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Abstract

Ethnopharmacological relevance: Selected Peruvian Amazon plants are macerated into sugar cane distillates to prepare alcoholic beverages used to improve male sexual performance. The tree bark from Campsiandra angustifolia Spruce ex Benth (Fabaceae), Swartzia polyphylla DC (Fabaceae), Minquartia guianensis Aubl. (Olacaceae) and Thynantus panurensis (Bureau) Sandwith (Bignoniaceae) usually are used as crude drugs in mixtures of several ingredients. Aim of study: Describe the chemical composition of the most traded traditional male enhancer beverages, namely "Levántate Lazaro" and "Siete veces sin sacarla", and their single crude drug constituents, as well as their inhibitory activity towards the enzyme phosphodiesterase-5. The presence of pro-sexual drugs such as Sildenafil® and derivatives was assessed in the samples. Materials and methods: Single plant constituents and the preparation mixtures were purchased in the Mercado Belen (Iquitos, Peru). Chemical profiling was carried out by HPLC-DAD-ESI-MS/MS. The extracts were assessed for phosphodiesterase-5 inhibition. The occurrence of pro-sexual drugs was determined by HPLC-DAD-ESI-MS/MS. Results: Chemical profiling allowed the identification of condensed tannins as the main constituents of C. angustifolia and S. polyphylla, hydrolysable tannins for M. guianensis, and C-glycosides for T. panurensis. The traditional preparations showed similar composition compared to the crude drugs. At 200 µg/mL, the traditional preparation "Levántate Lázaro" and "Siete veces sin sacarla" inhibited the phosphodiesterase-5 by 49.88% and 27.90%, respectively. No adulterations with pro-sexual drugs were found in the samples. From the crude drugs, low effect was found for the extracts of S. polyphylla and T. panurensis and high activity for C. angustifolia which inhibited the enzyme by 89.37% and 81.32% at 200 and 100 µg/mL, respectively. Conclusion: The traditional preparations used to improve sexual performance in the Peruvian Amazon showed activity as phosphodiesterase-5 inhibitors. The most active ingredient of the traditional preparations was C. angustifolia, with some contribution from T. panurensis. These results encourage additional studies, including animal models to confirm the male enhancer effect of the preparations.

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... We recently reported the chemical composition and potential male sexual enhancer activity of Campsiandra angustifolia, Minquartia guianensis, Swartzia polyphylla, and Tynanthus panurensis, as well as from two traditional preparations of the Peruvian Amazon. In our experiment, C. angustifolia was found to be a potent inhibitor of PDE-5 in vitro [12]. ...
... The inhibition of PDE-5 was carried out following the manufacturer's instructions of the kit (ab139460, Abcam, Cambdrige, UK), as described in Reference [12]. Crude extracts from stem and roots, as well as the main isolated compounds, were evaluated in concentrations ranging from 0-500 μg/mL. ...
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Aims: Proprietary Chinese medicines (pCMs) and health products, generally believed to be natural and safe, are gaining popularity worldwide. However, the safety of pCMs and health products has been severely compromised by the practice of adulteration. The current study aims to examine the problem of adulteration of pCMs and health products in Hong Kong. Methods: This study was conducted in a tertiary referral clinical toxicology laboratory in Hong Kong. All cases involving use of pCMs or health products which were confirmed to contain undeclared adulterants from 2005 to 2015 were retrospectively reviewed. Results: Four hundred and four cases involving the use of 487 adulterated pCMs or health products with a total of 1234 adulterants were identified. The adulterants consisted of approved drugs, banned drugs, drug analogues and animal thyroid tissue. The six most common categories of adulterants detected were NSAIDs (17.7%), anorectics (15.3%), corticosteroids (13.8%), diuretics and laxatives (11.4%), oral antidiabetic agents (10.0%) and erectile dysfunction drugs (6.0%). Sibutramine was the most common adulterant (n = 155). The reported sources of these illicit products included over-the-counter drug stores, Internet, Chinese medicine practitioners, etc. A significant proportion of patients (65.1%) had adverse effects attributable to these illicit products, including 14 severe and two fatal cases. Psychosis, iatrogenic Cushing syndrome and hypoglycaemia were the three most frequently encountered adverse effects. Conclusions: Adulteration of pCMs and health products with undeclared drugs poses severe health hazards to citizens. Public education and effective regulatory measures are essential to address the problem.
