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The biologically active constituents of Ganoderma lucidum (FR.) KARST. Histamine release-inhibitory triterpenes
Abstract
The MeOH extract of Ganoderma lucidum has an inhibitory action on histamine release from rat mast cells. From the physiologically active fraction of the extract, along with the known triterpenes ganoderic acids A and B, two new triterpenes were isolated and named ganoderic acids C and D. The structures of ganoderic acids C and D were determined to be 3β,7β,15α-trihydroxy-11,23-dioxo-5α-lanost-8-en-26-oic acid and 7β-hydroxy-3,11,15,23-tetraoxo-5α-lanost-8-en-26-oic acid respectively. Ganoderic acids C and D were shown to inhibit histamine release from rat mast cells. Quantitative analysis of these triterpenes was performed for the purpose of crude drug quality control.
... Antiallergic activity has been demonstrated by G. lucidum extracts, as well as some compounds isolated from this species, such as ganoderic acids, oleic acid, and cyclooctasulfur acid belonging to triterpenes [80]. A study showed that ganoderic acids C and D isolated from G. lucidum inhibit the release of histamine from mast cells [81]. The same effect was demonstrated for the chloroform extract of the G. lucidum culture medium. ...
... Cyclooctasulfur and oleic acid are responsible for the action of this extract. The mechanism of action of oleic acid, consisting of inhibition of histamine release and calcium uptake, results from the stabilization of the lipid bilayer of the cell membrane, whereas cyclooctasulfur affects membrane proteins [81][82][83]. The methanol extract of G. lucidum alleviates allergic pruritus through peripheral action. ...
... Furthermore, mast cells and H1 receptors have not been the primary sites of antipruritic action of this extract. It has been suggested to act through PAR2 and 5-HT2A receptors [81,84,85]. In patients with histamine-dependent allergic reactions, G. lucidum effectively regulates the balance between cytokines produced by Th1 and Th2 lymphocytes [35]. ...
This paper presents the current state of knowledge on the biological activity and possible medicinal applications of selected species of the genus Ganoderma: Ganoderma adspersum (Schulzer) Donk, Ganoderma applanatum (Pers.) Pat., Ganoderma carnosum Pat., Ganoderma lucidum (Curtis) P. Karst., Ganoderma pfeifferi Bres., Ganoderma resinaceum Boud. These inedible, wood-decaying fungi are pathogens that cause the enzymatic decomposition of wood. They are a valued natural medicinal resource and have been used in traditional Far Eastern medicine for centuries. Research conducted on these species using modern analytical methods has led to advances in knowledge of the potential therapeutic use of compounds isolated not only from basidiocarps but also from biomass obtained by in vitro methods. Recent pharmacological studies have confirmed the known traditional uses of these species, elucidated previously unknown mechanisms of biological action, and found evidence of new biological activities, such as anticancer, cytotoxic, antiallergic, and neuroprotective activities. Furthermore, the article updated the state of knowledge on the general mycological characteristics of these species.
... Methyl ganoderate D -G. lucidum [182,183] ...
... Methyl ganoderate A -G. lucidum [182] 114. ...
... Methyl ganoderate B -G. lucidum [182] 115. ...
Mahesh C.A. Galappaththi, Nimesha M. Patabendige, Bhagya M.
Premarathne, Kalani K. Hapuarachchi, Saowaluck Tibpromma, Dong-Qin Dai,
Nakarin Suwannarach, Sylvie Rapior, Samantha C. Karunarathna.
A review of Ganoderma triterpenoids and their bioactivities.
Biomolecules, Special Issue Fungal Metabolism - Enzymes and Bioactive Compounds
II, 13 (1), 24 (2023). doi:10.3390/biom13010024. hal-03912698
___ For centuries, Ganoderma has been used as a traditional medicine in Asian countries to prevent and treat various diseases. Numerous publications are stating that Ganoderma species have a variety of beneficial medicinal properties, and investigations on different metabolic regulations of Ganoderma species, extracts or isolated compounds have been performed both in vitro and in vivo. However, it has frequently been questioned whether Ganoderma is simply a dietary supplement for health or just a useful "medication" for restorative purposes. More than 600 chemical compounds including alkaloids, meroterpenoids, nucleobases, nucleosides, polysaccharides, proteins, steroids and triterpenes were extracted and identified from Ganoderma, with triterpenes serving as the primary components. In recent years, Ganoderma triterpenes and other small molecular constituents have aroused the interest of chemists and pharmacologists. Meanwhile, considering the significance of the triterpene constituents in the development of new drugs, this review describes 495 compounds from 25 Ganoderma species published between 1984 and 2022, commenting on their source, biosynthetic pathway, identification, biological activities and biosynthesis, together with applications of advanced analytical techniques to the characterization of Ganoderma triterpenoids.
... It has been studied that GA B isolated from Ganoderma species showed significant hepatoprotection property [100]. However, it was observed that when the doses of GA B were increased 10 times than the normal, it did not further reduce glutamic oxaloacetic transaminase and glutamic pyruvic transaminase levels in the serum of the mice [101]. ...
... Zhou et al., 2012 [109], reported neuroprotective effect of pre-administration of G. lucidum spores on rat hippocampus. Various studies have reported that the compounds, 4,4,14α-Trimethyl-5α-chol-7,9 (11)-diene-3-oxo-24-oicacid and methyl ganoderate B, have showed nerve growth factor-like neuronal survival-promoting effects [100,110], whereas the compounds 4,4,14α-Trimethyl-5α-chol-7,9 (11)-diene-3-oxo-24-oic-acid, methyl ganoderate B, methyl ganoderate A, GA S1, and GA T-Q showed brain-derived neurotrophic factor-like neuronal survival-promoting activities [100,[110][111][112]. Compounds such as n-butyl ganoderate H and methyl ganoderate A acetonide have shown specific antiacetylcholine terse activity and have been examined as possible drug candidates for the treatment of Alzheimer's and other related neurodegenerative diseases. The compounds lucidadiol, ganodermanondiol, and other Ganoderma triterpenes have shown moderate acetylcholinesterase inhibitory activity [113]. ...
... Zhou et al., 2012 [109], reported neuroprotective effect of pre-administration of G. lucidum spores on rat hippocampus. Various studies have reported that the compounds, 4,4,14α-Trimethyl-5α-chol-7,9 (11)-diene-3-oxo-24-oicacid and methyl ganoderate B, have showed nerve growth factor-like neuronal survival-promoting effects [100,110], whereas the compounds 4,4,14α-Trimethyl-5α-chol-7,9 (11)-diene-3-oxo-24-oic-acid, methyl ganoderate B, methyl ganoderate A, GA S1, and GA T-Q showed brain-derived neurotrophic factor-like neuronal survival-promoting activities [100,[110][111][112]. Compounds such as n-butyl ganoderate H and methyl ganoderate A acetonide have shown specific antiacetylcholine terse activity and have been examined as possible drug candidates for the treatment of Alzheimer's and other related neurodegenerative diseases. ...
