture (2)(3)(4)(5)(6). spectra were obtained on a VG 707EQ mass spectrometer.…”

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confidence: 99%

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Lignan Glycosides from the Heartwood of European Oak Quercus petraea

Dad¹,

Corbani²,

Manitto³

et al. 1989

J. Nat. Prod.

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Lignan Glycosides from the Heartwood of European Oak Quercus petraea

Dad¹,

Corbani²,

Manitto³

et al. 1989

J. Nat. Prod.

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“…The planar structure of 1 was the same as that of (+)-lyoniresinol, obtained as the deacetylated derivative from Gaultheria yunnanensis, with similar 1 H and 13 C NMR data [2]. [a] D for compound 1 ($0°, MeOH) differed from those for (+)-lyoniresinol ([a] D +68°, MeOH [2]) and epilyoniresinol ([a] D -28.9°, MeOH [3]) isolated from Grevillea robusta [3], however. In an NOEDF experiment, irradiation of H-7 at Compounds 2 and 3 were initially isolated as a mixture, by use of reversed-phase HPLC with MeOH-water (1:1) as mobile phase; they were, however, separated by use of a more polar mobile phase, MeOH-water (2:3).…”

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confidence: 73%

A new lignan from Aphanamixis polystachya

et al. 2006

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A new lignan, polystachyol (1), two lignan glycosides, lyoniside (2) and nudiposide (3), and a sterol, ergosta-4,6,8(14),22-tetraen-3-one (4), with stigmasterol, and oleic and linoleic acids, have been isolated from an MeOH extract of the dried bark of Aphanamixis polystachya. The structures of the isolated compounds were elucidated by analysis of 1D and 2D NMR and mass spectroscopic data. The compounds did not have growth inhibitory activity against HeLa cells.

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Stereochemistry and biosynthesis of (+)-lyoniresinol, a syringyl tetrahydronaphthalene lignan in Lyonia ovalifolia var. elliptica I: isolation and stereochemistry of syringyl lignans and predicted precursors to (+)-lyoniresinol from wood

Katayama

Suzuki

et al. 2007

J Wood Sci

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Steps leading to the biosynthesis of syringyl lignans and tetrahydronaphthalene and naphthalene lignans, especially the formation of the C2-C7′ linkage, have not been elucidated. Lyoniresinol is a typical syringyl lignan, as well as a tetrahydronaphthalene lignan found in Lyonia ovalifolia var. elliptica. To demonstrate the biosynthetic pathway for (+)-lyoniresinol, three putative biosynthetic intermediates of lyoniresinol, syringaresinol, 5,5′-dimethoxylariciresinol, and 5,5′-dimethoxysecoisolariciresinol, were isolated from wood. The identity of the putative intermediates was confirmed by spectroscopic analyses, as well as by comparison of spectral and chromatographic data with those of authentic samples previously synthesized. The stereochemistry (enantiomeric composition and absolute configuration) of the isolated lignans were determined as (±)-syringaresinol, (8S,8′S)-(−)-5,5′-dimethoxylariciresinol [46% enantiomeric excess (e.e.)],(8S,8′S)-(+)-5,5′-dimethoxysecoisolariciresinol (91% e.e.), and (8R,8′R)-(+)-lyoniresinol (42% e.e.). The absolute configurations of (+)-and (−)-5,5′-dimethoxylariciresinols, and (+)-and (−)-5,5′-dimethoxysecoisolariciresinols were determined by their synthesis (catalytic reduction) from (8R,8′R)-(+)-and (8S,8′S)-(−)-syringaresinols and by subsequent chiral high-performance liquid chromatography analysis.

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Minor Phenolic Constituents of Grevillea robusta and Hakea saligna

Cited by 8 publications

References 4 publications

Lignan Glycosides from the Heartwood of European Oak Quercus petraea

Lignan Glycosides from the Heartwood of European Oak Quercus petraea

A new lignan from Aphanamixis polystachya

Stereochemistry and biosynthesis of (+)-lyoniresinol, a syringyl tetrahydronaphthalene lignan in Lyonia ovalifolia var. elliptica I: isolation and stereochemistry of syringyl lignans and predicted precursors to (+)-lyoniresinol from wood

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