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The structure of the title compound, C17H20O4 [systematic name: (1aS,3aR,4aS,5aR)-15-(acetoxy)linden-7(11),8-trieno-12,8-lactone or (4aR,5S,5aR,6aS,6bR)-5-(acetoxymethyl)-4a,5,5a,6,6a,6b-hexahydro-3,6b-dimethylcyclopropa[2,3]indeno[5,6-b]furan-2(4H)-one, ent-chloranthalactone C], a natural product isolated from the whole plant Chloranthus japonicus Sieb., is a typical lindenane-type sesquiterpenoid. The molecule comprises a bicyclo[3.1.0]hexane ring (A/B system) bearing an acetoxymethyl (C-4) group, a bicyclo[4.3.0]nonane ring (B/C system) containing a double bond (C-8/9) and a chiral quaternary carbon (C-10), and a 7(11)-en-12,8-olide structural moiety on the cyclohexan-8-ene (C ring). In the tetracyclic skeleton, the 1,3-cyclopropane ring has a β-configuration, and atoms H-5 and H3-14 have α- and β-orientations, respectively. In the crystal, the molecules are assembled into a two-dimensional network by weak O...H/H...O interactions. Hirshfeld surface analysis illustrates that the greatest contributions are from H...H (55.2%), O...H/H...O (34.6%) and C...H/H...C (8.9%) contacts.

During our continuous efforts to pursue antifungal agents, some calycanthaceous alkaloid analogs showed diverse and promising bioactivities. Therefore, 34 new calycanthaceous alkaloid derivatives were further prepared and screened for bioactivities. As a result of the evaluation against a great deal of plant pathogen fungi, bacteria and human pathogenic fungi, a majority of them displayed potent bioactivity. In particular, compound b6 displayed remarkably activity and might be novel potential leading compound for further development of antifungal agent. The relationship between structure and biological activity was also discussed.

Zirconium tungsten phosphate (Zr2WP2O12 denoted as ZWP) is a negative thermal expansion material which can be used as filler in controlling the thermal expansion coefficient of other materials. In this study, dense ZWP ceramics without any additives was prepared via solid-state reaction method, by milling the as-synthesized powder for different times and sintering at 1300?C. The influence of the milling time, i.e. reduced particle sizes, on properties of the Zr2WP2O12 was investigated. The obtained samples were characterized by X-ray diffraction (XRD) method, scanning electron microscopy (SEM), thermal mechanical analysis (TMA), Raman spectroscopy and Vickers hardness tester. The results showed that the milled powders have high crystallinity with single phase orthorhombic structure. The ZWP ceramics exhibits NTE property with high density. With the increase of milling time the coefficient of thermal expansion changed from ?2.607 ? 10?6 1/K to ?3.914 ? 10?6 1/K. In addition, the grain sizes decrease and the relative density and HV hardness of the obtained ceramics increase confirming that grinding is an effective method to improve the performance of ZWP ceramics.

Phosphoglycerate dehydrogenase (PHGDH) is abnormally expressed in numerous malignant tumor cells and catalyzes the first step of serine biosynthesis, thus becoming a key drug target for antitumor treatment. In this study, compound B2 bearing a benzene-1,3-diamine scaffold was identified by structure-based virtual screening as a novel PHGDH inhibitor with moderate enzymatic activity. The structure-activity relationship study led to the discovery of compound C25 possessing improved enzymatic inhibitory activity and potent inhibitory activity on the proliferation of cells overexpressing PHGDH. The enzyme kinetic assay confirmed that C25 inhibited PHGDH in a nicotinamide adenine dinucleotide (NAD

Emerging evidence suggests the regulation of microglial phenotype balance between M1 and M2 will be a potential therapeutic strategy for microglia-mediated neuroinflammation in Alzheimer's disease (AD). Herein, we evaluated the anti-neuroinflammatory effects and the underlying mechanism of a natural cyathane diterpenoid sarcodonin A (1) derived from the mushroom Sarcodon scabrosus and its six new derivatives (2-7). Lipopolysaccharide (LPS)-activated primary microglia and microglia cell lines were used as models. The nitrite test and immunostaining showed that the derivative named 6 was more effective in inhibiting neuroinflammation. qRT-PCR, ELISA, and western blotting revealed that 6 showed more significant suppression on mRNA and protein expression of proinflammatory M1 markers of TNF-α, IL-6, IL-1β, iNOS, and COX-2, while more obvious potentiation on mRNA and protein levels of anti-inflammatory M2 markers of IL-10 and ARG-1. In mechanism, western blotting demonstrated that 6 inhibited LPS-induced activation of MAPK, and prevented LPS-stimulated nuclear translocation of NF-κB p65. Molecular docking revealed that 1 and 6 constructed interactions with iNOS. Collectively, the present study indicated that 1 and 6 might support neuroprotection by reversing LPS-induced microglia M1 polarization, implying that sarcodonin A can be a promising candidate for developing new therapeutics against AD by targeting microglia-mediated neuroinflammation.

