Coriander (Coriandrum sativum) Polyphenols and Their Nutraceutical Value against Obesity and Metabolic Syndrome.

Coriander is a widely used plant for its medicinal and biological properties. Both coriander essential oil and extracts are interesting sources of bioactive compounds and are widely used as spices in culinary practice due to their exclusive aroma and flavour. We focus our attention on coriander extracts that are rich in polyphenols. It is well known that plant polyphenols possess different biological activities and several functional foods contain this class of compounds. The polyphenol profile in an extract can be influenced by the plant part studied, the method of extraction and other parameters. This study performs a literature review using the words "coriander", "polyphenols" and "extraction" or "biological activity" in different databases such as PubMed, Google Scholar and Scopus. After that, we focus on the evidence of coriander polyphenols as protective agents against some inflammation-related diseases. Due to the bioactivities of coriander extract, this herb can be considered a valuable functional food against obesity, metabolic syndrome and diabetes.

Bioassay-Guided Isolation of Antiproliferative Compounds from Limbarda crithmoides (L.) Dumort.

Limbarda crithmoides (L.) Dumort (Asteraceae) n-hexane extract displayed high cell proliferation inhibitory activity against acute myeloid leukaemia cells (OCI-AML3) and was therefore subjected to a bioassay-guided multistep separation procedure. Two thymol derivatives, namely 10-acetoxy-8,9-epoxythymol tiglate (1) and 10-acetoxy-9-chloro-8,9-dehydrothymol (2), were isolated and identified by means of NMR spectroscopy. Both of them exhibited a significant dose-dependent inhibition of cell proliferation.

A Design of Experiment Approach for Ionic Liquid-Based Extraction of Toxic Components-Minimized Essential Oil from Myristica fragrans Houtt. Fruits †.

The effect of the addition of ionic liquids (ILs) during the hydrodistillation of Myristica fragrans Houtt. (nutmeg) essential oil was studied. The essential oil of M. fragrans is characterized by the presence of terpenes, terpenoids, and of phenylpropanoids, such as methyl eugenol and safrole, that are regarded as genotoxic and carcinogenic. The aim of the work was to determine the best ionic liquid to improve the yield of the extraction of M. fragrans essential oil and decrease the extraction of toxic phenylpropanoids. Six ILs, namely 1,3-dimethylimidazolium chloride (1), 1,3-dimethylimidazolium dimethylphosphate (2), 1-(2-hydroxyethyl)-3-methylimidazolium chloride (3), 1-(2-hydroxyethyl)-3-methylimidazolium dimethylphosphate (4), 1-butyl-3-methylimidazolium chloride (5), and 1-butyl-3-methylimidazolium dimethylphosphate (6), were prepared by previously reported, innovative methods and then tested. An experimental design was used to optimize the extraction yield and to decrease the phenylpropanoids percentage using the synthesized ILs. The influence of the molarity of ILs was also studied. MODDE 12 software established 0.5 M 1-butyl-3-methylimidazolium chloride as the best co-solvent for the hydrodistillation of M. fragrans essential oil.

An Ethnopharmacological, Phytochemical and Pharmacological Review on Lignans from Mexican Bursera spp.

The genus Bursera belongs to the family Burseraceae and has been used in traditional Mexican medicine for treating various pathophysiological disorders. The most representative phytochemicals isolated from this genus are terpenoids and lignans. Lignans are phenolic metabolites known for their antioxidant, apoptotic, anti-cancer, anti-inflammatory, anti-bacterial, anti-viral, anti-fungal, and anti-protozoal properties. Though the genus includes more than 100 species, we have attempted to summarize the biological activities of the 34 lignans isolated from selected Mexican Bursera plants.

Diterpenoids and Triterpenoids from the Resin of Bursera microphylla and Their Cytotoxic Activity.

A chemical study of the nonpolar fraction of a methanol-soluble extract of Bursera microphylla resin yielded a variety of di- and triterpenoids. In total, 15 compounds were isolated, of which three are new, namely, malabaricatrienone (1), malabaricatrienol (2), and microphyllanin (3). The antiproliferative activity of the major compounds was evaluated in different murine cancer cell lines (M12.C3.F6 and RAW264.7) and human cancer cells (A549, HeLa, and PC-3). The new compounds (1-3) did not show significant antiproliferative activity. The known compounds ariensin (4), burseran (5), and dihydroclusin diacetate (6) were effective against the RAW264.7 cell line, with IC50 values in the micromolar range.

