Two new phenylpropanoid glycosidic compounds from the pseudobulbs of Pleione bulbocodioides and their hepatoprotective activity.

Two new phenylpropanoid glycosidic compounds (a pair of epimers), named pleionosides K (1) and L (2), were isolated from the pseudobulbs of Pleione bulbocodioides (Franch.) Rolfe. Their structures, including absolute configurations, were elucidated by a combination of MS, NMR data, chemical methods and the comparison of experimental and calculated electronic circular dichroism (ECD). Their possible biosynthetic pathway was discussed in the text. Furthermore, the two compounds exhibited moderate hepatoprotective activity against N-acetyl-p-aminophenol (APAP)-induced HepG2 cell damage in in vitro assays, with cell survival rates of 25.83% and 28.82% at 10 µM, respectively, and antioxidant effect against H2O2-induced toxicity in human SK-N-SH cell, with increasing viability at 10 µM of 24.9% and 34.6%, respectively.

Hepatoprotective Glucosyloxybenzyl 2-Hydroxy-2-isobutylsuccinates from Pleione yunnanensis.

Nine new glucosyloxybenzyl 2-hydroxy-2-isobutylsuccinates, pleionosides M-U (1-9), and 12 known compounds (10-21) were isolated from the pseudobulbs of Pleione yunnanensis. Their structures and absolute configurations were established through a combination of HRESIMS and NMR data and supported by physical and chemical methods. Compounds 5, 6, 10, and 15 showed significant in vitro hepatoprotective activity against d-galactosamine (d-GalN)-induced toxicity in HL-7702 cells with increasing cell viability by 27%, 22%, 19%, and 31% compared to the model group (cf. bicyclol, 14%) at 10 µM, respectively. Compounds 4, 9, and 11 exhibited moderate hepatoprotective activity against N-acetyl-p-aminophenol (APAP)-induced toxicity in HepG2 cells with increasing cell viability by 9%, 16%, and 12% compared to the model group (cf. bicyclol, 9%) at 10 µM, respectively.

Phenanthrene, 9,10-dihydrophenanthrene and bibenzyl enantiomers from Bletilla striata with their antineuroinflammatory and cytotoxic activities.

Thirteen undescribed phenanthrene and bibenzyl derivatives, named blestanols A-M, including one pair of biphenanthrene enantiomers, two bis 9,10-dihydrophenanthrene ethers, five pairs of 9,10-dihydrophenanthrene/bibenzyl atropisomers, one racemic 9,10-dihydrophenanthrene/bibenzyl dimer, one 9,10-dihydrophenanthrenebibenzyl ether, two pairs of bibenzyl derivatives, and one stilbene, together with 12 known analogues were isolated from the tubers of Bletilla striata. The structures were elucidated via spectroscopic data analysis. 15 compounds were purified to yield enantiomers (a, b) via chiral-phase HPLC, and their configurations were determined by optical rotation values and the comparison of the experimental and calculated electronic circular dichroism (ECD) curves. Blestanols K-L possessed a cycloheptene moiety, which is rarely observed in bibenzyl derivatives. A putative biosynthetic pathway for the identified components is deduced. Among these compounds, 14 compounds showed inhibition of NO production, with IC50 values ranging from 5.0 to 19.0 µM. Eight compounds displayed selective cytotoxic activities against HCT-116, HepG2, BGC-823, A549 or U251 cancer cell lines, with IC50 values ranging from 1.4 to 8.3 µM. In addition, their structure-activity relationships are discussed briefly.

Characteristics and Transformation Mechanism of Nonmetallic Inclusions in 304 Stainless Steel during Heat Treatment at 1250 °C.

