New Lanostanoids from the Fungus Ganoderma concinna

González, Antonio G.; León, Francisco; Rivera, Augusto; Padrón, Juan I.; Gonzalez-Plata, Javier; Zuluaga, Juan C.; Quintana, José; Estévez, Francisco; Bermejo, Jaime

doi:10.1021/np010143e

Cited by 59 publications

(49 citation statements)

References 20 publications

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“…They are identified as ganoderic acid DM (1), 7) 5a-lanosta-7,9(11),24-triene-15a,26-dihydroxy-3-one (2), 8) ganodermadiol (3), 9) lucidumol B (4), 10) by comparison of the MS, NMR and optical rotation matched with published data (Fig. 2).…”

Section: Methodssupporting

confidence: 69%

“…The concentration of testosterone contributed by [4][5][6][7][8][9][10][11][12][13][14] C] testosterone was negligible. The sample was added to the solution at each concentration.…”

Section: Methodsmentioning

confidence: 99%

“…The radioactivity profile was determined with an imaging analyzer (FLA-5000 RF, Fuji Film Co., Ltd., Tokyo, Japan). The 5a-reductase activity was calculated from the percentage of the extent of the conversion of [4][5][6][7][8][9][10][11][12][13][14] C] testosterone to [4-14 C] dihydrotestosterone. Preparation of Methyl Ester (10) N-Methyl-N-nitrosop-toluenesulfonamide (1.25 g, 5.83 mmol) was dissolved in diethyl ether (60 ml), and was dropped into the solvent that included KOH (0.7 g, 12.5 mmol), EtOH (1.6 ml) and water (0.5 ml).…”

Section: Methodsmentioning

confidence: 99%

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5.ALPHA.-Reductase Inhibitory Effect of Triterpenoids Isolated from Ganoderma lucidum

Liu

Kurashiki²,

Shimizu

et al. 2006

Biological & Pharmaceutical Bulletin

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The microsomal enzyme steroid 5a-reductase [EC 1.3.99.5] catalyzes the NADPH-dependent reduction of D 4,5 double bond of a variety of 3-oxo-D 4 steroids.1) The principal circulating androgen is testosterone. In several androgen target tissues, like the prostate, testosterone is converted to 5a-dihydrotestosterone (DHT), which is the most potent natural androgen. This process amplifies of the androgenic response, perhaps because of the higher affinity of the androgen receptor for DHT than for testosterone.2) Both 5a-reductase and DHT perform critical roles physiologically and pathologically in man. The plasma level of DHT has been reported to be elevated in patients with either benign prostatic hyperplasia (BPH) or prostatic cancer. As a result, the inhibition of 5a-reductase has become a pharmacological strategy for the treatment of BPH as well as other DHT-related disorders such as acne and male pattern baldness.3)The study of the inhibition of 5a-reductase with organic molecules has lasted more than two decades; consequently, numerous nonsteroidal and steroidal compounds have been designed and synthesized as competitive, noncompetitive, and uncompetitive inhibitors of 5a-reductase. However, it should be noted that these inhibitors have the potential to cause adverse effects such as those reported for finasteride 4) -i.e., gynecomastia, impairment of muscle growth, and severe myopathy. Hence, the emergence of therapeutic materials having fewer side effects-preferably, edible natural products-would be highly desirable if their safety could be guaranteed.For thousands of years, mushrooms have been known as a source of medicine. In our previous screening of mushrooms, we discovered that the EtOH extract of Ganoderma lucidum (LEYSS.:FR.) KARST. (Ganodermataceae) (Fig. 1) showed the strongest 5a-reductase inhibitory activity. Also, the treatment of G. lucidum itself or the EtOH extract prepared from it significantly inhibited the growth of the ventral prostate induced by testosterone in rat. 5,6) In this paper, we report the isolation of the oxygenated lanostane-type triterpenoids with 5a-reductase inhibition, ganoderic acid DM (1) and 5a-lanosta-7,9(11),24-triene15a,26-dihydroxy-3-one (2) from G. lucidum and their inhibitory effects on 5a-reductase. EtOH Eextracts of Ganoderma lucidum Dried and chipped G. lucidum (15 kg) was extracted with 95% EtOH (126 l) at room temperature for 24 h by using blender. The extracts were filtered through ADVANTEC No. 2 filter paper, concentrated under vacuum, and then freeze-dried. The extracts (571.1 g) were stored in Ϫ20°C before assay. MATERIALS AND METHODS MaterialsDried and chipped G. lucidum (200 g) was extracted with 30% EtOH at room temperature for 24 h by using blender. The extracts were filtered through ADVANTEC No. 2 filter paper, concentrated under vacuum, and then freeze-dried. The extracts (10 g) were stored in Ϫ20°C before assay.The 95% EtOH extracts (571 g) was fractionated into three fractions 5a a-Reductase inhibitory activity-guided fractionation of the EtOH ext...

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Section: Methodssupporting

confidence: 69%

“…The concentration of testosterone contributed by [4][5][6][7][8][9][10][11][12][13][14] C] testosterone was negligible. The sample was added to the solution at each concentration.…”

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

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5.ALPHA.-Reductase Inhibitory Effect of Triterpenoids Isolated from Ganoderma lucidum

Liu

Kurashiki²,

Shimizu

et al. 2006

Biological & Pharmaceutical Bulletin

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“…La señal que se encuentra a δ 0,94 con multiplicidad de doblete (j = 6,3 Hz), se asignó al Me-21. De acuerdo con datos bibliográficos Arisawa, et al, 1986;Arisawa, et al,1988;Morigiwa, et al, 1986;González, et al, 2002), las señales en δ 5,43, 5,94 y 5,57, que integran para un protón cada una, se asignan respectivamente a los protones vinílicos (H-C11), (H-C7) y (H-C24) de un núcleo Lanosta-7,9,(11) -dieno; con cadena lateral insaturada en el C24.…”

Section: I4unclassified

Estudio químico de la fracción de acetato de etilo del hongo Ganoderma lucidum cultivado en desechos agroindustriales

Ordosgoitia

Martínez

Chavez

et al. 2016

Rev. Acad. Colomb. Cienc. Ex. Fis. Nat.

