Antitumor sterols from the mycelia of Cordyceps sinensis

Bok, Jin Woo; Lermer, Leonard; Chilton, J.E.; Klingeman, H. G.; Towers, G.H.N.

doi:10.1016/s0031-9422(99)00128-4

Cited by 300 publications

(186 citation statements)

References 26 publications

(26 reference statements)

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“…6B, 2005 column chromatography and identified as ergosterol and ergosterol 5α,8α-peroxide respectively, by comparison of their 1 H and 13 C NMR spectra with those reported in the literature. 7,8 The neocyclocitrinols (3) were obtained from the methanol phase. The hydroxyanthraquinones we reported before in another cultivation of the fungus, 5 were also obtained from this methanol phase.…”

Section: Resultsmentioning

confidence: 99%

C25 steroid epimers produced by Penicillium janthinellum, a fungus isolated from fruits Melia azedarach

Marinho¹,

Rodrigues‐Filho²,

Ferreira³

et al. 2005

J. Braz. Chem. Soc.

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O fungo Penicillium janthinellum, obtido de Melia azedarach, produziu ergosterol, ergosterol 5α,8α-peróxido e uma mistura de esteróides C25 epiméricos de ocorrência restrita na natureza. Os esteróides C25, denominados neociclocitrinóis, possuem o mesmo sistema tetracíclico de anéis presente no ciclocitrinol, o qual foi isolado do fungo Penicillium citrinum, associado a uma esponja, com o mesmo esqueleto biciclo[4:4:1] nos anéis A/B, mas com cadeias laterais diferentes. O P. janthinellum isolado de M. azedarach, foi cultivado sobre milho branco e os três esteróides foram isolados por vários procedimentos cromatográficos e identificados por cuidadosa análise dos dados de RMN, principalmente correlações 1 H -13 C em duas dimensões bem como COSY e TOCSY 1 H -1 H. A origem biossintética dos ciclocitrinóis é discutida.A plant-derived fungus, Penicillium janthinellum, obtained from Melia azedarach, produced ergosterol and ergosterol 5α,8α-peroxide along with a mixture of rare C25 steroid epimers. The C25 steroids, named neocyclocitrinols, shows exactly the same tetracyclic ring system present in cyclocitrinol, which was isolated from a sponge-derived Penicillium citrinum, with the same bicyclo [4:4:1] skeleton at A/B rings, but showing different side chains. The P. janthinellum was cultivated over white corn and the three steroids were isolated by several silica gel based chromatographic procedures and identified by extensive NMR methods, mainly 1 H -13 C correlations and 1 H -1 H COSY and TOCSY. The biosynthetic origin of the cyclocitrinols is also discussed. Keywords: endophytic fungi, Melia azedarach, Penicillium janthinellum, neocyclocitrinols IntroductionSteroid and steroid derived secondary metabolites are frequently found in filamentous fungi. 1 Ergosterol (1) is the precursor of many other microbial steroids. 2 Most of the ergosterol metabolism begins with an oxidative process in double-bonds at C-5(6) and C-7(8) letting to ergosterol 5,8-peroxide, 3 being the endo regioisomer (5α,8α-peroxide) (2) the most frequent, and then hydroxylated products at A/B/C rings are formed. 4 In the present work we have found these sorts of compounds in our chemical studies of endophytic filamentous fungi associated with Meliaceae plants. We previously described the production of polyketides by a Penicillium janthinellum, isolated from fruits of Melia azedarach. 5 Now we report the production of a pair of steroid epimers with a very unusual C25 skeleton, in addition to the regular steroids (1 and 2), when the fungus was cultivated over white corn. These epimers, which are represented here by the structural formula 3, contains a rare bicyclo [4:4:1] system at rings A/B, as in cyclocitrinol (4) and isocyclocitrinol (5) obtained by Amagata et al. 6 from P. citrinum, isolated from a marine sponge. 6 Herein we present spectroscopic evidences, which further support the bicycle system of these compounds and firmly establish the side chain of the new steroid neocyclocitrinol (3). Biosynthetic considerations regard the origin of these st...

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Section: Resultsmentioning

confidence: 99%

C25 steroid epimers produced by Penicillium janthinellum, a fungus isolated from fruits Melia azedarach

Marinho¹,

Rodrigues‐Filho²,

Ferreira³

et al. 2005

J. Braz. Chem. Soc.

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“…An extract was obtained from P. ostreatus which suppressed proliferation of breast cancer (MCF-7, MDA-MB-231) and colon cancer (HT-29, HCT-116) cells, without affecting proliferation of epithelial mammary MCF-10A and normal colon FHC cells [125]. Flow cytometry revealed that the inhibition of cell proliferation by P. ostreatus was associated with the cell cycle arrest at G0/G1 phase in MCF-7 and HT-29 cells.…”

Section: Other Immunotherapy Substances From Pleurotus Speciesmentioning

confidence: 99%

Effectiveness of Immunotherapies from Oyster Mushroom (Pleurotus species) in the Management of Immunocompromised Patients