Cuprous oxide (Cu2O) has attracted plenty of attention for potential nonlinear photonic applications due to its superior third-order nonlinear optical property such as two-photon absorption. In this paper, we investigated the two-photon excitation induced carrier dynamics of a Cu2O thin film prepared by radio-frequency magnetron sputtering, using the femtosecond transient absorption experiments. Biexponential dynamics including an ultrafast carrier scattering (< 1 ps) followed by a carrier recombination (> 50 ps) were observed. The time constant of carrier scattering under two-photon excitation is larger than that under one-photon excitation, due to the different transition selection rules and smaller absorption coefficient of the two-photon excitation.

Signal transducer and activator of transcription 3 (STAT3) is identified as a promising target for multiple cancer therapy and attracts widespread concern. Herein, we reported the discovery of a series of 2-acetyl-7-phenylamino benzofuran derivatives as STAT3 inhibitors using scaffold fusion strategy. Further structure activity relationship study led to the discovery of compound C6, which displayed the most potent anti-proliferation activities against MDA-MB-468 cells (IC50 = 0.16 μM). Western blot assay demonstrated that C6 inhibited the activation of STAT3 (Tyr705) without influencing the phosphorylation of STAT1 (Tyr701). Further mechanistic studies indicated that C6 caused a notable G2/M cycle-arresting and early apoptosis in a concentration-dependent manner in MDA-MB-468 cells. Finally, molecular modelling study elucidated the binding mode of C6 in STAT3 SH2 domain.

Persistently activated signal transducer and activator of transcription 3 (STAT3) plays an important role in the development of multiple cancers, and therefore is a potential therapeutic target for cancer prevention. Herein, we report the rational design, synthesis, and biological evaluation of novel potent STAT3 inhibitors based on BBI608. Among them, compound A11 exhibited the most potent in vitro tumor cell growth inhibitory activities toward MDA-MB-231, MDA-MB-468 and HepG2 cells with IC50 values as low as 0.67 ± 0.02 μM, 0.77 ± 0.01 μM and 1.24 ± 0.16 μM, respectively. Fluorescence polarization (FP) assay validated the binding of compound A11 in STAT3 SH2 domain with the IC50 value of 5.18 μM. Further mechanistic studies indicated that A11 inhibited the activation of STAT3 (Y705), and thus reduced the expression of STAT3 downstream genes CyclinD1 and C-Myc. Simultaneously, it induced cancer cell S phase arrest and apoptosis in a concentration-dependent manner. An additional in vivo study revealed that A11 suppressed the MDA-MB-231 xenograft tumor growth in mice at the dose of 10 mg/kg (i.p.) without obvious body-weight loss. Finally, molecular docking study further elucidated the binding mode of A11 in STAT3 SH2 domain.

Sarcodonin G, one of the cyathane diterpenoids isolated from the mushroom Sarcodon scabrosus, possesses pronounced neurotrophic activity but ambiguous mechanical understanding. In this work, sarcodonin G was chosen as a lead compound to prepare a series of 19- O-benzoyl derivatives by semisynthesis and their neuritogenic activities were evaluated. 6 and 15 (10 μM) were investigated with opposite effects in PC12 cells. 6 exhibited a superior activity to sarcodonin G by promoting NGF-induced neurite outgrowth, while 15 showed an inhibitory effect. Supportingly, 6 and 15 (20 μM) significantly induced and suppressed neurite extension in primary cultured rat cortical neurons, respectively. In mechanism, the two derivatives were revealed to influence NGF-induced neurite outgrowth in PC12 cells through the regulation of PKC-dependent and -independent ERK/CREB signaling as well as the upstream TrkA receptor phosphorylation. Furthermore, a possible pattern of interaction among NGF, 6/15 and TrkA was presented using molecular simulations. It revealed that 6/15 may contribute to the stabilization of the NGF-TrkAd5 complex by establishing several hydrophobic and hydrogen-bond interactions with NGF and TrkA, respectively. Taken together, 6 and 15 modulate PKC-dependent and -independent ERK/CREB signaling pathways possibly by influencing the binding affinity of NGF to the receptor TrkA, and finally regulate neurite outgrowth in PC12 cells.

