Lanostane triterpenes from the fungus Pisolithus tinctorius

Zamuner, M L M; Cortez, Diógenes Aparı́cio Garcia; Filho, Benedito Prado Dias; Lima, Matheus P.; Rodrigues‐Filho, Edson

doi:10.1590/s0103-50532005000500028

Cited by 10 publications

(10 citation statements)

References 13 publications

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“…On the other hand, lanosterol derivatives isolated in the fruiting bodies of this species showing small subtle differences from those found in the mycelium (Table 1), as 24-methyl and 24-ethyl-lanostan-8, 24 (28)-dien-3, 22, 23-triol-22-acetate (Lobo, De Abreu, Prabhakar, & Godinho, 1985;Zamuner et al, 2005), pisosterol, pisosterol acetate (Gill, Kiefe, Skelton, & White, 1989;Zamuner et al, 2005), 3-oxo-pisolactona (De Abreu et al, 1991;Lobo et al, 1988), epi-pisosterol and pisosteral . Some authors distinguish these differences at carbon-23 and they propose that derivates of lanosterol less oxidized participate in the processes of fixation and mycorrhizal formation Zamuner et al, 2005).…”

Section: Resultados Y Discusiónmentioning

confidence: 89%

“…Some authors distinguish these differences at carbon-23 and they propose that derivates of lanosterol less oxidized participate in the processes of fixation and mycorrhizal formation Zamuner et al, 2005). It is also known that even in the same species, mycorrhizal isolates from different sources show morphological variations and cause differential effects on plant growth when used as inoculants (Castellano & Molina, 1989), which could also be mediated by secondary metabolites, but it is necessary to confirm this with further studies on mycorrhizae of P. arhizus in vivo, due to the limitations of asymbiotic culture conditions of this piece of research.…”

Section: Resultados Y Discusiónmentioning

confidence: 99%

“…Una señal doble a δ 0,92 (0,91), J = 6,6 Hz, se asignó a los protones del metilo H-21 y dos señales dobles a δ 1,04 (1,01) y 1,07 (1,02), J = 6,8 Hz, que integraron para tres protones cada una, se asignaron a H-26 y H-27. Con estos datos y de acuerdo con la literatura, los compuestos 1 y 2 fueron identificados como 22-R-lanostan-8, 24 (28)-dien-3β, 22-diol y 22-R-lanostan-28-metil-8,24(28)-dien-3β, 22-diol, respectivamente (Baumert et al, 1997;Zamuner, Cortez, Dias-Filho, Lima, & Rodrigues-Filho, 2005).…”

Section: Resultados Y Discusiónunclassified

“…Por otro lado, los derivados de lanosterol aislados en los cuerpos fructíferos de esta especie muestran pequeñas diferencias sutiles de las que se encuentran en el micelio (Tabla 1), tal como 24-metil y 24-etil-lanostan-8, 24 (28)-dien-3, 22, 23-triol-22-acetat (Lobo, De Abreu, Prabhakar, & Godinho, 1985;Zamuner et al, 2005), pisosterol, pisosterol acetato (Gill, Kiefe, Skelton, & White, 1989;, 3-oxo-pisolactona (De Abreu et al, 1991;Lobo et al, 1988), epi-pisosterol y pisosteral . Algunos autores distinguen estas diferencias en el carbono-23 y proponen que los derivados de lanosterol menos oxidados participan en los procesos de fijación y la formación de micorrizas .…”

Section: Resultados Y Discusiónunclassified

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IDENTIFICACIÓN DE UN DERIVADO DE LANOSTEROL PROCEDENTE DEL HONGO CULTIVADO Pisolithus arhizus (Scop.) Rauschert

