Phenylpropanoids as the biologically active compounds of the medicinal plants and phytopharmaceuticals

In the present paper are discussed the results of the investigations of the phenylpropanoids of the medicinal plants which are of the great interest as the sources of the neurotropic, adaptogenic, immunostimulating, antioxidative, and hepatoprotective preparations. There were shown the necessity of using of the standard samples of triandrin (Rhodiola rosea L. tissue cultures, Salix viminalis L. barks), rosavin (Rhodiola rosea L. rhizomes), syringin, or eleutheroside B [Eleutherococcus senticosus (Rupr. et Maxim.) Maxim. rhizomes, Syringa vulgaris L. barks], and silybin [Silybum marianum (L.) Gaertn. fruits] for purpose of the standardization of the corresponding drugs and pharmaceuticals. It was shown also the significance of γ-schizandrin, chicoric acid, rosmarinic acid and lavandoside for purposes of the standardization of raw material and preparations of Schizandra chinensis Baill. fruits and seeds, Echinacea purpurea (L.) Moench. herbs, Melissa officinalis L. herbs and Lavandula spica L. flowers respectively.

Dualistic Properties of Cosmetic Formulations Based on Phenylpropanoids from <i>Ajuga reptans</i>

Our continued interest in the research and development of cosmetic active ingredients deriving from natural sources led us to investigate the potential of a purified extract of Ajuga reptans, a plant belonging to the family Labiatae and known for its traditional use in skin healing. The extracts deriving from a biotechnology platform are composed by meristematic cell culture, developed in the frame of a NTFP (non-timber forest product) project, and characterized by high content in phenylpropanoid, of which teupolioside represents the majority component. The latter is a phenylpropanoid glucoside, structurally correlated echinacoside and known in the literature for the antioxidant properties. This study was conducted with the purpose of evaluating the applicability of the Ajuga reptans extract within different cosmetic formulations. In particular, Photochemiluminescence (PCL) was used to proof the antioxidant capacity of cosmetic formulations containing the product, in relation to the change of the title of teupolioside. Furthermore, UVA and UVB filtering properties were also investigated. The results of the study showed relevantly antioxidant capacity of the finished formulation against superoxide anion, which is the main reactive oxygen species responsible for skin aging and significant synergic capacities to filter UV radiation.

Two new phenylpropanoids from Micromelum integerrimum

AIM: To investigate the chemical and bioactive constituents from the stems and leaves of Micromelum integerrimum. METHOD: The chemical constituents were isolated and purified by silica gel, Sephadex LH-20, and HPLC. Their structures were mainly elucidated on the basis of extensive 1D- and 2D-NMR spectroscopy and mass spectrometry. Their cytotoxicity and antimicrobial activities were tested by the SRB and turbidimetric methods, respectively. RESULTS: Two new phenylpropanoids and two known coumarins were obtained, and their structures were identified as microintegerrin A(1), microintegerrin B(2), scopoletin(3), and scopolin(4). All of the compounds were tested for their cytotoxicity against three cancer cell lines(HeLa, A549, and BGC-823) and for antimicrobial activity against the fungus Candida albicans and the bacterium Staphylococcus aureus. CONCLUSION: Two new phenylpropanoids 1 and 2 were isolated and identified from the stems and leaves of M. intgerrimum. None of the compounds showed cytotoxic or antimicrobial activity at the tested concentration of 20 ?g·mL–1.

Response Mechanisms to Flooding Stress in Mulberry Revealed by Multi-Omics Analysis

Abiotic stress,including flooding,seriously affects the normal growth and development of plants.Mulberry(Morus alba),a species known for its flood resistance,is cultivated worldwide for economic purposes.The transcriptomic analysis has identified numerous differentially expressed genes(DEGs)involved in submergence tolerance in mulberry plants.However,a comprehensive analyses of metabolite types and changes under flooding stress in mulberry remain unreported.A non-targeted metabolomic analysis utilizing liquid chromatographytandem mass spectrometry(LC-MS/MS)was conducted to further investigate the effects of flooding stress on mulberry.A total of 1,169 metabolites were identified,with 331 differentially accumulated metabolites(DAMs)exhibiting up-regulation in response to flooding stress and 314 displaying down-regulation.Pathway enrichment analysis identified significant modifications in many metabolic pathways due to flooding stress,including amino acid biosynthesis and metabolism and flavonoid biosynthesis.DAMs and DEGs are significantly enriched in the Kyoto Encyclopedia of Genes and Genomes(KEGG)pathways for amino acid,phenylpropanoid and flavonoid synthesis.Furthermore,metabolites such as methyl jasmonate,sucrose,and D-mannose 6-phosphate accumulated in mulberry leaves post-flooding stress.Therefore,genes and metabolites associated with these KEGG pathways are likely to exert a significant influence on mulberry flood tolerance.This study makes a substantial contribution to the comprehension of the underlying mechanisms implicated in the adaptation of mulberry plants to submergence.