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ResumenEstudios en hongos han revelado que poseen un alto valor nutricional, comprobada acción farmacológica de los metabolitos secundarios producidos en sus cuerpos fructíferos, siendo muchas las especies estudiadas, destacando entre estas el hongo macromiceto Ganoderma lucidum, del cual se han aislado compuestos tipo terpenoides y sus derivados, de importancia biológica, mostrando efectividad en la disminución de la presión sanguínea, propiedades antinflamatorias, antivirales, hipoglicémicas e inmunoprotectoras. Por otro lado, el cultivo de hongos promueve la solución a problemas de tipo ambiental, ya que puede hacerse en desechos agroindustriales. El objetivo fue estudiar la composición química del hongo G. lucidum, cultivado en desechos agroindustriales y determinar diferencias entre los metabolitos obtenidos, con respecto a los de la especie del hongo en su estado silvestre. Para ello, se cultivó G. lucidum, en desechos agroindustriales y se estudió químicamente la fracción de acetato de etilo (AcOEt), mediante cromatografía de columna, cromatografía de capa fina, cromatografía en capa fina preparativa. Además de técnicas de análisis de estructuras CG-EM, RMN-1 H, IR. Los resultados indicaron que la separación cromatografía, permitió la caracterización de 8 compuestos. De forma general, se puede concluir que el hongo cultivado, presenta una composición de metabolitos secundarios similar a la reportada en distintas investigaciones sobre la especie en su estado silvestre, estableciéndose que el compuesto mayoritario corresponde al ganoderiol B. © 2016. Acad. Colomb. Cienc. Ex. Fis. Nat. Palabras clave: Ganoderma lucidum; Cultivo; Estudio químico; Metabolitos secundarios.Chemical study of fraction ethyl acetate in the fungus Ganoderma lucidum, grown in agro-industrial waste. AbstractStudies in fungi have revealed that they have a high nutritional value, proven pharmacological action of the secondary metabolites produced in their fruiting bodies, being many species studied, emphasizing among these, the macromycete Ganoderma lucidum, from which have been isolated compounds type terpenoids and its derivatives, with biological significance, showing effectiveness in the lowering blood pressure, anti-inflammatory properties, antiviral, hypoglycemic and immunoprotective. On the other hand, mushroom cultivation promotes the solution to environmental problems, since it can be done in agro-industrial wastes. The objective was to study the chemical composition of the fungus G. lucidum, grown in agro-industrial wastes and to determine differences between the metabolites obtained, with respect to those of the species of the fungus in their wild state. To do so, G. lucidum, was cultivated in agro-industrial wastes and the ethyl acetate fraction was studied, throught chromatography column thin layer chromatography, preparative thin-layer chromatography. In addition, GC-MS, NMR-1 H, IR analysis techniques were done. The results and preparative indicated that the chromatographic separation allowed the characterization of 8 com...

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“…They are predominantly found on plant surfaces such as leaf, stem bark and fruit waxes (Jäger et al, 2009). These compounds reportedly exhibit a wide spectrum of biological activities including anti-inflammatory (Ko et al, 2007;Mosa et al, 2011), antitumor (Gonzalez et al, 2002) and antimicrobial activity (Motlhanka et al, 2010;Kiplimo et al, 2011). The importance of plant derived triterpenes as new targets for drug development cannot be overemphasised.…”

Section: Introductionmentioning

confidence: 99%

Antibacterial activity of two triterpenes from stem bark of Protorhus longifolia

Mosa¹,

Nhleko²,

Dladla³

et al. 2014

J. Med. Plants Res.

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Antibiotic resistance of pathogenic strains has hugely contributed to the wide spread of new and reemerging infectious diseases. There is thus the need for the discovery of new (non-penicillin based) antibiotics. The triterpenes [3β-hydroxylanosta-9,24-dien-21-oic acid (1) and methyl-3β-hydroxylanosta-9,24-dienoate (2)] isolated from stem bark of Protorhus longifolia (Benrh.) Engl. were evaluated for their antibacterial activity against a panel of selected general and antibiotic resistant Gram positive and Gram negative bacteria. The antibacterial activity of the compounds was determined using disc diffusion method. The compounds exhibited antibacterial activity against most of the tested bacteria with minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC) values ranging from 0.16 to 5.00 mg/ml and 0.63 to 5.00 mg/ml, respectively. The triterpenes did not exhibit any bacterial DNA damaging effects, but apparently affected the microbial cell membrane integrity. The triterpenes could be a potentially effective antimicrobial agent to combat infectious diseases.

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New Lanostanoids from the Fungus Ganoderma concinna

Cited by 59 publications

References 20 publications

5.ALPHA.-Reductase Inhibitory Effect of Triterpenoids Isolated from Ganoderma lucidum

5.ALPHA.-Reductase Inhibitory Effect of Triterpenoids Isolated from Ganoderma lucidum

Estudio químico de la fracción de acetato de etilo del hongo Ganoderma lucidum cultivado en desechos agroindustriales

Antibacterial activity of two triterpenes from stem bark of Protorhus longifolia

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