Yolanda Rios Gomez

Organic Chemistry, Medicinal Chemistry

PhD
33.88

Publications

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    ABSTRACT: Herbivory activates the synthesis of allelochemicals that can mediate plant-plant interactions. There is an inverse relationship between the activity of xylophages and the abundance of epiphytes on Ipomoea murucoides. Xylophagy may modify the branch chemical constitution, which also affects the liberation of allelochemicals with defense and allelopathic properties. We evaluated the bark chemical content and the effect of extracts from branches subjected to treatments of exclusion, mechanical damage and the presence/absence of epiphytes, on the seed germination of the epiphyte Tillandsia recurvata. Principal component analysis showed that branches without any treatment separate from branches subjected to treatments; damaged and excluded branches had similar chemical content but we found no evidence to relate intentional damage with allelopathy; however 1-hexadecanol, a defense volatile compound correlated positively with principal component (PC) 1. The chemical constitution of branches subject to exclusion plus damage or plus epiphytes was similar among them. PC2 indicated that palmitic acid (allelopathic compound) and squalene, a triterpene that attracts herbivore enemies, correlated positively with the inhibition of seed germination of T. recurvata. Inhibition of seed germination of T. recurvata was mainly correlated with the increment of palmitic acid and this compound reached higher concentrations in excluded branches treatments. Then, it is likely that the allelopathic response of I. murucoides would increase to the damage (shade, load) that may be caused by a high load of epiphytes than to damage caused by the xylophages.
    Full-text · Article · Dec 2015 · PLoS ONE
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    ABSTRACT: Heliopsis longipes (Asteraceae) is a plant whose roots are commonly used in Mexican cuisine as a substitute for hot pepper. This plant is also used in traditional medicine for its therapeutical properties. Previous reports detected the presence of affinin—an alkamide with analgesic properties—in extracts of H. longipes. Here, we describe the development of a high-performance liquid chromatography-UV detector method for the determination of the alkamide affinin (1) as the major component in fresh and dry roots of H. longipes. Compound 1 was quantitatively determined employing a Kromasil 100 C18 3 μm particle size column, using the isocratic mobile phase acetonitrile-water (55 + 45). The flow rate was 0.8 mL/min and the UV detection was at 213 nm. The limits of detection and quantitation were 0.0009 and 7.6 μg/mL, respectively. Compound 1 showed good linearity in the 75 to 150 μg/mL range; recovery was within 99.3 and 101.9 %. Quantities of affinin measured by this method ranged between 6.9 and 8.5 mg per gram of the dry and fresh roots; thus 1 could be used as marker for H. longipes. The LC method described here proved to be reliable, reproducible, accurate, and could be used for quality control of H. longipes medicinal materials. In addition, its volatile chemical composition is described and was assessed via GC-MS using headspace solid-phase microextraction; compounds were identified by matching against the standard mass spectral database of the National Institute of Standards and Technology (NIST). Twenty-eight recognized compounds represent 99.9 % of the total relative content of constituents from H. longipes roots.
    Full-text · Article · Nov 2015 · Food Analytical Methods
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    María Yolanda Rios
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    ABSTRACT: Flourensia species are dominant plants that are adapted to semidesertic and desertic regions. It is believed that they are successful plants because they employ several protection mechanisms, including the formation of a waxy film on their aerial parts to protect them from dehydration. This waxy film contains chemical compounds that are capable of inhibiting the growth of other plants and of acting as allelopathic and herbicidal agents and as germination inhibitors. These plants also limit herbivory, and they exhibit insecticidal, insect antifeedant, antibacterial, antifungal, antialgal, and antitermite activities. Sesquiterpenes, flavonoids, benzofurans, chromenes, coumarins, lupan triterpenes, aliphatic lactones, and aromatic and acetilenic compounds have all been isolated from the organic extracts of Flourensia species. Monoterpenes, sesquiterpenes, and aliphatic hydrocarbons are the main constituents found in their essential oils. This review is an overview of the chemical constituents and of the biological activities of Flourensia species.
