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Review on rosmarinic acid extraction, fractionation and its anti-diabetic potential

Ngo YL, Lau CH, Chua LS

Food Chem Toxicol, 2018 Nov;121:687-700.
PMID: 30273632 DOI: 10.1016/j.fct.2018.09.064

Rosmarinic acid is a bioactive phytochemical that can be found in many herbs as ethnomedicines. It possesses remarkable pharmacological activities, and thus leading to its exploration as a therapeutic drug in diabetes treatment recently. This article reviews the extraction and fractionation techniques for plant-based natural rosmarinic acid and its anti-diabetic potential based on literature data published in journals, books, and patents from 1958 to 2017. Factors affecting the performance of rosmarinic acid extraction and fractionation such as operating temperature, time, solvent to sample ratio and eluent system are compiled and discussed in detail. The inhibitory action of rosmarinic acid against sugar digestive enzymes, and protective action towards pancreatic β-cell dysfunction and glucolipotoxicity mediated oxidative stress are also critically reviewed. The optimal parameters are largely dependent on the applied extraction and fractionation techniques, as well as the nature of plant samples. Previous studies have proven the potent role of rosmarinic acid to control plasma glucose level and increase insulin sensitivity in hyperglycemia. Although rosmarinic acid is readily absorbed by human body, its mechanism after consumption is remained unclear. Intensive studies should be well planned to determine the dosage and toxicity level of rosmarinic acid for efficacy and safe consumption.

Matched MeSH terms: Cinnamates/chemistry
Fulltext Neuroprotective Effects of 7-Geranyloxycinnamic Acid from Melicope lunu ankenda Leaves

Abdulwanis Mohamed Z, Mohamed Eliaser E, Jaafaru MS, Nordin N, Ioannides C, Abdull Razis AF

Molecules, 2020 Aug 15;25(16).
PMID: 32824120 DOI: 10.3390/molecules25163724

Neurodegenerative diseases (NDDs) are chronic conditions that have drawn robust interest from the scientific community. Phytotherapeutic agents are becoming an important source of chemicals for the treatment and management of NDDs. Various secondary metabolites have been isolated from Melicope lunu-ankenda plant leaves, including phenolic acid derivatives. However, their neuroprotective activity remains unclear. Thus, the aim of this study is to elucidate the in vitro neuroprotective activity of 7-geranyloxycinnamic acid isolated from Melicope lunu-ankenda leaves. The neuroprotective activity was evaluated in differentiated human neuroblastoma (SH-SY5Y) cells by monitoring cell viability using 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT). Moreover, the potential to impair apoptosis in differentiated cells was investigated employing the Annexin V-FITC assay, acridine orange and propidium iodide (AO/PI) staining, and fluorescence microscopy. Morphological assessment and ultrastructural analysis were performed using scanning and transmission electron microscopy to evaluate the effect of 7-geranyloxycinnamic acid on surface morphology and internal features of the differentiated cells. Pre-treatment of neuronal cells with 7-geranyloxycinnamic acid significantly protected the differentiated SH-SY5Y cells against H2O2-induced apoptosis. Cytoskeleton and cytoplasmic inclusion were similarly protected by the 7-geranyloxycinnamic acid treatment. The present findings demonstrate the neuroprotective potential of 7-geranyloxycinnamic acid against H2O2-induced neurotoxicity in neuronal cells, which is an established hallmark of neuronal disorders.