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Ethnopharmacological relevance: The bark of Trichilia catigua A. Juss. (Meliaceae), popularly known as “big catuaba”, is traditionally used in Brazilian folk medicine for its neuroactive potential as memory stimulant, and antinociceptive and antidepressant effects. Aim of the study: To study the aqueous extract of T. catigua bark as dual inhibitor of monoamine oxidase A (MAO-A) and acetylcholinesterase (AChE). To explore its antioxidant potential through interaction with xanthine/xanthine oxidase (X/XO) pathway, and to attempt a correlation between its phenolic profile and effects displayed. Materials and methods: The phenolic profiling was achieved by HPLC-DAD-ESI/MSn and UPLC-ESI-QTOF-MS analyses. The capacity to inhibit hMAO-A was assessed in vitro, as was that for AChE, evaluated in rat brain homogenates. The direct inhibition of the X/XO pathway and the scavenging of superoxide anion radical were the selected in vitro models to explore the antioxidant potential. The cytotoxic effects were assayed with the human neuronal cells SH-SY5Y by MTT reduction, after direct exposure. Results: Twenty-six compounds were identified and quantified (551.02 ± 37.61 mg/g of lyophilized extract). The phenylpropanoid substituted flavan-3-ols were the most representative compounds (~81% of quantified mass). The extract inhibited hMAO activity in a concentration-dependent manner (IC50 = 121.06 ± 2.13 g/mL). At 200 g/mL a competitive inhibition of AChE activity was observed, as reflected by the increase of Km (from 0.122 ± 0.018 to 0.195 ± 0.035) calculated from Michaelis-Menten fitted equations. In addition, it was demonstrated that the extract directly inhibits the X/XO pathway (IC50 = 121.06 ± 2.13 g/mL) and also imbalance the oxidative stress acting as superoxide anion radical scavenger (EC50 = 104.42 ± 10.67 g/mL), an oxidative by-product of this reaction. All these neuroprotective and neurotrophic effects were displayed within the non-toxic range of concentrations (0.0063-0.500 g/mL) to SH-SY5Y cells. Conclusion: Our results validate the traditional use of T. catigua bark for its neuroactive and neuroprotective potential. A novel approach upon its application towards the management of neurodegenerative and related symptomatology was likewise demonstrated.
Article
Ethnopharmacological relevance: In the Peruvian Amazon, the use of medicinal plants is a common practice. However, there is few documented information about the practical aspects of their use and few scientific validation. The starting point for this work was a set of interviews of people living in rural communities from the Peruvian Amazon about their uses of plants. Protozoan diseases are a public health issue in the Amazonian communities, who partly cope with it by using traditional remedies. Validation of these traditional practices contributes to public health care efficiency and may help identify new antiprotozoal compounds. Aims of study: to inventory and validate the use of medicinal plants by rural people of Loreto region. Materials and methods: Rural mestizos were interviewed about traditional medication of parasite infections with medicinal plants. Ethnopharmacological surveys were undertaken in two villages along Iquitos-Nauta road (Loreto region, Peru), namely 13 de Febrero and El Dorado communities. Forty-six plants were collected according to their traditional use for the treatment of parasitic diseases, 50 ethanolic extracts (different parts for some of the plants) were tested in vitro on Plasmodium falciparum (3D7 sensitive strain and W2 chloroquine resistant strain), Leishmania donovani LV9 strain and Trypanosoma brucei gambiense. Cytotoxic assessment (HUVEC cells) of the active extracts was performed. Two of the most active plants were submitted to preliminary bioguided fractionation to ascertain and explore their activities. Results: From the initial plants list, 10 were found to be active on P. falciparum, 15 on L. donovani and 2 on the three parasites. The ethanolic extract from Costus curvibracteatus (Costaceae) leaves and Grias neuberthii (Lecythidaceae) bark showed strong in vitro activity on P. falciparum (sensitive and resistant strain) and L. donovani and moderate activity on T. brucei gambiense. Conclusions: The Amazonian forest communities in Peru represents a source of knowledge on the use of medicinal plants. In this work, several extracts with antiprotozoal activity were identified. This work contributes to validate some traditional uses and opens subsequent investigations on active compounds isolation and identification.
