Nitrile-Containing Phenolic Glucosides from the Leaves of Glochidion acuminatum

Abstract

From the EtOAc-soluble fraction of a MeOH extract of the leaves of Glochidion acuminatum, six new compounds along with five known ones were isolated. The structures of the new compounds were elucidated to be two gallates, a p-hydroxybenzoate and an (S)-2-(4-hydroxycyclohex-1-en-1-yl)acetate of a nitrile-containing phenolic glucoside, methyl 2-(2-hydroxyphenyl)acetate β-D-glucopyranoside, and (S)-methyl 2-[4-sulfooxycyclohex-1-en-1-yl]acetate on the basis of spectroscopic evidence.

Phenolic glycosides from the peels of durian fruits Durio zibethinus L.

“…Similarly, an HMBC cross‐peak from H‐1′ ( δ H 5.66) to the carbonyl carbon ( δ C 166.6) indicated that the glucose is connected to C‐7 of the p ‐hydroxybenzoyl aglycone. From the above observation, the 1 H‐ and 13 C NMR data of 1 were found to be similar as those of grevilloside J, [ 5 ] except for the replacement of the p ‐hydroxybenzyl group in grevilloside J by the p ‐hydroxybenzoyl group in 1 . The relative configuration of 1 was suggested as shown in Fig.…”

Distinctive Arbutin‐Containing Markers: Chemotaxonomic Significance and Insights into the Evolution of Proteaceae Phytochemistry

“…Taken together, the biosynthetic connections within the classes of unusual arbutin ester moieties that we have identified from relictual Proteaceae and more successful taxa from this family are consistent with the chemotaxonomic significance of these unusual molecules (Figure 5). [9,20h,21b,22,24,28–30,31] Specifically, we note that arbutin derivatives containing phenylalanine‐derived esters (blue fragments) have only been identified in Bellendena , Persoonia , Cenarrhenes , Protea , Agastachys , Helicia , Orites , Helicopsis , Grevillea , and Hakea genera to date (Figure 5). All genera are found in the family Proteaceae and these members span the phylogeny, including relictual and more successful members.…”

“…Benzoyl acetate or oxidized coumaroyl substituents (e. g., blue fragments within arbutin esters 1 c , 1 d , 1 i – 1 k , and 4 a – 4 d ) likely derive from the biosynthesis of phenylalanine [26] . Robustaside E ( 4 a ) was isolated from Grevillea ‘ Poorinda Queen’, [22] grevillosides L and M ( 4 b and 4 c ) were obtained from Grevillea robusta , [21b] and compound 4 d was found in Protea neriifolia [20h] . All of these are plant species are from the family Proteaceae.…”

Natural Products Containing the Nitrile Functional Group and Their Biological Activities

“…Arg. (Euphorbiaceae) 49 (Figure 9). The degalloylated analogue of 90 had been previously isolated from Ehretia philippinensis A. DC.…”