Matched MeSH terms: Cinnamates/chemistry*
Exploring the potential of biologically active phenolic acids from marine natural products as anticancer agents targeting the epidermal growth factor receptor

Roney M, Issahaku AR, Huq AM, Soliman MES, Tajuddin SN, Aluwi MFFM

J Biomol Struct Dyn, 2024;42(24):13564-13587.
PMID: 37909584 DOI: 10.1080/07391102.2023.2276879

The epidermal growth factor receptor (EGFR) dimerizes upon ligand bindings to the extracellular domain that initiates the downstream signaling cascades and activates intracellular kinase domain. Thus, activation of autophosphorylation through kinase domain results in metastasis, cell proliferation, and angiogenesis. The main objective of this research is to discover more promising anti-cancer lead compound against EGRF from the phenolic acids of marine natural products using in-silico approaches. Phenolic compounds reported from marine sources are reviewed from previous literatures. Furthermore, molecular docking was carried out using the online tool CB-Dock. The molecules with good docking and binding energies scores were subjected to ADME, toxicity and drug-likeness analysis. Subsequently, molecules from the docking experiments were also evaluated using the acute toxicity and MD simulation studies. Fourteen phenolic compounds from the reported literatures were reviewed based on the findings, isolation, characterized and applications. Molecular docking studies proved that the phenolic acids have good binding fitting by forming hydrogen bonds with amino acid residues at the binding site of EGFR. Chlorogenic acid, Chicoric acid and Rosmarinic acid showed the best binding energies score and forming hydrogen bonds with amino acid residues compare to the reference drug Erlotinib. Among these compounds, Rosmarinic acid showed the good pharmacokinetics profiles as well as acute toxicity profile. The MD simulation study further revealed that the lead complex is stable and could be future drug to treat the cancer disease. Furthermore, in a wet lab environment, both in-vitro and in-vivo testing will be employed to validate the existing computational results.Communicated by Ramaswamy H. Sarma.

Matched MeSH terms: Cinnamates/chemistry
Fulltext Communal microaerophilic-aerobic biodegradation of Amaranth by novel NAR-2 bacterial consortium

Chan GF, Rashid NA, Chua LS, Ab llah N, Nasiri R, Ikubar MR

Bioresour Technol, 2012 Feb;105:48-59.
PMID: 22182471 DOI: 10.1016/j.biortech.2011.11.094

A novel bacterial consortium, NAR-2 which consists of Citrobacter freundii A1, Enterococcus casseliflavus C1 and Enterobacter cloacae L17 was investigated for biodegradation of Amaranth azo dye under sequential microaerophilic-aerobic condition. The NAR-2 bacterial consortium with E. casseliflavus C1 as the dominant strain enhanced the decolorization process resulting in reduction of Amaranth in 30 min. Further aerobic biodegradation, which was dominated by C. freundii A1 and E. cloacae L17, allowed biotransformation of azo reduction intermediates and mineralization via metabolic pathways including benzoyl-CoA, protocatechuate, salicylate, gentisate, catechol and cinnamic acid. The presence of autoxidation products which could be metabolized to 2-oxopentenoate was elucidated. The biodegradation mechanism of Amaranth by NAR-2 bacterial consortium was predicted to follow the steps of azo reduction, deamination, desulfonation and aromatic ring cleavage. This is for the first time the comprehensive microaerophilic-aerobic biotransformation pathways of Amaranth dye intermediates by bacterial consortium are being proposed.

Matched MeSH terms: Cinnamates/chemistry
Fulltext Profiling of phenolic compounds and their antioxidant and anticancer activities in pandan (Pandanus amaryllifolius Roxb.) extracts from different locations of Malaysia

Ghasemzadeh A, Jaafar HZ

BMC Complement Altern Med, 2013;13:341.
PMID: 24289290 DOI: 10.1186/1472-6882-13-341

Phytochemicals and antioxidants from plant sources are of increasing interest to consumers because of their roles in the maintenance of human health. Most of the secondary metabolites of herbs are used in a number of pharmaceutical products.

Matched MeSH terms: Cinnamates/chemistry
Evaluation of the genotoxicity of Orthosiphon stamineus aqueous extract

Muhammad H, Gomes-Carneiro MR, Poça KS, De-Oliveira AC, Afzan A, Sulaiman SA, et al.

