Phytochemistry and Biological Activities of Werneria and Xenophyllum species / Fitoquímica y actividades biológicas de especies de Werneria y Xenophyllum

Plants of the genera Werneria (Asteraceae) and Xenophyllum (genus extracted from Werneria) are used in traditional medicine of Latin America for the treatment of mountain sickness, hypertension and gastrointestinal disorders. Only a small number of species of these genera have been studied, leading to the isolation of compounds belonging to the classes of benzofurans, chromenes, acetophenones, coumarates, diterpenes and pyrrolizidine alkaloids. Some of the plant extracts and/or compounds have shown antimicrobial, anti-HIV, hypotensive and photoprotective activities.

Las plantas de los géneros Werneria (Asteraceae) y Xenophyllum (género extraido de Werneria) son usadas en la medicina tradicional de América Latina para el tratamiento del mal de montaña, hipertensión y desórdenes gastrointestinales. Solo un pequeño número de especies de estos géneros ha sido investigado, lográndose aislar compuestos que pertenecen a las clases de benzofuranos, cromenos, acetofenonas, cumaratos, diterpenos y alcaloides pirrolizidínicos. Algunos de los extractos y/o compuestos de dichas plantas han mostrado actividades antimicrobianas, anti-HIV, hipotensoras y fotoprotectoras.

Bioactive Compounds from Plants Used in Peruvian Traditional Medicine.

It is estimated that there are as many as 1400 plant species currently used in traditional Peruvian medicine; however, only a few have undergone scientific investigation. In this paper, we make a review of the botanical, chemical, pharmacological and clinical propierties of the most investigated Peruvian medicinal plants. The plant species selected for this review are: Smallanthus sonchifolius (yacon), Croton lechleri (sangre de grado), Uncaria tomentosa/U. guianensis (uña de gato), Lepidium meyenii (maca), Physalis peruviana (aguaymanto), Minthostachys mollis (muña), Notholaena nivea (cuti-cuti), Maytenus macrocarpa (chuchuhuasi), Dracontium loretense (jergon sacha), Gentianella nitida (hercampuri), Plukenetia volubilis (sacha inchi) and Zea mays (maiz morado). For each of these plants, information about their traditional uses and current commercialization is also included.

Essential oil characterization of two Azorean Cryptomeria japonica populations and their biological evaluations.

Essential oils from foliage, bark and heartwood of Cryptomeriajaponica D. Don from Azores Archipelago (Portugal) were analyzed by GC and GC-MS. Two populations, of black and reddish heartwood color, were studied. The main compounds found in the foliage of both populations were alpha-pinene (9.6-29.5%), (+)-phyllocladene (3.5-26.5%), ent-kaur-16-ene (0.2-20.6%), sabinene (0.5-19.9%) and limonene (1.4-11.5%), with a large variation in individual compounds from each population. Heartwood oils were characterized by a high content of cubebol (2.8-39.9%) and epi-cubebol (4.1-26.9%) isomers, which were absent in the foliage. Elemol and eudesmol isomers were found in the foliage and heartwood oils, while (+)-phyllocladene was absent in heartwood. Black and reddish bark oils were composed of the diterpenes dehydroferruginol (1.9-5.1%) and ferruginol (2.6-11.5%), along with the sesquiterpenes delta-cadinene (10.4-15.9%), alpha-muurolene (3.3-5.4%), epi-zonarene (4.0-5.0%), cubenol (9.3-14.0%), tau-muurolol (4.8-10.7%), beta-eudesmol (3.0-9.9%), gamma-eudesmol (1.9-7.0%) and hedycariol (1.4-6.2%). Azorean C. japonica oils exhibited significant chemical differences compared with native plants from Asia. The essential oils showed moderate antimicrobial activity against the pathogenic fungus Cryptococcus neoformans and human pathogenic bacteria (especially against multidrug-resistant Mycobacterium tuberculosis). The antimicrobial activity of the essential oils may be attributed to compounds such as ent-kaur-16-ene, (+)-phyllocladene, ferruginol and elemol, which are present in different proportions within the complex oil mixture. These results suggest a potential use for C. japonica oils obtained from wood industry leftovers.