Chemical Composition and Biological Activities of Fragrant Mexican Copal (Bursera spp.).

Copal is the Spanish word used to describe aromatic resins from several genera of plants. Mexican copal derives from several Bursera spp., Protium copal, some Pinus spp. (e.g., P. pseudostrobus) and a few Fabaceae spp. It has been used for centuries as incense for religious ceremonies, as a food preservative, and as a treatment for several illnesses. The aim of this review is to analyze the chemical composition and biological activity of commercial Mexican Bursera copal.

Hinokinin, an emerging bioactive lignan.

Hinokinin is a lignan isolated from several plant species that has been recently investigated in order to establish its biological activities. So far, its cytotoxicity, its anti-inflammatory and antimicrobial activities have been studied. Particularly interesting is its notable anti-trypanosomal activity.

Cannabinoids as multifaceted compounds.

Since ancient times, Cannabis and its preparations have found various applications such as for medical, recreational and industrial purposes. Subsequently the 1930s, legislation in many countries has restricted its use due to its psychotropic properties. More recently, the discovery of endocannabinoid system, including new receptors, ligands, and mediators, its role in maintaining the homeostasis of the human body and the possible implication in various physiological and pathophysiological processes has also been understood. Based on this evidence, researchers were able to develop new therapeutic targets for the treatment of various pathological disorders. For this purpose, Cannabis and cannabinoids were subjected for the evaluation of their pharmacological activities. The renewed interest in the medical use of cannabis for its potential therapeutic application has prompted legislators to take action to regulate the safe use of cannabis and products containing cannabinoids. However, each country has an enormous heterogeneity in the regulation of laws. Here, we are pleased to show a general and prevailing overview of the findings regarding cannabinoids and the multiple research fields such as chemistry, phytochemistry, pharmacology and analytics in which they are involved.

NADES-Assisted Extraction of Polyphenols from Coriander Seeds: A Systematic Optimization Study.

Coriandrum sativum L. seeds are widely recognized for their traditional use in medicine. Among the most investigated components, the terpenoid linalool and monounsaturated petroselinic acid have attracted interest for their nutritional value. Instead, minor attention was paid to the polyphenolic fraction, resulting still being incomplete today. This study aimed to develop a systematic approach in which green natural deep eutectic solvents (NADES) were combined with conventional (maceration, MAC) or non-conventional (ultrasound-assisted extraction, UAE) techniques in a one-step methodology to recover polyphenols from coriander seeds. The NADES system choline chloride-citric acid (ChCl:CA, 1:1) was firstly evaluated, coupled with MAC or UAE, and then compared with ChCl-Urea (ChCl:Ur, 1:1) and ChCl-Glucose (ChCl:Glu, 1:1) under optimal conditions (20 min extraction time). The system ChCl:Ur UAE significantly improved the extraction of chlorogenic acid and its isomer (453.90 ± 4.77 and 537.42 ± 1.27 µg/g, respectively), while the system ChCl:Glu UAE improved the extraction of protocatechuic, caffeic and p-coumaric acids (131.13 ± 6.16, 269.03 ± 4.15 and 57.36 ± 0.06 µg/g, respectively). The highest levels of rutin were obtained with ChCl:CA-based NADES when the MAC technique was applied (820.31 ± 28.59 µg/g). These findings indicate that the NADES composition could be appropriately modulated to tailor extraction towards higher levels of a desirable bioactive for further applications.

Influence of choline chloride-based NADES on the composition of Myristica fragrans Houtt. essential oil.

Natural deep eutectic solvents (NADES) have emerged as green extracting solvents in recent years. In this study, a variety of choline chloride (ChCl)-based natural deep eutectic solvents (NADES) were used as co-solvents for the hydrodistillation of nutmeg with the aim to obtain M. fragrans essential oil (EO) in higher yield and with a lower content of toxic phenylpropenoids (e.g. myristicin and safrole). The influence of ChCl-based NADES as additives in the hydrodistillation process was studied. The results showed that NADES additives improved the yield of the extracted essential oil and influenced its composition leading to a decrease in toxic phenylpropenoids. Best results were achieved by using ChCl-CA NADES ultrasound-assisted pretreatment coupled with traditional 2 â€‹h Clevenger hydrodistillation that increased the yield of the EO from 0.98% (traditional) to 1.41% and a decrease of the phenylpropenoids amount in the essential oil.