J Ethnopharmacol, 2011 Jan 27;133(2):647-53.
PMID: 21044879 DOI: 10.1016/j.jep.2010.10.055

Orthosiphon stamineus, Benth, also known as Misai Kucing in Malaysia and Java tea in Indonesia, is traditionally used in Southeastern Asia to treat kidney dysfunctions, diabetes, gout and several other illnesses. Recent studies of Orthosiphon stamineus pharmacological profile have revealed antioxidant properties and other potentially useful biological activities thereby lending some scientific support to its use in folk medicine. So far the genotoxicity of Orthosiphon stamineus extracts has not been evaluated. In this study the genotoxic potential of Orthosiphon stamineus aqueous extract was investigated by the Salmonella/microsome mutation assay and the mouse bone marrow micronucleus test.

Matched MeSH terms: Cinnamates/chemistry
Fulltext Bioprospecting the Curculigoside-Cinnamic Acid-Rich Fraction from Molineria latifolia Rhizome as a Potential Antioxidant Therapeutic Agent

Ooi DJ, Chan KW, Sarega N, Alitheen NB, Ithnin H, Ismail M

Molecules, 2016 Jun 17;21(6).
PMID: 27322226 DOI: 10.3390/molecules21060682

Increasing evidence from both experimental and clinical studies depicts the involvement of oxidative stress in the pathogenesis of various diseases. Specifically, disruption of homeostatic redox balance in accumulated body fat mass leads to obesity-associated metabolic syndrome. Strategies for the restoration of redox balance, potentially by exploring potent plant bioactives, have thus become the focus of therapeutic intervention. The present study aimed to bioprospect the potential use of the curculigoside-cinnamic acid-rich fraction from Molineria latifolia rhizome as an antioxidant therapeutic agent. The ethyl acetate fraction (EAF) isolated from M. latifolia rhizome methanolic extract (RME) contained the highest amount of phenolic compounds, particularly curculigoside and cinnamic acid. EAF demonstrated glycation inhibitory activities in both glucose- and fructose-mediated glycation models. In addition, in vitro chemical-based and cellular-based antioxidant assays showed that EAF exhibited high antioxidant activities and a protective effect against oxidative damage in 3T3-L1 preadipocytes. Although the efficacies of individual phenolics differed depending on the structure and concentration, a correlational study revealed strong correlations between total phenolic contents and antioxidant capacities. The results concluded that enriched phenolic contents in EAF (curculigoside-cinnamic acid-rich fraction) contributed to the overall better reactivity. Our data suggest that this bioactive-rich fraction warrants therapeutic potential against oxidative stress-related disorders.

Matched MeSH terms: Cinnamates/chemistry
In vitro effects of active constituents and extracts of Orthosiphon stamineus on the activities of three major human cDNA-expressed cytochrome P450 enzymes

Pan Y, Abd-Rashid BA, Ismail Z, Ismail R, Mak JW, Pook PC, et al.

Chem Biol Interact, 2011 Mar 15;190(1):1-8.
PMID: 21276781 DOI: 10.1016/j.cbi.2011.01.022

Orthosiphon stamineus (OS) has been traditionally used to treat diabetes, kidney and urinary disorders, high blood pressure and bone or muscular pain. To assess the possibility of drug-herb interaction via interference of metabolism, effects of four OS extracts of different polarity and three active constituents (sinensetin, eupatorin and rosmarinic acid) on major human cDNA-expressed cytochrome P450 (CYP) enzymes were investigated. Three substrate-probe based high-performance liquid chromatography (HPLC) assays were established to serve as activity markers for CYP2C9, CYP2D6 and CYP3A4. Our results indicate that OS extracts and constituents exhibited differential modulatory effects on different CYPs. While none of the OS components showed significant inhibition on CYP2C9, eupatorin strongly and uncompetitively inhibited CYP2D6 activity with a K(i) value of 10.2μM. CYP3A4 appeared to be the most susceptible enzyme to OS inhibitory effects. It was moderately inhibited by OS dichloromethane and petroleum ether extract with mixed-type and noncompetitive inhibitions (K(i)=93.7 and 44.9μg/mL), respectively. Correlation study indicated that the inhibition was accounted for by the presence of eupatorin in the extracts. When IC(50) values of these extracts were expressed in volume per dose unit to reflect inhibitory effect at recommended human doses from commercially available products, moderate inhibition was also observed. In addition, CYP3A4 was strongly and noncompetitively inhibited by eupatorin alone, with a K(i) value of 9.3μM. These findings suggest that co-administration of OS products, especially those with high eupatorin content, with conventional drugs may have the potential to cause drug-herb interactions involving inhibition of major CYP enzymes.

