Identification of Abies sibirica L. Polyprenols and Characterisation of Polyprenol-Containing Liposomes

Abstract

The needles of conifer trees are one of the richest sources of natural polyprenols. Polyprenol homologs from Abies sibirica L. lipophilic 80% purified extract were analyzed and quantified. In total, 10 peaks (Prenol-11 to Prenol-20) were observed in the ultra-high-performance liquid chromatography–diode array detector (UHPLC-DAD) chromatogram of Siberian fir with the most abundant compound being Prenol-15 (relative amount 37.23 + 0.56% of the total polyprenol yield). Abies sibirica L. polyprenol solubility and incorporation efficiency into liposomes were studied in various commercially available lecithin mixtures (Phosal IP40, Phosal 75SA, and Lipoid P45). The resulting multilamellar polyprenol liposomes were morphologically characterized by Light and Transmission Electron Microscopy, and the liposome size was discovered to be polymodal with the main peak at 1360 nm (90% of the volume). As polyprenols are fully soluble only in lipids, a liposomal formulation based upon co-solubilization and a modified ethanol injection method of polyprenols into the ethanol-phospholipid system was developed for the entrapment and delivery of polyprenols for potential commercial applications in food supplement and cosmetic industries.

A new approach for analysis of polyprenols by a combination of thin‐film chemical deposition and matrix‐assisted laser desorption/ionization time‐of‐flight mass spectrometry

“…The m/z values of the remaining signals in the mass spectrum were also in good agreement (mass error ≤3 ppm) with the theoretical values of [M − H + Ba] + ions of other polyprenol homologues (from Pre‐12 to Pre‐20). The pattern of Abies sibirica L. polyprenols acquired with the proposed approach was consistent with those obtained by Vanaga et al in a study of the lipophilic extract from Abies sibirica L. using a combination of ultrahigh‐performance liquid chromatography with diode‐array detection and high‐resolution MS 12 …”

“…Nowadays, the main approach to the quantitative and qualitative analysis of polyprenols is reversed‐phase high‐performance liquid chromatography (RP‐HPLC) with ultraviolet detection 9,10 or electrospray ionization (ESI) mass spectrometry 11,12 . Among other chromatographic techniques, supercritical fluid chromatography 13 and thin‐layer chromatography 14 are used for characterization of the polyprenol profile in biological samples of different origin.…”

The Biomedical Importance of the Missing Pathway for Farnesol and Geranylgeraniol Salvage

“…Plants are probably the group of organisms where these metabolites have been most extensively studied [34]. Plants such as the acacia tree, Acacia caven, contain great amounts of farnesol (FOH) [35]; geranylgeraniol (GGOH) is particularly abundant in annatto (Bixa orellana) [36], as is solanesol in Nicotiana tabacum [37], and polyprenols of 13 isoprenic units in conifer extracts [38]. Medium-length isoprenoid alcohols of 3-4 isoprenic units in length serve as components of plant membranes [23,39].…”

Development and validation of the chromatography-mass spectrometry technique for polyprenols quantitative assessment

“…Полипренолы представляют собой класс природных длинноцепочечных изопреноидных спиртов с общей формулой Н-(С 5 Н 8 ) n -H, где n -число изопреновых единиц, соединенных в положении «голова -хвост», с гидроксильной группой на одном конце и атомом водорода на другом [1]. Полипренолы являются природными биорегуляторами, принимающими непосредственное участие в синтезе гликопротеинов клеточных мембран, обладают выраженной гепатопротекторной активностью, а также иными видами фармакологического действия, что обуславливает интерес к данным веществам как к перспективному лекарственному средству [2].…”

“…Мицеллы из производных полипренолов могут быть рассмотрены в качестве системы доставки лекарственных средств [13]. Основными источниками получения субстанции полипренолов являются гинкго двулопастный (Ginkgo biloba L.) и хвойные деревья, такие как пихта сибирская (Abies sibirica L.), ель обыкновенная (Picea abies L.), сосна сибирская (Pinus sibirica L.), сосна обыкновенная (Pinus sylvestris L.) [1]. Готовые извлечения из растительного сырья представляют собой сложные смеси гомологов полипренолов и сопутствующих веществ, что требует внедрения особых подходов к стандартизации полученных продуктов.…”