A novel sesquiterpenoid dimer, named multistalide C (1), together with two known congeners, shizukaols C (2) and D (3), was isolated from the whole plant of Chloranthus japonicus Sieb. The structures of compounds 1-3 were elucidated by extensive HR-ESI-MS, 1D, and 2D NMR spectroscopic analysis. Compounds 1-3 exhibited significant toxic effects on brine shrimp larvae (Artemia salina). The absolute configuration of 1 was established by CD/TDDFT calculations. The related compound chlorahololide A was also reinvestigated. The previous assignment of the absolute configuration of chlorahololide A and several related sesquiterpenoid dimers, based on an incorrect application of the exciton chirality method, is criticized.

A cuprous oxide (Cu2O) thin film was prepared by radio-frequency (RF) magnetron sputtering. The crystal structure, linear transmission spectrum and film thickness were characterized by X-ray diffraction (XRD), ultraviolet–visible–near infrared (UV–Vis–NIR) absorption spectroscopy and ellipsometry. By performing the pump-probe and [Formula: see text]-scan technique, respectively, nondegenerate and degenerate two-photon absorption (D-TPA) coefficients of the Cu2O thin film at several different excitation wavelengths were experimentally determined. The nondegenerate two-photon absorption (ND-TPA) coefficient always exhibits larger magnitude than the corresponding D-TPA coefficient. In particular, the ND-TPA coefficient shows a maximum value of [Formula: see text][Formula: see text]cm/GW. This study indicates that the cuprous oxide could be a potential material for ultrafast nonlinear photonic devices based on two-photon absorption due to its large ND-TPA coefficient.

Two new sesquiterpenes, namely, 1β,10β-dihydroxy-eremophil-7(11), 8-dien-12,8-olide (1) and 8,12-epoxy-1β-hydroxyeudesm-3,7,11-trien-9-one (2), together with three known sesquiterpenoids, shizukolidol (3), 4α-hydroxy-5α(H)-8β-methoxy-eudesm-7(11)-en-12,8-olide (4), and neolitacumone B (5), and two known monoterpenes, (3R,4S,6R)-p-menth-1-en-3,6-diol (6) and (R)-p-menth-1-en-4,7-diol (7), were isolated from the whole plant of Chloranthus japonicus Sieb. Their structures were elucidated on the basis of spectroscopic data analysis and comparison with those of related known compounds. Compounds 4–7 were isolated from this plant for the first time.

This study describes the activity-guided isolation of antioxidant agents from tartary buckwheat bran (TBB). The ethanol crude extract of oil-free TBB was partitioned sequentially into ethyl acetate, n-butanol, and residual aqueous fractions. The ethyl acetate fraction (EAF) had the highest phenolic and flavonoid contents and showed the strongest antioxidant activity. EAF was superior to rutin and inferior to vitamin C (Vc) in DPPH radical scavenging ability, had an advantage over rutin and Vc in ABTS radical scavenging ability, and again surpassed rutin and quercetin in reducing power. Then EAF was subjected to column chromatography, and isolated compounds were identified using nuclear magnetic resonance data by comparing with those reported in the literature. Finally, the bioassay-guided fractionation of the crude ethanol extract of TBB afforded three known compounds (quercetin, p-hydroxybenzoic acid, and daucosterol) responsible for antioxidant activity. p-Hydroxybenzoic acid and daucosterol we...

Secoscabronine M (1) is a hemiacetal cyathane diterpenoid that was isolated from the fruiting bodies of the basidiomycete Sarcodon scabrosus (Fr.) Karst. Compound 1 possesses a novel structure with a bond cleavage between C-3 and C-4. The structure of the new compound was elucidated by means of spectroscopic methods, including two-dimensional nuclear magnetic resonance experiments. The absolute configuration of 1 was established by analysis of circular dichroism spectroscopy and also by employing time-dependent density functional theory calculations. In addition, compound 1 was confirmed to be an equilibrium mixture of two epimers (15S and 15R) at position C-15 in polar solvents by one-dimensional nuclear magnetic resonance analysis. Chirality 4:386–390, 2012. © 2012 Wiley Periodicals, Inc.

