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Lanostane-type triterpenoids from the fruiting body of Ganoderma calidophilum
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To search for active anti-cancer constituents in the fruiting body of Ganoderma calidophilum, we have successfully isolated four previously undescribed spiro-lactone lanostane triterpenoids (spiroganocalitones A-D), two previously undescribed lanostanoids (ganodecalones A and B) together with twenty-three known ones. The structures of the six previously undescribed compounds were elucidated based on 1D, 2D-NMR, and HRMS analyses. Ganoderone A showed moderate cytotoxic activity against K562, BEL7402, and SGC790 cell lines with IC50 values of 7.62, 6.28, and 3.55 μM, respectively.
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... Recent research on chemical constituents of Ganoderma species showed that lanostane-type triterpenoids are the main characteristic natural products [4], and more than 400 lanostanoids have been isolated from the fungi of Ganoderma. These small molecule compounds have attracted considerable attention due to their extensive biological and pharmacological activities [5,6], including cytotoxic [7][8][9], hepatoprotective [10,11], anti-inflammatory [12][13][14], antidiabetic [15,16], neuroprotective [17], antiviral [18], antiaging [19], and antioxidant [20][21][22] effects. The genus Ganoderma is used as a healthy food and has been traditionally used for the prevention of numerous diseases or various pathological conditions, including complementary cancer therapy, especially a broad-spectrum application for the treatment of cancer. ...
... Ganoderma luteomarginatum, used as folk medicinal Ganoderma species, is a rare species mainly distributed in Hainan Province in China [25], where a pharmacodynamic molecular basis has been brought into focus in recent years [26,27]. In our ongoing endeavor to explore bioactive natural products, several species of Ganoderma have been studied, and a series of active compounds have been found [7,15,[28][29][30][31]. The fruiting bodies of G. luteomarginatum have been widely used as a healthy food to prevent tumors. ...
... In addition, three ganoderic aldehydes (5, 23, 24) and one ganoderic acid (3) were also found. The β-configuration of OH-15 in new ganoderic acid (3) from G. luteomarginatum was consistent with the previously discovered ganoderic acid derivatives from this fungus [27], which was opposite of that shown in the corresponding compounds from other Ganoderma species [7,12,50]. Moreover, norlanostanoids with 24 carbon atoms often occur in Ganoderma. ...
Macrofungus Ganoderma luteomarginatum is one of the main species of Ganoderma fungi distributed in Hainan province of China, the fruiting bodies of which have been widely used in folk as a healthy food to prevent tumors. To explore the potential cytotoxic constituents from G. luteomarginatum, the phytochemical investigation on the ethyl acetate soluble fraction of 95% ethanolic extract from the fruiting bodies of this fungus led to the isolation of twenty-six lanostane triterpenoids (1–26), including three undescribed ones (1–3), together with eight ergostane steroids (27–34). The structures of three new lanostane triterpenoids were elucidated as lanosta-7,9(11)-dien-3β-acetyloxy-24,25-diol (1), lanosta-7,9(11)-dien-3-oxo-24,26-diol-25-methoxy (2), and lanosta-8,20(22)-dien-3,11,23-trioxo-7β,15β-diol-26-oic acid methyl ester (3) by the analysis of 1D, 2D NMR, and HRESIMS spectroscopic data. All isolates were assayed for their cytotoxic activities using three human cancer cell lines (K562, BEL-7402, and SGC-7901) and seven lanostane triterpenoids (1, 2, 7, 13, 18, 22, and 24), and one ergostane steroid (34) showed definite cytotoxicity with IC50 values that ranged from 6.64 to 47.63 μg/mL. Among these cytotoxic lanostane triterpenoids, compounds 2 and 13 showed general cytotoxicity against three human cancer cell lines, while compounds 1 and 18 exhibited significant selective cytotoxicity against K562 cells with IC50 values of 8.59 and 8.82 μg/mL, respectively. Furthermore, the preliminary structure–cytotoxicity relationships was proposed.
