Ganoderenic acid D
(Synonyms: 灵芝烯酸D) 目录号 : GC36114Ganoderenic acid D 是一种灵芝提取物 (GLE),三萜。 Ganoderenic acid D 通过诱导细胞周期停滞和细胞凋亡 apoptosis 来抑制癌细胞的增殖。
Cas No.:100665-43-8
Sample solution is provided at 25 µL, 10mM.
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Ganoderenic acid D is a triterpene identified from the effective compounds of Ganoderma lucidum extract (GLE). Ganoderenic acid D inhibits the proliferation of cancer cells by inducing cell cycle arrest and apoptosis[1].
[1]. Zhao RL, et al. Network pharmacology analysis of the anti-cancer pharmacological mechanisms of Ganoderma lucidum extract with experimental support using Hepa1-6-bearing C57 BL/6 mice. J Ethnopharmacol. 2018 Jan 10;210:287-295.
Cas No. | 100665-43-8 | SDF | |
别名 | 灵芝烯酸D | ||
Canonical SMILES | CC1(C)C(CCC2(C)C3=C(C4(C(CC(C4(CC3=O)C)/C(C)=C/C(CC(C)C(O)=O)=O)=O)C)C(O)CC12)=O | ||
分子式 | C30H40O7 | 分子量 | 512.63 |
溶解度 | Soluble in DMSO | 储存条件 | Store at -20°C |
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1 mg | 5 mg | 10 mg | |
1 mM | 1.9507 mL | 9.7536 mL | 19.5072 mL |
5 mM | 0.3901 mL | 1.9507 mL | 3.9014 mL |
10 mM | 0.1951 mL | 0.9754 mL | 1.9507 mL |
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Network pharmacology analysis of the anti-cancer pharmacological mechanisms of Ganoderma lucidum extract with experimental support using Hepa1-6-bearing C57 BL/6 mice
J Ethnopharmacol 2018 Jan 10;210:287-295.PMID:28882624DOI:10.1016/j.jep.2017.08.041.
Ethnopharmacological relevance: Ganoderma lucidum (GL) is an oriental medical fungus, which was used to prevent and treat many diseases. Previously, the effective compounds of Ganoderma lucidum extract (GLE) were extracted from two kinds of GL, [Ganoderma lucidum (Leyss. Ex Fr.) Karst.] and [Ganoderma sinense Zhao, Xu et Zhang], which have been used for adjuvant anti-cancer clinical therapy for more than 20 years. However, its concrete active compounds and its regulation mechanisms on tumor are unclear. Aim of the study: In this study, we aimed to identify the main active compounds from GLE and to investigate its anti-cancer mechanisms via drug-target biological network construction and prediction. Materials and methods: The main active compounds of GLE were identified by HPLC, EI-MS and NMR, and the compounds related targets were predicted using docking program. To investigate the functions of GL holistically, the active compounds of GL and related targets were predicted based on four public databases. Subsequently, the Identified-Compound-Target network and Predicted-Compound-Target network were constructed respectively, and they were overlapped to detect the hub potential targets in both networks. Furthermore, the qRT-PCR and western-blot assays were used to validate the expression levels of target genes in GLE treated Hepa1-6-bearing C57 BL/6 mice. Results: In our work, 12 active compounds of GLE were identified, including Ganoderic acid A, Ganoderenic acid A, Ganoderic acid B, Ganoderic acid H, Ganoderic acid C2, Ganoderenic acid D, Ganoderic acid D, Ganoderenic acid G, Ganoderic acid Y, Kaemferol, Genistein and Ergosterol. Using the docking program, 20 targets were mapped to 12 compounds of GLE. Furthermore, 122 effective active compounds of GL and 116 targets were holistically predicted using public databases. Compare with the Identified-Compound-Target network and Predicted-Compound-Target network, 6 hub targets were screened, including AR, CHRM2, ESR1, NR3C1, NR3C2 and PGR, which was considered as potential markers and might play important roles in the process of GLE treatment. GLE effectively inhibited tumor growth in Hepa1-6-bearing C57 BL/6 mice. Finally, consistent with the results of qRT-PCR data, the results of western-blot assay demonstrated the expression levels of PGR and ESR1 were up-regulated, as well as the expression levels of NR3C2 and AR were down-regulated, while the change of NR3C1 and CHRM2 had no statistical significance. Conclusions: The results indicated that these 4 hub target genes, including NR3C2, AR, ESR1 and PGR, might act as potential markers to evaluate the curative effect of GLE treatment in tumor. And, the combined data provide preliminary study of the pharmacological mechanisms of GLE, which may be a promising potential therapeutic and chemopreventative candidate for anti-cancer.
Constituents of various wood-rotting basidiomycetes
Phytochemistry 2000 Jul;54(6):603-10.PMID:10963454DOI:10.1016/s0031-9422(00)00165-5.