    Full-text · Article · Nov 2015 · Chemistry & Biodiversity
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    ABSTRACT: The fungus Fusarium oxysporum f. sp. gladioli is one of the main pathogenic microorganisms of the ornamental genus Gladiolus. The attack of this microorganism includes corms and different plant phenological stages. In this study, different microscopic techniques and fluorochromes were used to evaluate the effect of J. curcas oil and acylglycerides, namely trilinolein, triolein, monomyristin and dimyristin, on the morphology, membrane integrity (%), viability (%) and germination (%) of F. oxsporum f sp. gladioli. Phase-contrast optical photomicrographs and scanning microscopy showed that J. curcas oil and the triglycerides triolein and trilinolein caused the formation of numerous vacuoles, alterations in the morphology of the outer covering of the mycelium and conidia, and inhibition of membrane activity in the fungus during 24h of incubation. The fluorochromes used detected no permanent damage to the viability of the conidia. The high germination percentage of the conidia of Fusarium oxysporum f. sp. gladioli indicates that the damage caused by the application of the treatments was fungistatic rather than fungicidal and did not cause cell death.
    Full-text · Article · Nov 2015
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    ABSTRACT: A group of sixteen iridoids isolated from plants used as anti-inflammatory remedies in Mexican folk medicine were evaluated for their potential to inhibit cyclooxygenase-1 (COX-1) and cyclooxygenase-2 (COX-2) enzymes. From these assays, loganic acid (10) was identified as the most promising compound with both COX-1 (36.0±0.6%) and COX-2 (80.8±4.0%) inhibition at 10μM. Compound 10 shows a better inhibition against the COX-2 enzyme. Other iridoids tested in the present study showed weak or no inhibition against these enzymes. Furthermore, herein are presented key interactions of iridoid 10 with COX-1 and COX-2 enzymes through molecular docking studies. These studies suggest that 10 exhibits anti-inflammatory activity due to COX inhibition.
    Full-text · Article · Aug 2015 · Bioorganic & medicinal chemistry letters
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    ABSTRACT: Capsaicinoids are the compounds responsible for the pungency of chili peppers. These substances have attracted the attention of many research groups in recent decades because of their antinociceptive, analgesic, anti-inflammatory, and antiobesity proper- ties, among others. There are nearly 160 capsaicinoids reported in the literature. Approximately 25 of them are natural products, while the rest are synthetic or semi-synthetic products. A large amount of NMR data for the capsaicinoids is dispersed throughout literature. Therefore, there is a need to organize all this NMR data in a systematic and orderly way. This review summarizes the 1 H and 13 C NMR data on 159 natural and synthetic capsaicinoids, with a brief discussion of some typical and relevant aspects of these NMR data.
    No preview · Article · Jan 2015 · Magnetic Resonance in Chemistry
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    María Yolanda Rios · Horacio F. Olivo
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    ABSTRACT: Alkamides are a group of bioactive natural compounds showing broad structural variability and an important range of biological activities, such as immunomodulatory, antimicrobial, antiviral, larvicidal, insecticidal, diuretic, pungent, analgesic, cannabimimetic, and antioxidant activities. These natural products are also involved in the potentiation of some antibiotics and the inhibition of prostaglandin biosynthesis, RNA synthesis, and the arachidonic acid metabolism. Many plant species containing alkamides have been used in traditional medicine by different civilizations around the world. Alkamides represent a class of lipidic compounds structurally related to animal endocannabinoids. Based on the structural similarity of these compounds to anandamide (N-arachidonoylethanolamine), an endogenous cannabinoid cerebral neurotransmitter, alkamides are highly active in the central nervous system. Despite their several biological activities, their immunomodulatory and analgesic properties are most important therapeutic applications.