Ganoderma a traditional Chinese medicine popularly used for complementary cancer therapy and longevity for centuries. The vast amount of study has been performed on the medicinal properties of Ganoderma lucidum. G. lucidum contains various compounds with a high grade of biological activity, which increase the immunity. Several of these substances belong to the triterpenoids and polysaccharides. Proteins, sterols, phenols, lipids, etc., are also present. Ganoderma triterpenes are important secondary metabolites of G. lucidum. Ganoderma triterpenes are lanostane tetracyclic terpenes which have been reported to possess antioxidant, antitumor, anti-human immunodeficiency virus, anticancer, anti-inflammation, cytotoxic, hepatoprotective, and neuroprotective activities. This review deals with most important triterpenes isolated from Ganoderma and their therapeutic effects.
... Ganoderma lucidum has been used for the treatment of histamine-mediated allergic reactions including asthma and contact dermatitis (Chen and Chang 1987). The methanolic extract of this mushroom has an inhibitory action on histamine release from rat mast cells (Kohda et al. 1985). It has exhibited potential therapeutic effect against the lesion of the kidney, decreased excretion of protein in urine, and serum sickness nephritis caused by immune complex in rats. ...
... It has been found that cyclo-octasulfur and ganoderic acids C and D suppressed the histamine release of histamine from rat mast cells. Cyclo-octasulfur from this mushroom has also been reported to interact with membrane proteins to inhibit Ca uptake resulting in a blockade of histamine release (Kohda et al. 1985;Tasaka et al. 1988). Anti-allergic effects of triterpenoids and polysaccharide extracts from G. tsugae were studied using mast cells, T-cell line, primary T cells, and macrophage cells. ...
Emergence of resistance in microorganisms against the current armamentarium of drugs along with severe side effects encountered with usage of synthetic drugs has resurrected natural products and herbal based drug industries. Among various sources of natural products, fungi have always been a key supplier of bioactive molecules of high medicinal importance. Over the years, fungi from the division Basidiomycota have been of keen interest due to isolation of putative bioactive compounds from them. The genus Ganoderma consists of wood-degrading polypore mushrooms which have been traditionally used in China and other Asian countries for the treatment of various ailments. Several species of genus Ganoderma exhibited anti-inflammatory, antitumor, antioxidant, antidiabetic, antiviral, antibacterial, antifungal, and immunomodulatory properties which are attributed to the presence of various bioactive compounds such as terpenoids, polysaccharides, steroids, fatty acids, and proteins in them. The aim of this chapter is to summarize the research progress on general pharmacological effects of Ganoderma.
... The bioactive substances in Phellinus are important as health-beneficiary. Phellinus and Ganoderma is an excellent herbal resource of immunoregulatory, anticancerous, antioxidants and liver-protectants (Kohda;1985). ...
... The bioactive substances in Phellinus are important as health-beneficiary. Phellinus and Ganoderma is an excellent herbal resource of immunoregulatory, anticancerous, antioxidants and liver-protectants (Kohda;1985). ...
edicinal mushrooms plays important role in immunomodulation as they contains number of bioactive compounds The search for novel polysaccharides with immune enhancing properties seems from the basic shortcomings of existing therapies. Majority of chemical compounds, which have been identified as cytotoxic to cancer cells, are also toxic to normal cells. Hence, the discovery and identification of safer new drugs, without severe side effects, has become an important goal of research in the biomedical sciences.A future significant observation is the ability of all the mushroom polysaccharides when administered to significantly reduce the side effects so often encountered. Therefore current review enlightened the important bioactive polysaccharides from medicinal mushroom with immunomodulation
... Moreover, trivial names of ganoderic acids and lucidenic acids are confusing because identical compounds were given different names or different compounds were named identically. These naming issues are mostly in papers published by four research groups in the 1980s (Hirotani et al., 1985(Hirotani et al., , 1987Kikuchi et al., 1985aKikuchi et al., ,b, 1986aKohda et al., 1985;Nishitoba et al., 1984Nishitoba et al., , 1985aNishitoba et al., ,b,c, 1986aNishitoba et al., ,b, 1987aNishitoba et al., ,b,c, 1988aNishitoba et al., ,b, 1989 (Table 1, Fig. 1, Table S1). For example, Nishitoba et al. (1984Nishitoba et al. ( , 1985a reported (3) as ganoderic acid C. Kohda et al., 1985 reported (3) as ganoderic acid D, but later (3) was renamed as ganoderic acid C1 by Kikuchi et al. (1986a). ...
... For example, Nishitoba et al. (1984Nishitoba et al. ( , 1985a reported (3) as ganoderic acid C. Kohda et al., 1985 reported (3) as ganoderic acid D, but later (3) was renamed as ganoderic acid C1 by Kikuchi et al. (1986a). Kohda et al. (1985) named (4) as ganoderic acid C and Kikuchi et al. (1985a) named (4) as ganoderic acid D. It (4) was later renamed as ganoderic acid D2 by Nishitoba et al. (1985b) and as ganoderic acid C2 by Kikuchi et al. (1986a). reported (4) as ganoderic acid E. Hirotani et al., 1985 reported (9) as ganoderic acid C. Nishitoba et al. (1985a) reported (5) as ganoderic acid D and Nishitoba et al. (1985b) renamed it as ganoderic acid D1. ...
... The acidic ethyl acetate soluble materials (AESM, crude triterpenoids) were purified from G. tsugae, then ganoderic acid A (1), B (2), C (3), D (4), E (5), C5 (6), C6 (7), G (8), and ganoderenic acid D (9) were isolated using semi-preparative HPLC. All these triterpenoids are physiologically active compounds containing activities of anti-cancer (16) , anti-oxidation (17) , antiallergy (18) , and liver-protection (19) . This research used these nine ganoderic acids as standard compounds to establish a fast and accurate reverse-phase HPLC method. ...
... More than 100 mg of ganoderic acid A can be obtained from 5 g of AESM by isolating twice. Ganoderic acid A is usually used as the marker compound because it is the major triterpenoid in G. tsugae (18) . ...
Ganoderma product has the highest sale volume in the health food market in Taiwan. The most widely-used raw material is the species of G. tsuage. Nine triterpenoids were isolated from the fruiting body of G. tsugae and their structures were identified, using 1H NMR and FT-IR, as ganoderic acid A (1), B (2), C (3), D (4), E (5), C5 (6), C6 (7), G (8) and ganoderenic acid D (9). A reverse-phase HPLC method was also established for the determination of these nine triterpenoids. Among these compounds, ganoderic acid E, C5, C6, G and ganoderenic acid D were analyzed for the first time by reverse-phase HPLC. The separation was carried out on a C18 reverse-phase column with a gradient elution of acetonitrile and 2% acetic acid (1/4 and 1/2, v/v) as mobile phase at a flow-rate of 0.8 mL/min and detection at 252 nm. Regression equation revealed the linear relationship (correlation coefficient: 0.9990-0.9999) between the peak-area ratios and concentrations of ganoderic acids. The recoveries of nine ganoderic acids were between 96.85-105.09%. The relative standard deviations of nine ganoderic acids range from 0.8-4.8% (intraday) and 0.7-5.1% (interday). The total contents of the nine ganoderic acids in eight Ganoderma samples were between 0.28-2.20%.
