lanostane triterpenes

Poria cocos is traditionally used as both food and medicine. Triterpenoids in Poria cocos have a wide range of pharmacological activities, such as diuretic, sedative and tonic properties. In this study, the anti-tumor activities of poricoic acid A (PAA) and poricoic acid B (PAB), purified by high-speed counter-current chromatography, as well as their mechanisms and signaling pathways, were investigated using a HepG2 cell model. After treatment with PAA and PAB on HepG2 cells, the apoptosis was obviously increased ( p < 0...

Sixteen triterpenoids with various skeletal types, five phenylpropanoid derivatives, and two flavonoids were isolated from a propolis sample produced by Apis mellifera collected in the Atlantic Forest of Midwest Brazil. Among these compounds, six triterpenes, namely 3β,20R-dihydroxylanost-24-en-3-yl-palmitate, (23E)-25-methoxycycloartan-23-en-3-one, 24-methylenecycloartenone, epi-lupeol, epi-a-amyrin, and epi-β-amyrin are being reported for the first time in propolis, while cycloartenone, (E)-cinnamyl benzoate, and (E)-cinnamyl cinnamate are new findings in Brazilian propolis...

Polyporenic acids N-R ( 1 - 5 ), five novel 24-methylene lanostane triterpenes along with seven known polyporenic acids ( 6 - 12 ), were identified from the fruiting bodies of Buglossoporus quercinus . The isolation of compounds 1 - 12 was performed by a combination of multistep flash chromatography and reversed-phase high-performance liquid chromatography (HPLC). The structure determination was carried out by extensive spectroscopic analysis, including 1D and 2D nuclear magnetic resonance (NMR) and high-resolution electrospray ionization mass spectrometry (HR-ESI-MS) experiments...

A new Lanosta-7,9(11),22-trien-3,15,20-triol named Anomanol B 1, together with five known compounds: manniindole 2 , arborinine 3 , polycarpol 4, 8,9-dimethoxyphenanthridin-6(5 H )-one 5 and 3-O- β -D-glucopyranosyl- β -sitosterol 6 were isolated from the stem bark extract of Anonidium mannii by routine chromatography techniques. 8,9-dimethoxyphenanthridin-6(5 H )-one 5, was reported from natural origin for the first time. The structures of the compounds were established by comprehensive elucidation of spectroscopic data and by comparison with literature data...

A preliminary phytochemical investigation on the 90% MeOH extract from the twigs and needles of the vulnerable conifer Keteleeria fortunei led to the isolation and characterization of 17 structurally diverse triterpen-26-oic acids, including nine previously undescribed ones (fortunefuroic acids A-I, 1 - 9 ) featuring a rare furoic acid moiety in the lateral chain. Among them, 1 - 5 are uncommon 9β H -lanostane-type triterpenoic acids. Friedo-rearranged triterpenoids 6 and 7 feature a unique 17,14-friedo-lanostane skeleton, whereas 9 possesses a rare 17,13-friedo-cycloartane-type framework...

Seven [4 + 2]-type triterpene-diterpene hybrids derived from a rearranged or a normal lanostane unit (dienophile) and an abietane moiety (diene), forrestiacids E-K ( 1 - 7 , respectively), were further isolated and characterized from Pseudotsuga forrestii (a vulnerable conifer endemic to China). The intriguing molecules were revealed with the guidance of an LC-MS/MS-based molecular ion networking strategy combined with conventional phytochemical procedures. Their chemical structures with absolute configurations were established by spectroscopic data, chemical transformation, electronic circular dichroism calculations, and single-crystal X-ray diffraction analysis...

Wolfiporia cocos is commonly used as a traditional Chinese medicine for its diuretic, tonifying, and invigorating effects on the spleen. However, the epidermis of W. cocos is discarded as scrap during harvesting because of its low price, resulting in a great waste of resources and environmental pollution. In this work, the epidermis of W. cocos was studied and three new lanostane triterpenoids were isolated. The structures were determined using NMR and HRESIMS, with absolute configurations established by comparison of the calculated and experimental ECD spectra...