A novel cyathane diterpenoid, designated scabronine M (1), was isolated from the fruiting bodies of the mushroom Sarcodon scabrosus together with 10 known compounds. The structure of the new compound was elucidated on the basis of extensive spectroscopic analysis including 2D-NMR. Among these compounds, only scabronine M (1) significantly inhibited dose-dependently NGF-induced neurite outgrowth in PC12 cells without cytotoxicity, possibly through suppressing the phosphorylation of the receptor Trk A and the extracellular signal regulated kinases (ERK). This is the first report of novel neurite outgrowth-inhibiting activity in PC12 cells of this group of diterpenoids.

Nano-crystalline diamond (NCD) films with good adhesion were deposited on flexible copper substrate with Ni interlayer by Microwave Plasma Chemical Vapor Deposition (MPCVD). In this paper, two-stage method was used to improve the adhesion between the copper substrates and the diamond films. The effect of deposition time of the first stage on the morphology, crystal structure, non-diamond phase and adhesive properties of diamond films was investigated. The performance and structure of the diamond films were studied by Scanning Electron Microscope (SEM), Raman Spectroscopy (Raman) and X-Ray Diffraction (XRD). The results showed that the films were nano-crystalline diamond films positively. Impress method was used to examine the adhesion between diamond film and the substrate. When deposition time is 1.5h, the adhesion between diamond film and the copper substrate is better than the others. When it was 2.5h or longer, because the graphite layers existed as intermediate, the adherence between the diamond films and copper substrates was very poor. Therefore, the diamond films were easily peeled off from the substrates. Otherwise, the second stage called annealing process after the deposition played an important role to the adhesion. The films would be easily peeled off by curling without the annealing process.

Two new highly oxygenated fasciculol-type lanostane derivatives, fasciculols H and I (1 and 2, resp.), together with five known compounds, 3-7, were isolated from the fruiting bodies of the Chinese toxic mushroom Naematoloma fasciculare. Their structures were elucidated on the basis of spectroscopic analyses including 2D-NMR (HMBC, HSQC, NOESY, (1)H,(1)H-COSY). Compounds 5-7 were identified for the first time in this mushroom. Compounds 1, 3, 4, and 5 were evaluated for inhibitory activity against human glioma cell line U87 and nuclear factor-κB.

TiN thin films were deposited by Arc Ion Plating(AIP) with or without Magnetic Filter(AIP or MFAIP) on silicon(Si) and high-speed steel(HSS) substrates,respectively.Scanning Electron Microscope(SEM),X-ray Diffraction(XRD),nanoindentation and microscratch tests were applied for microstructure and property investigation.SEM data showed that the AIP films are plagued with macro-particles(MPs),while the MFAIP films have no or less MPs.XRD showed that the MFAIP films have more obvious preferred orientation at (111) than the AIP films.Scratch Crack Propagation Resistance(CPRs) was introduced to evaluate the film adhesion properties in a scratch test.MFAIP films had higher adhesion.AIP films were susceptible to failure as the CPRs was lower.The MFAIP films had higher hardness than the AIP ones, due to the reason of less MPs in MFAIP films and more obvious preferred orientation.It was proposed that the MPs were effectively removed with the magnetic filter, so the properties of the MFAIP films were greatly improved.

Two novel cyathane diterpenoids, designated scabronines K (1) and L (2), were isolated from the fruiting bodies of the basidiomycete Sarcodon scabrosus together with four known analogues, sarcodonins G (3), A (5), M (6), and scabronine H (4). Their structures were elucidated on the basis of extensive spectroscopic analysis including 2D-NMR (HMBC, HSQC, ROESY, (1)H,(1)H-COSY) and MS experiments. The isolated compounds were evaluated for nerve growth factor (NGF)-mediated neurite outgrowth using rat pheochromocytoma (PC12) cells as a model system of neuronal differentiation. Among these compounds, only sarcodonins G and A (3 and 5) at 25 μM showed significant neurite outgrowth (neuritegenesis)-promoting activity in the presence of 20 ng/mL NGF after 24h treatment. Their structure-neurite inducing activity relationship was also discussed.