The chromosome-scale genome assembly of Jasminum sambac var. unifoliatum provides insights into the formation of floral fragrance

Jasmine [Jasminum sambac(L.) Ait.], a tropical and subtropical plant emits a sweet, heady fragrance during flower opening. However, the molecular mechanisms underlying this phenomenon remain largely unknown. In the present study, integrated Illumina sequencing, Pacbio sequencing, and high-throughput chromatin conformation capture(Hi-C) scaffolding was used to generate a 495.60 Mb genome assembly of J.sambac var. unifoliatum cultivar ‘Fuzhou Single-petal’(JSU-FSP), with contig N50 of 16.88 Mb;96.23% of the assembly was assigned to 13 pseudochromosomes. The genome harbors 30 989 protein-coding genes, and 49.47% of the assembled sequences are repetitive sequences. The analysis of duplication modes showed that 51% of genes were duplicated through dispersed duplication, and expanded gene families are mainly involved in photosynthesis, which may be responsible for the light-loving characteristic specific to jasmine. Transcriptome analysis revealed that at least 35 structural genes involved in the biosynthesis of volatile terpenes(VTs), volatile phenylpropanoid/benzenoids(VPBs),fatty acid-derived volatiles(FADVs), and indole were highly expressed in the flower-opening stage, both preharvest and postharvest, and are proposed to be important in endowing flower aroma. Additionally, at least 28 heat shock protein(HSP) and 11 β-glucosidase(BGLU) genes may be involved in the formation of floral fragrance. These findings provide insights into the formation of the floral fragrance of jasmine and will promote germplasm utilization for breeding improved jasmine varieties.

Widely Untargeted Metabolome Profiling Provides Insight into Browning and Nutritional Quality Changes in Short-Term Stored Fresh-Cut Potato(Solanum tuberosum L.)Shreds

Potato(Solanum tuberosum L.)is susceptible to enzymatic browning after fresh processing,resulting in color change and potential alteration in the nutritional quality.In this study,a popular potato cultivar,Feiwuruita,was used to profile the metabolites involved in color and nutritional quality changes in fresh shreds stored at 0 and 4 h at 25°C(designated CK and CK4H,respectively).The shreds turned brown within 4 h of storage.In all,723 metabolites consisting 12 classes of compounds were detected in the samples,largely lipids,phenolic acids,alkaloids,amino acids and derivatives,flavonoids,organic acids,nucleotides and derivatives.Of these,163 metabolites accumulated differentially between CK and CK4H shreds.Polyphenolic compounds(phenolic acids and flavonoids)mostly increased in the shreds after 4 h storage.Conversely,the short-term storage drastically reduced lipid compounds(25 LysoPC and 19 LysoPE),while essential alkaloids and terpenoid compounds that are beneficial to human health increased in accumulation.The findings present global metabolome and nutritional composition changes in short-term stored shreds of Feiwuruita.This study provides important foundation for future studies on browning prevention/reduction and for better utilization of Feiwuruita.

Induced Accumulation of Polyphenolics and Flavonoids in Cyanobacteria under Salt Stress Protects Organisms through Enhanced Antioxidant Activity

Induced accumulation of polyphenolics and flavonoids in cyanobacterial strains grown under different salt concentrations is correlated with their growth under stress conditions and enhanced antioxidant activity. Plectonema boryanum, Hapalosiphon intricatus, Anabaena doliolum and Oscillatoria acuta grown for 21 days under different salt concentrations (80, 160, 240, 320 and 400 mM) in BG11 medium showed differential growth responses in terms of biomass, total protein, chlorophyll content, total content of polyphenol, flavonoid and carotenoid, accumulation of phenolic acids (gallic, caffeic, chlorogenic, ferullic and vanillic) and flavonoids (rutin and quercetin). Cyanobacterial extracts showed prominent free radical scavenging antioxidant activity (AOA) in terms of % DPPH discoloration. Highly significant (p < 0.05) and strong correlation was found between TPC and AOA (r = 0.974). Other positive but non-significant (p < 0.05) correlations were observed between AOA and gallic acid (r = 0.893) and AOA and caffeic acid (r = 0.931). Significant and strong correlation was also observed between gallic and caffeic acid (r = 0.973). Positive but lesser magnitude correlations were recorded between TPC and caffeic acid (r = 0.905), TPC and gallic acid (r = 0.920), gallic and vanillic acid (r = 0.916) and caffeic and vanillic acid (r = 0.814). An integrated combination of growth parameters, salt-induced accumulation of phenylpropanoids and stress-derived subsequent antioxidant property of cyanobacterial extracts is thought to provide evidence that secondary metabolic changes can act as the possible alternative mechanism to overcome stress-induced damages in cells.