Dihydrochalcones and benzoic acid derivatives from Piper dennisii.

Two new dihydrochalcones (1, 2), as well as eight known compounds, piperaduncin C (3), 2',6'-dihydroxy-4'-methoxydihydrochalcone (4), 4,2',6'-trihydroxy-4'-methoxydihydrochalcone (5), 4-hydroxy-3,5-bis(3-methyl-2-butenyl)-benzoic acid (6), 3,5-bis(3-methyl-2-butenyl)-4-methoxybenzoic acid (7), 4-hydroxy-3-(3-methyl-2-butenoyl)-5-(3-methyl-2-butenyl)-benzoic acid (8), 2,2-dimethyl-8-(3-methyl-2-butenyl)-2H-1-chromene-6-carboxylic acid (9), and 3-(3',7'-dimethyl-2',6'-octadienyl)-4-methoxybenzoic acid (10) were isolated from the leaves of Piper dennisii Trelease (Piperaceae), using a bioassay-guided fractionation to determine their antileishmanial potential. Among them, compound 10 exhibited the best antileishmanial activity (IC50 = 20.8 µM) against axenic amastigote forms of Leishmania amazonensis, with low cytotoxicity on murine macrophages. In the intracellular macrophage-infected model, compound 10 proved to be more active (IC50 = 4.2 µM). The chemical structures of compounds 1-10 were established based on the analysis of the spectroscopic data.

Actividad antifúngica de cuatro plantas usadas en la medicina tradicional peruana. Aislamiento de 3'- formil ­ 2',4',6' ­ trihidroxidihidrochalcona, principio activo de Psidium acutangulum / Antifungal activity of four plants used in traditional Peruvian medicine. Isolation of 3'-formyl-2 ', 4', 6'-trihydroxydihydrochalcone, active ingredient of Psidium acutangulum

En el presente trabajo se evaluó la actividad antifúngica de los extractos etanólicos de Thevetia peruviana (Pers.) K. Schum. (Apocynaceae), Spondias mombin L. (Anacardiaceae), Calycophyllum spruceanum (Benth.) Hook. f. ex K. Schum. (Rubiaceae) y Psidium acutangulum DC (Myrtaceae), cuatro plantas utilizadas en la medicina tradicional peruana contra las infecciones micóticas de la piel. El extracto etanólico de Psidium acutangulum fue el más activo contra los hongos evaluados (Candida albicans, Sporothrix schenckii y Trychophyton mentagrophytes), por lo que fue sometido a fraccionamiento biodirigido que condujo al aislamiento de 3'-formil-2',4',6'- trihidroxidihidrochalcona. Este compuesto mostró concentraciones inhibitorias mínimas en el rango de 16-512 µg/mL contra los hongos Cryptococcus neoformans, S. schenckii y varias especies de Candida. Los resultados obtenidos apoyan el uso de Psidium acutangulum en la medicina tradicional peruana. Su actividad antifúngica se debe principalmente a la 3'-formil-2',4',6'- trihidroxidihidrochalcona.

Cytotoxic and anti-infective sesquiterpenes present in Plagiochila disticha (Plagiochilaceae) and Ambrosia peruviana (Asteraceae).

A pharmacological screening of the ethanol extract and fractions of two Peruvian medicinal plants, Plagiochila disticha and Ambrosia peruviana, led to the isolation and characterization of three ENT-2,3-secoaromadendrane-type sesquiterpenoids, named plagiochiline A ( 1), I ( 2), and R ( 3), as well as of two pseudoguaianolids, damsin ( 4) and confertin ( 5), which exhibited significant cytotoxic activity against a panel of human tumor cell lines. Compounds 1, 4, and 5 were also investigated for their in vitro antileishmanial, trypanocidal, and antituberculosis activity against Leishmania amazonensis axenic amastigotes and Trypanosoma cruzi trypomastigotes, as well as against MDR and sensitive strains of Mycobacterium tuberculosis, respectively.