... Compound (2) of the NMR spectra exhibited characteristic α-glucosyl and β-glucosyl signals. In addition to the signals of the GAA [25], 14 proton signals (from 4.28 to 6.04 ppm) and 12 carbon signals (from 62.7 to 96.5 ppm) corresponding to two glucose moiety structures were observed. The attachment of the glucose moiety to C-26 of GAA was confirmed by the HMBC correlation from the anomeric proton of Glu H-2 a (δ H 5.48, d, J = 3.5, 9.8 Hz) to C-26 (δ C 176.2). ...
Glycosylation occurring at either lipids, proteins, or sugars plays important roles in many biological systems. In nature, enzymatic glycosylation is the formation of a glycosidic bond between the anomeric carbon of the donor sugar and the functional group of the sugar acceptor. This study found novel glycoside anomers without an anomeric carbon linkage of the sugar donor. A glycoside hydrolase (GH) enzyme, amylosucrase from Deinococcus geothermalis (DgAS), was evaluated to glycosylate ganoderic acid F (GAF), a lanostane triterpenoid from medicinal fungus Ganoderma lucidum, at different pH levels. The results showed that GAF was glycosylated by DgAS at acidic conditions pH 5 and pH 6, whereas the activity dramatically decreased to be undetectable at pH 7 or pH 8. The biotransformation product was purified by preparative high-performance liquid chromatography and identified as unusual α-glucosyl-(2→26)-GAF and β-glucosyl-(2→26)-GAF anomers by mass and nucleic magnetic resonance (NMR) spectroscopy. We further used DgAS to catalyze another six triterpenoids. Under the acidic conditions, two of six compounds, ganoderic acid A (GAA) and ganoderic acid G (GAG), could be converted to α–glucosyl-(2→26)-GAA and β–glucosyl-(2→26)-GAA anomers and α-glucosyl-(2→26)-GAG and β-glucosyl-(2→26)-GAG anomers, respectively. The glycosylation of triterpenoid aglycones was first confirmed to be converted via a GH enzyme, DgAS. The novel enzymatic glycosylation-formed glycoside anomers opens a new bioreaction in the pharmaceutical industry and in the biotechnology sector.
... Modern research has shown that the main bioactive compounds in G. lucidum are polysaccharides and ganoderic acids, a group of triterpenes [6,7]. Over one hundred highly oxygenated and pharmacologically active triterpenes have been isolated from this mushroom [8], and these compounds have been proven to display wideranging biological activities; some of these are cytotoxicity against Meth-A cells [9,10], promotion of apoptosis of hepatoma HuH-7 cells [11], inhibition of histamine release [12], inhibition of angiotensin converting enzyme [13], and antitumor promoting [14] and cholesterol synthetic inhibiting [15,16] effects. ...
By means of 5α-reductase inhibitory activity-guided fractionation, a new lanostanoid, 15α-hydroxy-3-oxolanosta- 7, 9(11), 24(E)-trien-26-oic acid, named as ganoderic acid TR, was isolated from the ethanol extract of the fruiting bodies of Ganoderma lucidum (Fr.) Karst (Ganodermataceae). The compound showed potent inhibitory activity with an IC50 of 8.5 μM. Modified Mosher's method established the S-configuration of the secondary hydroxyl group at C-15. In addition, a carboxyl group on the side chain of ganoderic acid TR is essential to elicit the inhibitory activity because of the considerably lower activity of its methyl ester.
... Ethanolic extracts of Japanese edible mushrooms namely H. marmoreus, F. velutipes, Pholiota nameko, and P. eryngii show remarkable antiallergic effects in mice by oxazolone-induced type IV allergy after oral application. Inhibition of histamine release from the rat mast cells was done by compounds such as Ganoderic acids C (8d) and D (8e) and cyclooctasulfur (compounds from G. lucidium) 47,48 . Regression of severe allergic symptoms was observed in a patient suffering from thromboangitis obliterans and also in a patient with urticaria. ...
Mushrooms can be considered as a prolific resource for drugs as per previous literature surveys. Their constituent bioactive components are broadly classified such as phenols, flavonoids, triterpenoids, saponins. Whole mushrooms or mainly fruiting bodies extracts and compounds isolated from their mycelium are of immense pharmacological importance. Extraction employing suitable solvents leads to the isolation of various principle compounds. Pure compounds can also be isolated from natural material or can be synthesized chemically. 80-85% of all medicinal mushroom products are isolated from fruiting bodies. 15% of all products are obtained from mycelia. Cultivation of mushrooms requires minimal resources; therefore the development of cultivation farm helps for creating employment for various people in many parts of the country. Many kinds of literature have already reported the detailed chemical bioactive constituents of the extracts prepared from mushrooms via various extraction methods. These compounds are of immense therapeutic importance, and some of them have already become a part of clinical trials as an adjuvant therapy along with the conservative therapy applied for patients suffering from cancer in various countries like China, Japan. The next most crucial part is the development of suitable galenic formulations in the form of capsules, tea or tablets which depends on the isolated material. Mixing of several mushroom components is also becoming common and will be of course beneficial to mankind shortly.
... Ethanolic extracts of the edible Japanese basidiomycetes H. marmoreus, F. velutipes, Pholiota nameko, and Pleurotus eryngii show significant antiallergic effects in mice [77]. Some compounds from G. lucidum (ganoderic acids C and D) have been shown to inhibit the histamine release from rat mast cells [78,79]. Eating of Tricholoma populinum led to the regression of severe allergic symptoms in a patient with thromboangiitis obliterans and in another patient with urticaria [80]. ...
... Then 1 H and 13 C-NMR were obtained, and the 1 H-and 13 C-NMR signal assignments were conducted, and assisted with spectra of distortionless enhancement, using polarization transfer (DEPT), heteronuclear single quantum coherence (HSQC), heteronuclear multiple bond connectivity (HMBC), 1 H-1 H correlation spectroscopy (COSY), and nuclear Overhauser effect spectroscopy (NOESY; shown in Figures S4-S10). Among the 36 signals in the 13 C-NMR spectrum of compound (1), 30 signals corresponding to the triterpenoid structure of GAA [24] were completely assigned, while a significant downfield shift of C-15 (82.7 ppm) and a minor shift of C-6, C-7, C-8, C-17, and C-30 were observed. The other six peaks from 62 to 106 ppm (105.3, ...
Functional bacteria that could biotransform triterpenoids may exist in the diverse microflora of fish intestines. Ganoderic acid A (GAA) is a major triterpenoid from the medicinal fungus Ganoderma lucidum. In studying the microbial biotransformation of GAA, dozens of intestinal bacteria were isolated from the excreta of zebrafish. The bacteria’s ability to catalyze GAA were determined using ultra-performance liquid chromatography analysis. One positive strain, GA A07, was selected for functional studies. GA A07 was confirmed as Bacillus sp., based on the DNA sequences of the 16S rRNA gene. The biotransformed metabolite was purified with the preparative high-performance liquid chromatography method and identified as GAA-15-O-β-glucoside, based on the mass and nuclear magnetic resonance spectral data. The present study is the first to report the glycosylation of Ganoderma triterpenoids. Moreover, 15-O-glycosylation is a new microbial biotransformation of triterpenoids, and the biotransformed metabolite, GAA-15-O-β-glucoside, is a new compound.
