New alkaloids from the fruiting bodies of Ganoderma sinense
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ABSTRACT: Electronic Supplementary Material
Supplementary material is available for this article at 10.1007/s13659-011-0026-4 and is accessible for authorized users.
SUBMITTER: Liu J
PROVIDER: S-EPMC4131651 | biostudies-literature | 2011 Oct
REPOSITORIES: biostudies-literature
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Project description:A polysaccharide named GSP-2 with a molecular size of 32 kDa was isolated from the fruiting bodies of Ganoderma sinense. Its structure was well elucidated, by a combined utilization of chemical and spectroscopic techniques, to be a β-glucan with a backbone of (1→4)- and (1→6)-Glcp, bearing terminal- and (1→3)-Glcp side-chains at O-3 position of (1→6)-Glcp. Immunological assay exhibited that GSP-2 significantly induced the proliferation of BALB/c mice splenocytes with target on only B cells, and enhanced the production of several cytokines in human peripheral blood mononuclear cells and derived dendritic cells. Besides, the fluorescent labeled GSP-2 was phagocytosed by the RAW 264.7 cells and induced the nitric oxide secretion from the cells.
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Project description:Six new lanostane-type triterpenoids, namely leucocontextins S-X (1-6), together with twelve known compounds, were isolated from the fruiting bodies of Ganoderma leucocontextum. Their structures were established by MS and NMR data.
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Project description:Ganoderma resinaceum is usually used as ethnomedicine for immune-regulation, hyperglycemia, and liver disease. To date, only a few chemical constituents have been reported from G. resinaceum. In this study, fifteen nortriterpenoids including six new nortriterpenoids (1-6) and nine known analogs (7-15), were separated and purified from the fruiting bodies of G. resinaceum. New compounds were identified as lucidone I (1), lucidone J (2), lucidone K (3), lucidone I (4), ganosineniol B (5), and ganosineniol C (6), based on analysis of extensive spectroscopic data (high resolution mass spectrometry (HRMS), nuclear magnetic resonance (NMR), infrared (IR), and ultraviolet (UV)). The known compounds were assigned as lucidone A (7), lucidone B (8), lucidone H (9), lucidone E (10), lucidone F (11), lucidone D (12), lucidone C (13), ganoderense F (14), and ganosineniol A (15), by comparing their spectroscopic data with those reported in the literature. Compounds 3, 4, and 7-13 were examined for α-glucosidase inhibitory activity and display no significant activity, but the finding may support that the side chain of ganoderma triterpenoids played an important role in α-glucosidase inhibitory activity.
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Project description:A water-soluble glycopeptide (PGY), fractionated and purified from the aqueous extract of the fruiting bodies of Ganoderma lucidum via two-step dialysis, anion exchange, and gel permeation chromatography, was constituted of two moieties of carbohydrate and peptide. Carbohydrate characterization with component analysis, methylation analysis, periodate oxidation, Smith degradation, enzymic hydrolysis, and IR and NMR experiments demonstrated that the carbohydrate moiety possessed a backbone of approximately 33 (1-->3)-linked beta-d-glucopyranosyl residues and side chains, at positions 6, of single alpha-l-arabinofuranosyl residues for every three Glcp residues in the main chain. On the basis of the results of amino acid composition and trypsin digestion, the peptide moiety, shown to consist of Arg, Ser, Ala, and Gly in a ratio of 1:1:2:2, exhibited the sequence of Ser-Arg-[(Ala)2(Gly)2] and was O-attached to the carbohydrate moiety via Ser. To contribute toward our understanding of the structure-activity relationship, a series of expected derivatives generated from PGY by trypsin digestion, debranching, and NaIO4 oxidation following reduction experiments, including PTC, DB-PGY, and PPP, were obtained. All of them, as well as PGY and a reference compound (butylated hydroxytoluene, BHT), were evaluated with two conventional antioxidant testing systems of 1,1-diphenyl-2-picrylhydrazyl (DPPH) and superoxide radical scavenging and found to have their respective antioxidant activities in a concentration-dependent manner. Comparable radical-scavenging activities observed between PTC and PGY demonstrated that the removal of Ala and Gly in a peptide moiety did not result in the variation of biological functions of PGY. However, it was very interesting to note that the scavenging activity of PPP was higher for DPPH radicals, with an SC(50) value of 116.4 +/- 5.1 microg/mL, and lower for superoxide radicals, with an SC(50) value of 205.2 +/- 14.4 microg/mL, than that of PGY with corresponding SC(50) values of 133.5 +/- 5.5 and 140.5 +/- 7.7 microg/mL, and, moreover, DB-PGY displayed the weakest scavenging potency in the tested samples, indicating that the carbohydrate moiety, in particular the side chain of nonreducing end units of Araf residues as the functional region, played a vital role in the structure and antioxidant activity. In addition, compared with the SC(50) value of BHT, PGY showed lower DPPH radical-scavenging activity but possessed higher superoxide radical-quenching potency, suggesting that it could be presented as a possible new source of natural antioxidants.