Pholiols L-S ( 1 - 8 ), eight undescribed triterpenes were isolated from the sporocarps of the mushroom Pholiota populnea . Various chromatographic techniques, such as open column chromatography, flash chromatography, gel filtration, preparative thin layer chromatography, and HPLC, were applied to purify the compounds. The structure elucidation was carried out by spectroscopic analysis, including 1D (1 H NMR and 13 C JMOD) and 2D NMR (1 H-1 H COSY, HSQC, HMBC and NOESY) and HRESIMS experiments. The isolated compounds had lanostane ( 1 - 7 ) or trinorlanostane ( 8 ) skeletons; all of them were substituted with 3-hydroxy-3-methylglutaroyl group or its 6-methyl ester...

A new lanostane-type triterpene, namely 3-oxo-5α-lanosta-7,9(11)-dien-24-oic acid methyl ester ( 2 ), and three known compounds including ganoderal A ( 1 ), ganoderiol B ( 3 ) and ganodermenonol ( 4 ) were isolated from the fruiting bodies of Ganoderma lucidum by silica gel column chromatography and Sephadex LH-20 column chromatography. Their structures were determined by extensive NMR data and mass spectral analysis. The in vitro cytotoxic activity of the isolated compounds against SK-Hep-1, HepG2, Hela and Hela/VCR cancer cell lines was assessed by using MTT assay...

Neurotrophins such as nerve growth factor (ngf) and brain-derived neurotrophic factor (bdnf) play important roles in the central nervous system. They are potential therapeutic drugs for the treatment of neurodegenerative diseases, including Alzheimer's disease and Parkinson's disease. In this study, we investigated the neurotrophic properties of triterpenes isolated from fruiting bodies of Laetiporus sulphureus and a mycelial culture of Antrodia sp. MUCL 56049. The structures of the isolated compounds were elucidated based on nuclear magnetic resonance (NMR) spectroscopy in combination with high-resolution electrospray mass spectrometry (HR-ESIMS)...

Investigation of the chloroform and ethyl acetate extracts of the edible mushroom Pholiota populnea led to the isolation of eight triterpenes, the undescribed natural products pholiols E-K and the known (+)-clavaric acid. HRESIMS and 1D and 2D NMR spectroscopy were employed to determine the structures of the undescribed compounds. The NOESY spectra were used to assign the relative configurations of triterpenes. The isolated compounds were screened for their anti-inflammatory activity on cyclooxygenase (COX-1 and COX-2), and lipoxygenase (5-LOX and 15-LOX) inhibitory assays...

Chemical investigation on the medicinal fungus Ganoderma australe led to the identification of ten new nor-lanostane triterpenes, namely two hexa-nor ones, ganoaustratetraenones A (1) and B (2), five penta-nor ones, ganoaustraldehydes A-E (3-7), and three tetra-nor ones ganoaustrenoic acids A-C (8-10). The chemical structures along with the absolute configurations were determined by extensive spectroscopic analysis of 1D & 2D NMR and HRESIMS data. The postulated biosynthesis pathways of these compounds were proposed...

Ganoderma lucidum is a famous edible and medicinal fungus. Through a bioactive phytochemical investigation of the ethanolic extracts of the fruiting bodies of G. lucidum, twenty-nine triterpenoids, including eleven previously undescribed triterpenoids, were isolated and characterized based on spectroscopic data. The inhibitory effects of all the triterpenes against fatty acid amide hydrolase (FAAH) were found to be in the range of 30-60% at 100 μM. Methyl ganoderate A displayed the strongest inhibitory activity (61%) against FAAH...

Twelve new lanostane triterpenoids ( 1 - 5 , 7 - 13 ) were isolated from the fruiting bodies of the fungus Ganoderma australe . The structures of the new compounds were elucidated by extensive 1D and 2D NMR, and HRESIMS spectroscopic analysis. All the triterpenes are featured by 20(22) E configurations which are uncommon in the Ganoderma triterpene family. The absolute configuration of the C-25 of compounds 1 , 2 , and 6 were determined by the phenylglycine methyl ester (PGME) method. A postulated biosynthetic pathway for compound 1 was discussed...

