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A decoction prepared from the aerial parts of Melampodium divaricatum showed antinociceptive and antihyperalgesic responses when tested in the formalin model in mice. From the CH2 Cl2 fraction of the decoction, two non-previously reported secondary metabolites, 3-O-ß-D-glucopyranosyl-16α-hydroxy-ent-kaurane (1) and melampodiamide (2) [(2'R*,4'Z)-2'-hydroxy-N-[(2S*,3S*,4R*)-1,3,4-trihydroxyoctadec-2-yl]tetracos-4-enamide] were separated and characterized by spectroscopic, spectrometric, and computational techniques. The flavonoids isoquercitrin and hyperoside, which possessed noted antinociceptive properties, were obtained from the active AcOEt fraction of the decoction. The chemical composition of the essential oil of the plant was also analyzed by gas chromatography-mass spectrometry. The major constituents were (E)-caryophyllene, germacrene D, ß-elemene, δ-elemene, γ-patchoulene, and 7-epi-α-selinene. Headspace solid-phase microextraction analysis detected (E)-caryophyllene as the main volatile compound of the plant.

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Individuals experiencing unsheltered homelessness face significant barriers to accessing water, sanitation, and hygiene services, but the risks associated with this lack of access and barriers to service provision have been largely understudied. We analyzed water samples upstream and downstream of three homeless encampments in the San Diego River watershed and interviewed service providers from public and nonprofit sectors to assess local perceptions about challenges and potential solutions for water and sanitation service provision in this context. Water upstream from encampments contained detectable levels of caffeine and sucralose. Escherichia coli concentrations downstream of the encampments were significantly greater than concentrations upstream, but there was no significant change in the concentrations of other pollutants, including caffeine and sucralose. The HF183 marker of Bacteroides was only detected in one sample upstream of an encampment and was not detected downstream. Overall, there was insufficient evidence to suggest that the encampments studied here were responsible for contributing pollution to the river. Nevertheless, the presence of caffeine, sucralose, and HF183 indicated that there are anthropogenic sources of contamination in the river during dry weather and potential risks associated with the use of this water by encampment residents. Interviews with service providers revealed perceptions that the provision of water and sanitation services for this population would be prohibitively expensive. Interviewees also reported perceptions that most riverbank residents avoided contact with service providers, which may present challenges for the provision of water and sanitation service unless trust is first built between service providers and residents of riverine encampments.

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Chemical investigation of the leaves from Ageratina glabrata yielded four new thymol derivatives, namely: 10-benzoyloxy-8,9-dehydro-6-hydroxythymol isobutyrate (4), 10-benzoyloxy-8,9-dehydrothymol (5), 10-benzoyloxythymol (6) and 10-benzoyloxy-6,8-dihydroxy-9-isobutyryl-oxythymol (7). In addition, (8S)-10-benzoyloxy-8,9-epoxy-6-hydroxythymol isobutyrate (1), together with other two already known thymol derivatives identified as 10-benzoyloxy-8,9-epoxy-6-methoxythymol isobutyrate (2) and 10-benzoyloxy-8,9-epoxythymol isobutyrate (3) were also obtained. In this paper, we report the structures and complete assignments of the ¹H and (13)C-NMR data of compounds 1-7, and the absolute configuration for compound 1, unambiguously established by single crystal X-ray diffraction, and evaluation of the Flack parameter. The in vitro antiprotozoal assay showed that compound 1 and its derivative 1a were the most potent antiamoebic and antigiardial compounds. Both compounds showed selectivity and good antiamoebic activity comparable to emetine and metronidazole, respectively, two antiprotozoal drugs used as positive controls. In relation to anti-propulsive effect, compound 1 and 1a showed inhibitory activity, with activities comparable to quercetin and compound 9, two natural antipropulsive compounds used as positive controls. These data suggest that compound 1 may play an important role in antidiarrheal properties of Ageratina glabrata.