... Ethanolic extracts of the edible Japanese basidiomycetes H. marmoreus, F. velutipes, Pholiota nameko, and Pleurotus eryngii show significant antiallergic effects in mice [77]. Some compounds from G. lucidum (ganoderic acids C and D) have been shown to inhibit the histamine release from rat mast cells [78,79]. Eating of Tricholoma populinum led to the regression of severe allergic symptoms in a patient with thromboangiitis obliterans and in another patient with urticaria [80]. ...
... A further loss of an H 2 O molecule formed the next fragment ion at m/z 433. Ganoderic acid was proven to exhibit significant pharmacological activities by means of anti-histamine, anti-hypercholesterolemic, antibacterial and capacity to scavenge free radicals (Kohda et al., 1985;Komoda et al., 1989;Zhu et al., 1999;Wang and Liu, 2008). Other research has implicated that ganoderic acid DM isolated from Ganoderma lucidum (Curtis) P. Karst. ...
A cupric reducing antioxidant capacity (CUPRAC)-guided purification approach was performed on a methanol extract of Lentinus squarrosulus (LsqMeOH) by using reversed phase-high performance liquid chromatography. Using reversed phase-high performance liquid chromatography, three fractions were separated arbitrarily named FR1, FR2 and FR3. Results showed that FR2 exhibited the highest antioxidant activity in CUPRAC assay (A450, 0.86) but not significantly different from LsqMeOH (A450, 0.84). FR1 and FR3 showed much lower absorbance, with values (A450, 0.21) and (A450, 0.36) respectively at 1 mg ml⁻¹. The most active fraction (F3) was further subjected to LC-MS/MS to obtain its detailed chemical profile. Uridine, ganoderic acid derivative, and flavonoids were the first time being found in L. squarrosulus antioxidative fractions. The present results indicate that the fraction extracts of L. squarrosulus possess antioxidant properties and can be used as free radical inhibitors. Therefore, this research suggested the potentials of L. squarrosulus as a source of antioxidant extract to be used in food industries (functional food).
... ganoderic acids (Paterson 2006;Bishop et al. 2015;Guthmann 2016). One investigation found that ganoderic acids C and D (concentration 0.4 and 2 mg/ml), isolated from G. lucidum, inhibited histamine release from rat mast cells that was induced by compound 48/80 and concanavalin A (ConA) (Kohda et al. 1985). The chloroform extract from the culture medium had similar effects. ...
Allergies are an increasing problem worldwide, and new strategies for prophylaxis and therapy are urgently needed. Medicinal mushrooms present such an opportunity. Antiallergic activities have been found for Agaricus subrufescens, Armillaria ostoyae, Flammulina velutipes, Ganoderma lucidum and G. tsugae, Inonotus obliquus, Phellinus linteus, Pleurotus ostreatus and P. pulmonarius, Tricholoma populinum, and some further mushroom species. Nevertheless, most effects have been detected only in vitro and/or in animal assays, and responsible bioactive compounds have not yet been identified. Besides, only a limited number of mushroom species has been investigated for antiallergic activities until now. The chapter gives an overview about mushrooms with antiallergic activities and describes the challenges for the exploration of the antiallergic potential of mushrooms.
... Its pharmaceutical effects include enhanced health and longevity. 1 The major secondary metabolites of G. lucidum are lanostane triterpenoid natural products, and more than 150 lanostanes, including ganoderic acids, ganolucidic acids and lucidic acids have been isolated from Ganoderm spp. 2 These compounds exhibit various biological activities such as anti-HIV activity, 3-5 angiotensin converting enzyme inhibitory effect, 6,7 cholesterol synthesis inhibitory effect, 8,9 anti-histamine releasing activity, 10 and potential anticancer activities. 2,[11][12][13][14] One Ganoderma triterpenoid was shown to specifically interact with tubulin proteins, which play an important role in cell growth and differentiation. ...
A new lanostane triterpene was extracted from Ganoderma lucidum using cellulose-dissolving ionic liquids. The structure of the isolated compound was elucidated by spectroscopic analysis, including NMR, MS, and a modified Mosher’s method. The newly isolated lanostane natural product was named ganoderic acid Σ.
... In addition to lucidumol C described above, six known compounds (Fig. 2) were identified by comparing their physicochemical and spectral data with those in the literature . These compounds were identified as lucidumol A (2) [9], ergosterol palmitate (3) [10], ergosta-7,22-dien-3b-yl palmitate (4) [11, 12], ergosterol (5) [13] , ergosterol peroxide (6) [14], ganoderic acid A (7) [15]. Cytotoxic activities of the isolated compounds were evaluated against HCT-116, Caco-2, HepG2 and HeLa cell lines (Table 2). ...
A new oxygenated lanostane-type triterpene, named lucidumol C, together with six known compounds, was isolated from the chloroform extract of the fruiting bodies of Ganoderma lingzhi. Structures were established based on extensive spectroscopic and chemical studies. Potential cytotoxic activities of the isolated compounds were evaluated against human colorectal carcinoma (HCT-116, Caco-2), human liver carcinoma (HepG2), and human cervical carcinoma (HeLa) cell lines using WST-1 reagent. Selectivity was evaluated using normal human fibroblast cells (TIG-1 and HF19). Among the compounds, lucidumol C showed potent selective cytotoxicity against HCT-116 cells with an IC50 value of 7.86 ± 4.56 lM and selectivity index (SI) > 10 with remarkable cytotoxic activities against Caco-2, HepG2 and HeLa cell lines.
... Also, GA-β has been seen to exhibit immune-modulator action decreasing the burden of the active immune system by reducing IL-5, but increasing CD8 + , IFN-γ, IL-10, and IL-12 production of specific allergen-stimulated PBMCs. These effects have been observed to be significant for attaining immune competence in GA-R, S Antihepatotoxic activity [34] B, C2, and G Anti-ageing activity [35,36] Ganoderic acid, GA-A, B, C, and D Antioxidative activity [37] GA-A, B, G, and H Antinociceptive activity [38] GA-Me Arrest cell cycle, apoptosis [39,40] Ganoderic acid, GA-C, and D Histamine inhibition [38,41,42] Ganoderic acid, GA-A, F, and DM Anti-inflammatory activity [43][44][45] GA-Y, F, H, B, D, K, and S Antihypertensive activity [46] GA-Me, Mf, and Y Hypercholesterolemic activity [38,47] GA-Sz Anticomplement activity [48] GA-T Anti-metastatic, anti-invasion [ [61,62] asthmatic patients [81]. In addition, GA-S is known to suppress the thromboxanes and prostaglandins exhibiting the amphipathic effect on the platelets aggregation [77,83,84]. ...
