Terrestrins A-G: p-terphenyl derivatives from the inedible mushroom Thelephora terrestris

Seven p-terphenyl derivatives named terrestrins A-G together with three known ganbajunin B, thelephantins F and H, were isolated from the methanol extract of fruiting bodies of the Japanese inedible mushroom Thelephora terrestris (Thelephoraceae). Their structures were elucidated by means of high-resolution MS, 2D NMR, IR and UV spectroscopy, and X-ray crystallographic analysis.     

Thelephantins I-N; p-terphenyl derivatives from the inedible mushroom Hydnellum caeruleum

Phytochemical investigation of the methanolic extract of the fruiting bodies of the inedible mushroom Hydnellum caeruleum resulted in the isolation of six p-terphenyl derivatives named thelephantins I-N (1-6), together with a known compound, dihydroaurantiacin dibenzoate (7). These structures were determined by high-resolution MS, 2D NMR, IR and UV spectroscopic analysis, and by the chemical reactions.     

Thelephantins D-H: five p-terphenyl derivatives from the inedible mushroom Thelephora aurantiotincta

Five p-terphenyl derivatives named thelephantins D-H (1-5) together with nine known compounds, thelephantins A-C (6-8), ganbajunin E (9), p-hydroxylbenzoic acid (10), ganbajunin C (11), thelephorin A (12), 2-O-methylatromentin (13) and atromentin (14), were isolated from the methanolic extract of fruit bodies of the Thelephoraceous Basidiomycete Thelephora aurantiotincta. Their structures were elucidated by high-resolution MS, 2D NMR, IR and UV spectroscopic analysis.     

Lanostane triterpenoids from cultivated fruiting bodies of the basidiomycete Ganoderma orbiforme

A new 3,4-seco-27-norlanostane triterpene, ganoboninketal D (1), a new lanostane, (24S)-3-oxo-7α,24,25-trihydroxylanosta-8-ene (2), together with six known lanostanes (3–8), were isolated from cultivated fruiting bodies of the basidiomycete Ganoderma orbiforme. The structures were elucidated on the basis of NMR spectroscopic and mass spectrometry data, and the structures 1 and 2 were further confirmed by chemical correlations to ganoboninketal C and ganodermanondiol, respectively. All isolated compounds were inactive in the antitubercular and antimalarial activity assays against Mycobacterium tuberculosis H37Ra and Plasmodium falciparum K1, respectively, except that compound 8 exhibited weak antitubercular activity (MIC 50 μg/ml).     

Lanostane triterpenoids from the medicinal mushroom Ganoderma tsugae

Two undescribed lanostane triterpenoids, tsugaric acids G (1) and H (2), and a known compound, N-(3′α,4′β-dihydroxy-2′β-(hydroxymethyl)-1′β-(cyclobutyl) palmitamide (3) were isolated from the fruiting bodies of Ganoderma tsugae and characterized on the basis of spectroscopic and spectrometric analysis, especially 2D NMR and HRMS. Compounds 1 and 2 were also characterized by an LC-ESI-MS analytical approach and were compared with the fragmentation patterns of reported compounds. Compound 3 significantly exhibited anti-HCV activity.     

Thelephantins A,B and C: three benzoyl p-terphenyl derivatives from the inedible mushroom Thelephora aurantiotincta

Three benzoyl p-terphenyl derivatives named thelephantins A, B and C were isolated from the ethyl acetate extract of fruit bodies of the Thelephoraceous Basidiomycete Thelephora aurantiotincta. Their structures were elucidated by analysis of high-resolution 2D NMR, MS, IR and UV spectra.     

Curtisians E-H: four p-terphenyl derivatives from the inedible mushroom Paxillus curtisii

Four p-terphenyl derivatives named curtisians E-H (1-4) were isolated from the methanolic extract of fruit bodies of the Basidiomycete Paxillus curtisii by a combination of Sephadex LH-20, silica gel column chromatography and preparative reversed phase HPLC. The relative stereochemistries of the curtisians were elucidated by 2D NMR, MS, IR and UV spectroscopy with the absolute configurations at C(3a-3d) of the side chains being established as S by GC-MS on a chiral column previously used for separation of authentic standards.     