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From the leaves of Ageratina cylindrica, in addition to the described [(2S)-2-{4-formyl-5-hydroxy-2-[(2-methylpropanoyl)oxy]phenyl}oxiran-2-yl]methyl benzoate (cylindrinol A, 8), seven new thymol derivatives were isolated and named cylindrinols B - H (1 - 7). The structures of these compounds were established as (2-{4-(hydroxymethyl)-2-[(2-methylpropanoyl)oxy]phenyl}oxiran-2-yl)methyl benzoate (1), (2-{4-formyl-2-[(2-methylpropanoyl)oxy]phenyl}oxiran-2-yl)methyl benzoate (2), (2-{4-[(acetyloxy)methyl]-2-[(2-methylpropanoyl)oxy]phenyl}oxiran-2-yl)methyl benzoate (3), [2-(2-[(2-methylpropanoyl)oxy]-4-{[(2-methylpropanoyl)oxy]methyl}phenyl)oxiran-2-yl]methyl benzoate (4), [2-(5-hydroxy-2-[(2-methylpropanoyl)oxy]-4-{[(2-methylpropanoyl)oxy]methyl}phenyl)oxiran-2-yl]methyl benzoate (5), 2-{4-(hydroxymethyl)-2-[(2-methylpropanoyl)oxy]phenyl}prop-2-en-1-yl benzoate (6), and 2-hydroxy-2-[2-hydroxy-4-(hydroxymethyl)-phenyl]-3-[(2-methylpropanoyl)oxy]propyl benzoate (7), by spectroscopic means. Compounds 1 showed moderate antiprotozoal activity on both protozoa. Compounds 4 and 5 showed selectivity on Giardia lamblia trophozoites. All isolated compounds were less active than two antiprotozoal drugs, metronidazole and emetine, used as positive controls. Compound 5 exhibited a high inhibitory effect on hyperpropulsive movement of the small intestine in rats; its effect was best than loperamide, antidiarrheal drug used as a positive control.

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The aqueous extract of the leaves of Ageratina cylindrica afforded six new ent-kaurenoic acid glycosides together with the known diterpenoid paniculoside V, the flavonoid astragalin, chlorogenic acid, and L-chiro-inositol. The structures were elucidated mainly by NMR and MS methods, and the absolute configuration was established by vibrational circular dichroism spectroscopy. The new compounds showed moderate antiprotozoal activity against Entamoeba histolytica and Giardia lamblia trophozoites.

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The leaves of Ageratina cylindrica afforded a thymol derivative that was characterized by physical and spectroscopical methods as (8S)-8,9-epoxy-6-hydroxy-l0-benzoyloxy-7-oxothymol isobutyrate (1). The absolute configuration of 1 was established as 8S by vibrational circular dichroism spectroscopy in combination with density functional theory calculations and by evaluation of the Flack and Hooft X-ray parameters. Compound 1 showed weak antiprotozoal activity against Entamoeba histolytica and Giardia lamblia trophozoites and a high inhibitory effect on hyperpropulsive movement of the small intestine in rats.

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The antiviral activity of extracts obtained from Ageratina havanensis (Kunth) R.M.King & H.Rob., Asteraceae, against rabbit vesivirus (RaV) (Caliciviridae) and human herpes simplex viruses type 1 and 2 (HSV-1, HSV-2) (Herpesviridae) were analyzed, and the main metabolites from the most active extract were isolated and characterized. The antiviral properties were investigated by measuring the inhibition of viral-induced cytopathic effect in Vero cells. The strongest inhibitory effects were found for ethyl acetate extract from leaves (SI=5 for RaV and SI=5.4 for HSV-1). The crude ethyl acetate extract was further fractionated by chromatographic methods and the structures of isolated compounds were established through comprehensive spectroscopic analyses, including IR, 2D NMR and MS. Four flavonoids were identified: 5,4'-dihydroxy-7-methoxyflavanone (sakuranetin), 3,5,4'-trihydroxy-7-methoxyflavanone (7-methoxyaromadendrin), 4'-O-β-D-glucosyl-5,3'-dihydroxy-7-methoxyflavanone (4'-O-β-D-glucosyl-7-methoxy-eriodictyol) and 4'-O-β-D-glucosyl-5-hydroxy-7-methoxyflavanone (4'-O-β-D-glucosylsakuranetin). This is the first report on antiviral activity for Ageratina havanensis.