    Full-text · Chapter · Dec 2014
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    ABSTRACT: Natural products from plants have great potential as novel fungicide sources for controlling pathogenic fungi. The aims of this study were to examine the chemical composition of the leave powders and extract (Hexane, methanol and water) of Mexican plants and to test in vitro, their efficacy as antifungal potential against Fusarium oxysporum f. sp. gladioli. All the species showed antifungal activity in the methanol extract. Chemical analysis of leave powders and extracts of Byrsonima crassifolia, Ocimum basilicum, Persea americana, Psidium guajava and Spondias purpurea by gas chromatography and spectrometry of masses (CG-MS) analysis showed that 89 volatile compounds were present. Leave powders and extracts contained the following: sesquiterpenes (46.06%), fatty acids (23.6%), diterpenes (14.6%), phenolic compound (11.23%) and monoterpenes (4.7%). Sesquiterpenes were not detected in B. crassifolia. The powders and leaf of extract, at 5% (hexane and methanol) revealed remarkable antifungal effect in the growth inhibition of Fusarium oxysporum f.sp. gladioli with a range of 15 to 67%. The high chemical diversity of the analyzed plant species results in different effects on the development of the fungus.
    Full-text · Article · Dec 2014 · African journal of microbiology research
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    ABSTRACT: Application of plant derivatives, including Jatropha curcas seed oil, is among the newest alternative methods for controlling Fusarium oxysporum f. sp. gladioli, one of the most widespread and destructive gladiolus fungi. Phorbol esters are considered the main toxic compounds in J. curcas seeds; therefore, knowing the amount of these compounds for the possible application of the oil as fungicide is of utmost importance, including the identification and evaluation of the fungicidal effect of its compounds. In this study, phorbol ester content in the seed oil of a native J. curcas species from the state of Chiapas, Mexico, was almost negligible (0.15 mg g−1). The result of the fractionation indicates that triacylglycerides were the dominant lipids. Further methanolysis of J. curcas seed oil and its fractions gave 49% oleic acid. Antifungal assays showed that the seed oil of J. curcas at 2.5 mg mL−1 inhibited the growth rate of F. oxysporum f. sp. gladioli to about 0.77 cm day−1, while the effect of the G1-G9 fractions, obtained by column chromatography, tested on this parameter was variable. The best inhibitory concentration for G3-G9 fractions was 200 mg L−1. In G4 fraction at a similar concentration, the lowest percentage germination (about 57%) was observed. From the active compounds and commercial triacylglycerides tested, no pattern was associated with concentration-inhibition in the growth rate assay, while the lowest percentage germination was with the commercial triolein at 500 mg L−1 (30% approximately).
    Full-text · Article · Dec 2014
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    ABSTRACT: The new 2-acetyl-8-methoxynaphthol (1) and five new "dimeric" napthopyranones, karwinaphthopyranones A1 and A2 (2 and 3) and karwinaphthopyranones B1-B3 (4-6), possessing a methoxy group at C-5', were isolated together with four other known compounds from the dried fruits of Karwinskia parvifolia. The structures of compounds 2-6 were determined by spectroscopic data interpretation. Cell culture assays showed that some of these compounds possess antiproliferative activities in representative human cancer cell lines, with half-maximal growth inhibitory concentrations in the micromolar range.
    Full-text · Article · Nov 2014 · Journal of Natural Products
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    ABSTRACT: Non-insulin dependent diabetes mellitus is a multifactorial disease that links different metabolic routes; a point of convergence is the enzyme PTP-1B which turns off insulin and leptin receptors involved in glucose and lipid metabolism, respectively. Pentacyclic acid triterpenes such as oleanolic acid (OA) have proved to be excellent PTP-1B inhibitors, thus, the purpose of current work was to generate a series of derivatives that improve the pharmacological effect of OA. Our findings suggest that the presence of the carboxylic acid and/or its corresponding reduction product carbinol derivative (H-bond donor) in C-28 is required to maintain the inhibitory activity; moreover, this is further enhanced by ester or ether formation on C-3. The most active derivatives were cinnamoyl ester (6) and ethyl ether (10). Compound 6 showed potent in vitro inhibitory activity and significantly decrease of blood glucose levels on in vivo experiments. Meanwhile, 10 showed contrasting outcomes, since it was the compound with higher inhibitory activity and selectivity over PTP-1B and has improved interaction with site B, according with docking studies, the in vivo antidiabetic effect was similar to oleanolic acid. In conclusion, oleanolic acid derivatives have revealed an enhanced inhibitory effect over PTP-1B activity by increasing molecular interactions with either catalytic or allosteric sites and producing a hypoglycaemic effect on non insulin dependent diabetes mellitus rat model.