Article
Ethnopharmacological relevance: Maca - Lepidium meyenii Walp has been cultivated and used by Andean people for over 1,300 to 2000 years in Peru as food and medicine. Starting in the late 1990's it has developed into an important herbal medicine in China and is now cultivated there widely, too. Aim of study: This study aims to provide an insight into the emergence of maca on the global market as an alternative remedy to treat reproductive health related problems in both men and women and to critically assess these health claims. Methodology: A search of electronic databases such as EMBASE and a hand-search was done to acquire peer-reviewed articles and reports about maca. Results and discussion: Lepidium meyenii is used traditionally as a tonic, fertility enhancer for both humans and cattle, and to treat a variety of ailments such as rheumatism, respiratory disorders and anaemia among others. Maca root is cooked, baked, fermented as a drink and made into porridge. In the last twenty years, maca was introduced onto the global market and demand has dramatically grown over this time with its promotion on the internet, as the 'Peruvian Ginseng' for libido and fertility enhancement. It has also been said to treat menopausal symptoms, erectile dysfunction and benign prostatic hyperplasia. The sky-rocketing demand for the plant has seen a shift from traditional cultivation methods to mass production practices with the use of fertilisers and also pesticides; as maca is now grown in areas other than the Andes such as in the Yunnan province in China. This can potentially affect the phytochemistry and composition of the plant and thus, the quality, safety and efficacy of maca products. Meanwhile, research into maca's medicinal properties has followed the spike in popularity of maca and has been focused mainly on maca's aphrodisiac and fertility enhancing properties. So far, the in vivo studies and clinical trials conducted have yielded inconclusive results. Some of the key limitations reside in methodology and sample size. Chemical profiling, led to the discovery of new compounds unique to maca, such as, 'macamides' and also other active metabolites like the glucosinolates; to which the medicinal effects of maca have been ascribed but cannot be confirmed due to lack of data. Conclusions: To date, the health claims of maca cannot be fully supported from a scientific standpoint and more research is needed. It appears that the indigenous local knowledge about the health benefits of maca has been dragged out of context to fit the demands of a growing market for herbal remedies. This globalisation (or hype esp. in China) also has had serious consequences for the local producers in Peru. The lack of protocols to regulate the production and marketing of maca during this rapid expansion, poses a threat to both the safety of consumers and the sustainability of supply.
Article
Intracellular cyclic AMP and/or cyclic GMP are characterized in the 1960th. These second messengers, hydrolysed specifically by cyclic nucleotide phosphodiesterase (PDE), play a major role in intracellular signalling. Natural products have been a rich source of drug discovery, Theophylline and Methylxanthine originated from tea leaves used for asthma treatment, whereas, Papaverine, a natural isoquinolein originated from Papaver somniferum traditionally used in impotency, altogether as caffeine where firstly described as PDE-inhibiting compounds. Since that time, the knowledge in PDE field has been drastically increased, allowing the design and development of new therapeutic drugs acting against different pathologies in the nanomolar range. During this period some natural compounds have been identified as PDE inhibitors and used in that context to investigate their therapeutic potential effects. The aim of this literature review is to point out the reported data and demonstrating the contribution of natural characterized molecules as PDE inhibitors in various pathologies that can open new fields of research for drug discovery, notably in epigenetic regulation.
Article
A dichloromethane extract of the roots from the Panamanian plant Swartzia simplex exhibited a strong antifungal activity in a bioautography assay against a genetically modified hypersusceptible strain of Candida albicans. At-line HPLC activity based profiling of the crude extract enabled a precise localization of the antifungal compounds, and dereplication by UHPLC-HRESIMS indicated the presence of potentially new metabolites. Transposition of the HPLC reversed-phase analytical conditions to medium-pressure liquid chromatography (MPLC) allowed an efficient isolation of the major constituents. Minor compounds of interest were isolated from the MPLC fractions using semipreparative HPLC. Using this strategy, 14 diterpenes (1-14) were isolated, with seven (5-10, 14) being new antifungal natural products. The new structures were elucidated using NMR spectroscopy and HRESIMS analysis. The absolute configurations of some of the compounds were elucidated by electronic circular dichroism spectroscopy. The antifungal properties of these compounds were evaluated as their minimum inhibitory concentrations in a dilution assay against both hypersusceptible and wild-type strains of C. albicans and by assessment of their antibiofilm activities. The potential cytological effects on the ultrastructure of C. albicans of the antifungal compounds isolated were evaluated on thin sections by transmission electron microscopy.
Article
IntroductionThe Food and Drug Administration defines an aphrodisiac drug product as “any product that bears labeling claims that it will arouse or increase sexual desire, or that it will improve sexual performance.” Presently, there are no approved medications for the treatment of lowered desire for women, and many opt for “natural” products.AimThe aim of this article was to review the most popular and currently used aphrodisiac products marketed in the United States. The safety and efficacy of animal- and plant-based aphrodisiacs, vitamins and minerals, and popular over-the-counter combination supplements have been reviewed.Methods An English PubMed literature search was performed using the key words “sexuality,” “sex,” “aphrodisiac,” and “sexual enhancer.” Approximately 50 articles were reviewed by the authors. The authors used relevant case series, case-controlled, and randomized clinical trial data.Main Outcome MeasuresProducts were evaluated based on the quality of research, and their known efficacy and safety considerations. Products with low risk and potential benefit for sexual response based on prior research studies were highlighted.ResultsResearch has demonstrated that the risks of yohimbine, Spanish fly, mad honey, and Bufo toad may outweigh any benefit, and these products should be avoided. Other products, such as Maca, Tribulus, Ginkgo, and ginseng, have limited but emerging data. Randomized clinical trial data are often lacking, but future research should be performed to further elucidate the efficacy and safety of these products.Conclusion Future randomized clinical trials are warranted before health care practitioners can recommend most aphrodisiac products. There remain some medical concerns with drug interactions, purity, reliability, and safety. West E and Krychman M. Natural aphrodisiacs—A review of selected sexual enhancers. Sex Med Rev **;**:**–**.