Evolutions of two typical types of nonmetallic inclusions, i.e., inclusions based on CaO-SiO2-Al2O3 and MnO-SiO2-Al2O3 of 304 stainless steel were investigated in laboratory-scale experiments under isothermal heat treatment at 1250 °C for 0, 30, 60 and 120 min. Results show inclusion population density increases at the first stage and then decreases while their average size decreases and then increases. Moreover, almost no Cr2O3 content within the inclusion before the heat treatment, but Cr2O3 content increases gradually along with increasing heat treatment time. Furthermore, the increasing of Cr2O3 content in the inclusions would increase their melting points and reduce their plasticities. The experimental results and thermodynamic analysis indicate that there are three steps for inclusion evolution during the heat treatment process, in which Ostwald ripening plays an important role in inclusion evolution, i.e., inclusions grow by absorbing the newly formed small-size MnO-Cr2O3 inclusions.

Sesquiterpenoids, phenolic and lignan glycosides from the roots and rhizomes of Clematis hexapetala Pall. and their bioactivities.

Approximately 17 compounds were isolated from a 60% EtOH aqueous extract of the roots and rhizomes of Clematis hexapetala Pall., including three new guaianolide sesquiterpenoids with 5/7/5-fused rings and 3S-configuration (1-3), five new prenylated tetra-substituted phenolic glycosides (4-8) with 6/6-fused 9H-benzopyran skeleton (5) and 6/7-fused 7,10-dihydro-benzoxepin skeleton (6-8), one new isoferulyl glucoside (9), two new furofuran lignan diglucosides (10-11), and six known compounds. The chemical structures of the new compounds were elucidated via spectroscopic data and electronic circular dichroism (ECD) analyses in combination with a modified Mosher's method. The possible biosynthetic relationships of prenylated tetra-substituted phenols were postulated. In the in vitro assays, compound 16 exhibited moderate TNF-α secretion inhibitory activity with IC50 value of 3.419 µM. Compounds 14-16 displayed potent PTP1B enzymatic inhibitory activities with inhibition ratios of 48.30-86.00%. And compound 16 showed significant PTP1B enzymatic inhibition with IC50 value of 4.623 µM.

Atropisomeric bi(9,10-dihydro)phenanthrene and phenanthrene/bibenzyl dimers with cytotoxic activity from the pseudobulbs of Pleione bulbocodioides.

Bulbocodioidins E-H (1-4), four pairs of undescribed racemic bi(9,10-dihydro)phenanthrene and phenanthrene/bibenzyl atropisomers, along with four known compounds (5-8) were isolated from the ethanol extract of the pseudobulbs of Pleione bulbocodioides. Their structures were established by HRESIMS and comprehensive NMR spectroscopic data analysis. Their absolute configurations were elucidated by comparison of their experimental and calculated ECD (electronic circular dichroism) curves. Furthermore, compound 4a displayed cytotoxic activity against colon cancer (HCT-116), liver cancer (HepG2), and breast cancer (MCF-7) cell lines with IC50 values of 7.6, 3.8 and 3.4 µM, respectively. Compound 6 showed cytotoxic activity against breast cancer cell lines (MCF-7) with IC50 value of 5.4 µM.

Phenanthrenequinone enantiomers with cytotoxic activities from the tubers of Pleione bulbocodioides.

Eight new phenanthrenequinones (four pairs of enantiomers), named bulbocodioidins A-D (1-4), have been isolated from the ethanolic extract of tubers of Pleione bulbocodioides. Their structures, including absolute configurations, were determined by extensive NMR analysis combined with experimental and calculated ECD (electronic circular dichroism) data analyses. Compounds 1-4 possessed a 9(10)H-phenanthren-10(9)-one structure, which is a rarely reported instance from natural sources. Their possible biosynthetic pathway was discussed in the text. The cytotoxic effects of the isolated phenanthrenequinones were evaluated in several human cancer cell lines, and compounds 1a and 4a exhibited marked cytotoxic activities.

New dammarane triterpenoid saponins from the leaves of Cyclocarya paliurus.

Three new dammarane triterpenoid saponins, cyclocariosides O-Q (1-3), were isolated from the ethanolic extracts of the leaves of Cyclocarya paliurus. The structures of these compounds were elucidated by spectroscopic methods.

[Chemical constituents from tuber of Bletilla striata].

