Labdane diterpene glycosides with 6-deoxy-L-idose from Aster spathulifolius Maxim.

Uchio, Yasuto; Nagasaki, Masaharu; Eguchi, Shizuko; Matsuo, Akihiko; Nakayama, Mitsuru; Hayashi, Shûichi

doi:10.1016/0040-4039(80)80175-4

Cited by 29 publications

(20 citation statements)

References 13 publications

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“…The structure of 2, including relative stereochemistry and identity of the sugar moiety, was determined in a manner comparable to that of 1. The aglycone core of 2 was identified as labda-7,14-dien-13(R)-ol by comparison of the NMR data and optical rotation (negative value) with the literature data [14], [15], [16]; this assignment is in agreement with all other known natural glycosides comprising the same aglycone. As a result, the new compound 2 was assigned as 13-hydroxylabda-7,14-diene 13(R)-O-a-L-arabinopyranoside (2).…”

supporting

confidence: 79%

Diterpene Glycosides fromEgletes viscosa

Lee

Graf

et al. 2005

Planta med

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A phytochemical investigation of the CHCl (3)-soluble extract of the entire plant of Egletes viscosa (Asteraceae), collected in Peru, afforded two new labdane glycosides, 13-hydroxy-7-oxolabda-8,14-diene 13( R)- O-alpha- L-arabinopyranoside and 13-hydroxylabda-7,14-diene 13( R)- O-alpha- L-arabinopyranoside, along with four known compounds. The structures of the new compounds were elucidated by spectroscopic and chemical methods.

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supporting

confidence: 79%

Diterpene Glycosides fromEgletes viscosa

Lee

Graf

et al. 2005

Planta med

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“…21 The sulphated glycopeptidolipid from the Mycobacterium avium cell wall (10) has a 6-deoxy-L-talose residue. 22 Some terpenoids were also found conjugated to L-sugars such as L-idose from Aster spathulifolius Maxim (11) 23 and L-galactose from the marine octocoral Muricea cf. purpurea.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of l-hexoses and their related biomolecules

2013

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Carbohydrates either conjugated or as free entities are major players in numerous biological processes. The desire to comprehend the nature of their functions and further develop therapeutic and diagnostic applications has fuelled the recent upsurge in the glycoscience field. Mainly accessed through chemical synthesis, homogeneous and well-defined sugar constructs are on high demand for structure-activity evaluation. Although the d-sugars, particularly the d-hexoses, have dominated the carbohydrate landscape, L-hexoses also attracted attention because they are known components of important polysaccharides, antibiotics, and other natural products. Nonetheless, the L-hexose-based materials needed for making building blocks for sugar assemblies are rare and are usually expensive if commercially available. Thus, intense efforts were focused on the development of innovative and reliable methods for the acquisition of L-hexoses and their derivatives. This review outlines several efficient and cost-effective routes for the chemical syntheses of L-hexoses, particularly focusing on approaches that utilize commercially abundant sugars as starting materials. A sampling of the applications of the generated L-hexoses in preparing biologically relevant compounds is also provided.

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“…For instance, Yersinia enterocolitica serovars O:1.2a,3 and O:2a,2b,3 have a trisaccharide repeating unit (i.e., 6 ) consisting only of 6‐deoxy‐ L ‐altrose units 7. The tetracyclic triterpene Datiscoside C ( 7 ) isolated from the plant Datisca glomerata contains a 6‐deoxy‐ L ‐alloside,8 and 6‐deoxy‐ L ‐idose occurs in the diterpene glycoside 8 isolated from Aster spathulifolius Maxim 9 . L ‐Rhamnose (6‐deoxy‐ L ‐mannose) and L ‐fucose (6‐deoxy‐ L ‐galactose) are common L ‐sugars widely present in Nature.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of All Eight Stereoisomeric 6‐Deoxy‐L‐hexopyranosyl Donors – Trends in Using Stereoselective Reductions or Mitsunobu Epimerizations

2014

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The synthesis of all eight rare but biologically important 6‐deoxy‐L‐hexoses as their thioglycoside glycosyl donors starting from the commercially available L‐rhamnose or L‐fucose is reported. The synthesis of all eight 6‐deoxy‐L‐hexoses was accomplished using a variety of epimerization methods, which revealed some general trends. The stereoselective reduction of 4‐oxopyranosides could be predicted by the Cram chelation model, while Mitsunobu conditions led to elimination in some substrates.

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Labdane diterpene glycosides with 6-deoxy-L-idose from Aster spathulifolius Maxim.

Cited by 29 publications

References 13 publications

Diterpene Glycosides fromEgletes viscosa

Diterpene Glycosides fromEgletes viscosa

Synthesis of l-hexoses and their related biomolecules

Synthesis of All Eight Stereoisomeric 6‐Deoxy‐L‐hexopyranosyl Donors – Trends in Using Stereoselective Reductions or Mitsunobu Epimerizations

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