Article
ABSTRACT Oligomeric proanthocyanidins were successfully identified by UHPLC-PDA-HRMSn in a selection of plant derived materials (jujube fruit, Fuji apple, fruit pericarps of litchi and mangosteen, dark chocolate, and grape seed and cranberry extracts). The identifies of around 247 proanthocyanidins were theoretically predicted by computing high accuracy masses based on the degree of polymerization, flavan-3-ol components, the member of A-type linkage and galloyls. MSn fragments allowed characterization on flavan-3-ol based on the monomer, connectivity, and location of A-type bonds. Identification of doubly or triply charged ions of 50 PAs was made based on theoretical calculations. A single catechin standard and molar relative response factors (MRRFs) were used to quantify the well separated PAs. The ratios of the SIM peak counts were used to quantify each of the un-separated isomers. This is the first report of direct determination of proanthocyanidins in plant-derived foods and the proanthocyanidins containing epifisetinidol unit in grape seeds.
Article
The aims of this study were the evaluation of polyphenols and vitamin C content, and antioxidant capacity of dehydrated pulp powder and the dried flour obtained from the skin and seeds residue remaining after pulp preparation from camu-camu (Myrciaria dudia). Fifty-three different phenolics were characterised by HPLC-DAD-ESI-MS-MS and UPLC-HR-QTOF-MS-MS. The phenolic content of camu-camu flour was higher than that of the pulp powder (4007.95mg/100g vs. 48.54mg/100g). In both products the flavonol myricetin and conjugates, ellagic acid and conjugates and ellagitannins were detected. Cyanidin 3-glucoside, and quercetin and its glycosides were only found in the pulp powder, while proanthocyanidins were only present in the flour (3.5g/100g, mean degree of polymerisation 3). The vitamin C content was lower in pulp powder (3.5%) than in the flour (9.1%). The radical-scavenging capacity of both powders was determined by the DPPH, ABTS and ORAC assays, and was higher for camu-camu flour as could be expected for its higher phenolics and vitamin C content. Comparative analyses with fresh camu-camu berries indicate that some transformations occur during processing. Analysis of fresh berries showed that ellagic acid derivatives and ellagitannins were mainly present in the seeds, while proanthocyanidins were present both in the seeds and skin.
Article
Ethnopharmacological relevance: Up until now, the plant pharmacopoeia of the Chayahuita, an ethnic group from the Peruvian Amazon, has been poorly defined. This paper details the uses of medicinal plants within this community, as recorded in two villages of the Paranapura basin, Soledad and Atahualpa de Conchiyacu. This study aimed to describe the basis of the Chayahuita traditional medical system, to document part of the medicinal plant corpus, and to compare it with data from other Amazonian ethnic groups. Material and methods: Methodology was based (i) on field prospection with 26 informants (ethnobotanical walks methodology), (ii) semi-structured interviews including 93 people (49 men and 44 women) focused on the most recent health problem experienced and on the therapeutic options chosen, (iii) individual or group thematic discussions relating to disease and treatments, (iv) 6-months of participants' observations between May 2007 and May 2008. At the end of the project in May 2008 a workshop was organized to cross-check the data with the help of 12 of the most interested informants. Results: Six hundred and seventeen voucher specimens were collected, corresponding to 303 different species, from which 274 (belonging to 83 families) are documented here. Altogether 492 recipes were recorded, corresponding to a global figure of 541 therapeutic uses and a total of 664 use reports. The main therapeutic uses are related to dermatological problems (103 uses; 19%), gastro-intestinal complaints (69 uses; 13%) and malaria/fevers (52 uses; 10%). Diseases are analysed according to Chayahuita concepts, and for each disease the species having a high frequency of citation are listed, and the most frequently used remedies are described. Whenever possible, comparisons with other Amazonian groups have been drawn. Conclusion: Chayahuita nosology and medical ethnobotany appear to draw their inspiration from a common panamazonian root. Despite the fact that a certain number of medicinal plants are shared with other nearby groups, there seem to be specific uses for some species, thus highlighting the originality of the Chayahuita pharmacopoeia. Presently there is a certain disinterest in the most traditional area of the Chayahuita medical ways, and the role of the penutu (shaman) seems to be less highly-valued than in the past. Nonetheless, the use of medicinal plants in phytotherapeutic treatment is very much a living, shared knowledge.