Medicinal plants from the Yanesha (Peru): evaluation of the leishmanicidal and antimalarial activity of selected extracts.

AIM OF THE STUDY: Ninety-four ethanolic extracts of plants used medicinally by the Yanesha, an Amazonian Peruvian ethnic group, for affections related to leishmaniasis and malaria were screened in vitro against Leishmania amazonensis amastigotes and against a Plasmodium falciparum chloroquine resistant strain. MATERIALS AND METHODS: The viability of Leishmania amazonensis amastigote stages was assessed by the reduction of tetrazolium salt (MTT) while the impact on Plasmodium falciparum was determined by measuring the incorporation of radio-labelled hypoxanthine. RESULTS AND CONCLUSIONS: Six plant species displayed good activity against Plasmodium falciparum chloroquine resistant strain (IC(50) < 10 microg/ml): a Monimiaceae, Siparuna aspera (Ruiz & Pavon), A. DC., two Zingiberaceae, Renealmia thyrsoidea (Ruiz & Pavon) Poepp. & Endl. and Renealmia alpinia (Rottb.), two Piperaceae (Piper aduncum L. and Piper sp.) and the leaves of Jacaranda copaia (Aubl.) D. Don (Bignoniaceae). Eight species displayed interesting leishmanicidal activities (IC50 < 10 microg/ml): Carica papaya L. (Caricaceae), Piper dennisii Trel (Piperaceae), Hedychium coronarium J. König (Zingiberaceae), Cestrum racemosum Ruiz & Pav. (Solanaceae), Renealmia alpinia (Rottb.) Zingiberaceae, Lantana sp. (Verbenaceae), Hyptis lacustris A. St.-Hil. ex Benth. (Lamiaceae) and Calea montana Klat. (Asteraceae). Most of them are used against skin affections by Yanesha people. Results are discussed herein, according to the traditional use of the plants and compared with data obtained from the literature.

A multipronged approach to the study of peruvian ethnomedicinal plants: a legacy of the ICBG-Peru Project.

A multidisciplinary and international team of scientists was assembled in the early 1990s to conduct an ethnobotanical study of plants used by the Aguaruna people of the Peruvian Amazon forest. The initial ethnobotanical project, carried out under the auspices of an International Cooperative Biodiversity Grant (ICBG), led to the collection of approximately 4000 plant species. Some members of the original team of scientists have continued this collaboration by focusing on potential sources of new anticancer, anti-infective, and wound-healing agents. This effort has uncovered several secondary metabolites representing a wide variety of chemical diversity. In this short review we describe some bioactive compounds of interest as part of our continuing collaboration.

Anti-infective and cytotoxic compounds present in Blepharodon nitidum.

A pharmacological screening of the ethanol extract and fractions of Blepharodon nitidum led to the isolation of fourteen compounds, two of which, 24-hydroperoxycycloart-25-en-3beta-ol and 25-hydroperoxycycloart-23-en-3beta-ol, exhibited in vitro anti- Mycobacterium tuberculosis and antileishmanial activities, as well as significant cytotoxic activity against a panel of human tumor cell lines.

Isolation of cytotoxic metabolites from targeted peruvian amazonian medicinal plants.

The antiproliferative bioassay-guided fractionation of five Peruvian plants, Doliocarpus dentatus, Picramnia sellowii, Strychnos mitscherlichii, Iryanthera juruensis, and Croton alnifolius, led to the isolation and identification of their different major cytotoxic constituents, betulinic acid (1), nataloe-emodin (2), bisnordihydrotoxyferine (4), 2',4'-dihydroxy-6'-methoxy-3,4-methylenedioxydihydrochalcone (5), and 2',4'-dihydroxy-4,6'-dimethoxydihydrochalcone (6) and 12-O-tetradecanoylphorbol-13-acetate (7), respectively. Eight human tumor cell lines and two nontumorigenic cell lines were used in this investigation. Their in vitro activity against Mycobacterium tuberculosis is also reported.