Antiviral Activity of Ficus rubiginosa Leaf Extracts against HSV-1, HCoV-229E and PV-1.

Ficus rubiginosa plant extract showed antimicrobial activity, but no evidence concerning its antiviral properties was reported. The antiviral activity of the methanolic extract (MeOH) and its n-hexane (H) and ethyl acetate (EA) fractions against Herpes simplex virus-1 (HSV-1), Human coronavirus (HCoV) -229E, and Poliovirus-1 (PV-1) was investigated in the different phases of viral infection in the VERO CCL-81 cell line. To confirm the antiviral efficacy, a qPCR was conducted. The recorded cytotoxic concentration 50% was 513.1, 298.6, and 56.45 µg/mL for MeOH, H, and EA, respectively, assessed by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl-2H-tetrazolium bromide (MTT) assay after 72 h of treatment. The Ficus rubiginosa leaf extract inhibited the replication of HSV-1 in the early stages of infection, showing a complete inhibition up to 0.62, 0.31, and 1.25 µg/mL. Against HCoV-229E, a total inhibition up to 1.25 µg/mL for MeOH and H as well as 5 µg/mL for EA was observed. Otherwise, no activity was recorded against PV-1. The leaf extract could act directly on the viral envelope, destructuring the lipid membrane and/or directly blocking the enriched proteins on the viral surface. The verified gene inhibition suggested that the treatments with M, H, and EA impaired HSV-1 and HCoV-229E replication, with a greater antiviral efficiency against HSV-1 compared to HCoV-229E, possibly due to a greater affinity of Ficus rubiginosa towards membrane glycoproteins and/or the different lipid envelopes.

Protective effects of Commiphora erythraea resin constituents against cellular oxidative damage.

By bioguided fractionation of the hexane extract of Commiphora erythraea resin we isolated four furanosesquiterpenoids that were tested for their protective activity against oxidative stress. Furanodienone and 1,10(15)-furanogermacra-dien-6-ones showed to be potent inhibitors of lipid peroxidation (IC(50) of -0.087 µM), being more active than the methoxylated analogues. Furthermore, using BV2 microglial cells, we found that furanodienone from C. erythraea is able to counteract LPS-induced cell death and decrease LPS-induced NO generation thus protecting microglial cells from LPS-induced cytotoxicity. Finally, docking studies were undertaken to gain insight into the possible binding mode of the isolated compounds at 5-LOX binding site.

Cucurbitacin IIb, a steroidal triterpene from Ibervillea sonorae induces antiproliferative and apoptotic effects on cervical and lung cancer cells.

Chemical studies on Ibervillea sonorae (S. Watson) Greene root led to isolation and chemical characterization of diverse cucurbitacin triterpenoid compounds such as kinoin A, B, C, and their glucosides. In previous studies, we demonstrated that kinoin A inhibits the cell proliferation on diverse cell line and induce apoptosis in HeLa cells. Therefore, the study of the isolated compounds from the extracts continued to be necessary. The objective of the present work was to isolate and chemically characterize the active compounds of the methanolic extract of the roots of I. sonorae and to evaluate their antiproliferative activity and induction of apoptosis. By chromatographic column separation and using NMR spectroscopy experiments, cucurbitacin IIb (CIIb), known as 23,24-dihydrocucurbitacin F or hemslecin B, was isolated and identified for the first time as a chemical constituent of the crude methanolic extract of this plant. The antiproliferative activity of CIIb was evaluated by MTT assay, and the apoptosis induction capacity was monitored by annexin V-FITC/propidium iodide using flow cytometry. CIIb showed a pronounced effect on the proliferation of HeLa and A549 tumor cells, with IC50 of 7.3 and 7.8 µM, respectively, but was less effective against L929 non-cancerous murine cell line. Apoptosis induction capacity of CIIb on HeLa and A549 was monitored by annexin V-FITC/propidium iodide using flow cytometry. Exposure of HeLa and A549 with CIIb (8 µM) for 24 h increased 56.9 and 52.3% respectively of the total apoptosis compared to the negative control (p < 0.005). CIIb, isolated for the first time from I. sonorae, showed antiproliferative activity against HeLa and A549 cell lines by inducing cell death by apoptosis.