Article
The stem bark of Minquartia guianensis is used by the Quijos Quichua people of Ecuador's Amazonian lowlands in an infusion drunk to treat intestinal parasitic infections, lung cancer, and tuberculosis and is applied topically to treat muscular pain and skin irritations. Using the in vitro P-388 murine lymphocytic leukemia cytotoxicity bioassay to guide fractionation of the CHCl 3 extract of M. guianensis stem bark, the novel cytotoxic polyacetylene (-)-17-hydroxy-9,11,13,15-octadecatetraynoic acid [1] was isolated. The P-388 ED 50 of the pure compound is 0.18 μg/ml, and it is also active in the brine shrimp larvicidal bioassay, with an LC 50 of 5.06 7mu;g/ml (95% confidence interval 3.68-6.98). These biological activities could account for the alleged efficacy of the plant in folk usage.
Article
Polyphenol profile of Citrus juices of sweet orange, tangerine, lemon and grapefruit from Spanish cultivars was obtained by High-Performance Liquid Chromatography with Diode Array Detection coupled to Electrospray ionization and Triple Quadrupole Mass Spectrometry. Fifty eight phenolic compounds of five different classes were identified in these Citrus juices. Flavanone: O-dihexoside of naringenin; flavones: apigenin-7-O-rutinoside-4'-O-glucoside, luteolin-7-O-neohesperidoside-4'-O-glucoside, luteolin-6-C-glucoside, 6,8-di-C-acylhexosides of chrysoeriol and diosmetin, 6C- and 8C-glucoside-O-pentoside of apigenin, apigenin-6-C-hexoside-O-hexoside and apigenin-8-C-hexoside-O-acylrhamnoside; flavonols: 7-O-rutinosides of quercetin, kaempferol, isorhamnetin and tamarixetin, kaempferol-3-O-rutinoside, isorhamnetin-3-O-rutinoside-7-O-glucoside, tamarixetin-3-O-rutinoside-7-O-glucoside, isorhamnetin-3-O-hexoside-7-O-rhamnosylhexoside, 3-O-rhamnoside-7-O-rhamnosylhexoside of quercetin and isorhamnetin and kaempferol-3-O-rhamnosylhexoside-7-O-rhamnoside; hydroxycinnamic acids: O-hexoside of ferulic and sinapic acid; and, coumarins: O-hexoside and O-rhamnosylhexoside of scopoletin, had not previously been reported in Citrus juices to our knowledge. Structures have been assigned on the basis of the complementary information obtained from retention time, UV-visible spectra, scan mode MS spectra, and fragmentation patterns in MS(2) spectra obtained using different collision energies. A structure diagnosis scheme is provided for the identification of different phenolic compounds.
Article
Lichexanthone, 17-hydroxy,9,11,13,15-octadecatetraynoic acid and fatty acid esters (mixture) of erythrodiol (12-oleanene-3,28-diol, 3-β-form), and betulin (20-(29)-lupen-3,28-diol) were isolated. The structure of the new triterpene, 13,28-epoxy-3-acetoxy-11-oleanene, 3β,13β form, was determined by X-ray diffraction. The triterpenes occur mainly as C-3-O-palmitates.
Article
The success of synthetic phosphodiesterase type-5 (PDE-5)-inhibitor drugs (viz sildenafil, vardenafil and tadalafil), which are constituents of popular brands (viz Viagra, Levitra and Cialis, respectively) for the treatment of erectile dysfunction in males, has led to their widespread use as adulterants in herbal dietary supplements (HDSs). There have been reports that not only these three approved drugs but also their unapproved analogues have been found in HDSs. The problem is becoming more complex, as concealed, structurally modified analogues are increasingly being used. Also, counterfeits of the popular brands have emerged.Fortunately, it has become possible to detect these drugs and their derivatives as adulterants and counterfeits by using modern sensitive and selective analytical techniques [e.g., liquid chromatography with tandem mass spectrometry, Fourier transform (FT) with near infrared spectrometry, and FT with Raman spectroscopy], although some conventional approaches have also been employed.We critically review the literature, and present generalized strategies, including flow charts, for characterizing adulteration of PDE-5 inhibitors in HDSs, and detecting and categorizing counterfeit products.
Article
The use of aphrodisiacs dates back thousands of years in Chinese, Indian, Egyptian, Roman, and Greek cultures. Although the scientific basis of these substances was not understood, aphrodisiacs were valued for their ability to enhance the sexual experience. Their use allowed for human procreation and the ability to obtain a sexually fulfilling relationship. Aphrodisiacs used historically include ambrein, Bufo toad, Spanish fly, yohimbine, Tribulus terrestris, horny goat weed, muira puama, MACA root, Panax ginseng, nutmeg, saffron, and cacao. Previous studies on these substances have shown potential aphrodisiac properties using animal models and in human clinical trials. Aphrodisiacs were shown to relax corpus cavernosum smooth muscle tissue in animals, improve erection quality in humans and animals, or increase sexual behavior and satisfaction in humans and animals. Although most studies showed positive effects of aphrodisiacs on sexual enhancement, more studies are needed to understand their mechanism of action. The need for clinical trials using larger populations is also evident to prove the effectiveness of aphrodisiacs for human use. This paper will review recent scientific studies conducted on these commonly used aphrodisiacs, and determine whether the results support or refute their use for human sexual enhancement.