Matched MeSH terms: Cinnamates/chemistry
Fulltext Uridine from Pleurotus giganteus and Its Neurite Outgrowth Stimulatory Effects with Underlying Mechanism

Phan CW, David P, Wong KH, Naidu M, Sabaratnam V

PLoS One, 2015;10(11):e0143004.
PMID: 26565787 DOI: 10.1371/journal.pone.0143004

Neurodegenerative diseases are linked to neuronal cell death and impairment of neurite outgrowth. An edible mushroom, Pleurotus giganteus was found to stimulate neurite outgrowth in vitro but the chemical constituents and the underlying mechanism is yet to be elucidated. The chemical constituents of P. giganteus (linoleic acid, oleic acid, cinnamic acid, caffeic acid, p-coumaric acid, succinic acid, benzoic acid, and uridine) were tested for neurite outgrowth activity. Uridine (100 μM) was found to increase the percentage of neurite-bearing cells of differentiating neuroblastoma (N2a) cells by 43.1 ± 0.5%, which was 1.8-fold higher than NGF (50 ng/mL)-treated cells. Uridine which was present in P. giganteus (1.80 ± 0.03 g/100g mushroom extract) increased the phosphorylation of extracellular-signal regulated kinases (ERKs) and protein kinase B (Akt). Further, phosphorylation of the mammalian target of rapamycin (mTOR) was also increased. MEK/ERK and PI3K-Akt-mTOR further induced phosphorylation of cAMP-response element binding protein (CREB) and expression of growth associated protein 43 (GAP43); all of which promoted neurite outgrowth of N2a cells. This study demonstrated that P. giganteus may enhance neurite outgrowth and one of the key bioactive molecules responsible for neurite outgrowth is uridine.

Matched MeSH terms: Cinnamates/chemistry
Chemical characterization and antimicrobial activity of rhizome essential oils of very closely allied Zingiberaceae species endemic to Borneo: Alpinia ligulata K. Schum. and Alpinia nieuwenhuizii Val

Yusoff MM, Ibrahim H, Hamid NA

Chem Biodivers, 2011 May;8(5):916-23.
PMID: 21560240 DOI: 10.1002/cbdv.201000270

Two poorly studied, morphologically allied Alpinia species endemic to Borneo, viz., A. ligulata and A. nieuwenhuizii, were investigated here for their rhizome essential oil. The oil compositions and antimicrobial activities were compared with those of A. galanga, a better known plant. A fair number of compounds were identified in the oils by GC-FID and GC/MS analyses, with large differences in the oil composition between the three species. The rhizome oil of A. galanga was rich in 1,8-cineole (29.8%), while those of A. ligulata and A. nieuwenhuizii were both found to be extremely rich in (E)-methyl cinnamate (36.4 and 67.8%, resp.). The three oils were screened for their antimicrobial activity against three Gram-positive and three Gram-negative bacteria and two fungal species. The efficiency of growth inhibition of Staphylococcus aureus var. aureus was found to decline in the order of A. nieuwenhuizii>A. ligulata ∼ A. galanga, while that of Escherichia coli decreased in the order of A. galanga>A. nieuwenhuzii ∼ A. ligulata. Only the A. galanga oil inhibited the other bacteria and the fungi tested.

