Comparison of some secondary metabolite content in the seventeen species of the Boraginaceae family

Abstract

Context: The Boraginaceae family comprises plants that have important therapeutic and cosmetic applications. Their pharmacological effect is related to the presence of naphthaquinones, flavonoids, terpenoids, phenols, or purine derivative – allantoin.Objective: In the present study, comparison of some secondary metabolite content and phytochemical relationship between 17 species of the Boraginaceae family were analyzed.Materials and methods: High performance capillary electrophoresis (HPCE) was used to perform a chemometric analysis in the following Boraginaceae species: Anchusa azurea Mill., Anchusa undulata L., Borago officinalis L., Buglossoides purpurocaerulea (L.) I.M. Johnst., Cerinthe minor L., Cynoglossum creticum Mill, Echium italicum L., Echium russicum J.F. Gmel., Echium vulgare L., Lindelofia macrostyla (Bunge) Popov (syn. Lindelofia anchusoides (Lindl.) Lehm.), Lithospermum officinale L., Nonea lutea (Desr.) DC., Omphalodes verna Moench (syn. Cynoglossum omphaloides L.), Pulmonaria mollis Wulfen ex Hornem., Pulmonaria obscura Dumort., Symphytum cordatum Waldst. & Kit ex Willd., and Symphytum officinale L.Results: Six active compounds in shoot extracts (allantoin, p-hydroxybenzoic acid, rutin, hydrocaffeic acid, rosmarinic acid, and chlorogenic acid) and four compounds in root extracts (allantoin, hydrocaffeic acid, rosmarinic acid, and shikonin) were identified. The presence and abundance of these compounds were used for the characterization of the species and for revealing their phytochemical similarity and differentiation.Discussion and conclusion: The present study provides the first comprehensive report of the extraction and quantification of several compounds in Boraginaceae species (some of them for the first time). Among the 17 species studied, species with potentially high pharmacological activity were recognized.

De Novo Transcriptome Assembly and Characterization of Lithospermum officinale to Discover Putative Genes Involved in Specialized Metabolites Biosynthesis

“…Unigenes annotated as HMGCS1, HMGCR, PMVK, and MVD, the four key enzymes of MVA pathway, and PGT, the key enzyme for shikonin biosynthesis, were highly expressed in the root tissue compared to stem and leaf of L. officinale. Previous studies have shown shikonin accumulation in the root of L. officinale [5] while MVA biosynthesis pathway is known to be highly upregulated and specific to the roots. Expression trend for unigenes assigned to shikonin biosynthetic pathway thus is consistent with previously reported metabolome analysis for different tissues of L. officinale.…”

“…To gain an insight on the highly active biological processes in leaf, stem, and root of L. officinale, RNA-sequencing reads for each tissue were mapped on the de novo transcriptome assembly and unigene expression was measured in FPKM value. Among highly expressed unigenes (FPKM value > 50), 500 unigenes were common across all tissues, while 186, 333, and 346 unigenes were specific to the Zeatin biosynthesis (5) Monobactam biosynthesis (5) Valine, leucine and isoleucine biosynthesis (8) Various types of N-glycan biosynthesis (13) Biotin metabolism (10) N-Glycan biosynthesis (18) One carbon pool by folate (14) Pantothenate and CoA biosynthesis (17) Flavonoid biosynthesis (13) Other glycan degradation (8) Selenocompound metabolism (11) Geraniol degradation (5) Arginine biosynthesis (21) Riboflavin metabolism (14) Aminoacyl-tRNA biosynthesis (22) Sphingolipid metabolism (16) Fatty acid elongation (10) Biosynthesis of unsaturated fatty acids (11) Terpenoid backbone biosynthesis (27) Fatty acid biosynthesis (14) alpha-Linolenic acid metabolism (11) Citrate cycle (TCA cycle) (18) Alanine, aspartate and glutamate metabolism (29) Phenylalanine, tyrosine and tryptophan biosynthesis (27) Inositol phosphate metabolism (25) Metabolism of xenobiotics by cytochrome P450 (8) Drug metabolism -cytochrome P450 (7)…”

“…De Novo Transcriptome Assembly and Characterization of Lithospermum officinale to Discover Putative Genes Involved in Specialized Metabolites Biosynthesis* the roots [5] with proven antibacterial, anti-inflammatory, antitumor, and anti-angiogenesis properties [2]. Naphthoquinone compounds are also used as a source of dye in the food, textile, and cosmetic industries for their characteristic brilliant red color.…”

“…Medicinal properties and industrial applications of shikonin and its derivatives have led to increase in its demand and have inspired several studies focused on increasing its synthesis through genetic engineering, chemosynthesis, and two-stage culture biosynthesis [6]. Besides shikonin, several specialized metabolites including rutin, pyrrolizidine alkaloid, allantoin, chlorogenic acid, rosmarinic acid, and lithospermic acid, among others, are accumulated in L. officinale [5]. Despite the wide pharmacological importance of these metabolite classes, their biosynthetic pathways are still unclear.…”

TLC-densitometric analysis of allantoin in Symphytum officinale L. roots

“…Several chromatographic methods have been developed for determination of allantoin in biological material, while only some of them refer to its quantification in complex plant material. Thus far, the analysis of allantoin in plant matrix was only performed by HPLC in Zea mays and rice (5)(6)(7) and high-performance capillary electrophoresis (HPCE) in comfrey root (8). Due to their simplicity, relatively low cost and short time of analysis, TLC methods are widely used for the separation of secondary metabolites in plant extracts.…”