Article
High-performance liquid chromatography-electrospray ionization mass spectrometry (HPLC-ESI-MS) and tandem mass spectrometry (MS(n)) were used to investigate the phenolic constituents in methanol, water, and methanol/water extracts of Eucalyptus globulus Labill. bark. Twenty-nine phenolic compounds were identified, 16 of them referenced for the first time as constituents of E. globulus bark, namely, quinic, dihydroxyphenylacetic, and caffeic acids, bis(hexahydroxydiphenoyl (HHDP))-glucose, galloyl-bis(HHDP)-glucose, galloyl-HHDP-glucose, isorhamentin-hexoside, quercetin-hexoside, methylellagic acid (EA)-pentose conjugate, myricetin-rhamnoside, isorhamnetin-rhamnoside, mearnsetin, phloridzin, mearnsetin-hexoside, luteolin, and a proanthocyanidin B-type dimer. Digalloylglucose was identified as the major compound in the methanol and methanol/water extracts, followed by isorhamnetin-rhamnoside in the methanol extract and by catechin in the methanol/water extract, whereas in the water extract catechin and galloyl- HHDP-glucose were identified as the predominant components. The methanol/water extract was shown be the most efficient to isolate phenolic compounds identified in E. globulus bark.
Article
High-performance liquid chromatography-mass spectrometry (HPLC-MS(n)) detected aspalathin and nothofagin, C-glycosides of apigenin and luteolin, and four eriodictyol-C-glycoside isomers in unfermented and fermented rooibos teas. The fermented drink contained 10-fold higher levels of aspalathin and nothofagin and a 4-fold lower eriodictyol-C-glycoside content than the fermented tea. The total flavonoid contents in 500 mL servings of the teas were 84 (fermented) and 159 mumol (unfermented). Following the ingestion of 500 mL of the teas by 10 volunteers, 0-24 h urine and plasma samples were collected for analysis. HPLC-MS(n) identified eight metabolites in urine. These were O-linked methyl, sulfate, and glucuronide metabolites of aspalathin and an eriodictyol-O-sulfate. The main compound excreted was an O-methyl-aspalathin-O-glucuronide (229 nmol) following ingestion of the unfermented drink and eriodictyol-O-sulfate (68 nmol) after ingestion of the fermented beverage. The overall metabolite levels excreted were 82 and 352 nmol, accounting for 0.09 and 0.22% of the flavonoids in the fermented and unfermented drinks, respectively. Most of the aspalathin metabolites were excreted within 5 h of tea consumption, suggesting absorption in the small intestine. Urinary excretion of the eriodictyol-O-sulfate occurred mainly during the 5-12 h collection period, indicative of absorption in the large intestine. Despite exhaustive searches, no flavonoid metabolites were detected in plasma.
Article
The methanolic extract of Swartzia polyphylla DC. heartwood had antibacterial activity against cariogenic bacteria, the mutans Streptococci. The chromatographic purification of the extract afforded seven flavonoids. Among them, three known isoflavanones, dihydrobiochanin A, ferreirin and darbergioidin, and one new isoflavanone, 5,2',4'-trihydroxy-7-methoxyisoflavanone (dihydrocajanin) had potent antibacterial activity against cariogenic bacteria. This effect was not detected on isoflavone derivatives. A comparative antibacterial study of various flavonoids was further performed, and their structure-activity relationship was discussed.
Article
Fractionation of an ethanolic extract of Swartzia polyphylla, guided in part by an assay for inhibition of protein kinase C, led to the isolation of the known flavonoids biochanin A, dihydrobiochanin A, ferreirin, dalbergioidin, and naringenin, and one new prenylated isoflavonone, dihydrolicoisoflavone [1].