A Basidiomycetes fungus belonging to polypore family of mushrooms, Ganoderma lucidum (GL), has been known since a long time for their myriad therapeutic indications. Renowned as an invaluable resource of cardinal mycoconstituents they encompass numerous terpenoids polysaccharides and proteins. Possessing the therapeutically potent lanosteroidal skeleton, terpenoids are upheld for their invariable participation in therapeutically diverse bioactivities. Polysaccharides and proteins exhibiting distinguishable bioactivities provide this oriental mushroom with additional edges over immune function and anti-cancer potential. This review is a concerted effort to throw light upon the therapeutic versatility of the fungus, shadowed by various other natural products. An effort has been made towards conglomerating the mycoconstituents decisive for the many activities portrayed by this fungus. More importantly, this review seeks to fathom the inextricable role played by derivatives in modulating signaling cascades such as downregulation of various mitogenic pathways, inhibiting growth factors, or upregulating certain pathways enhancing cellular integrity.
... The fruiting bodies of G. lucidum are widely used in China, Japan, and Korea as a valuable crude drug, particularly in the treatment of chronic hepatitis, nephritis, hepatopathy, neurasthenia, arthritis, bronchitis, asthma, gastric ulcer, and insomnia (Namba, 1994). Triterpenoids are the main chemical constituents of G. lucidum, and these compounds have been shown to produce inhibitory effects on HIV-1 protease (Min et al., 1998), anti-tumor effects (Stanley et al., 2005;Sliva, 2006;Mü ller et al., 2006), inhibitory effects on histamine release (Kohda et al., 1985), as well as antimicrobial (Wang and Ng, 2006), anti-inflammatory (Tung et al., 2013;Dudhgaonkar et al., 2009), and antioxidant activities (Zhu et al., 1999). In addition, polysaccharides from G. lucidum have been shown to possess hypoglycemic (Hikino and Mizuno, 1989), immunostimulant (Kino et al., 1989;Soccol et al., 2010), antitumor, and anti-inflammatory activities (Joseph et al., 2011). ...
Two new lanostane triterpenes, 3α,12β,15α-triacetoxy-5α-lanosta-7,9(11),24-trien-26-oic acid (1) and 5α-lanosta-8,24-diene-26,27-dihydroxy-3,7-dione (2), together with sixteen known compounds (3–18) were isolated from the fruiting bodies of the Vietnamese mushroom Ganoderma lucidum. Their chemical structures were determined by extensive spectroscopic (IR, HR-EI-MS, 1D and 2D NMR) analyses. Potential cytotoxic activities of these compounds were evaluated against human non-small cell lung adenocarcinoma (A549), breast adenocarcinoma (MCF-7), and prostatic small cell carcinoma (PC-3). Among the compounds, 3α,12β,15α-triacetoxy-5α-lanosta-7,9(11),24-trien-26-oic acid (1) showed significant cytotoxic activity against PC-3 cells with an IC50 of 11.5 μM. In studies of anti-angiogenesis activity, ganoderic acid F (17) was found to have the most potent inhibitory effect on the formation of capillary-like structures of human umbilical vein endothelial cells.
... However, the eosinophils in BALF and Th2 cytokines IL-4 and IL-5 and were not significantly suppressed by G. tsugae [22,23]. Since early in vitro study suggested that triterpenoids suppressed histamine release from mast cells [24], our study further demonstrated that triterpenoids fraction from G. tsugae significantly inhibited eosinophils, IL-4, IL-5, PGE2, eotaxin levels, and thus airway hyperactivity [25]. ...
This study was to investigate antiallergic effects of triterpenoids (Gt-TRE) and polysaccharide (Gt-PS) extracts from Ganoderma tsugae, using mast cell line RBL-2H3, T cell line EL4, primary T cells, and transfected RAW264.7 macrophage cells. The results showed that histamine secreted from activated RBL-2H3 mast cells was significantly suppressed by Gt-TRE but not Gt-PS. Interleukin- (IL-) 4 secreted from activated EL4 cells was significantly suppressed by Gt-TRE but not Gt-PS. Further primary CD4+ T cells cultures also confirmed that Gt-TRE (
5
~
50
µg/mL) significantly suppressed Th2 cytokines IL-4 and IL-5 secretions but had no effect on Th1 cytokines IL-2 and interferon (IFN)-γ. Gt-PS did not affect IL-4 and IL-5 secretions until higher doses (400, 500 µg/mL) and significantly suppressed IFNγ secretions but enhanced IL-2 at these high doses. The reporter gene assay indicated that Gt-TRE inhibited but Gt-PS enhanced the transcriptional activity of NF-κB in activated transfected RAW264.7 cells and transfected EL4 cells. IL-4 secreted by this transfected EL-4 cells was also significantly decreased by Gt-TRE but not by Gt-PS, suggesting that these two fractions may exert different effects on NF-κB related cytokines expression. These data suggested that triterpenoids fraction of Ganoderma tsugae might be the main constituents to alleviate allergic asthma.
... Ganoderma lucidum and ginseng have been claimed by traditional health food practitioners as being able to improve health, enhance strength, and prevent tumors. Some literatures have reported that Ganoderma lucidum exhibits the ability to prevent tumors (15) , inhibit histamine-release (16) , decrease cholesterol synthesis (17) , and protect against hepatorelated diseases (18,19) . Ginseng has been shown to carry the liver-protection activity via a cytochrom P450 inhibition to reduce CCl4-induced hepatic lipid peroxidation (20,21) . ...
Proper regulation of the acclaimed functionality and safety of the health food is a consensus among the health authorities of every nation. The objective of this study is focused on the methods development for safety and functionality of hepatic injury prevention of health food using CCl4-induced hepatotoxicity as model. The result from this study could provide some useful information for setting a feasible and reasonable evaluating method for regulatory purpose. In this study, we have shown that in the untreated rats, administration of CCl4 at 0.05 and 0.20 mL/ kg, BW caused the increase of SGOT activities from 118 ± 25 to 328 ± 42 and 670 ± 95 (U/L), respectively; SGPT activities from 48 ± 5 to 170 ± 18 and 535 ± 123 (U/L), respectively. In the rats treated with silymarin for 7 days at 140 mg/ kg, BW prior the administration of CCl4 could attenuate the liver injury induced by CCl4 at 0.05 and 0.20 mL/ kg, BW. Similar results were obtained when pretreated with Ganoderma lucidum and red ginseng. However, none of the pre-treatment can effectively prevent or reduce the liver injury induced by CCl4 at higher dosage (0.40 and 0.80 mL/ kg, BW). In addition, we have also found that no toxic effects were observed when pretreated with silymarin, Ganoderma lucidum and red ginseng for 7 and 30 days as judged by the pathological examination and serum enzyme activities. The results of this study might provide some useful information for the Department of Health with a scientific and objective means to evaluate the safety and functionality for the hepatic injury prevention of health foods.