    Full-text · Article · Sep 2014 · European Journal of Medicinal Chemistry
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    ABSTRACT: The need for new bioinsecticidal compounds motivates the study of natural products. Therefore, we studied the activity of Crescentia alata Kuth (Lamiales: Bignoniaceae) against Spodoptera frugiperda (J. E. Smith) (Lepidoptera: Noctuidae). We showed that C. alata has bioinsectidal activity. After 7 days of exposure to C. alata fractions in the diet at 200 ppm, fractions 3, 4 and 7 caused 90.7% weight loss in the larvae, and at 100 ppm, fractions 2, 4, 7 and 8 caused 90.1% weight loss with respect to the control. After 14 days of exposure to fractions 4 and 7 at 200, 100, and 50 ppm, the larvae had lost 94% of their weight compared to the control. There were large differences in larval mortalities between treatments, and fractions 5 and 6 at 200, 100, and 50 ppm induced the highest mortalities, which ranged from 65 to 80%. Possibly the iridoids identified from the C. alata fruit fractions are responsible for the antifeedant activity and mortality of S. frugiperda. This is the first report of C. alata fractions being evaluated as biocides of S. frugiperda.La búsqueda de nuevos compuestos bioinsecticidas motiva el estudio de los productos naturales. Crescentia alata fue estudiada en contra de Spodoptera frugiperda. En este estudio se muestra la actividad bioinsectida de C. alata. Después de siete días de exposición de las fracciones en la dieta a 200 ppm las fracciones: 3, 4 y 7; indujeron un 90.76 % de reducción del peso, a 100 ppm las fracciones 2, 4, 7 y 8 redujeron el peso larval en un 90.1 % con respecto al testigo. Después de 14 días de exposición las fracciones 4 y 7 indujeron una reducción del peso larval en un 94 % con respecto del testigo. En la mortalidad larval existió una gran diferencia entre los tratamientos, la fracción 5 y 6 a 200, 100 y 50 ppm produjeron una alta mortalidad (65 a 80 %). Los iridoides identificados en las fracciones activas de C. alata, sean posiblemente los responsables de la actividad antialimentaria y mortalidad en S. frugiperda.
    Full-text · Article · Jun 2014 · Florida Entomologist
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    ABSTRACT: Stansin 6 a tetrasaccharide resin glycoside isolated from the root of Ipomoea stans was evaluated as anticonvulsant and neuroprotective in kainic acid-induced seizures of rats. Intraperitoneal injection of kainic acid (10mg/kg) induced typical behavioral seizures such as wet dog shakes and limbic seizures, and histopathological changes in the hippocampus (degeneration and loss of pyramidal cells in CA1 to CA4 areas). Stansin 6 (10-80mg/kg) had no effect on the behavior of rats and did not induce hippocampal damage. Pretreatment with stansin 6 inhibited convulsions in rats from kainic acid-induced seizures, reduced the degeneration pattern in the CA3 region, decreased astrocytic reactivity, and reduced the expression of IL-1β and TNF-α induced by kainic acid. These results suggest that stansin 6 possesses neuroprotective and anticonvulsant activities.
    Full-text · Article · May 2014 · Bioorganic & Medicinal Chemistry Letters
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    ABSTRACT: Asthma is a chronic inflammatory disorder that causes contraction in the smooth muscle of the airway and blocking of airflow. Reversal the contractile process is a strategy for the search of new drugs that could be used for the treatment of asthma. This work reports the semisynthesis, ex vivo relaxing evaluation and SAR studies of a series of 18 coumarins. The results pointed that the ether derivatives 1-3, 7-9 and 13-15 showed the best activity (Emax = 100%), where compound 2 (42 μM) was the most potent, being 4-times more active than theophylline (positive control). The ether homologation (methyl, ethyl and propyl) in position 7 or positions 6 and 7 of coumarins lead to relaxing effect, meanwhile formation of esters generated less active compounds than ethers. The SAR analysis showed that it is necessary the presence of two small ether groups and the methyl group at position 4 (site 3) encourage biological activity through soft hydrophobic changes in the molecule, without drastically affecting the cLogP.