Arc ion plating(AIP) has higher deposition rates, whereas macro-particles (MPs) make the film properties decreasing. In this paper, AIP with or without magnetic filter (MF or AIP) and composition of AIP followed with magnetic filter (MFAIP) were designed to deposit TiN films on silicon (Si) and high-speed steel(HSS), respectively. Scanning electron microscope (SEM), nanoindentation and microscratch tests were investigated. SEM showed that both the MF and the MFAIP films had a superfine layer among the columnar crystals grown vertically against substrate surface. However, the columnar crystals of MF films were leptosomatic and well-orientational, while MFAIP ones were coarse and short, and even ragged in size and orientation. Nanoindentation test results showed the highest hardness for MF films and the lowest one for AIP films. A new parameter Scratch Crack Propagation Resistance (CPRs) was introduced to evaluate the film adhesion properties in a scratch test. MF films had the highest adhesion. AIP films were most susceptible to failure as the CPRs was the lowest, although the Lc1 was higher than MFAIP ones. It was proposed that the MPs were effectively removed with the MF, and the MF layers were superfine to improve the properties of the films.

The title compound, C23H35NO2, is an amide derivative of the lactone (+)-sclareolide, and was synthesized from natural sclareol. In the molecular structure, the two six-membered rings (AandB) of the labdane skeleton aretrans-fused, and adopt chair conformations. There is an intramolecular N—H...O hydrogen bond present forming anS(7) ring motif. In the crystal, O—H...O hydrogen bonds link the molecules into helical chains propagating along theb-axis direction. The chains are linkedviaC—H...π interactions, forming a three-dimensional structure.

The title compound, C30H42N2O7[systematic name: (1S,4S,5S,7S,8S,9S,10S,11S,13R,14S,16S,17R)-20-ethyl-4,8,9-trihydroxy-1,14,16-trimethoxyaconitan-4-yl 2-aminobenzoate], isolated from roots ofAconitum sinomontanumNakai, is a typical aconitane-type C19-diterpenoid alkaloid, which crystallizes with two independent molecules in the asymmetric unit. The conformations of the two independent molecules are closely similar. Each molecule comprises four six-membered rings (A,B,DandE) including one six-membered N-containing heterocyclic ring (E), and two five-membered rings (CandF). RingsA,BandEadopt chair conformations, while ringDdisplays a boat conformation. Five-membered ringsCandFexhibit envelope conformations. IntramolecularN—H...O hydrogen bonds between the amino group and carbonyl O atom help to stabilize molecular structure. In the crystal, O—H...O hydrogen bonds link the molecules into zigzag chains propagating in [010].

The title compound, C15H22O3·H2O, is a natural producr isolated fromChloranthus japonicus, which is a eudesmane sesquiterpenoid. The twotrans-fused six-membered rings have chair confomations. In the crystal, O—H...O hydrogen bonds link the components into corrugated layers parallel to thebcplane. There are C—H...O interactions present within and between the layers.

Seven known metabolites, dianhydro-aurasperone C (1), isoaurasperone A (2), fonsecinone A (3), asperpyrone A (4), asperazine (5), rubrofusarin B (6) and (R)-3-hydroxybutanonitrile (7), were isolated from the culture of Aspergillus sp. KJ-9, a fungal endophyte isolated from Melia azedarach and identified by spectroscopic methods. All isolates were evaluated in vitro against several phytopathogenic fungi (Gibberella saubinetti, Magnaporthe grisea, Botrytis cinerea, Colletotrichum gloeosporioides and Alternaria solani) and pathogenic bacteria (Escherichia coli, Bacillus subtilis, Staphyloccocus aureus and Bacillus cereus). Compounds 3 and 7 were active against almost all phytopathogenic fungi tested with minimum inhibitory concentration (MIC) range of 6.25-50 μM. Moreover, compound 3 was active against all pathogenic bacteria with MIC in the range of 25-100 μM. Compound 7 is a rare new natural product isolated from a natural source for the first time, and the detailed NMR data of 1 were first assigned.

The title compound (common name: sclaral), C16H28O2, is a sclareolide derivative, which was synthesized from sclareolide itself. In the molecule, the two six-membered rings,AandB, of the labdane skeleton adopt chair conformations and the five-membered O-containing heterocyclic ringCdisplays an envelope conformation, with the methine C atom of the fused C—C bond as the flap. In the crystal, molecules are linked by O—H...O hydrogen bonds, forming chains propagating along [100].

The title compound [systematic name: [(1α,14α,16β)-20-ethyl-8,9,10-trihydroxy-1,14,16-trimethoxyaconitan-4-yl 2-aminobenzoate], C30H42N2O8, a natural C19-diterpenoid alkaloid, possesses an aconitane carbon skeleton with four six-membered rings and two five-membered rings. The fused ring system contains two chair, one boat, one twist-boat and two envelope conformations. Intramolecular N—H...O hydrogen bonds are observed between the amino and carbonyl groups. The molecules are linked togetherviaO—H...O hydrogen bonds, forming a three-dimensional framework.