During this period of time, mushroom experience changes in functional aspects and consumption areas. Due to its magnificent role in promoting health, it was considered one of the most healthy sources of food. Agaricus spp., Marcrolepoita spp., Auricularia spp, Armillaria spp, Pholoita, Hericium, Grifola spp, Flammulina, and Hypsizygus spp. are some most commonly consumed mushrooms in the world. They provide inexpensive means of nutritious and tasty food worldwide. However, ancient people are also very much aware of their holistic function towards health and that was why they used mushrooms for medicinal purposes in the past onwards. Mushroom plays an important role in the treatment of some lethal diseases like cancer, inflammation, autoimmune disorders, allergy, hypertension, arthritis, hyperglycemia, atherosclerosis, and many more. Meanwhile, researchers still focus on other functions of mushrooms in health science and also explore their anticancerous activity. However, many findings are left to be found in the future. This review paper throws light on the various important mushrooms and their functions related to human health, and also ongoing research towards treating some critical diseases.
In recent years, the health benefits of mushrooms are being realized in an exponential manner. Mushrooms are an interesting group of organisms, which attracted and distracted people alike since times immemorial. They appear and disappear mysteriously. Many legends are associated with them. Their potential in medicine for health benefits was appreciated only during the late 1990s. When their medicinal properties were recognized, their importance immediately gained significance, and now they are at the forefront of the treatment of some dreaded diseases. Their potentialities in the health sector have grown tremendously due to the identification and isolation of bioactive compounds, which are being explored further as nutraceuticals. This appreciation was first limited to a few well-known species, but now a consensus seems to have emerged that every mushroom possesses one or other traits which accrue health benefits to man. There are around 7000 edible species among 16,000 mushroom species recorded the world over. Of these, around 3000 are perhaps the prime edible species of which around 200 have been experimentally grown, 100 economically cultivated, and 30 commercially cultivated in one or other parts of the world, and about 6 species are grown on the industrial scale. Further, around two dozen species have been investigated for their nutraceutical traits. In the near future, it is anticipated that the mushrooms possessing medicinal properties are likely to become a potential source of new biological drugs for counteracting lifestyle diseases. The health benefits of mushrooms, nutraceuticals, and pharmaceuticals derived from them have been discussed in this chapter.KeywordsMushroomsMedicinal valueBioactive compoundsNutraceuticals
As part of our ongoing research on bioactive fungal metabolites, two new metabolites were isolated from a fungus of the Stictidaceae (strain MSX62440), dasyscyphins F and G (1 and 3), along with the known dasyscyphin C (2). Compound 1 was characterized by HRMS and 1D and 2D NMR data, and its absolute configuration established by ECD spectroscopy. A structural revision of dasyscyphin C (2) was based on NMR data and verified by ECD calculations. Compound 3 was previously reported as a synthetic product, and its identity confirmed by comparison with NMR data in the literature, and its absolute configuration was established by ECD spectroscopy. Compounds 1 and 2 showed moderate cytotoxicity and antimicrobial activity.
Five novel C30 triterpenoids, ganoderic acids Mg (10), Mh (11), Mi (12), Mj (13) and Mk (14), were isolated from the mycelial mat of a G. lucidum strain, which produces C27 lucidenic acids in the fruiting body. Their structures were determined by spectroscopic analysis and chemical conversion.
Ganoderma lucidum is one of the most famous medicinal fungi and is traditional Chinese medicine with various biological activities in Asian countries. To clarify its pharmacodynamic material basis, 15 lanostane triterpenoidswere obtained from the fruiting bodies of G. lucidum, including 8 previously undescribed lanostanoids. Their structures, including absolute configuration, were established based on ultraviolet, infrared, high-resolution electrospray ionisation mass spectrometry, 1D and 2D nuclear magnetic resonance, and X-ray crystallographic analysis. Ganoluciduone A was an unusual octonorlanostane, which was isolated from Ganoderma for the first time. In addition, the anti-inflammatory activities of all isolates were evaluated by observing their inhibitory effects on nitric oxide production in RAW264.7 cells activated by a lipopolysaccharide. Ganoluciduone B exhibited moderate inhibitory activity on nitric oxide production, with an inhibition rate of 45.5% at a concentration of 12.5 μM.
A preliminary relationship was illustrated between the structural characteristics and corresponding immunomodulatory activities of G. lucidum polysaccharides. Two polysaccharides (GLP-1 and GLP-2) were purified from Ganoderma lucidum extracts by gradient ethanol precipitation and a Q-Sepharose Fast Flow (QFF) strong anion-exchange column. The monosaccharide composition, high-performance gel permeation chromatography-multi-angle laser light scattering-refractive index (HPGPC-MALLS-RI), Fourier-transform infrared spectroscopy (FT-IR), atomic force microscopy (AFM), methylation analysis, and nuclear magnetic resonance (NMR) were used to characterize these polysaccharides. The GLP-1 polysaccharide was elucidated as D-galactoglucan with a flexible random linear conformation that mainly composed of →6)-β-D-Glcp-(1→, →6)-α-D-Galp-(1→, and →3)-β-D-Glcp-(1→ residues. GLP-2 was found to be a relatively homogeneous β-D-glucan that possessing →6)-β-D-Glcp-(1→ and →3)-β-D-Glcp-(1→ residues packaged into a spherical conformation. Immunomodulatory activities in vivo demonstrated that GLP-1 produced better protection of the spleen and thymus and was more effective for promoting hematopoiesis and improving IgA levels in serum. Our results suggest that the immunomodulatory activities of G. lucidum polysaccharides are highly corresponded to their structural characteristics such as carbohydrate composition, molecular weight and advanced conformation. This study provides a preliminary basis for studying the relationship between polysaccharide structure characterization and pharmacological activities.
So far, more than 20 species of Ganoderma (Lingzhi) fungi have been studied, including G. lucidum, G. sinense, G. japonicum, G. capense, G. australe, G. tsugae, G. applanatum, G. tropicus, G. boniense, G. duropora, G. resinaceum, G. theaecolum, G. cochlear, G. atrum, G. formosanum, G. boninense, G. colossum, G. concinna, G. amboinense, G. pfeifferi, and G. orbiforme. Over 600 compounds were isolated and identified from the genus Ganoderma. The components in Ganoderma contained triterpenes, meroterpenoids, steroids, alkaloids, nucleosides, nucleobases, and polysaccharides, in which triterpenes were the main compounds, and more than 300 triterpenes obtained from it. With the use of new technology of separation and purification, the other types of compounds, such as meroterpenoids, alkaloids, nucleosides, and polysaccharides were reported in recent years. Herein, the structural classifications and characteristics and separation methods were summarized.
Ganoderma lucidum, as food, tea, dietary supplement, and medicine, is widely used in China and Eastern Asian countries. In order to discover its anti-inflammatory constituents and provide some references for the usage of G. lucidum and G. sinense, two official species in China, the fruiting bodies of G. lucidum were studied, leading to the isolation of six new triterpenoids (1-6) and 27 known analogues (7-33). Compound 4 exhibited the most potent inhibition on nitric oxide (NO) production induced by lipopolysaccharide (LPS) in RAW264.7 macrophage cells. The production of IL-6 and IL-1β, as well as the expression of iNOS, COX-2 and NF-κB were dose-dependently reduced by 4. The phosphorylations of IκBα and IKKβ in LPS-induced macrophage cells were blocked by 4. Therefore, 4 could be used as a potential anti-inflammatory candidate and the total triterpenoids might be developed as value-added functional food for the prevention of inflammation. In combination of previous studies, it should be cautious for the interchangeable usage of G. lucidum and G. sinense.