Two triterpenoids and other constituents from Petasites tricholobus

Two migrated ursane skeleton triterpenoids, one is D:B-friedoursane-3alpha,16alpha-dihydroxy-7alpha,8alpha-epoxy-5(10)-ene, named petatrichol A (1) and the other one represents a novel triterpenoid carbon framework, named petatrichol B (2), along with 10 known compounds were isolated from the rhizome of Petasites tricholobus. Their structures were elucidated on the basis of spectroscopic methods (IR, EIMS, HRMS, 1D and 2D NMR). The triterpenoids were assayed against Escherichia coli, Staphylococcus aureus and Bacillus subtilis. Compounds 1 and 2 exhibited significant antibacterial activity against B. subtilis.     

Purification and characterization of isocitrate lyase from the wood-destroying basidiomycete Fomitopsis palustris grown on glucose

Isocitrate lyase (EC 4.1.3.1), a key enzyme in the glyoxylate cycle, was purified 76-fold with 23% yield as an electrophoretically homogeneous protein from the wood-destroying basidiomycete Fomitopsis palustris grown on glucose. The native enzyme has a molecular mass of 186 kDa, consisting of three identical subunits of 60 kDa. The K(m) for DL-isocitrate was found to be 1.6 mM at the optimum pH (7.0). The enzyme required Mg(2+) (K(m) 92 microM) and sulfhydryl compounds for optimal activity. The enzyme activity was strongly inhibited by oxalate and itaconate with a K(i) of 37 and 68 microM, respectively. The inhibition by the glycolysis and tricarboxylic acid cycle intermediates and related compounds suggested that the isocitrate lyase was a regulatory enzyme playing a crucial role in the fungal growth.     

Degradation of cellulose by the major endoglucanase produced from the brown-rot fungus Fomitopsis pinicola

An endoglucanase that is able to degrade both crystalline and amorphous cellulose was purified from the culture filtrates of the brown-rot fungus Fomitopsis pinicola grown on cellulose. An apparent molecular weight of the purified enzyme was approximately 32 kDa by SDS-PAGE analysis. The enzyme was purified 11-fold with a specific activity of 944 U/mg protein against CMC. The partial amino acid sequences of the purified endoglucanase had high homology with endo-beta-1,4-glucanase of glycosyl hydrolase family 5 from other fungi. The K(m) and K(cat)values for CMC were 12 mg CMC/ml and 670/s, respectively. The purified EG hydrolyzed both cellotetraose (G4) and cellopentaose (G5), but did not degrade either cellobiose (G2) or cellotriose (G3).     

Two lanostane triterpenoids from Abies koreana

Two lanostane-type triterpenoids, namely, 24(E)-3,4-seco-9betaH-lanosta-4(28),7,24-triene-3,26-dioic acid and 24(E)-3-oxo-9betaH-lanosta-7,24-dien-26-ol were isolated from the root bark of Abies koreana. Their structures were established based on spectroscopic analyses. Compound 2 exhibited marginal cytotoxicity against human tumor cell lines.     

Insulin mimetic lanostane triterpenes from the cultivated mushroom Ganoderma orbiforme

Two new lanostane triterpenes, ganorbifoins A and B (1-2), together with the known compound (25S,3′S)-(+)-12α-hydroxy-3α-(3′-hydroxy-4′-methoxycarbonyl-3′-methylbutiryloxy)-24-methyllanosta-824-(31)-dien-26-oic acid (3) were isolated from the cultivated fruiting bodies of Ganoderma orbiforme. The structures of isolates were determined by extensive analysis of NMR and HRESIMS. All compounds induced glucose uptake in zebrafish-based system at the concentration of 10 μM. And the best performing compound is ganorbifoin A. Compounds 2 and 3 exhibited an inhibitory effect on nitric oxide production in LPS-induced BV-2 microglia cells at the concentration of 20 μM.     

Polyhydroxyserratane triterpenoids from Diphasiastrum complanatum

Serratane triterpenoids were identified from Diphasiastrum complanatum (L.) Holub, including serratane-3alpha,14alpha,15alpha,20beta,21beta,24,29-heptol (1), 3alpha,20beta,21beta-trihydroxyserrat-14-en-24-oic acid (2), 3beta,20beta,21beta-trihydroxyserrat-14-en-24-oic acid (3), 3alpha,20beta,21beta-trihydroxy-16-oxoserrat-14-en-24-oic acid (4), and 16-oxolyclanitin-29-yl E-4'-hydroxyl-3'-methoxycinnamate (5) on the basis of their spectroscopic data as well as nine known analogs.     