Microbial transformation of diosgenin (3β-hydroxy-5-spirostene) using white-rot fungus Coriolus versicolor afforded four previously unreported polyhydroxylated steroids, 25(R)-spirost-5-en-3β,7α,15α,21-tetraol (5), 25(R)-spirost-5-en-3β,7β,12β,21-tetrol (6), (25R)-spirost-5-en-3β,7α,12β,21-tetraol (7), and (25R)-spirost-5-en-3β,7β,11α,21-tetraol (8), along with three known congeners, 25(R)-spirost-5-en-3β,7β-diol (2), 25(R)-spirost-5-en-3β,7β,21-triol (3), and 25(R)-spirost-5-en-3β,7β,12β-triol (4). These structures were elucidated by 1D and 2D NMR as well as HR-ESIMS analysis. In addition, we provide evidence for two new microbial hydroxylations of diosgenin: C-21 primary carbon hydroxylation and C-15 hydroxylation. The 3β-hydroxyl group and double bond in the B-ring of diosgenin were found to be important structural determinants for their activity.

Secoscabronine M (1) is a hemiacetal cyathane diterpenoid that was isolated from the fruiting bodies of the basidiomycete Sarcodon scabrosus (Fr.) Karst. Compound 1 possesses a novel structure with a bond cleavage between C-3 and C-4. The structure of the new compound was elucidated by means of spectroscopic methods, including two-dimensional nuclear magnetic resonance experiments. The absolute configuration of 1 was established by analysis of circular dichroism spectroscopy and also by employing time-dependent density functional theory calculations. In addition, compound 1 was confirmed to be an equilibrium mixture of two epimers (15S and 15R) at position C-15 in polar solvents by one-dimensional nuclear magnetic resonance analysis.

Biotransformation of paeonol (1) with the white-rot basidiomycete Coriolus versicolor afforded two metabolites, 2,4-dihydroxyacetophenone (2) and 2,5-dihydroxy-4-methoxyacetophenone (3), which were identified by spectroscopic methods. Compound 3 showed higher antioxidative, antibacterial, antifungal activities than 1 or 2. The results demonstrate for the first time that C. versicolor has the capacities to catalyze hydroxylation and demethylation reactions on the aromatic compound.

The novel diterpenoids, scabronine K (I) and L (II) are isolated from the fruiting bodies of the basidiomycete S.scabrosus together with four known analogues.

The title compound, C13H11Cl2N3O2, was obtained by the reaction of eugenol and cyanuric chloride. The dihedral angle between the benzene and triazine rings is 87.56 (4)°. Two C atoms of the allyl group are disordered over two sites in a 0.72 (2):0.28 (2) ratio.

observed in the mass spectra showed the molecular formula to be C 30 H 50 O 2 . The 1 H NMR spectrum revealed the presence of seven methyl groups: H 0.86 (3H, d, J = 6.7 Hz, H-23), 0.72 (3H, s, H-24), 0.87 (3H, s, H-25), 1.00 (3H, s, H-26), 1.07 (3H, s, H-27), 1.11 (3H, s, H-28); one of them was attached to a tertiary methyl, while the other six were attached to a quaternary carbon. The signal of the proton connected with the hydroxyl group carbon consisted of two parts: 3.34 (1H, d, J = 10.7 Hz) and 3.42 (1H, d, J = 10.7 Hz), while the signal of the secondary methyl carbon connected with the hydroxyl group appeared at C 71.9, showing that this hydroxyl group was attached to C-30 [11]. The 1 H and 13 C NMR (CDCl 3 ) data agreed with those of literature data [11, 12], so compound 1 was identified as 30-hydroxy-3-friedelanone. Compound 2 was obtained as a white amorphous powder (mp 272–273C), and the molecular ion peak ([M] + , m/z 442) observed in the mass spectra indicated that the molecular formula is C 30 H 50 O 2 . The 1 H and 13 C NMR (CDCl 3 ) data agreed with the literature data [11, 12], so compound 2 was identified as 29-hydroxy-3-friedelanone. Compound 3 was obtained as a white amorphous powder (mp 266–268C) and had the molecular C 30 H 50 O according to the mass spectra ([M + H] + , m/z 427). The 1 H and 13 C NMR (CDCl 3 ) data were in agreement with the literature [13, 14], so