Matched MeSH terms: Cinnamates/chemistry
Phytochemical profile of Orthosiphon aristatus extracts after storage: Rosmarinic acid and other caffeic acid derivatives

Chua LS, Lau CH, Chew CY, Ismail NIM, Soontorngun N

Phytomedicine, 2018 Jan 15;39:49-55.
PMID: 29433683 DOI: 10.1016/j.phymed.2017.12.015

BACKGROUND: Orthosiphon aristatus (Blume) Miq. is a medicinal herb which is traditionally used for the treatment of diabetes and kidney diseases in South East Asia. Previous studies reported higher concentration of antioxidative phytochemicals, especially rosmarinic acid (ester of caffeic acid) and other caffeic acid derivatives in this plant extract than the other herbs such as rosemary and sage which are usually used as raw materials to produce rosmarinic acid supplement in the market.
PURPOSE: The phytochemical profile of O. aristatus was investigated at different storage durations for quality comparison.
METHODS: The phytochemicals were extracted from the leaves and stems of O. aristatus using a reflux reactor. The extracts were examined for total phenolic and flavonoid contents, as well as their antioxidant capacities, in terms of radical scavenging, metal chelating and reducing power. The phytochemical profiles were also analyzed by unsupervised principal component analysis and hierarchical cluster analysis, in relation to the factor of storage at 4 °C for 5 weeks.
RESULTS: The leaf extract was likely to have more phytochemicals than stem extract, particularly caffeic acid derivatives including glycosylated and alkylated caffeic acids. This explains higher ratio of total phenolic content to total flavonoid content with higher antioxidant capacities for the leaf extracts. Rosmarinic acid dimer and salvianolic acid B appeared to be the major constituents, possibly contributing to the previously reported pharmacological properties. However, the phytochemical profiles were found changing, even though the extracts were stored in the refrigerator (4 °C). The change was significantly observed at the fifth week based on the statistical pattern recognition technique.
CONCLUSION: O. aristatus could be a promising source of rosmarinic acid and its dimer, as well as salvianolic acid B with remarkably antioxidant properties. The phytochemical profile was at least stable for a month stored at 4 °C. It is likely to be a good choice of herbal tea with comparable radical scavenging activity, but lower caffeine content than other tea samples.

Matched MeSH terms: Cinnamates/chemistry
Fulltext The Antioxidant and Xanthine Oxidase Inhibitory Activity of Plumeria rubra Flowers

Mohamed Isa SSP, Ablat A, Mohamad J

Molecules, 2018 Feb 13;23(2).
PMID: 29438299 DOI: 10.3390/molecules23020400

Plumeria rubra Linn of the family Apocynaceae is locally known in Malaysia as "Kemboja". It has been used by local traditional medicine practitioners for the treatment of arthritis-related disease. The LCMS/MS analysis of the methanol extract of flowers (PR-ME) showed that it contains 3-O-caffeyolquinic acid, 5-caffeoquinic acid, 1,3-dicaffeoquinic acid, chlorogenic acid, citric acid, 3,3-di-O-methylellagic acid, kaempferol-3-O-glucoside, kaempferol-3-rutinoside, kaempferol, quercetin 3-O-α-l-arabinopyranoside, quercetin, quinic acid and rutin. The flower PR-ME contained high amounts of phenol and flavonoid at 184.632 mg GAE/g and 203.2.2 mg QE/g, respectively. It also exhibited the highest DPPH, FRAP, metal chelating, hydrogen peroxide, nitric oxide superoxide radical scavenging activity. Similarly, the XO inhibitory activity in vitro assay possesses the highest inhibition effects at an IC50 = 23.91 μg/mL. There was no mortality or signs of toxicity in rats at a dose of 4 g/kg body weight. The administration of the flower PR-ME at doses of 400 mg/kg to the rats significantly reduced serum uric acid 43.77%. Similarly, the XO activity in the liver was significantly inhibited by flower PR-ME at doses of 400 mg/kg. These results confirm that the flower PR-ME of P. rubra contains active phytochemical compounds as detected in LCMS/MS that contribute to the inhibition of XO activity in vitro and in vivo in reducing acid uric level in serum and simultaneously scavenging the free radical to reduce the oxidative stress.

Matched MeSH terms: Cinnamates/chemistry

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