Quantitative analysis of cucurbitane-type triterpenes in Ibervillea sonorae extracts: Relationship study with their antiproliferative activity.

Ibervillea sonorae (Cucurbitaceae) is a Mexican plant commonly used by local population for its hypoglycaemic activity. Root extracts showed also other different biological activities, including antimicrobial, antifungal, antioxidant and anti-inflammatory activity. Main components of this plant are cucurbitacins, steroid-like triterpenes that possess, among others, antiproliferative activity. In previous studies, kinoin A and cucurbitacin IIb extracted from I. sonorae showed antiproliferative and apoptotic effects against different cancer cell lines. Based on all the above, a RP-HPLC method was developed and validated for the quantitative analysis of these two compounds in I. sonorae root extracts obtained with different extraction conditions. In the present study, the quantitative analysis of kinoin B diglycoside in all the extracts was performed as well. As a result, no direct correlation was found between the antiproliferative activity (IC50) against human cervical cancer cell line (HeLa) and the composition of the above three compounds. Only a slight statically significant negative correlation was observed between IC50s and the content of kinoin A (r = 0.29, p = 0.12), meaning that, at least in part, this is the main compound among the three, contributing to the antiproliferative activity on the real samples. Accordingly, a synergistic effect by the phytocomplex components can account for the observed antiproliferative activity of the methanolic extracts towards HeLa cells.

Impact of conventional/non-conventional extraction methods on the untargeted phenolic profile of Moringa oleifera leaves.

The impact of different extraction methods, namely maceration, homogenizer-assisted extraction, rapid solid-liquid dynamic extraction, microwave-assisted extraction and ultrasound-assisted extraction, on polyphenols of Moringa oleifera leaves was studied. The phenolic composition of alcoholic (methanol 100%) and hydroalcoholic (methanol/water 50:50, v/v) extracts was compared by using an untargeted metabolomics-based profiling approach followed by multivariate statistics. With this aim, ultra-high-pressure liquid chromatography coupled to a quadrupole-time-of-flight mass spectrometry was used to profile phenolic compounds under the different extraction conditions. Besides, the in vitro antioxidant activities of Moringa leaves were also investigated as ferric reducing antioxidant power (FRAP) and oxygen radical absorbance capacity (ORAC). The metabolomic approach allowed to putatively annotate 262 phenolic compounds. In particular, glycosidic forms of quercetin (i.e., quercetin 3-O-galactoside, quercetin 3-O-glucoside, and quercetin 4'-O-glucoside) were the most represented compounds among flavonoids. Furthermore, protocatechuic acid was found to be the most abundant hydroxybenzaldheyde derivative, while the isomeric forms of hydroxybenzoic acid characterized the phenolic acids class. Overall, the extractions in methanol 100% were found to be the most effective for phenolic compounds recovering, when compared with those in methanol/water (50:50, v/v). Homogenizer-assisted extraction of M. oleifera leaves using 100% methanol allowed extracting the highest amounts of polyphenols (35.19 mg/g) and produced the highest oxygen radical absorbance capacity (536.27 µmol Trolox Equivalents/g). The supervised orthogonal projection to latent structures discriminant analysis identified phenolic acids as the phenolic class mostly affected by the different extraction technologies. These findings demonstrate that each extraction method promoted the recovery of specific phenolic subclasses with different efficiencies.

Chemistry and pharmacology of collinin, active principle of Zanthoxylum spp.

Collinin is a geranyloxycoumarins isolated in small amounts from plants of the Rutaceae family. Synthetic schemes were recently developed allowing to handle collinin in sufficient quantities to put in evidence valuable biological effects. The aim of this review is to examine the phytochemical and pharmacological properties of this compound.

Two new lignans from the resin of Bursera microphylla A. gray and their cytotoxic activity.

