Glycosylated constituents isolated from the trunk of Abies holophylla and their anti-inflammatory and neurotrophic activity

Bioactive Phenylpropanoid Glycosides, Dimers, and Heterodimers from the Bark of Cinnamomum cassia (L.) J.Presl

“…The coupling constants of relevant protons ( J H‑1′–H‑2′ = 7.8 Hz, J H‑2′–H‑3′ = 8.0 Hz, J H‑3′–H‑4′ = 9.0 Hz, J H‑4′–H‑5′ = 7.9 Hz, and J H‑1″–H‑2″ = 3.0 Hz) and the key ROESY correlations (Figure ) between H-1″ and Ha-4″/O H -3″ and between H-2″ and Hb-4″ showed that compound 1 contained the 6- O -(β- erythro -apiofuranosyl)-β-glucopyranosyl group. The absolute configurations of the glucopyranosyl and apiofuranosyl units in isolate 1 were established by acid hydrolysis. , The chromatographic peaks of derivative products of the glucopyranosyl, apiofuranosyl, l -Glc, d -Glc, and d -Api (derived from d -apiofuranosyl-containing astrapterocarpanoside A) respectively appeared at t R 19.5, 31.2, 17.9, 19.6, and 31.3 min, which showed that the glucopyranosyl and apiofuranosyl were d -Glc and d -Api (for HPLC analysis conditions, see the related section in the Supporting Information). The comparison of experimental 13 C NMR data of 1 and calculated 13 C NMR data of 1′ -(1′ R ,2′ R ,3′ S ,4′ S ,5′ R ,1″ R ,2″ R ,3″ R ), 1′ -(1′ R ,2′ R ,3′ S ,4′ S ,5′ R ,1″ S ,2″ R ,3″ S ), 1′ -(1′ R ,2′ R ,3′ S ,4′ S ,5′ R ,1″ R ,2″ R ,3″ S ), and 1′ -(1′ R ,2′ R ,3′ S ,4′ S ,5′ R ,1″ S ,2″ R ,3″ R ) confirmed the attribution of the absolute configuration of its apiofuranosyl as (1″ R , 2″ R , 3″ R ) (Figure ).…”

“…We described the specific details for enzymatic hydrolysis, acid hydrolysis, alkaline hydrolysis, quantum chemical calculation, DPPH radical scavenging assay, oxygen radical absorbance capacity assay, α-glucosidase inhibitory assay, and molecular docking in the relevant sections of the Supporting Information.…”

“…The absolute configurations of the glucopyranosyl and apiofuranosyl units in isolate 1 were established by acid hydrolysis. 22,30 The chromatographic peaks of derivative products of the glucopyranosyl, apiofuranosyl, L-Glc, D-Glc, and D-Api (derived from D-apiofuranosyl-containing astrapterocarpanoside A) 30 respectively appeared at t R 19.5, 31.2, 17.9, 19.6, and 31.3 min, which showed that the glucopyranosyl and apiofuranosyl were D-Glc and D-Api (for HPLC analysis conditions, see the related section in the Supporting Information). The comparison of experimental 13 C NMR data of 1 and calculated 13 C NMR data of 1′-…”

“…The optical rotation of 10a ([α] D 25 −19.1 (c 0.02, MeOH)) was similar to that of (8R,8′R)-secoisolariciresinol ([α] D 20 −37.5 (c 0.10, MeOH)), which showed that the absolute configurations in 10a were (8R, 8′R). 34 A precise comparison of its 1D NMR data with those of 1−3 and acid hydrolysis 22 Compound 11 was isolated as a brown oil, and the molecular formula of 11 was determined as C 18 H 18 O 4 by HRESIMS. The planar structure of isolate 11 was built up by a detailed analysis of NMR data of 11 (Table S11, Supporting Information).…”

Abies holophylla Leaf Essential Oil Alleviates Allergic Rhinitis Based on Network Pharmacology

“…Abies holophylla is an evergreen coniferous species which is distributed widely in East Asia [27]. In traditional medicine, Abies species were widely used for treating pulmonary diseases, colds, and rheumatic diseases [28,29]. Abies species contain diverse sources of volatile bioactive compounds such as phenols, terpenoids, and sesquiterpenoids [30,31].…”