Diterpenoids and triterpenoids from Euphorbia guyoniana

Two new compounds with tigliane and cycloartane skeletons: 4,12-dideoxy(4alpha)phorbol-13-hexadecanoate (1) and 24-methylenecycloartane-3,28-diol (2), respectively, in addition of four known diterpenoids and 13 triterpenoids: 3-benzoyloxy-5,15-diacetoxy-9,14-dioxojatropha-6(17),11-diene (4), ent-abieta-8(14),13(15)-dien-16,12-olide (5), ent-8alpha,14alpha-epoxyabieta-11,13(15)-dien-16,12-olide (6), ent-3-hydroxyatis-16(17)-ene-2,14-dione (7), 3beta-hydroxytaraxer-14-en-28-oic acid (8), beta-sitosteryl-3beta-glucopyranoside-6'-O-palmitate (9), multiflorenyl acetate (10), multiflorenyl palmitate (11), peplusol (12), 24-methylenecycloartanol (3), lanosterol (13), euferol (14), butyrospermol (15), cycloartenol (16), obtusifoliol (17), cycloeucalenol (18) and beta-sitosterol (19), were isolated from the roots of Euphorbia guyoniana. Their structures were established on the basis of physical and spectroscopic analysis, including 1D and 2D homo- and heteronuclear NMR experiments (COSY, HSQC, HMBC and NOESY) and by comparison with the literature data.     

Lanostane triterpenoids from mycelial cultures of the basidiomycete Ganoderma weberianum

Eight undescribed lanostane triterpenoids (1–8) were isolated from cultures of the basidiomycete Ganoderma weberianum TBRC-BCC 60642. The structural types of lanostane constituents were different between mycelial cultures and fruiting bodies. Lanostanes 2, 3 and 6 showed moderate antimalarial activity against Plasmodium falciparum K1 (IC₅₀ 10–15 μM).     

Triterpenoids from Gentiana scabra

Five triterpenoids, (20S)-dammara-13(17),24-dien-3-one, (20R)-dammara-13(17),24-dien-3-one, chirat-16-en-3-one, chirat-17(22)-en-3-one and 17beta,21beta-epoxyhopan-3-one, were isolated from the rhizomes and roots of Gentiana scabra together with five known ones, chiratenol, hop-17(21)-en-3-one, hop-17(21)-en-3beta-ol, lupeol and alpha-amyrin. The structures of new compounds were elucidated on the basis of spectroscopic studies.     

药用拟层孔菌石油醚提取物的GC-MS分析及各相提取物生物活性

通过形态学和分子生物学分析,实验菌株为药用拟层孔菌。采用不同有机溶剂提取药用拟层孔菌子实体,分别获得石油醚、氯仿、乙酸乙酯和甲醇提取物。采用GC-MS方法,分析药用拟层孔菌石油醚提取物中的化学成分,同时对不同有机溶剂提取物的生物活性进行检测。结果表明:药用拟层孔菌石油醚提取物中共鉴定出46个化合物。体外抑制肿瘤细胞活性实验表明,在100μg/m L时,不同有机溶剂提取物都表现出抑制肿瘤细胞活性。其中,石油醚提取物在50μg/m L时,其对NCI-H460和SGC-7901肿瘤细胞的抑制率分别为99.03%和82.57%。甲醇提取物在8mg/m L时,DPPH自由基清除率达93.35%。     

Cycloartane triterpenoids from Guarea macrophylla

Nine cycloartane triterpenoids, including two new derivatives 22,25-dihydroxy-cycloart-23E-en-3-one and 24-methylenecycloartane-3 beta,22-diol have been isolated from leaves of Guarea macrophylla. The structures were elucidated by interpretation of spectral data, mainly 1H and 13C NMR, including bidimensional analysis (HOMOCOSY, HMQC and HMBC).     

Tetracyclic triterpenoids from the leaves of Azadirachta indica

Two new tetracyclic triterpenoids zafaral [24,25,26,27-tetranorapotirucalla-(apoeupha)-6alpha-methoxy-7alpha-acetoxy-1,14-dien-3,16-dione-21-al] (1) and meliacinanhydride [24,25,26,27-tetranorapotirucalla-(apoeupha)-6alpha-hydroxy,11alpha-methoxy-7alpha,12alpha-diacetoxy,1,14,20(22)-trien-3-one] (2) have been isolated from the methanolic extract of neem leaves along with two known constituents nimocinol and isomeldenin. Their structures and the relative configurations were determined by spectroscopic methods ((1)H and (13)C NMR, IR, and MS) and 2D NMR experiments.