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.
Highlights
Hippophae rhamnoides L. (Elaeagnaceae), known as “Sea buckthorn” and “Vitamin tree”, is a spiny deciduous shrub
liquid chromatography–mass spectrometry (LC/MS)-based analysis combined with our in-house built UV library, and Thin-layer chromatography (TLC) analysis of the solvent-partitioned fractions suggested that the BuOH-soluble fraction contained the majority of the organic acid derivatives
Phytochemical examination of the extracts of H. rhamnoides fruits resulted in the isolation of seven organic acid derivatives: one malate derivative (1), five citrate derivatives (2–6), and one quinate derivative (7)
Summary
Hippophae rhamnoides L. (Elaeagnaceae), known as “Sea buckthorn” and “Vitamin tree”, is a spiny deciduous shrub. (Elaeagnaceae), known as “Sea buckthorn” and “Vitamin tree”, is a spiny deciduous shrub. It has historically been used for medicinal purposes worldwide, especially in Central and Southeastern Asia. In China, its pharmacological use was revealed more than a thousand years ago through the records of Sibu Yidian from the Tang Dynasty and Jing Zhu Ben Cao from the Qing dynasty [1]. Its bark and fruits have been used as Tibetan folk medicine to treat pulmonary disorders, cough, fever, and tumors [3]. For the past 50 years, several medicinal preparations based on H. rhamnoides have been clinically used to treat radiation damage, oral inflammation, burns, and gastric ulcers, and more than 300 preparations have been reported in the literature [4]
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