Article
To determine the effect of oral administration of a purified lipidic extract from Lepidium meyenii (MacaPure M-01 and M-02) on the number of complete intromissions and mating in normal mice, and on the latent period of erection (LPE) in rats with erectile dysfunction. Mice and rats were randomly divided into several experimental and control groups. A 10% ethanol suspension of M-01 and M-02 was orally administered for 22 days to the experimental groups according to the dosage specified by the experimental design. On day 22, 30 minutes after the dose was administered to the male mice, 2 virgin female mice were placed with 1 male mouse. The number of complete intromissions of each male mouse in 3 hours was recorded. In an assessment of 1 day of mating, each male mouse was cohabited with 5 estrous female mice overnight. The number of sperm-positive females was recorded. The LPE was measured to assess the sexual function in rats with erectile dysfunction. By using a YSD-4G multifunction instrument, an electric pulse at 20 V was applied to stimulate the rat's penis, and the duration from the start of the stimulus to full erection was measured in seconds as the LPE. In the normal male mice, the number of complete intromissions during the 3-hour period was 16.33 +/- 1.78, 46.67 +/- 2.39, and 67.01 +/- 2.55 for the control group, M-01 group, and M-02 group, respectively. In the assessment of mating, the number of sperm-positive females increased from 0.6 +/- 0.7 in the control group to 1.5 +/- 0.5 in the M-01 experimental group. The LPE of male rats with erectile dysfunction was 112 +/- 13 seconds with a regular diet (control group). The oral administration of M-01 at a dose of 180 or 1800 mg/kg body weight and M-02 at a dose of 45, 180, or 1800 mg/kg body weight reduced the LPE to 54 +/- 12 seconds, 54 +/- 13 seconds, 71 +/- 12 seconds, 73 +/- 12 seconds, and 41 +/- 13 seconds, respectively. The LPE of the surgical rats treated with M-01 at the lowest dose (45 mg/kg) was 121 +/- 12 seconds; thus, the change was not significant. Oral administration of M-01 and M-02 enhanced the sexual function of the mice and rats, as evidenced by an increase in the number of complete intromissions and the number of sperm-positive females in normal mice, and a decrease in the LPE in male rats with erectile dysfunction. The present study reveals for the first time an aphrodisiac activity of L. meyenii, an Andean Mountain herb.
Article
The fragmentation behavior of 18 chlorogenic acids that are not substituted at position 1 has been investigated using LC-MS(4) applied to a methanolic coffee bean extract and commercial cider (hard cider). Using LC-MS(3), it is possible to discriminate between each of the three isomers of p-coumaroylquinic acid, caffeoylquinic acid, feruloylquinic acid, and dicaffeoylquinic acid, and a hierarchical key has been prepared to facilitate this process when standards are not available. MS(4) fragmentations further support these assignments, but were not essential in reaching them. The distinctive behavior of 4-acyl and 3-acyl chlorogenic acids compared with the 5-acyl chlorogenic acids is a key factor permitting these assignments. The fragmentation patterns are dependent upon the particular stereochemical relationships between the individual substituents on the quinic acid moiety. Fragmentation is facilitated by 1,2-acyl participation and proceeds through quinic acid conformers in which the relevant substituents transiently adopt a 1,3-syn-diaxial relationship. Selected ion monitoring at m/z 529 clearly indicated the presence in coffee of six caffeoylferuloylquinic acid isomers, whereas previously only two or three had been demonstrated. The hierarchical key permitted specific structures to be assigned to each of the six isomers. These assignments are internally consistent and consistent with the limited data previously available.
Article
Phosphodiesterases (PDEs) play a decisive role in cyclic nucleotide-mediated intracellular signaling. As PDEs are expressed in a variety of tissues, selectivity is a prerequisite for a therapeutically applicable PDE inhibitor. Sildenafil, vardenafil, and tadalafil are selective for PDE5, with vardenafil exhibiting the highest potency and minimal inhibition of other PDEs, with the exception of PDE6. Tadalafil is extremely selective for PDE5, but also potently inhibits PDE11, an enzyme with unknown physiological function. As PDE1 is expressed in the brain, myocardium, and vascular smooth muscle cells, nonselectivity with respect to this enzyme (selectivity: tadalafil>vardenafil>sildenafil) may result in vasodilation and tachycardia. Inhibition of PDE6 (selectivity: tadalafil>vardenafil congruent with sildenafil), which is expressed only in retina and functions in visual transduction, can transiently disturb vision. PDE5 inhibitors may also indirectly inhibit PDE3 by increasing cyclic guanosine monophospate levels, thereby elevating heart rate and vasodilation while inhibiting platelet aggregation.
Article
Viagra has had a profound influence on the search for natural products with erectile-dysfunction activity. To date the "natural" equivalent is not in existence but several pure compounds from nature, e.g., Yohimbine, Citrulline, two pyrano-isoflavones, berberine, forskolin and others, have either been re-examined or are new potential candidates. Intense activity exists in the area of testing semi-purified plant extracts for erectile dysfunction activity.
Article
A phytochemical analysis of the methanol extract of Tynanthus panurensis bark led to the isolation of one new phenylpropanoid glycoside, eugenol-O-[beta-D-xylopyranosyl-(1-->5)-O-beta-D-apiofuranosyl-(1-->6)-O-beta-D-glucopyranoside], the known verbascoside, isoverbascoside, and leucosceptoside, along with the known flavonoid apigenin 8-C-[beta-D-xylopyranosyl-(1-->6)-beta-D-glucopyranoside], namely, katchimoside. Their structures were established by NMR and ESIMS experiments. Additionally, a quantitative study of the phenylpropanoid glycosides fraction of T. panurensis bark and of the hydroalcoholic extract prepared according to the traditional recipe was performed by combining high-performance liquid chromatography diode array detection with positive electrospray ionization tandem mass spectrometry. The new eugenol derivate was found to be the most abundant phenylpropanoid glycoside in both dried bark (19.5 mg/g) and hydroalcoholic extract (0.24 mg/mL). The antioxidant activity of all the isolated compounds and of the methanol and hydroalcoholic extract of the bark was determined by measuring the free radical scavenging effects using the Trolox equivalent antioxidant capacity method. The traditional hydroalcoholic extract showed a moderate activity.