Two new lignans, namely 7-O-podophyllotoxinyl butyrate (1) and dihydroclusin 9-acetate (2), were isolated from the dichloromethane fraction of a methanol extract of Bursera microphylla (Burseraceae), along with eight known lignans (3-10). Their structures were determined by means of comprehensive spectroscopic analysis. Lignans 2-6 were tested for their anti-proliferative activity on the cancer cell lines LS180, A549 and HeLa, and on a non-cancer cell line, ARPE-19. Only compounds 4 and 5 showed an interesting activity on HeLa cells.

The Hexane Fraction of Bursera microphylla A. Gray Induces p21-Mediated Anti-Proliferative and Pro-Apoptotic Effects in Human Cancer-Derived Cell Lines.

Bursera microphylla (BM), one of the common elephant trees, is widely distributed in the Sonoran Desert in Mexico. The Seri ethnic group in the Sonoran Desert uses BM as an anti-inflammatory and painkiller drug for the treatment of sore throat, herpes labialis, abscessed tooth, and wound healing. Dried stems and leaves of BM are used in a tea to relieve painful urination and to stimulate bronchial secretion. Furthermore, BM is used for fighting venereal diseases. To investigate the effects of the hexane fraction of resin methanol extract (BM-H) on cell growth, the acute myeloid cell line (OCI-AML3) was treated with 250, 25, or 2.5 µg/mL of BM-H. The first 2 concentrations were able to significantly decrease OCI-AML3 cell number. This reduced cell number was associated with decreased S-phase, blockade of the G2/M phase of the cell cycle, and increased cell death. Similar results were obtained on all tested tumor cell lines of different origins. We found that blockade of the cell cycle was due to upregulation of p21 protein in a p53-independent way. Increase of p21 was possibly due to upstream upregulation of p-ERK (which stabilizes p21 protein) and downregulation of p-38 (which promotes its degradation). Regarding cell death, activation of caspase-3, but not of caspase-8 or -9, was detectable after BM-H treatment. In conclusion, these data suggest that the BM's hexane fraction inhibited proliferation of cell lines mainly by a p21-dependent, p53-independent mechanism and promoted apoptosis through activation of caspase-3, but not caspase-8 or -9.

A novel cyathane diterpene, cyrneine A, induces neurite outgrowth in a Rac1-dependent mechanism in PC12 cells.

We examined the effects of cyrneine A, a novel diterpene isolated from the mushroom Sarcodon cyrneus, on morphology of rat pheochromocytoma cells (PC12). In response to cyrneine A, PC12 cells extended their neurites, an effect partially blocked by the extracellular signal-regulated kinase (ERK) kinase inhibitor PD98059, but not by the protein kinase C inhibitor GF109203X, nor the phosphatidylinositol-3-kinase inhibitor wortmannin. Cyrneine A did not activate ERK at any of the time points tested (5-120 min), indicating that only the basal activity of ERK is required for cyrneine A-induced neurite outgrowth. As transcriptional regulation is required for neurite extension, the activity of three major transcription factors was determined. Cyrneine A enhanced activation of the transcription factors activator protein-1 (AP-1) and nuclear factor-kappaB, but not CREB, and this was accompanied by enhanced c-fos expression. Moreover, we determined the role of Rac1, a small GTPase protein of the Rho family that regulates actin dynamics, in cyrneine A-induced neurite outgrowth. Treatment with cyrneine A led to actin translocation and subsequently, to accumulation of F-actin at the tip of neurites. Rac1 activity was increased by cyrneine A and expression of a dominant-negative Rac1 mutant significantly inhibited the cyrneine A-induced extension of neurites. These results suggest that cyrneine A induces neurite outgrowth in a Rac1-dependent mechanism.

Optimisation of a Naviglio-assisted extraction followed by determination of piperine content in Piper longum extracts.

Studies were made to increase the yield of piperine extraction using Naviglio Extractor® solid-liquid dynamic extractor (SLDE) from fruits of Piper longum. The effects of ratio w/v were investigated and optimised for the best method. The maximum yield of piperine (317.7 mg/g) from P. longum fruits was obtained in SLDE 1:50 ethanol extract. Extraction yields of piperine obtained from Soxhlet extraction, decotion (International Organization for Standardization) and conventional maceration extraction methods were found to be 233.7, 231.8 and 143.6 mg/g, respectively. The results of the present study indicated that Naviglio Extractor® is an effective technique for the extraction of piperine from long pepper.