In Vitro Action of <i>ent</i>-Manoyl Oxides against <i>Leishmania donovani</i>

Garcı́a-Granados, Andrés; Liñán, Emilio; Martı́nez, Antonio; Rivas, Francisco; Mesa-Valle, Concepción; Castilla-Calvente, Juan José; Osuna, Antonio

doi:10.1021/np9603636

Cited by 15 publications

(11 citation statements)

References 17 publications

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“…8). Ribenone (61) and, its ent-6 -hydroxy (62) and 1,2-dehydro (64) derivatives, inhibited the growth of the pathogenic protozoon Leishmania donovani [5]. Several ent-manoyl oxides, epimers at C-13 of ribenone (61) and metabolites 64 y 68, isolated from Croton oblongifolius [8h], exhibited strong activity against gastric carcinoma (KATO-3) and moderate activity against other types of carcinoma.…”

Section: Natural Ent-13-epi-manoyl Oxides and Analoguesmentioning

confidence: 99%

“…Incubation of methyl ester 144 with C. lunata yielded an ent-6 -hydroxy derivative (170, 8%), as well as 159 (3%), previously isolated with R. nigricans, whereas with its 13-epimer (145), monohydroxylations at C-11 (161, 26%) and C-6 (171, 18%), and dihydroxylations at C-6/C-11 (172, 3%), or at C-3/C-11 (163, 3%), were produced by entface [49]. C. lunata improved the yield of metabolite 161 (carbomanoyl) with regard to R. nigricans, a compound that inhibits the activity of the AC enzyme [7e, 50], and also inhibits the growth of the protozoon Leishmania donovani [5]. The action of F. moniliforme on the methyl ester epimers 144 and 145 was similar producing ent-1 -hydroxylation in both substrates (159, 23%; 173, 14 %) [49], improving the yield of metabolite 159, previously obtained from the incubations with C. lunata or R. nigricans.…”

Section: Semi-synthetic Ent-manoyl Oxidesmentioning

confidence: 99%

“…In this context, the microbial transformation of manoyl oxides by filamentous fungi has been used to introduce hydroxyl groups, at positions difficult to achieve, by chemical means, on the substrates. The main interest of the biotransformations of manoyl oxides has been to achieve new poly-functionalized compounds, due to the wide variety of biological properties that have been described for these compounds, including anti-inflammatory [3], anti-hypertensive [4], anti-leishmanial [5], antibacterial [6], enzyme stimulation [7], cytotoxic [8], phytotoxic [9] and insecticidal [10], most of these being covered in two reviews [11].…”

Section: Introductionmentioning

confidence: 99%

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Manoyl-Oxide Biotransformations with Filamentous Fungi

Garcı́a-Granados¹,

Martı́nez²,

Parra³

et al. 2007

COC

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Microbial transformations of manoyl oxides by filamentous fungi have been used to introduce hydroxyl groups, regio-and stereoselectively, into substrates at positions difficult to achieve by chemical means. The principal objective of most papers published in this field has been to produce new, highly oxygenated, bioactive manoyl-oxide compounds that present a large diversity of biological properties. The manoyl oxides most frequently studied at present are forskolin and its derivatives, the pharmacological activity of which is related to their ability to activate AC (adenylate cyclase), thus generating an increase in intracellular cAMP (cyclic adenosine monophosphate). The microbial hydroxylation of forskolin and 1,9-dideoxyforskolin has been extensively studied, using the fungi Scopuloriopsis sp., Syncephalastrum sp., Neurospora crassa, Mortierella isabellina and several Aspergillus sp.. Other biotransformation studies of natural manoyl oxides and hemi-synthetic enantio derivatives, carried out via the biomimetic cyclization of ent-8 -hydroxylabda-13(16),14-dienes, have used filamentous fungi Curvularia lunata, Cunninghamella elegans, Fusarium moniliforme, Gibberella fujikuroi, Gliocladium roseum, Mucor plumbeus, Rhizopus nigricans and Neurospora crassa. In some cases, the new hydroxylations were introduced at the same positions as in natural forskolin, yielding some noteworthy products that show biological activities.