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Project description:Eleven new cyclohexane-type meroterpenoids (1, 3-5, 7, 8, 11-15) and four known similar meroterpenoids (2, 6, 9, and 10) were isolated from Ganoderma cochlear. Their structures and absolute configurations at stereogenic centers were elucidated by using HRESIMS, NMR spectroscopy and computational methods. In addition, the structure of the known meroterpenoid, cochlearol G (2), was revised, and the absolute configurations at the stereogenic centers of known meroterpenoids 9 and 10 were determined. All the isolated meroterpenoids were evaluated for their activities against renal fibrosis and triple negative breast cancer, and their insulin resistance. The results of the renal fibrosis study showed that meroterpenoid 11 inhibits over-expression of fibronectin, collagen I and α-SMA. Results of the wound healing study revealed that 4, 6 and 8 significantly inhibit migration of BT549 cells. Observations made in Western blotting experiments showed that 6 decreases the levels of TWIST1 and ZEB1, and increases the level of E-cadherin. Finally, meroterpenoids 7, 9, 11, and 15 significantly up-regulate p-AMPK protein expression in normal L6 myotubes cells.
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Project description:Ganoderma fungi have long been used as functional foods and traditional medicines in Asian countries. Ganoderma ahmadii is one of the main species of Ganoderma fungi distributed in Hainan province of China, the fruiting bodies of which have been used in folk to lower blood sugar for a long time. A chemical investigation of the fruiting bodies of Ganoderma ahmadii led to the isolation of seven new meroterpenoids, named ganoduriporols F-L (1-7). The chemical structures of the compounds were elucidated by spectroscopic data including HRESIMS and 2D NMR. Compounds 5-7 represent the first examples of ganoduriporol-type meroterpenoids bearing oxepane rings in their skeletons. Compounds 1-4 showed inhibitory activity against protein tyrosine phosphatase 1B (PTP1B) comparable to the positive control Na3VO4, with IC50 values of 17, 20, 19, and 23 ?M, respectively.
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Project description:A basidiomycete fungus used in Chinese herbal medicine
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Project description:We conducted a study of Ganoderma lucidum metabolites and isolated 35 lanostane-type triterpenoids, including 5 new ganoderols (1-5). By spectroscopy, we compared the structures of these compounds with known related compounds in this group. All of the isolated compounds were assayed for their effect against the human breast carcinoma cell line MDA-MB-231 and hepatocellular carcinoma cell line HepG2. Corresponding three-dimensional quantitative structure-activity relationship (3D-QSAR) models were built and analyzed using Discovery Studio. These results provide further evidence for anti-cancer constituents within Ganoderma lucidum, and may provide a theoretical foundation for designing novel therapeutic compounds.
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Project description:Two low-molecular-weight polysaccharides (GLP-1 and GLP-2) were purified from Ganoderma leucocontextum fruiting bodies, and their physicochemical properties and antioxidant activities were investigated and compared in this study. The results showed that GLP-1 and GLP-2 were mainly composed of mannose, glucose, galactose, xylose, and arabinose, with weight-average molecular weights of 6.31 and 14.07 kDa, respectively. Additionally, GLP-1 and GLP-2 had a similar chain conformation, crystal structure, and molecular surface morphology. Moreover, GLP-1 exhibited stronger antioxidant activities than GLP-2 in five different assays: 2,2'-azino-bis(3-ethylbenzthiazoline-6-sulfonic acid) (ABTS), hydroxyl radical, superoxide anion radical, ferric reducing antioxidant power (FRAP), and oxygen radical antioxidant capacity (ORAC). The main linkage types of GLP-1 were found to be →4)-α-D-Glcp-(1→, →4)-β-D-Glcp-(1→, →3)-β-D-Glcp-(1→, →6)-β-D-Galp-(1→, →6)-α-D-Glcp-(1→, →4,6)-α-D-Glcp-(1→, and Glcp-(1→ by methylation analysis and nuclear magnetic resonance (NMR) spectroscopy. In addition, GLP-1 could protect NIH3T3 cells against tert-butyl hydroperoxide (tBHP)-induced oxidative damage by increasing catalase (CAT) and glutathione peroxidase (GSH-Px) activities, elevating the glutathione/oxidized glutathione (GSH/GSSG) ratio, and decreasing the malondialdehyde (MDA) level. These findings indicated that GLP-1 could be explored as a potential antioxidant agent for application in functional foods.
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Project description:In the 1H NMR-guided fractionation of extracts from the edible mushroom Lactarius deliciosus, two new azulene-type sesquiterpenoids, 7-isopropenyl-4-methyl-azulene-1-carboxylic acid (1) and 15-hydroxy-3,6-dihydrolactarazulene (2), together with seven known compounds were characterized. Their structures were determined on basis of spectroscopic evidence, as well as by comparing with literature data. Amongst the known metabolites, the 13C NMR assignment of 15-hydroxy-6,7-dihydrolactarazulene (3) is reported here for the first time. Moreover, 7-acetyl-4-methylazulene-1-carbaldehyde (5) displayed a moderate antibacterial activity against Staphylococcus aureus. *Digital image of L. deliciosus. Retrieved March 17, 2017 from https://upload.wikimedia.org/wikipedia/commons/e/e3/Lactarius_deliciosus_1_(1).jpg .
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