Eleven new 9,19-cycloartane triterpenes (1-9, 11-12) and one undescribed lanostane-type aglycone (10) were identified from the aerial parts of Cimicifuga yunnanensis . The new structures were elucidated by analysis of spectroscopic data. Compounds 3-5, 7-9, and 11, without obvious cytotoxicity at 50 μM, were evaluated for inhibiting the mRNA expressions of atherosclerosis-related factors of CD147 (extracellular matrix metalloproteinase inducer, EMMPRIN), matrix metalloproteinase 2 (MMP-2) and MMP-9 in phorbol-12-myristate-13-acetate (PMA) induced Human monocytic THP-1 cells by using a quantitative real-time PCR method (q-PCR)...

A preliminary phytochemical investigation on the MeOH extract of the twigs and needles of Pseudotsuga gaussenii (a 'vulnerable' plant endemic to China) led to the isolation and characterization of 25 structurally diverse mono- and dimeric triterpenoids. 19 of them are previously undescribed, including eight cucurbitane-type triterpenoids (gaussenols A-H, 1-8, resp.), one serratene-type triterpene (gaussenol I, 9), and 10 triterpenic dimers (gaussenols J-S, 10-19, resp.). Their chemical structures were elucidated by means of spectroscopic data, some chemical transformations, the modified Mosher's method, and single crystal X-ray diffraction analyses...

A chemical study on the epidermis of cultivated edible mushroom Wolfiporia cocos resulted in the isolation and identification of 46 lanostane triterpenoids, containing 17 new compounds ( 1 - 17 ). An experimental determination of their anti-inflammatory activity showed that poricoic acid GM ( 39 ) most strongly inhibited NO production in LPS-induced RAW264.7 murine macrophages with an IC50 value at 9.73 μM. Furthermore, poricoic acid GM induced HO-1 protein expression and inhibited iNOS and COX2 protein expression as well as the release of PGE2 , IL-1β, IL-6, TNF-α, and reactive oxygen species (ROS) in LPS-induced RAW264...

An investigation of the fruiting bodies of edible mushroom Ganoderma lucidum produced 13 steroids, containing one new lanostane-type triterpene compound, named ganoderterpene A ( 1 ). Nuclear magnetic resonance and high-resolution electrospray ionization mass spectrometry data were used to deduce these structures. All the isolates were evaluated for their ability to suppress NO generation in BV-2 microglial cells treated with lipopolysaccharide (LPS) and exhibited moderate to strong inhibition effects, with IC50 values in the range 7...

Nine new mono-, di-, and trisulfated triterpene penta- and hexaosides, kurilosides A3 ( 1 ), D1 ( 2 ), G ( 3 ), H ( 4 ), I ( 5 ), I1 ( 6 ), J ( 7 ), K ( 8 ), and K1 ( 9 ) and two desulfated derivatives, DS-kuriloside L ( 10 ), having a trisaccharide branched chain, and DS-kuriloside M ( 11 ), having hexa- nor -lanostane aglycone with a 7(8)-double bond, have been isolated from the Far-Eastern deep-water sea cucumber Thyonidium (=Duasmodactyla) kurilensis (Levin) and their structures were elucidated based on 2D NMR spectroscopy and HR-ESI mass-spectrometry...

Lanostane triterpenoids are thought to be the main underlying preclinical antitumor secondary metabolites of the genus Ganoderma. To further explore the potential cytotoxic triterpenoids from Ganoderma luteomarginatum, the ethyl acetate soluble fraction of 95% ethanolic extract was systematically studied. Twelve previously undescribed lanostane-type triterpene acids were isolated from the fruiting bodies of G. luteomarginatum, and their structures were elucidated by extensive spectroscopic analyses. Among them, 11 compounds have an unusual β-configuration for OH-15...