    Full-text · Article · Mar 2014 · European Journal of Medicinal Chemistry
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    ABSTRACT: Flourensia genus (Asteraceae) includes about 40 species of resinous shrubs characterized for its leaves surfaces covered with a characteristic oil-fatty film. These plants grow in arid and semiarid regions throughout the American continent. Plants belonging to Flourensia genus show important activities, like insecticidal (García et al., 2007), insect antifeedant (Diaz Napal et al., 2009; Faini et al., 1997a), antibacterial (Joray et al., 2011), antifungal (Jasso de Rodríguez et al., 2012), herbicidal, in-hibitors on the germination and in growth of plants (Diaz Napal et al., 2009; Silva et al., 2012) and as tyrosinase inhibitors (Chiari et al., 2010). F. resinosa S.F. Blake (Asteraceae) is a dominant plant at the semi-desertic zone known as "Cerro del Señor" (20 26 0 10 00 N, 99 05 0 42 00 W, 1915 m above sea level), Ixmiquilpan, Hidalgo, where its aerial parts were collected and identified in October 27, 2007 by M.C. Ramiro Ríos-Gómez from the Facultad de Estudios Superiores Zaragoza, UNAM, México. A voucher specimen (number 11839) was deposited at FESZ Herbarium, UNAM. 2. Previous work F. resinosa is an evergreen shrub up to 2.5 m growing in semiarid environments in central regions of Mexico. As its name suggests, this plant secretes large amounts of resin, which is deposited on its leaves and aerial parts. This resin contains
    Full-text · Article · Dec 2013 · Biochemical Systematics and Ecology
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    Myriam Arriaga-Alba · María Yolanda Rios · Myrna Déciga-Campos
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    ABSTRACT: Context: Heliopsis longipes (A. Gray) Blake (Asteraceae), commonly known in Mexico as "chilcuage" or "chilcuan", is widely used as an analgesic and anesthetic agent. Affinin, the major metabolite of this plant, and the ethanol extract of the plant have shown antinociceptive properties in mice. H. longipes plant produces a complex mixture of antioxidant chlorophylls and polyamines as well as a number of possible antimutagens. Objective: The current study evaluated the potential utilization of the natural product affinin isolated from H. longipes ethanol extract as an antimutagenic and possibly anticarcinogenic agent. Materials and methods: The Ames assay was used to assess the mutagenic properties of affinin (12.5, 25 and 50 µg/plate) that was added to several mutagens with or without S9 metabolic activation in Salmonella typhimurium (TA98, TA100 and TA102 strains). Results: Heliopsis longipes extract and affinin were not toxic as a reduction in the number of His(+) revertant bacteria colonies. Affinin (25 and 50 µg/plate) significantly reduced the frameshift mutations that were generated by 2-aminoanthracene (2AA) (40%) and reduced the oxidative DNA damage generated by norfloxacin (NOR) (37-50%). Affinin possessed antioxidant properties that were able to reduce 2AA- and NOR-induced mutations in S. typhimurium TA98 and TA102, respectively. Discussion and conclusion: Affinin, the principal metabolite of H. longipes, is not mutagenic and possesses antimutagenic activity. These plants are currently used to treat some pain symptoms in Mexico; and antimutagen activity determined could be important to treat some pain symptoms related to antiradical activity.