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The structure of the known 2''-O-α-rhamnosyl-4''-O-methylvitexin (apigenin-8-C-α-rhamnosyl-(1→2)-ß-4-O-methylglucopyranoside), isolated from the leaves of Piper ossanum, was revised to acacetin-8-C-neohesperidoside (acacetin-8-C-α-rhamnosyl-(1→2)-ß-glucopyranoside or 2''-O-α-rhamnosyl-4'-O-methylvitexin) (1). The NMR data and theoretical calculations established the preferred conformation of 1, which is controlled by CH/π interactions. This phenomenon explains the unusual chemical shifts of some protons in the molecule, besides other weak intramolecular interactions such as the anomeric effect, the Δ2 effect, and several hydrogen bonds.

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Fractionation with n-hexane/ethyl acetate (1:1 v/v) by open column chromatography of the oleoresin from Pinus oocarpa Schiede yielded two diterpenes, pimaric acid (1) and dehydroabietic acid (5), the sesquiterpene longifolene (3) and a diterpenic mixture containing pimaric acid (1), isopimaric acid (4) and dehydroabietic acid (5). Subsequently, the isolated compounds, the mixture of 1, 4 and 5, the oleoresin and the dehydroabietic acid methyl ester (2), were tested in vitro against epimastigotes of Trypanosoma cruzi, the causative agent of Chagas disease. The most active compounds were 1, 3 and the oleoresin, being as active as nifurtimox, a drug effective in the treatment of acute infection by American trypanosomiasis and used in this work as positive control.

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As a defense mechanism of the leaves of Rhus javanica (Anacardiaceae) against the aphid Melaphis chinensis (Aphididae) attack, tannic acid is rapidly accumulated and forms galls along the midrib of the leaves resulting in a unique natural medicine Gallae Rhois. Tannic acid was found to inhibit the oxidation of L-3,4-dihydroxyphenylalanine (L-DOPA) catalyzed by tyrosinase (EC 1.14.18.1) with an IC50 of 22 microM. The aphid would detoxify the ingested toxic tannic acid to relatively nontoxic gallic acid, whereas the non-adapted pink bollworm Pectinophora gossypiella larvae are sensitive to the ingested tannic acid.

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Anisic acid (p-methoxybenzoic acid) was characterized as a tyrosinase inhibitor from ani-seed, a common food spice. It inhibited the oxidation of L-3,4-dihydroxyphenylalanine (L-DOPA) catalyzed by tyrosinase with an IC50 of 0.60 mM. The inhibition of tyrosinase by anisic acid is a reversible reaction with residual enzyme activity. This phenolic acid was found to be a classical noncompetitive inhibitor and the inhibition constant K(I) was obtained as 0.603 mM. Anisic acid also inhibited the hydroxylation of L-tyrosine catalyzed by tyrosinase. The lag phase caused by the monophenolase activity was lengthened and the steady-state activity of the enzyme was decreased by anisic acid.

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A novel tetrahydroxypyrrolizidine alkaloid (6) was obtained from rosmarinine degradation in 23% yield (isolated from Senecio callosas).

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Two new oleanane-type triterpenes, characterized as 3-oxo-11alpha,12alpha-epoxy-oleanan-28,13beta-olide and 3-oxo-olean-11-en-28,13beta-olide , were isolated from the fruits and seeds of Cedrela montana (Meliaceae). In addition, the known compounds oleanonic acid, a mixture of beta-sitosterol and stigmasterol, and the limonoid photogedunin were also isolated. The structures of the new compounds were established by spectroscopic methods, including 2D NMR.

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The roots and aerial parts of Tephrosia major Micheli, afforded a new prenylated-beta-hydroxychalcone, characterized as 2',6'-dihydroxy-3'-prenyl-4'-methoxy-beta-hydroxychalcone. In addition, seven prenylated flavonoids, two rotenoids, beta-sitosterol, stigmasterol, lupeol and quercetin were isolated. The structure of the new beta-hydroxy chalcone was established by spectroscopic methods, including 2D NMR experiments.

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