Oloke¹

2015

IJI

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Abstract:In the recent years, mushrooms are distinguished as important natural resources of immunotherapy which can be used as immunomodulating and immunostimulating in the management of some immunodeficiency diseases such as cancer, tumour, HIV, tuberculosis etc. Mushroom of the genus Pleurotus are good sources of several bioactive compounds which are able to augment or complement a desired immune response. Such bioactive compounds are polysaccharopeptides, polysaccharide-proteins, functional proteins (ubiquinone-9, nebrodeolysin, ubiquitin-like peptide and glycoprotein), glucans, proteoglycans and many others. Most of these bioactive compounds follow the immunomodulatory pathway mechanism of polysaccharide (β-glucan) from mushrooms by stimulating activities for both innate and adaptive immune systems. They proliferate and activate innate immune system components such as natural killer (NK) cells, neutrophils, and macrophages, and stimulate cytokines expression and secretion. These cytokines in turn activate adaptive immunity through the promotion of Bcells for antibodies production and stimulation of T-cell differentiation to T helper (Th1 and Th2) cells, which mediate cell and humoral immunities, respectively. In this review, the immunotherapeutic potential of oyster mushroom in relation to bioactive compounds produced is shown and this suggests that the oyster mushrooms are one of the most important natural products and functional foods.

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“…It was also recorded that a polysaccharide fraction from an ethanol-precipitable aqueous extraction of that fungus inhibited the proliferation and differentiation of the human leukemic U937 cells (55). Further studies on this species resulted in the isolation of bioactive sterols, which exhibited anti-tumor activities against various tumor cell lines such as the K562, Jurkat (T-lymphoblastic), HL-60 (promyelocytic leukemia), WM1341 (malignant melanoma) and RPMI (multiple myeloma) (56). An ethanolic extract from this fungus as well as cordycepin, a newly-discovered bioactive compound, were reported to possess anti-oxidant and anti-tumor activities such as inhibiting cell proliferation, and inducing apoptosis in colorectal and hepatocellular cancer (57).…”

Section: ------------------------------------------------------------mentioning

confidence: 99%

Fungal metabolites modulating NF-κB activity: An approach to cancer therapy and chemoprevention (Review)

Petrova

Reznick²,

Wasser³

et al. 2008

Oncol Rep

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Abstract.Fighting cancer is considered one of the most important areas of research in medicine and immunology. Due to the ability of cancer cells to mutate and become resistant to available drugs, new scientific approaches, focused on molecular mechanisms of carcinogenesis, are needed. A new direction in cancer treatment has arisen, devoted to the adjuvant use of natural bioactive compounds in conventional chemotherapy. This kind of research is gaining more attention. In particular, fungi can be used not only as strong immunoceuticals but also as a source of potent metabolites, capable of penetrating cell membranes and interfering with particular signal transduction pathways linked to processes such as inflammation, cell differentiation and survival, carcinogenesis, and metastasis. One such a crucial pathway involved in the above-mentioned processes, is the activation of the nuclear transcription factor κB (NF-κB). This review compiles the available data on fungal metabolites, known to modulate the activity of NF-κB, thus demonstrating their potential use as novel anti-cancer agents in the rapidly advancing field of molecular therapy. Contents1. Introduction 2. Fungal metabolites modulating NF-κB activity 3. Perspectives IntroductionCancer is the second most predominant cause of death in the modern world, after cardiovascular diseases, taking many human lives every year. Depending on the stage of cancer progression, treatments include surgical operation, radiotherapy and chemotherapy. However, their side effects cause serious damage and suffering to patients. As an alternative to these treatment methods, immunotherapy is now gaining more attention than ever. Immunotherapy substantially reduces the side effects and the inherent pain of cancer sufferred by patients and helps to overcome cancer growth, even in the last stages of the disease.Despite the observed success of most of the chemotherapeutic regimes, cellular adaptations have enabled tumor cells to evade many of these drugs. The nuclear transcription factor κB (NF-κB) is one of the factors responsible for cellular chemoresistance. It is a dimeric transcription factor belonging to the Rel/NF-κB family of transcription factors (1-4). The NF-κB complex is maintained in the cytoplasm in an inactive form by the inhibitory protein κB (IκBα), belonging to a family of inhibitory proteins, IκBs. The major activator of NF-κB is the IκB kinase complex (IKK). This complex is composed of two catalytic subunits, IKK-α and -ß and a regulatory subunit, IKK-γ (also known as NEMO) (2). The NF-κB pathway is triggered by bacterial and viral infections as well as pro-inflammatory cytokines and chemokines [e.g., tumor necrosis factor α (TNF-α), lipopolysaccharide (LPS), interleukins (IL-1, IL-6)], all of which activate the IKK complex. After activation, the IKK complex phosphorylates NF-κB-bound IκBs, thereby targeting them for proteasomal degradation. Simultaneously, the NF-κB dimers are released and free to enter the nucleus where transcriptional activation of target genes be...

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Antitumor sterols from the mycelia of Cordyceps sinensis

Cited by 300 publications

References 26 publications

C25 steroid epimers produced by Penicillium janthinellum, a fungus isolated from fruits Melia azedarach

C25 steroid epimers produced by Penicillium janthinellum, a fungus isolated from fruits Melia azedarach

Effectiveness of Immunotherapies from Oyster Mushroom (Pleurotus species) in the Management of Immunocompromised Patients

Fungal metabolites modulating NF-κB activity: An approach to cancer therapy and chemoprevention (Review)

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