New Amides and Phenylpropanoid Glucosides from the Fruits of Piper retrofractum

Two new amides(E)-N-cinnamoyl-2-methoxypiperidine(1)and(R)-1-(2-oxopyrrolidin-3-yl)-5,6-dihydropyridin-2(1H)-one(2),four new amide glucosides,retrofractosides A-D(3-6),and two new phenylpropanoid glucosides,retrofractosides E(7)and F(8),together with 24 known compounds(9-32)were isolated from the fruits of Piper retrofractum.The chemical structures of these new compounds were elucidated based on extensive spectroscopic analysis.All of these isolates(1-32)were evaluated for inhibitory activity against mouse platelet aggregation induced by the peptide AYPGKF-NH2.(E)-N-(Tetrahydro-2H-pyran-2-yl)cinnamamide(9)showed a weak inhibitory efect,with an inhibition ratio of 52.0%at a concentration of 150μM.

Verbascoside—A Review of Its Antitumor Activities

Cancer is a set of diseases including abnormal growth of cells that can spread to another tissue. Verbascoside (or acteoside) is a naturally occurring, water-soluble secondary metabolite with significant biological properties, which is distributed widely in plant kingdom. Verbascoside is pharmacologically active compounds with many recent evidences that support its biological activities and safety. This review focuses on the recent studies that concerned with the antitumor activities of verbascoside alone and as a synergistic agent as well as nanoproduct. It also shows the latest advances in its antitumor effects, cytotoxic selectivity and its efficiencies in treating cancer, in vitro and/or vivo.

Studies on chemical constituents of Ailanthus altissima(Mill.)Swingle and their antioxidant activity

Ailanthus altissima(Mill.)Swingle is a deciduous tree belonging to the Simaroubaceae family.The root and stem bark are traditional medicines for treating many diseases,such as diarrhea,dreaminess and intestinal tract bleeding.Phytochemical investigation of Ailanthus altissima(Mill.)Swingle led to the isolation of eight compounds.Chemical structures of these compounds were identified by analyzing their NMR spectroscopic data.Among them,compounds 1,4,5,6 and 8 were isolated from Ailanthus Desf.for the first time.The antioxidant activities of these compounds were determined by DPPH radical scavenging method.

A novel phenylpropanoid glycosides and a new derivation of phenolic glycoside from Paris Polyphylla var. yunnanensis

A novel phenylpropanoid glycosides 1, named parispolyside E and a novel derivation of phenolic glycoside 2, named parispolyside G, as well as two known flavonoid glycosides were isolated from the rhizome of Paris polyphylla var. yunnanensis. Their structures were elucidaed by spectroscopic methods.

Antioxidant and Cytotoxic Phenolic Compounds of Areca Nut(Areca catechu)

Areca catechu L.（Palmae）, commonly known as an important economical seed crop, is widely culti- vated in tropical and subtropical areas, including India, Southeast Asia, East Africa and New Guinea. Areca nut（frequently known as betel nut） is the ripe fruit of the tree A. catechu. Areca nut can be chewed and it is a common masticatory in tropical and subtropical countries. It was estimated in the early 1990s that 10% to 20% of the world＇s population chewed betel quid daily. Areca nut is commonly used in folklore medicine for treatment of various diseases such as dyspep sia, constipation, beriberi and oedema.

Effects of thiamine on Trichothecium and Alternaria rots of muskmelon fruit and the possible mechanisms involved

The effects of thiamine against pink and black spot rots caused by Trichothecium roseum and Alternaria alternata and modulation on the metabolism of reactive oxygen species （ROS） and phenylpropanoid pathway were investigated in this paper. In vitro test indicated that thiamine significantly inhibited mycelia growth and spore germination of T. roseum and A. alternata. Thiamine at 100 mmol L-1 effectively inhibited lesion development of muskmelon fruit inoculated with T. roseum or A. alternata, enhanced production rate of O2; and H2O2 content, activities of catalase （CAT）, ascorbate peroxidase （APX） and glutathione reductase （GR） in muskmelon fruit. Thiamine also affect phenylpropanoid pathway in muskmelon fruit by increasing the activities of phenylalanine ammonia lyase （PAL） and peroxidase （POD）, the content of total phenolic compounds, flavonoids and lignin. These results suggest that the effects of thiamine on pink and black spot rots in muskmelon fruits are associated with its direct fungitoxic against the pathogens and the modulation of O2- and H2O2 production, elimi- nating enzymes and phenylpropanoid pathway.