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Section: Natural Ent-13-epi-manoyl Oxides and Analoguesmentioning

confidence: 99%

Section: Semi-synthetic Ent-manoyl Oxidesmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Manoyl-Oxide Biotransformations with Filamentous Fungi

Garcı́a-Granados¹,

Martı́nez²,

Parra³

et al. 2007

COC

Self Cite

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“…Antimicrobial activity [103,104] Salvia candidissima [105] Salvia linariaefolia strong antibacterial activity [74] Salvia palestina antimicrobial activity [73] Sideritis hirsuta, S. nutans, S. perfoliata Against Leishmania donovani [150][151][152][153][154] Sideritis javalabrensis Anti-inflammatory activity [160,161,183,184] S. varoi subsp. cuatrecasasii, subsp.…”

Section: Coleus Forskohliimentioning

confidence: 99%

“…cuatrecasasii, subsp. nijarensis Inhibitors of the growth of the promastigote and amastigote forms of Leishmania donovani [150][151][152] Stachys chrysantha Antibacterial activity [98] Leguminosae Copaifera L. species Antimicrobial activity, cosmetic purposes [82,[222][223][224] Lythraceae Meliaceae Mimosaceae Nolanaceae Pinaceae ( …”

Section: Coleus Forskohliimentioning

confidence: 99%

Labdanes of Natural Origin-Biological Activities (1981-2004)

Chinou

2005

CMC

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Terpenoids is a class of natural compounds found in higher plants, mosses, liverworts, algae and lichens, as well as in insects, microbes or marine organisms. Through centuries many of these compounds have been used as ingredients of perfumes, drugs, narcotics or pigments. Labdanes, belonging to the bicyclic diterpenoids group, have been found as secondary metabolites in tissues of fungi, insects, marine organisms, and in essential oils, resins and tissues of higher plants. The diterpenes of labdane type, have been reported to have broad spectrum of biological activities. In this study, the reported bioactivities and/or uses of them, the last two decades (1981-2004), are selected as an attempt to underline their role in nature.

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In vitro Biological Activities of Gold(I) and Gold(III) Bis(N-Heterocyclic Carbene) Complexes

et al. 2017

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The aim of this research is to evaluate for the first time the in vitro leishmanicidal activity and inhibition of a-glucosidase and b-glucuronidase of new gold(I) and gold(III) complexes involving N-heterocyclic carbene (NHC) ligands, with the general formula [Au(X) n (NHC)R 2 ][BF 4 ] (X=Cl, OAc, R = various aromatic and aliphatic substituents). The Au(III) complexes were shown to have a significant antileishmanial activity, and were also found to be more potent inhibitors of a-glucosidase and b-glucuronidase enzymes than the standard drugs. Some complexes were also identified as potent anti-inflammatory agents with activity comparable to that of tested standard drugs, allopurinol and ibuprofen. These gold complexes were also evaluated for their in vitro cytotoxic activity against HeLa (cervical cancer), MCF-3 (breast cancer), and 3T3 (mouse fibroblast) cell lines.Recent advancements in transition-metal-based compounds have found wide medical applications. The use of cisplatin to treat ovarian cancer and the discovery of the gold-based drug auranofin to treat rheumatoid arthritis are among the numerous examples that have seen transition metal complexes combat human ailments. Nowadays, large libraries of platinum-, palladium-, ruthenium-and gold-containing molecules are being synthesized for therapeutic purposes. [1][2][3]

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In Vitro Action of ent-Manoyl Oxides against Leishmania donovani

Cited by 15 publications

References 17 publications

Manoyl-Oxide Biotransformations with Filamentous Fungi

Manoyl-Oxide Biotransformations with Filamentous Fungi

Labdanes of Natural Origin-Biological Activities (1981-2004)

In vitro Biological Activities of Gold(I) and Gold(III) Bis(N-Heterocyclic Carbene) Complexes

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