Ganoderma hainanense, an edible mushroom mainly distributed in Southern China, has long been used as a functional food with considerable health benefits. Bioassay-guided phytochemical research on the fruiting bodies of G. hainanense led to the isolation of 22 lanostane-type triterpenoids, including two new compounds 3-acetyl-ganodermadiol (1) and 3-acetyl-lucidumol B (2). In an in-vitro assay, sixteen out of the twenty-two triterpenoids were found to possess more potent α-glucosidase inhibitory activity than the positive control acarbose. Preliminary structure-activity relationship (SAR) analysis indicated that the side chain structures of these compounds could significantly influence the activity. Results of the present study revealed that lanostane-type triterpenoids with α-glucosidase inhibitory activity may contribute to the hypoglycaemic effects of G. hainanense in the folk usage, and also the potentiality to develop G. hainanense as dietary supplement for glycemic control.
Ganoderma lucidum is traditionally applied in various countries for treatment of variety of diseases. It is a prime example of an ancient remedy being of immense relevance to the modern era and known as mushroom of immortality as well as spirit mushroom. It has been used as a health promoting agent due to its wide pharmacological and nutraceutical activity and availability. Increasing awareness about fitness and health-promoting capability of G. lucidum pull the majority of people to get healthier lifestyles, propelling expansion of its market globally. The importance of Ganoderma lucidum has fascinated scientific community to carry out extensive phytochemical and pharmacological investigations. Different studies have been carried out, and a broad spectrum of its pharmacological actions has been established which include immunomodulatory, anticancerous, antioxidant, antidiabetic, hepatoprotective, neuroprotective, cardioprotective, antimicrobial, anti-inflammatory, anti-allergic, antiosteoporotic, suppression of angiogenesis, and antinociceptive properties. The current review is an attempt to explore the reported chemical composition and pharmacological activity. It will act as a reference for all researchers, scientists, and other health professionals who are working on this mushroom.
The secrets of Reishi : morphology, chemical constituents and therapeutic activities
Le ganoderme luisant est un polypore qui ressemble beaucoup à un morceau de bois verni. Ce champignon est considéré, depuis très longtemps, par les asiatiques comme une panacée qui est capable de rendre l’homme immortel. D’après plusieurs recherches scientifiques récentes, de nombreuses activités bénéfiques ont été mise en évidence, notamment l’activité antitumorale, antioxydante et immunostimulante. Des études sur la composition de ce polypore ont montré qu’il contient essentiellement des polysaccharides, des triterpènes et des protéines. S’il était rare et donc coûtait extrêmement cher dans le passé, actuellement, il est cultivable par plusieurs méthodes et entre dans la composition de nombreux compléments alimentaires commercialisés dans le monde. Les études approfondies en cours et dans l’avenir sur ce merveilleux champignon semblent très prometteuses. Nous pourrons espérer que le ganoderme luisant devienne le traitement de fond possédant peu d’effets indésirables pour plusieurs maladies chroniques comme le cancer, le diabète ...
Mots clés :
Ganoderma lucidum, β-D-glucanes, acides ganodériques, taxonomie, activités thérapeutiques, compléments alimentaires.
Key Words:
Reishi, glucans, ganoderic acids, medicinal mushroom, food supplements
Ganoderma triterpenes (GTs) are the major secondary metabolites of Ganoderma lucidum, which is a popularly used traditional Chinese medicine for complementary cancer therapy. The present study was to establish a fingerprint evaluation system based on Similarity Analysis (SA), Cluster Analysis (CA) and Principal Component Analysis (PCA) for the identification and quality control of G. lucidum. Fifteen samples from the Chinese provinces of Hainan, Neimeng, Shangdong, Jilin, Anhui, Henan, Yunnan, Guangxi and Fujian were analyzed by HPLC-PAD and HPLC-MS(n). Forty-seven compounds were detected by HPLC, of which forty-two compounds were tentatively identified by comparing their retention times and mass spectrometry data with that of reference compounds and reviewing the literature. Ganoderic acid B, 3,7,15-trihydroxy-11,23-dioxolanost-8,16-dien-26-oic acid, lucidenic acid A, ganoderic acid G, and 3,7-oxo-12-acetylganoderic acid DM were deemed to be the marker compounds to distinguish the samples with different quality according to both CA and PCA. This study provides helpful chemical information for further research on the anti-tumor activity and mechanism of action of G. lucidum. The results proved that fingerprints combined with chemometrics are a simple, rapid and effective method for the quality control of G. lucidum.
Secondary metabolites of higher fungi (mushrooms) are an underexplored resource compared to plant-derived secondary metabolites. An increasing interest in mushroom natural products has been noted in recent years. This chapter gives a comprehensive overview of the secondary metabolites from higher fungi, with 765 references highlighting the isolation, structure elucidation, biological activities, chemical syntheses, and biosynthesis of pigments, nitrogen-containing compounds, and terpenoids from mushrooms. Mushroom toxins are also included in each section.
This study investigated the physiological activities of different molecular weight (MW) fractions of crude polysaccharide from D\check{o}d\check{o}k (Codonopsis lanceolata). The crude polysaccharide cut off for each fraction was:
Twenty-nine lanostane triterpenoids (1-29) were obtained from the EtOH extract of fruiting bodies of the Ganoderma curtisii. Among them, compound 1 was a new lanostane triterpenoid and compounds 2-5 were isolated from the genus Ganoderma for the first time and their structures were unambiguously identified in this work. The NMR data of the four known lanostane triterpenoids (2-5) were reported for the first time because their structures were all tentatively characterized by interpreting the MS data from the methanol extract of G. lucidum or from the metabolites in rat bile after oral administration of crude extract of the fruiting bodies of G. lucidum using fragmentation rules. Their anti-inflammatory activities were tested by measuring their inhibitory effects on nitric oxide (NO) production in BV-2 microglia cells activated by lipopolysaccharide. Their IC50 values were in a range from 3.65 ± 0.41 and 28.04 ± 2.81 μM.
Ganoderma lucidum and Ganoderma sinense can be easily identified by TLC and HPLC based on the characteristic features of triterpenoid and the presence of ergosterol which is a characteristic constituent of many mushrooms. A discrimination of G. lucidum and G. sinense is only possible by a macro- and microscopic analysis.
Ganoderma lucidum is widely used throughout the world as a form of traditional medicine. Phytochemical investigation of the chloroform (CHCl3) extract of the fruiting body of G. lucidum resulted in the isolation of four lanostane-type triterpenoids. Based on various spectroscopic data, the isolated triterpenoids were identified as highly oxygenated lanostane-type triterpenoids, including four new compounds (1–4). Furthermore, in vitro bioassays using an adriamycin (ADM)-resistant human breast adenocarcinoma cell line (MCF-7/ADR) and measuring the nitric oxide production in LPS-stimulated macrophages showed that the isolated triterpenoids had no inhibitory effects on p-glycoprotein (p-gp).