Isolation and Expression Analysis of Two Genes Encoding Cinnamate 4-Hydroxylase from Cotton(Gossypium hirsutum)

Two genes （GhC4H1 and GhC4H2） that encode putative cotton cinnamate 4-hydroxylases that catalyze the second step in the phenylpropanoid pathway were isolated from developing cotton fibers. GhC4H1 and GhC4H2 each contain open reading frames of 1 518 base pairs （bp） in length and both encode proteins consisting of 505 amino acid residues. They are 90.89% identical to each other at the amino acid sequence level and belong to class I of plant C4Hs. GhC4H1 and GhC4H2 genomic DNA are 2 247 and 2 161 bp long, respectively, and contain two introns located at conserved positions relative to the coding sequence. GhC4HI and GhC4H2 promoters were isolated and found to contain many cis-elements （boxes P, L and AC-1 element） previously identified in the promoters of other phenylpropanoid pathway genes. Histochemical staining showed GUS expression driven by the GhC4H1 and GhC4H2 promoters in ovules and fibers tissues. GhC4H1 and GhC4H2 were also widely expressed in other cotton tissues. GhC4H2 expression reached its highest level during the elongation stage of fiber development, whereas GhC4H1 expression increased during the secondary wall development period in cotton fibers. Our results contribute to a better understanding of the biochemical role of GhC4H1 and GhC4H2 in cotton fiber development.

A New Phenylpropanoid Glycoside: Serratumoside A from Clerodendrum serratum

A new phenylpropanoid glycoside, serratumoside A, was isolated from the aerial parts of Clerodendrum serratum var. amplexifolium Moldenke. Its structure was determined by spectral and chemical methods.

Transcriptome analysis to identify candidate genes related to chlorogenic acid biosynthesis during development of Korla fragrant pear in Xinjiang

Korla fragrant pear(KFP)with special fragrance is a unique cultivar in Xinjiang,China.In order to explore the biosynthesis molecular mechanism of chlorogenic acid(CGA)in KFP,the samples at different development periods were collected for transcriptome analysis.High performance liquid chromatography analysis showed that CGA contents of KFP at 88,118 and 163 days after full bloom were(20.96±1.84),(12.01±0.91)and(7.16±0.41)mg/100 g,respectively,and decreased with the fruit development.Pears from these typical 3 periods were selected for de novo transcriptome assemble and 68059 unigenes were assembled from 444037960 clean reads.One‘phenylpropanoid biosynthesis’pathway including 57 unigenes,11 PALs,1 PTAL,64CLs,9 C4Hs,25 HCTs and 5 C3’Hs related to CGA biosynthesis was determined.It was found that the expression levels of 11 differentially expressed genes including 1 PAL,2 C4Hs,34CLs and 5 HCTs were consistent with the change of CGA content.Quantitative polymerase chain reaction analysis further showed that 8 unigenes involved in CGA biosynthesis were consistent with the RNA-seq data.These findings will provide a comprehensive understanding and valuable information on the genetic engineering and molecular breeding in KFP.

Cloning, bioinformatics and transcriptional analysis of caffeoyl-coenzyme A 3-O-methyltransferase in switchgrass under abiotic stress

Genes encoding enzymes involved in the lignin biosynthesis through phenylpropanoid pathway were not only associated with the lignin content, but also related to the abiotic stress resistances. As far as the production of liquid biofuels and cultivation within the marginal land are concerned, switchgrass could be the better candidate to determine the relationship between lower lignin content and physiological function under stress. Caffeoyl-coenzyme A 3-O-methyltransferase（CCoAOMT） is a key enzyme for the methylation reaction of lignin biosynthesis. For this purpose, we cloned a CCoAOMT gene from switchgrass and identified its expression patterns under abiotic stresses. The full-length CCoAOMT gene, designated PvCCoAOMT（Gen Bank accession no. KF041775）, was 1 005-bp in length, has an opening reading frame of 777 nucleotides encoding a 258-amino acid protein. The deduced amino acid sequence of PvCCoAOMT shared a high degree of similarity（up to 98%） with CCoAOMTs from Panicum virgatum allele（BAO20881）, Sorghum bicolor（XP002436550） and Zea mays（NP001131288）. Using quantitative real-time PCR（qRT-PCR）, the significant upregulation of PvCCoAOMT was observed in stem tissues at a later stage（24 h） after drought treatment, with the transcript level increasing 33-fold compared that of the controls. Moderate and insignificant inductions of PvCCoAOMT were also observed in both stems and leaves during the later stages after cold（48 h in stems, 12 h in leaves） and mechanical wounding（48 h in stems, 12 h in leaves） treatments, respectively. Our results showed the different expression patterns of PvCCoAOMT in drought, cold and mechanical wounding stresses. PvCCoAOMT can be highly induced by drought and cold stresses, which indicates that it may play a role in plant abiotic stress resistance, particularly in the regulation of drought and cold resistance.