Márquez-Fernández¹,

Herrera²,

Castellanos-Onorio³

et al. 2013

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de Tlaxcala. km 10.5 Autopista San Martín Texmelucan-Tlaxcala. C. P. 90122. Ixtacuixtla, Tlax. RESUMENL os hongos micorrizógenos se encuentran en asociación con las raíces de muchas plantas, incluyendo casi todas las especies de árboles como la familia Pinaceae. Algunos derivados triterpé-nicos de lanosterol se han aislado tanto del micelio como de los cuerpos fructíferos del hongo ectomicorrizógeno Pisolithus arhizus. En el presente trabajo, se cultivó una cepa de la especie P. arhizus, aislada de bosques de pino en Oaxaca en condiciones de laboratorio, con el fin de determinar qué tipo de compuestos se pueden encontrar en una cepa mexicana cultivada bajo condiciones asimbió-ticas y sus posibles implicaciones ecológicas. Los resultados confirman que, en la fermentación líquida in vitro del micelio, la cepa aislada de los bosques de México presenta el mismo tipo de triterpenos sin funcionalidad con el carbono-23 como otras cepas procedentes de bosques de Europa y Brasil, a pesar de que se utilizó un medio de cultivo PDA en lugar del medio de cultivo Melin-Norkrans. ABSTRACTM ycorrhizal fungi can be found in association with the roots of many plants, including almost all tree species such as the Pinaceae family. Some triterpene derivatives of lanosterol have been isolated both in the mycelium as well as in the fruiting bodies of the ectomycorrhizal fungus Pisolithus arhizus. In order to determine, what type of compounds can be found as well as any possible ecological implications involved in the case of a Mexican strain cultivated under asymbiotic conditions in the present research work, a strain isolated from P. arhizus from pine woods from Oaxaca was grown under laboratory conditions. These results confirm that the strain isolated from the forests of Mexico presents the same type of triterpenes unfunctionalized at carbon-23 in the in vitro liquid fermentation of mycelium, like other strains from forests in Europe and Brazil, despite the fact that they we used a PDA medium culture instead of a half Melin-Norkrans medium culture.

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Section: Resultados Y Discusiónmentioning

confidence: 89%

Section: Resultados Y Discusiónmentioning

confidence: 99%

Section: Resultados Y Discusiónunclassified

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IDENTIFICACIÓN DE UN DERIVADO DE LANOSTEROL PROCEDENTE DEL HONGO CULTIVADO Pisolithus arhizus (Scop.) Rauschert

Márquez-Fernández¹,

Herrera²,

Castellanos-Onorio³

et al. 2013

rchscfa

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“…Studies on natural compounds from fungi and particularly from P. tinctorius were conducted using sporocarp and mycelium (Tsantrizos et al, 2001;Montenegro et al, 2004;Zamuner et al, 2005). However, no apparent studies focused on the anticancer potential of other structures such as spores.…”

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confidence: 99%

Cytotoxicity Induced by Extracts ofPisolithus tinctoriusSpores on Human Cancer and Normal Cell Lines—Evaluation of the Anticancer Potential

Alves

Preto

Vasconcelos

et al. 2015

Journal of Toxicology and Environmental Health, Part A

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Recent advances in synthesis and biological activity of triterpenic acylated oximes

Bednarczyk–Cwynar

Zaprutko

2014

Phytochem Rev

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During the last few decades more and more attention has been paid to triterpenes—a group of compounds with five- or four-ring skeleton and carboxyl, hydroxyl or oxo groups. Triterpenes with unsubstituted C-3 hydroxyl group can be easily transformed into appropriate ketones and then into oximes. The carbonyl group can be created not only from the hydroxyl group at C-3 position, but also at C-2, C-12 or C-28 positions. Several methods of creation of two = NOH groups within one molecule of triterpene are known. There are also known triterpenes with two carbonyl groups, e.g. at C-3 and C-11 positions, which differ in reactivity: among them only C-3 group can be transformed into oxime. A reactive hydroxyimine group can undergo the action of acylating agents, such as carboxylic acids or their derivatives, also the ones with significant pharmacological activity. Acyl derivatives of triterpenic oximes exhibit important pharmacological activity. The biological tests performed with the use of cell cultures inoculated with viruses showed inhibitory activity of some triterpenic acyloximes against type 1 HSV (H7N1), ECHO-6 and HIV-1 viruses. Another acylated oximes derived from triterpenes shown cytotoxic or antiproliferative activity against many lines of cancer cells. In many cases the pharmacological effects of the tested acyloxyiminotriterpenes were comparable to those of appropriate standard drugs. One of the newest application of acyl derivatives of triterpenic oximes is their ability to form organogels.

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Lanostane triterpenes from the fungus Pisolithus tinctorius

Cited by 10 publications

References 13 publications

IDENTIFICACIÓN DE UN DERIVADO DE LANOSTEROL PROCEDENTE DEL HONGO CULTIVADO Pisolithus arhizus (Scop.) Rauschert

IDENTIFICACIÓN DE UN DERIVADO DE LANOSTEROL PROCEDENTE DEL HONGO CULTIVADO Pisolithus arhizus (Scop.) Rauschert

Cytotoxicity Induced by Extracts ofPisolithus tinctoriusSpores on Human Cancer and Normal Cell Lines—Evaluation of the Anticancer Potential

Recent advances in synthesis and biological activity of triterpenic acylated oximes

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