Phytochemical investigation of n-hexane and methanol extracts of fruiting bodies of the wood-rotting fungi Fomitopsis pinicola. Ganoderma lipsiense, Fomes fomentarius and Gloeophyllum odoratum led to the isolation and identification of several triterpene derivatives and some aromatic compounds derived from lignin. These are the new natural products, namely, pinicolic acid E (16alpha-hydroxy-3-oxolanosta-8,24-dien-21-oic acid) and pinicolol C (3-oxolanosta-7,9(11),24-trien-15alpha,21-diol) from the crust of F. pinicola, Ganoderenic acid D [(E)-7beta-hydroxy-3,11,15,23-tetraoxolanosta-8,20(22)-di en-26-oic acid] and ganoderic acid N (7beta,20-dihydroxy-3,11,15,23-tetraoxolanost-8-en-26-oic acid) from G. lipsiense and ergosterol peroxide (5alpha,8alpha-epi-dioxyergost-6-en-3beta-ol) as well as ergost-7-en-3-one from F. fomentarius. From G. odoratum, dehydroeburicoic acid [24-methylene-3-oxolanosta-7,9(11)-dien-21-oic acid], the dimethylacetal of 4,4,14alpha-trimethyl-24-oxo-5alpha-chol-8-en-21-oic acid and some aromatic compounds, of which 1-(4'-methoxyphenyl)-1,2-ethandiol is a new natural product, were isolated. Furthermore, a complete set of 13C NMR data of the steryl esters 3beta-linoleyloxyergosta-7,24(28)-diene, 3beta-linoleyloxyergosta-7,24-diene and 3beta-linoleyloxyergost-7-ene, which could be identified as a mixture in all investigated fungi, could be recorded. It was proved by HPLC and TLC investigations, that the crust on top of the fruiting bodies of F. pinicola consists of lanostane derivatives.
Extraction optimisation and isolation of triterpenoids from Ganoderma lucidum and their effect on human carcinoma cell growth
Nat Prod Res 2014;28(24):2264-72.PMID:25032738DOI:10.1080/14786419.2014.938337.
The response surface methodology was used to optimise the extraction conditions of Ganoderma lucidum based on a Box-Behnken design. A quadratic model sufficiently simulated the response of ganoderic acid H with a determination coefficient (R(2)) of 0.98. The optimal condition for extracting triterpenoids was determined to be 100.00% ethanol at 60.22°C for 6.00 h, under which the yield of the reference triterpenoid ganoderic acid H increased from 0.88 to 2.09 mg/g powder. Following extraction, triterpenoid-enriched fraction was further isolated into 23 fractions, and 7 fractions were identified as ganoderic acids A, B, D, G, H and I and Ganoderenic acid D. Of the seven triterpenoids, Ganoderenic acid D was most cytotoxic with IC50 values of 0.14 ± 0.01, 0.18 ± 0.02 and 0.26 ± 0.03 mg/mL in Hep G2, Hela and Caco-2 cells, respectively. While ganoderic acids A, G and H were relatively non-cytotoxic. The variation of inhibitory effects for these triterpenoids was likely related to their chemical structures.
[Determination of nine triterpenoid acids from Ganoderma lucidum of different producting areas by HPLC]
Zhongguo Zhong Yao Za Zhi 2012 Dec;37(23):3599-603.PMID:23477148doi
Objective: To establish an HPLC method for determining nine triterpenes contained in Ganoderma lucidum. Method: Chromatography conditions: Alltima C18 (4.6 mm x 150 mm, 5 microm) was adopted as the chromatographic column, with acetonitrile-0.04% formic acid solution as the mobile phase. The detective wavelength was set at 254 nm, and the column temperature was 15 degrees C. Result: The linearities of ganoderic acid C2, ganoderic acid G, ganoderenic acid B, ganoderic acid B, ganoderenic acid A, ganoderic acid A, lucideric acid A, Ganoderenic acid D, and ganoderic acid C1 ranged between 6.81-40.88, 6.38-38.25, 6.75-40.50, 6.38-38.25, 5.95-35.65, 5.90-35.25, 7.00-42.00, 6.20-37.15 and 6.05-36.4 mg x L(-1) (r = 0.999 4, 0.999 2, 0.999 4, 0.999 2, 0.999 2, 0.994 5, 0.999 0, 0.999 2 and 0.998 4). Their recoveries were 102.1%, 102.3%, 100.6%, 103.3%, 104.1%, 103.2%, 96.42%, 102.5% and 101.5%, with RSD being 1.5%, 0.96%, 1.9%, 1.3%, 1.7%, 2.5%, 0.62%, 2.9% and 1.3%. The content of triterpenes contained in G. lucidum samples from 31 different areas and under different cultivation conditions. Conclusion: The method is so feasible and highly reproducible that it can be used for quantitatie determination of the content of triterpenoid acid contained in G. lucidum.
Ultra Performance Liquid Chromatography-Quadrupole Time-of-Flight Mass Spectrometry (UPLC-Q-TOF-MS)-based metabolomic analysis of mycelial biomass of three Ganoderma isolates from the Lower Volta River Basin of Ghana
J Pharm Biomed Anal 2021 Oct 25;205:114355.PMID:34500238DOI:10.1016/j.jpba.2021.114355.
In this work, we sought to determine the differences and/or similarities in the metabolite composition of the mycelial biomass of three ganoderma isolates (Ganoderma LVRB-1, Ganoderma LVRB-9 and Ganoderma LVRB-17) from the Lower Volta River Basin of Ghana. The cultured mycelial mass of the three isolates were subjected to DNA sequencing. BLASTn searches of the internal transcribed spacer. (ITS) sequences of the isolates were conducted in the GenBank and the data obtained subjected to ITS phylogenetic analysis. Thereafter, extracts of the cultured mycelial biomass of the three isolates were subjected to untargeted ultra performance liquid chromatography-quadrupole time-of-flight mass spectrometry (UPLC-Q-TOF-MS)-based metabolomic analysis. A cursory examination of the total ion chromatograms of the isolates gave evidence of the differential levels of the metabolites present. Further analysis of the metabolomic data using multivariate analysis better captured these marked differences in terms of the presence and/or levels of the metabolites. Finally, four lanostane triterpenoids, namely ganoderic acid C6, ganoderenic acid A, Ganoderenic acid D and ganoderic acid G, together with two annotated compounds (ganoderic acids K and AM1) were detected in the mycelia biomass of the three ganoderma isolates from the Lower Volta River Basin of Ghana. The results provide the first ever metabolomic data on the chemical constituents of the mycelial biomass of ganoderma isolates from the Lower Volta River Basin of Ghana.