    Full-text · Article · Aug 2013 · Pharmaceutical Biology
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    ABSTRACT: Morolic (1) and moronic (2) acids are the main constituents of acetonic extract from Phoradendron reichenbachianum (Loranthaceae), a medicinal plant used in Mexico for the treatment of diabetes. The aim of the current study was to establish the sub-acute antidiabetic and antihyperlipidemic effects of compounds 1 and 2 over non insulin-dependent diabetic rat model. Also, to determine the antihyperglycemic action on normoglycemic rats by oral glucose tolerance test. Daily-administered morolic (1) and moronic (2) acids (50mg/kg) significantly lowered the blood glucose levels at 60% since first day until tenth day after treatment than untreated group (p<0.05). Moreover, analyzed blood samples obtained from diabetic rats indicated that both compounds diminished plasmatic concentration of cholesterol (CHO) and triglycerides (TG), returning them to normal levels (p<0.05). Also, pretreatment with 50mg/kg of each compound induced significant antihyperglycemic effect after glucose and sucrose loading (2g/kg) compared with control group (p<0.05). In vitro studies showed that compounds 1 and 2 induced inhibition of 11β-HSD 1 activity at 10μM. However, in silico analysis of the pentaclyclic triterpenic acids on 11β-HSD 1 revealed that all compounds had high docking scores and important interactions with the catalytic site allowing them to inhibit 11β-HSD 1 enzyme. In conclusion, morolic and moronic acids have shown sustained antidiabetic and antihyperglycemic action possibly mediated by an insulin sensitization with consequent changes of glucose, cholesterol and triglycerides, in part mediated by inhibition of 11β-HSD 1 as indicated by in vitro and in silico studies.
    Full-text · Article · Feb 2013 · Phytomedicine: international journal of phytotherapy and phytopharmacology
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    ABSTRACT: Phoradendron brachystachyum is a hemiparasitic plant widely distributed in México that belongs to the Viscaceae family. It has been commonly used in folk medicine as a substitute for the European mistletoe. In this chemical study, morolic acid was isolated as the major component (47.54% of the total composition of acetone extract) of this plant. In addition, 19 known compounds were identified: β-sitosteryl and stigmasteryl linoleates, β-sitosterol, stigmasterol, triacontanol, squalene, α- and β-amyrin, lupeol, lupenone, betulin aldehyde, betulon aldehyde, oleanolic aldehyde, betulinic acid, betulonic acid, moronic acid, morolic acid, oleanolic acid, flavonoids acacetin and acacetin 7-methyl ether. There have been no previous reports in the literature on the chemical composition of this potential natural source of hypoglycaemic and antihypertensive compounds.
    Full-text · Article · Feb 2013 · Natural Product Research
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    Full-text · Dataset · Nov 2012
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    M Angeles Ramírez-Cisneros · Yolanda Rios Gomez · Ramiro Ríos-Gómez · A Berenice Aguilar-Guadarrama
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    ABSTRACT: Krameria pauciflora is a species belonging to the Krameriaceae family. It has been used to treat inflammatory disorders in folkloric Mexican medicine; however, chemistry and pharmacological studies have not been carried out on this species. In this work, from the dichloromethane root extract of K. pauciflora, five cycloartane-type triterpenoids were isolated: cyclomargenyl-3-O-β-caffeoyl ester (1), cyclomargenyl-3-O-β-feruloyl ester (2), cyclomargenyl-3-O-β-coumaroyl ester (3), cyclomargenol (4, polysthicol), and cyclomargenone (5). Additionally, the lignane 6'-methoxyrataniaphenol was isolated. To the best of our knowledge, compounds 1-3 are new natural products, whereas compounds 4 and 5 are isolated for the first time in the Krameria genus and the Krameriaceae family. The structures of all of these compounds were established by 1D and 2D NMR spectroscopy including 1H, 13C, DEPT, COSY, HSQC, and HMBC experiments, as well as by EI mass spectrometry. There is an incomplete previous report about the spectroscopic data of compounds 4 and 5. However, in this work, a complete and unambiguous assignation has been realized. Due to the traditional use of this plant and other species from this genus, such as K. lappacea, cycloartanes isolated herein were evaluated by their inhibition of phospholipase A2, cyclooxygenase-1, and cyclooxygenase-2 enzymes. Cyclomargenyl-3-O-β-caffeoyl ester (1) showed inhibition of phospholipase A2, cyclooxygenase-1, and cyclooxygenase-2 target enzymes for nonsteroidal anti-inflammatory drugs. Both cyclooxygenases were inhibited by cyclomargenol (4); however, cyclomargenyl-3-O-β-feruloyl ester (2) showed inhibition only on cyclooxygenase-1.
    Full-text · Article · Nov 2012 · Planta Medica

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