Phytochemical Analysis of the Fruits of Sea Buckthorn (Hippophae rhamnoides): Identification of Organic Acid Derivatives

Abstract

Hippophae rhamnoides L. (Elaeagnaceae), commonly known as “Sea buckthorn” and “Vitamin tree”, is a spiny deciduous shrub whose fruit is known for its nutritional composition, such as vitamin C, and is consumed as a dietary supplement worldwide. As part of our ongoing efforts to identify structurally new and bioactive constituents from natural resources, the phytochemical investigation of the extract of H. rhamnoides fruits led to the isolation of one malate derivative (1), five citrate derivatives (2–6), and one quinate derivative (7). The structures of the isolated compounds were elucidated by analysis of 1D and 2D nuclear magnetic resonance (NMR) spectroscopic data and high-resolution electrospray ionization (HR-ESI) liquid chromatography–mass spectrometry (LC/MS) data. Three of the citrate derivatives were identified as new compounds: (S)-1-butyl-5-methyl citrate (3), (S)-1-butyl-1′-methyl citrate (4), and (S)-1-methyl-1′-butyl citrate (6), which turned out to be isolation artifacts. The absolute configurations of the new compounds were established by quantum chemical electronic circular dichroism (ECD) calculation, which is an informative tool for verifying the absolute configuration of organic acid derivatives. The isolated compounds 1–7 were evaluated for their stimulatory effects on osteogenesis. Compounds 1, 3, 4, 6, and 7 stimulated osteogenic differentiation up to 1.4 fold, compared to the negative control. These findings provide experimental evidence that active compounds 1, 3, 4, 6, and 7 induce the osteogenesis of mesenchymal stem cells and activate bone formation.

Oligo-FISH Can Identify Chromosomes and Distinguish Hippophaë rhamnoides L. Taxa

“…Its natural habitats include severe environments with excessive salinity, drought, cold, and heat [ 3 ]. H. rhamnoides is known for its nutritional, medicinal, and ecological values [ 4 ]; it has been shown to improve the health of consumers. Moreover, its berries, which are edible, are used as a general body-toning agent [ 3 ].…”

Metabolite and Bioactive Compounds Profiling of Meteora Sea Buckthorn Berries through High-Resolution NMR Analysis

“…The target of many analytical studies in the field of natural products is the organic acid composition of berries and seeds. Organic acids as bioactive components are known for their contribution in fresh fruit acidity and SB juice sourness [34]. Our analysis reveals seven organic acids.…”

Phytochemistry and pharmacology of sea buckthorn (Elaeagnus rhamnoides; syn. Hippophae rhamnoides): progress from 2010 to 2021

“…In addition, several other compounds (Fig. 10 ) were isolated from different parts of SB, including 1,5-dimethyl citrate ( 97 ), (S)-dimethyl malate ( 98 ), as well as norsesquiterpenoids vomifoliol ( 94 ) and ( +)-dehydrovomifoliol ( 95 ) from SB fruit (Baek et al 2020 ; Lee et al 2021 ); vomifoliol was also purified from SB leaves (Yang et al 2013 ), and vomifoliol 9- O -β-D-apiofuranosyl-(1 → 6)-β-D-glucopyranoside ( 96 ) from the seeds of H. rhamnoides ssp. sinensis (Gao et al 2015 ).…”