Changes in phenolic content,composition,and antioxidant activity of blood oranges during cold and on-tree storage

Citrus fruits are rich in phenolic compounds that possess several health benefits.However,few studies have focused on the changes in phenolic compounds in citrus fruits during postharvest storage.This study dynamically monitored the phenolic content,components and antioxidant activity of‘Tarocco’blood oranges during a period of 12-week cold storage and on-tree storage,respectively.We investigated the alteration mechanism of phenolic compounds in blood oranges by evaluating phenylpropanoid pathway-related enzyme activities and gene expression.Results showed that flavanones were the main phenolic compounds in blood oranges.Both storage methods mainly stimulated the accumulation of phenolic acids to improve total phenolic content,which reached the maximum at week 12.Nonetheless,blood oranges had a higher phenolic content and antioxidant activity under on-tree storage than cold storage.Furthermore,the enzyme activities and gene expression of the phenylpropanoid pathway demonstrated that the accumulation of phenolics in blood oranges during storage was highly related to the activation of the phenylpropanoid pathway.These results demonstrate that on-tree storage is a potential approach for extending the supply period of blood orange from the perspective of phenolic compounds.

Bioactive natural products from marine angiosperms:abundance and functions

This review explores the natural products of seagrass that are to be exploited for their bioactive potential.Beside from portraying the presence of a wide array of secondary compounds such as phenols,flavonoids,sterols and lipids from different seagrass species,the focus is on novel natural products projecting towards their biological applications.Though there are a significant number of reports on the abundance of secondary metabolites from seagrass and their bioactive derivatives,only a small number of reports explore their functional and defensive characteristics.Efforts have been made to collate the available information on seagrass natural products and clarify their function and metabolic pathway’s.It is emphasized that metabolic profiling of seagrass should be extensively progressed to obtain a deeper knowledge about the specific roles of each natural product.The investigation of seagrass natural products for their bioactive potential would most likely result in the detection of surprising and unexpected novel chemical structures and clinical leads that may be useful to mankind.

Clausena anisata(Willd.)Hook.f.ex Benth.(Rutaceae):ethnomedicinal uses,phytochemistry,pharmacological activities,toxicity,and clinical application

Clausena anisata(Willd.)Hook.f.ex Benth.is a plant extensively used in traditional medicine.Here,a synopsis of the research on various aspects of Clausena anisata(Willd.)Hook.f.ex Benth.is presented.An electronic literature review revealed that formulations containing Clausena anisata(Willd.)Hook.f.ex Benth.are used to manage and treat diabetes,eye problems,malaria,snake envenomation,malignancies,as well as venereal,gastrointestinal,reproductive,respiratory,dermatological,and odonatological ailments.To date,90 compounds have been isolated and characterized from extracts of Clausena anisata(Willd.)Hook.f.ex Benth.Crude extracts and isolated compounds from Clausena anisata(Willd.)Hook.f.ex Benth.possess anti-inflammatory,antimicrobial,antioxidant,antiplasmodial,antiproliferative,anti-human immunodeficiency virus-1,antimycobacterial,antihypertensive,and antidiabetic activities.These bioactivities can be attributed to alkaloids,coumarins,limonoids,and phenylpropanoids present in different parts of the plant.Although some studies have indicated moderate toxicity of the extracts,some of the dominant compounds in this species,such as estragole and carbazole alkaloids,are mutagenic or cytotoxic.A clinical trial utilizing a Ghanaian herbal formulation containing Clausena anisata(Willd.)Hook.f.ex Benth.was found to be effective in reducing pain associated with osteoarthritis.Research progress to date supports the traditional use of this species in herbal medicine.However,these studies do not explain the relationships between traditional uses,pharmacological activities,and mechanisms of action.Thus,further studies should be designed to understand the biochemical properties and physiological effects of Clausena anisata(Willd.)Hook.f.ex Benth.extracts,facilitating the development and utilization of this medicinal resource.