... The evaluation of cytotoxicity showed that compound 358 had no inhibitory effect against HL-60, SMMC-7721, A-549, MCF-7, and SW480 cell lines [62]. Huang et al. [53] searched for active anticancer components in the fruiting bodies of G. calidophilum and isolated a previously undescribed lanostanoid species named as ganodecalone B (359). Phytochemical investigation of lanostane triterpenoids from G. luteomarginatum isolated two types of previously undescribed C29 structures named as (5α, 23E)-27-norlanosta-8,23-dien-3,7,25-trione (360) and (5α,23E)-27-nor-3β-hydroxylanosta-8,23-dien-7,25dione (361) with an unusual 27-nor-lanostane carbon skeleton [285]. ...
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.
Four natural products of Ganoderma lucidum triterpenoids were semi-synthesized for the first time and the active compound endertiin B was demonstrated to play an anti-breast cancer role through the PI3K-AKT pathway.
A new sesquiterpenoid, named amoienacid (1), was isolated from the n-BuOH extract of the fruiting bodies of Amauroderma amoiensis. Its structure was elucidated by 1D and 2D NMR spectra as well as HR-ESI-MS data. The new isolate exhibited anti-acetylcholinesterase (AChE) activity with the percentage inhibition of 36.3% at a concentration of 100 μM.
Eight previously undescribed lanostane triterpenoids, ganodeweberiols A∼H (1−8), together with eighteen known compounds (9−26), were isolated from the fruiting bodies of Ganoderma weberianum. The structures and absolute configurations of the new compounds were determined by extensive spectroscopic analysis, as well as NMR chemical shifts and electronic circular dichroism (ECD) calculations. Compounds 2, 7, 12, and 14 showed significant α-glucosidase inhibitory activity with IC50 values ranging from 35.3 μM∼223.4 μM compared to the positive control acarbose (IC50, 304.6 μM). Kinetic study indicated that the most potent compound 12 was a mixed type inhibitor for α-glucosidase. Molecular docking simulation revealed the interactions of 12 with α-glucosidase. Additionally, Compounds 3 and 6 inhibited glucagon-induced hepatic glucose production in HepG2 cells with EC50 values of 42.0 and 85.9 μM, respectively. Further study revealed that compounds 3 and 6 inhibited hepatic glucose production by suppression glucagon-induced cAMP accumulation. Moreover, compounds 3 and 26 were active against HeLa cell line with IC50 values of 17.0 and 6.8 μM, respectively.
Eight new alkaloids, 3β-n-butylstemonamine (1), 8-oxo-3β-n-butylstemonamine (2), 3-n-butylneostemonine (3), 10-epi-3-n-butylneostemonine (4), 8-oxo-oxymaistemonine (5) protostemonine N4-oxide (6), (19S)-hydroxy-21-methoxystemofoline (7), and parvistemonine A (8), were isolated from the roots of Stemona parviflora, together with 17 known alkaloids. The structures of the new alkaloids were elucidated based on a comprehensive spectroscopic data analysis. The absolute configurations of 1-4 were determined by the ECD exciton chirality method and quantum ECD calculations. Protostemonine (10) and stemofoline (12) showed strong nematicidal activity against Panagrellus redivevus, with IC50 values of 0.10 and 0.46 μM, respectively.
Thirteen new sesquiterpenoids, including six guaiane type auranticanols A-F (1, 2, and 4-7) and seven carotene type auranticanols G-M (18-24) were isolated from the stems of Daphne aurantiaca Diels., along with fourteen known sesquiterpenoids (3, 8-17, 25-27) and two known tigliane diterpenoids (28, 29), and their structures were elucidated by extensively analyzing their MS and NMR spectroscopic data. A bioassay of anti-HIV activity indicated that compounds 11, 14, 19, and 28 showed definite activities with EC50 values of 2.138, 0.286, 1.773 and 0.000282 μg mL-1 and SI > 93.545, 93.787, 10.243, and 65 177.305, respectively. This journal is
The structures of eight novel triterpenoids, ganoderiol C (1), D (2), E (3), F (4), G (5), H (6), I (7), and ganolucidic acid E (8), isolated from the fruiting body of Ganoderma lucidum were determined by spectroscopic methods. In addition, the absolute configuration at C-23 of ganolucidic acid D (9) was determined from the CD spectrum of its p-dimethylaminobenzoate derivative.