Article
Adulteration of allegedly "natural herbal medicines" with undeclared synthetic drugs is a common and dangerous phenomenon of alternative medicine. The purpose of the study was to develop a procedure for detection of most common synthetic adulterants in herbal remedies, using high-pressure liquid chromatography-electrospray tandem mass spectrometry (LC-ESI-MS-MS). Eighty drugs belonging to various pharmacological classes were included in the study. For most drugs two transitions were monitored, using protonated or deprotonated molecules as precursor ions. The drugs were isolated from herbal remedies using simple methanol extraction. Chromatographic separation was done in gradient of acetonitrile-10 mM ammonium formate buffer (pH 3.0). Drugs tested were grouped in suites, comprising analgesic drugs, antibiotics, antidiabetic drugs, antiepileptic drugs, aphrodisiacs, hormones and anabolic drugs, psychotropic drugs, and weight reducing compounds. These suites were used according to the declared benefits of examined preparations. Limits of detection ranged from 5 pg to 1 ng per injected sample. Drug-free herbal remedy spiked with eight various pharmaceuticals occurring in adulterated herbal preparations was used for internal proficiency testing. The recoveries of spiked drugs ranged from 63 to 100%. The procedure was applied in everyday casework. Several undeclared drugs were identified in "herbal" remedies, like e.g. sildenafil, tadalafil, testosterone, or glibenclamide. Pharmacological properties of detected drugs always corresponded with the claims of the "natural" remedies. The method presents a valuable extension of standard GC-MS screening used for this purpose.
Article
The root of Scutellaria baicalensis, called Huangqin in Chinese, is one of the most commonly used traditional Chinese medicines for the treatment of hepatitis, tumors, diarrhea, and inflammatory diseases. The major chemical constituents of Huangqin are flavonoids. In the present paper, HPLC-DAD-ESI-MS(n) was used to analyze flavonoids in the roots of S. baicalensis. A total of 26 flavonoids were identified or tentatively characterized, including 5 C-glycosides, 12 O-glycosides, and 9 free aglycones. Two C-glycosides, apigenin-6-C-glucyl-8-C-arabinoside and chrysin-6,8-di-C-glucoside, together with some O-glycosides, are reported from S. baicalensis for the first time. This method is simple, reliable and sensitive, and could be used for the quality control of Huangqin and its related preparations.
Article
Fifty three O-glycosyl-C-glycosyl flavones with O-glycosylation on phenolic hydroxyl or on the C-glycosyl residue or combination of both forms have been studied by liquid chromatography-UV diode array detection-electrospray ionisation mass spectrometry ion trap in the negative mode. The study of the relative abundance of the main ions from the MS preferential fragmentation on -MS2 and/or -MS3 events allows the differentiation of the position of the O-glycosylation, either on phenolic hydroxyl or on the sugar moiety of C-glycosylation. In addition, it is possible to discriminate between O-glycosylation at 2'' and at 6'' positions. The occurrence of an abundant ion Y(0)(-) ([(M-H)-132/-146/-162](-), mono-O-pentosyl/rhamnosyl/hexosyl-C-glycosyl derivatives) after -MS2 fragmentation characterizes the O-glycosylation on phenolic hydroxyls. The preferential fragmentation leading to a relevant Z(1)(-) ([Y(1)-18](-)) fragment is characteristic of 2''-O-glycosyl-C-glycosyl derivatives. The 6''-O-glycosyl-C-glycosyl derivatives are characterized by (0,2)X(0)(-), which is generated by a global loss of the sugar moiety from the O-glycosylation at 6'' and the glycosidic fraction that involves the carbons 6''-3'' of the C-glycosyl residue ([(M-H)-162-120](-), in the case of 6''-O-hexosyl-C-hexosyl derivatives). Regarding the combined O-glycosylated compounds (both on phenolic hydroxyl and on sugar moiety at C-glycosylation), the main fragmentation on -MS2 events produces a Y(0)(-) characterizing the O-glycosylation on the phenolic hydroxyl, and the -MS3[(M-H)-->Y(0)](-) fragmentation of the O-glycosylation on the C-glycosyl residue.
  • G Schmeda-Hirschmann
G. Schmeda-Hirschmann et al. Journal of Ethnopharmacology 229 (2019) 167-179