Treatment of THP-1 cells with Uncaria tomentosa extracts differentially regulates the expression if IL-1beta and TNF-alpha.

Uncaria tomentosa, commonly known as cat's claw, is a medicinal plant native to Peru, which has been used for decades in the treatment of various inflammatory disorders. Uncaria tomentosa can be used as an antioxidant, has anti-apoptotic properties, and can enhance DNA repair, however it is best know for its anti-inflammatory properties. Treatment with Uncaria tomentosa extracts inhibits the production of the pro-inflammatory cytokine, TNF-alpha, which is a critical mediator of the immune response. In this paper, we showed that treatment of THP-1 monocyte-like cells with Uncaria tomentosa extracts inhibited the MAP kinase signaling pathway and altered cytokine expression. Using ELISA assays, we showed that treatment with Uncaria tomentosa extracts augmented LPS-dependent expression of IL-1beta by 2.4-fold, while inhibiting the LPS-dependent expression of TNF-alpha by 5.5-fold. We also showed that treatment of LPS-stimulated THP-1 cells with Uncaria tomentosa extracts blocked ERK1/2 and MEK1/2 phosphorylation in a dose-dependent manner. These data demonstrate that treatment of THP-1 cells with Uncaria tomentosa extracts has opposite effects on IL-1beta and TNF-alpha secretion, and that these changes may involve effects on the MAP kinase pathway.

Aegicerin, the first oleanane triterpene with wide-ranging antimycobacterial activity, isolated from Clavija procera.

An ethanol extract of the Peruvian plant Clavija procera, a member of the rare Theophrastaceae family, was fractionated using a colorimetric bioassay-guided protocol against Mycobacterium tuberculosis (MTB), yielding the oleanane triterpenoid aegicerin (1) as the active constituent. Its MIC values ranged between 1.6 and 3.12 microg/mL against 37 different sensitive and resistant MTB strains (1 H37Rv, 21 susceptible clinical isolates, 2 INH-resistant clinical isolates, and 13 MDR clinical isolates).

Larvicidal, antimycobacterial and antifungal compounds from the bark of the Peruvian plant Swartzia polyphylla DC.

The 95% ethanol extract of the bark of Swartzia polyphylla DC (Fabaceae) possesses important larvicidal, antimycobacterial and antifungal activity in vitro. Bioassay-guided studies performed on the crude ethanol extract afforded T-cadinol as the larvicidal and anti-Mycobacterium tuberculosis principle, while the antifungal activity of the extract is due to the presence of the flavonoids biochanin A and dihydrobiochanin A.

Antimicrobial and free radical scavenging activity of Gentianella nitida.

The antimicrobial and free radical scavenging activity of the ethanol extract and fractions of Gentianella nitida have been assessed. The most susceptible microorganisms were Candida albicans, Trichophyton mentagrophytes and Microsporum gypseum. The antifungal activity was concentrated in the 90% methanol and nonsoluble fractions, while the radical scavenging activity was stronger in the ethyl acetate and nonsoluble fractions.

Antimicrobial activity of selected Peruvian medicinal plants.

The antimicrobial activity of 36 ethanol extracts from 24 plants, all of them currently used in the Peruvian traditional medicine for the treatment of several infectious and inflammatory disorders, was tested by means of the agar-well diffusion assay against four bacteria (Bacillus subtilis, Staphylococcus aureus, Escherichia coli and Pseudomonas aeruginosa) and four fungi (Candida albicans, Trichophyton mentagrophytes, Microsporum gypseum and Sporothrix schenckii). Twenty-five (69%) extracts showed some degree of antimicrobial activity against at least one microorganism. The plants with the greatest antimicrobial activity were Cestrum auriculatum L. Heritier (Solanaceae), Iryanthera lancifolia Ducke Suesseng (Myristicaceae), Lepechinia meyenii (Walp.) Epling (Lamiaceae) and Ophryosporus peruvianus (Gmelin) King & H. Rob. (Asteraceae).