Ganoderma species is known as a functional mushroom used in many Asian countries. Triterpenoids, ganoderic acids, and lucidenic acids have been isolated from Ganoderma species (Ganodermataceae family), such as Ganoderma lucidum. Triterpenoids have been investigated for their biological activities, including antibacterial, antiviral, antitumor, antiosteoclastic differentiation activity, anti-HIV-1, hepatoprotection, antioxidation, antihypertension, cholesterol reduction, and antiaggregation functions. In this chapter, the sources, biosynthesis, biological functions (including cell cytotoxicity, cell apoptosis, cell cycle arrest, anti-invasion, autophagy, anti-inflammation, antiosteoclastogenesis, antiasthma, and antihepatitis B activity), and pharmacokinetics of lucidenic acids and ganoderic acids are considered in detail here. This chapter briefly summarizes the multiple functions of lucidenic acids and ganoderic acids and their potential for fighting against human diseases.
This research aimed to study the chemical constituents of fruiting bodies of wild Ganoderma australe (Fr.) Pat., Bull. of the Ganoderma P. Karst. genus. Compounds 1-14 were isolated by the combination of repeated silica gel chromatography, Sephadex LH-20, reversed-phase ODS column, and high performance liquid chromatography. The structures of the compounds were elucidated on the basis of nuclear magnetic resonance spectroscopy, mass spectrometry, IR, and UV spectra. As a result, fourteen compounds, including a new compound (1), were isolated and elucidated as Methyl ganoderenate G (1), Ganoderenic acid G (2), Ganoderenic acid A (3), Methyl ganoderenate A (4), Ganoderenic acid D (5), Ganoderenic acid F (6), Ganoderic acid AP (7), 7β,23α-dihydroxy-3,11,15-trioxolanosta-8,20E(22)-dien-26-oic acid (8), Elfvingic acid A(9), 3β,5α-dihydroxy-(22E,24R)-ergosta-7,22-dien-6-one(10), p-hydroxybenzoic acid (11), 3-hydroxy-4-methoxybenzoic acid (12), 9-octadecenoic acid,2,3-dihydroxypropyl ester (13), and β-sitosterol (14). This research isolated nine lanostane-type triterpenoids (Compounds 1-9) from G. australe for the first time.
Fungi have shown the ability to produce bioactive compounds or present biological activities beneficial to health. Many studies have been conducted to identify the bioactive compounds, as well as the extraction mechanisms, and evaluate their effects either in vivo or in vitro. Work was also done in the search for producing species, including production conditions; moreover, there have been studies to increase production of bioactive compounds. In this review is mentioned some work about the production, characterization, and evaluation of fungal bioactive compounds.
The structures of five new lanostanoid triterpenes isolated from the fungus Ganoderma lucidum were determined by spectroscopic methods.
The objective of this study was to prepare nanostructured lipid carrier (NLC)-based topical gel of Ganoderma Triterpenoids (GTs) and evaluate their effects on frostbite treatment. GT-NLCs was prepared by the high pressure homogenization method and then characterized by morphology and analyses of particle size, zeta potential, entrapment efficiency (EE), and drug loading (DL). The NLCs was suitably gelled for skin permeation studies in vitro and pharmacodynamic evaluation in vivo, compared with the GT emulgel. The GT-NLC remained within the colloidal range and was uniformly dispersed after suitably gelled by carbopol preparation. Transmission electron microscopy (TEM) study showed GT-NLCs was spherical in shape. The EE (%) and DL (%) could reach up to (81.84 ± 0.60)% and (2.13 ± 0.12)%, respectively. The result of X-ray diffractograms (XRD) showed that GTs were in an amorphous state in the NLC-gel. In vitro permeation studies through rat skin indicated that the amount of GTs permeated through skin of GT-NLCs after 24 h was higher than that of GT emulsion, and GT-NLCs increased the accumulative amounts of GTs in epidermis 7.76 times greater than GT emulsion. GT-NLC-gel was found to possess superior therapeutic effect for frostbite, compared with the GT emulgel. The NLC based topical gel of GTs could improve -their therapeutic effect for frostbite.
Copyright © 2015 China Pharmaceutical University. Published by Elsevier B.V. All rights reserved.
Ganoderma triterpenes (GTs) are the major secondary metabolites of Ganoderma lucidum, a traditional Chinese medicine, popularly used for complementary cancer therapy. GTs are lanostane-tetracyclic triterpenes. They have been reported to possess anti-tumor, anti-inflammation, antioxidant, antimicrobial and blood fat reducing effects. To date, 316 GTs have been found and their similar chemical structures have proved difficult to elucidate. This paper compiles 316 naturally occurring triterpenes from Ganoderma based on the literature published through January 2013 along with their structures, physiological activities and 13C-NMR spectral data.
The methanolic extract of fruit bodies of cultivated Ganoderma lucidum was separated by silica gel column chromatography and preparative thin-layer chromatography to give ten compounds. On the basis of spectral analysis, chemical procedures and gas chromatography, d-mannitol (1), ergosta-7, 22-dien-3β-yl palmitate (2), ergosterol (3), ergosta-7, 22-dien-3β-ol (4), 5α-lanosta-7,9(11),24-trien-3β,26-diol (5), ergosterol peroxide (6), 24,25,26-trihydroxy-5α-lanosta-7,9(11)-dien-3-one (7), 5α-lanosta-7,9(11)-dien-3β,24,25,26-tetraol (8) and 8,9-epoxyergosta-5,22-dien-3β,15-diol (9) were identified. Among these compounds, 8,9-epoxyergosta-5,22-dien-3β,15-diol was first separated from Ganoderma lucidum.
Lucidenic acid A (1) and a new lactone, lucidenolactone (2) were isolated from the fruiting bodies of Ganoderma lucidum. Their structures were elucidated by spectroscopic method and single-crystal X-ray analysis. Lucidenolactone (2) showed significant antiplatelet aggregation activity. The NMR spectral data of lucidenic acid A were also reassigned.
Oxygenated lanostanoid triterpenes including multiple pairs of C-3 stereoisomers and C-3/C-15 positional isomers were identified from the Chinese medicinal fungus Ganoderma lucidum (Fr.) Karst. Empirical rules based on the chromatographic behavior in reversed-phase HPLC were developed to correlate the molecular polarities due to the presence of an individual functional group. 13C NMR correlation of stereochemistry in these oxygenated triterpenes was also achieved. Biosynthetic studies indicated that oxygenated triterpenes in the 3α series were derived from those in the 3β series through an oxidationreduction pathway. Several oxygenated triterpenes inhibited cholesterol synthesis in the in vitro assay. Ganodermic acid S induced platelet aggregation by stimulating the hydrolysis of phosphatidylinositol 4,5-bisphosphate.
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