Eighteen compounds were isolated from the EtOAc soluble fraction of Bletilla striata by various chromatographic techniques, such as silica gel, ODS, Sephadex LH-20, RP-HPLC. Their structures were identified by spectroscopic methods and physicochemical properties, as 5-hydroxy-2-(p-hydroxybenzyl)- 3- methoxybibenzyl(1), shancigusins B(2), shanciguol(3),arundinan(4), 3',5-dihydroxy-2,4-di(p-hydroxybenzyl)-3-methoxybibenzyl(5), arundin(6), 3,3'-dihydroxy-2-(p-hydroxybenzyl)-5-methoxybibenzyl(7), 3, 3'-dihydroxy-2', 6'-bis(p-hydroxybenzyl)-5-methoxybibenzyl(8), 7-hydroxy-2,4-dimethoxyphenanthrene(9), bleformin B(10),nudol(11), 3,7-dihydroxy-2, 4-dimethoxyphenanthrene(12), 2, 7-dihydroxy-4-methoxy-9,10-dihydrophenathrene(13), bleformin D(14), 4,4'-dimethoxy-9,10-dyhydro-[6,1'-biphenanthrene]-2,2',7,7'-tetraol(15),gymconopin C(16),(2,3-trans)-2-(4-hydroxy-3-methoxyphenyl)-3-hydroxymethyl-10-methoxy-2,3,4,5-tetrahydro-phenanthro[2,1-b]furan-7-ol(17),shanciol(18). Among them, compound 1 was a new compound, Compounds 2-6,9,15-18 were isolated from this genus for the first time.

[Studies on glucosyloxybenzyl 2-isobutylmalates of Pleione bulbocodioides].

Ten glucosyloxybenzyl 2-isobutylmalates and one benzyl alcohol glycoside were isolated from the dry tuber of Pleione bulbocodioides, which is a specie of Orchidaceae family and its dry tuber is one of the main sources of traditional Chinese medicine "shanci-gu", by a combination of various column chromatographic methods, including ODS, macroporous adsorbent resin, Sepheadex LH-20, and preparative HPLC. Their structures were identified on the basis of chemical evidences and spectroscopic analysis asloroglossin (1), grammatophylloside A (2), cronupapine (3), (-)-(2R, 3S)-1-(4-ß-D-glucopyranosyloxybenzyl)-4-methyl-2-isobutyltartrate (4), vandateroside II (5), grammatophylloside B (6), bis [4-(ß-D-glucopyranosyloxy) -benzyl] (S) -2-isopropylmalate (7), gymnoside I (8), militarine (9), dactylorhin A (10), gastrodin (11). Compounds 1-7 were isolated from this genus for the firt time.

[Chemical constituents from Pleione bulbocodioides].

Fourteen compoumds were isolated from the ethyl acetate portion of the 95% ethanolic extract of Pleione bulbocodioides by a combination of various chromatographic techniques including silica gel, ODS, macroporous adsorbent resin, Sephadex LH-20, and preparative HPLC, of which ten compoumds were phenanthrenes and dihydrophenanthrenes, two compoumds were bibenzyls, one was lignan and a sterol. Their structures were identified on the basis of spectroscopic data as monbarbatain A(1), 2, 7, 2'-trihy-droxy-4, 4', 7'-trimethoxy-1, 1'- biphenanthrene(2), blestriarene A(3), pleionesin B(4), shanciol H(5), 17-hydroxy-7'-(4'-hy-droxy-3 '-methoxyphenyl)- 4-methoxy-9, 10, 7', 8'-tetrahydrophenanthro[2, 3-b]furan-8'-yl methyl acetate(6), 1-p-hydroxybenzyl-4-methoxy phenanthrene-2, 7-diol(7), 1-p-hydroxybenzyl-4-met-hoxy-9, 10-dihydrophenanthrene-2, 7-diol(8), hircinol(9), coelonin( 10), gigantol(11), batatasin 11 (12), syringaresinol(13) and ergosta4, 6, 8 ( 14) , 22-tetraen-3-one (14). Compounds 1-3, 9, 13 and 14 were isolated from this genus for the first time.