(+)- and (-)-Ganodilactone (1), a pair of novel meroterpenoid dimers possessing a unique 5′H-spiro[chroman-4,2′-furan]-2,5′-dione ring system, along with their biogeneticly-related compound, ganomycin I (2), were discovered from the fruiting bodies of Ganoderma leucocontextum. The structures and absolute configurations were assigned with the aid of 1D and 2D NMR spectra, HRESIMS analysis and ECD calculations. (±)-, (+)-, and (-)-ganodilactone (1) showed pancreatic lipase inhibitory activities and exhibited the IC50 values as 27.3, 4.0, and 2.5 μM, respectively.
Applanatumols A (1) and B [(±)-2], two unique meroterpenoids with a novel spiro[benzofuran-2,2′-bicyclo[3.2.2]nonane] ring system and a naturally unusual dioxacyclopenta[cd]inden motif, respectively, were isolated from Ganoderma applanatum. Their structures were determined using spectroscopic data. In particular, the absolute configurations of 1 and 2 were assigned by X-ray diffraction analysis using the Flack parameter and ECD calculations, respectively. A plausible biosynthetic pathway for 1 and 2 is proposed. The biological activities of 1 and 2 against renal fibrosis were accessed in rat proximal tubular epithelial cells.
Six new prenylated hydroquinones named ganocalidin A-F (1-6) and two new compounds of ganocalicine A (7) and B (8), together with sixteen known compounds (9-24) were isolated from an EtOAc extract of the fruiting body of Ganoderma calidophilum. The new compound structures were elucidated on the basis of spectroscopic data analysis including 1D, 2D NMR and MS. Compounds 1 and 7 showed inhibitory activity effects on β-hexosaminidase activity (IC50 9.44 and 9.14 μM, respectively), and significantly reduced the production of IL-4 and LTB4 by RBL-2H3 cells in response to antigen stimulation, suggesting that 1 and 7 possess anti-allergic activity.
1H- and 13C-nmr assignments of lanostanoids from Ganoderma lucidum were revised by 2D nmr, 1H-1H and 1H-13C shift correlation spectra, and distortionless enhancement by polarization transfer (DEPT) techniques for 13C-nmr. The assignments of five lanostanoids, ganodermenonol [1], ganodermadiol [2], ganodermatriol triacetate [33], ganodermanondiol [4], and the 3β-ol of 4 [6], were revised by the direct data, and those of ganodermanontriol [5] were revised by analogy to the five lanostanoids. The 1H-nmr assignments for acetate derivatives of 1, 2, 4, and 5 were also revised with the above data.
In situ synthesized TiC particle reinforced high-chromium Fe-based composite coating was fabricated on substrate of Q235 carbon steel by plasma transferred arc (PTA) process using the mixture of ferrotitanium, ferrochromium, ferroboron and ferrosilicium powders. The microstructure and wear properties of the composite coating were investigated by means of X-ray diffraction (XRD), scanning electron micrograph (SEM), energy dispersive X-ray analysis (EDS), microhardness tester and wear tester. Results indicat that the composite coating has a rapidly solidified microstructure consisting of in-situ the reinforcing TiC carbide, primary Cr7C3, (Cr,Fe)7C3 eutectics, and is metallurgically bonded to the Q235 steel substrate. TiC particles present granular, rod-like and dendrite shape in the composite coating. The composite coating has high microhardness and excellent wear resistance under dry-sliding wear test condition.
