[Flavonol glycosides from Lysimachia clethroides].

Eleven flavonol glycosides were isolated from the ethanol extract of Lysimachia clethroides by a combination of various chromatographic techniques including column chromatography over silica gel, Sephadex LH-20, and reversed-phase HPLC. Their structures were identified as astragalin (1), isoquercitrin (2), isorhamnetin-3-O-ß-D-glucopyranoside (3), quercetin-3-O-ß-D-6"-acetylglucopyranoside (4), quercetin-7-O-ß-D-glucopyranoside (5), prunin (6), 2-hydroxynaringin-5-O-ß-D-glucopyranoside (7), kaempferol-3-O-rutinonoside (8), kaempferol-3-O-robinobioside (9), rutin (10) and kaempferol-3,7-di-O-ß-D-glucopyranoside (11). Among them, compounds 4, 7 and 11 were obtained from the Lysimachia genus for the first time, while compounds 3, 5 and 9 were firstly reported from this plant. In the preliminary assays, compounds 2, 6 and 8 possessed significant inhibition against aldose reduc- tase, with IC50 values of 2.69, 1.00, 1.80 µmol · L(-1), respectively; none of compounds 1-11 exhibited obvious cytotoxic activity (IC50 > 10 µmol · L(-1)).

Three new norsesquiterpenoids from the seeds of Alpinia galanga.

From the seeds of Alpinia galanga Willd., three new norsesquiterpenoid racemic mixtures, galanols A-C (1-3) were isolated, along with three known sesquiterpenoids (4-6). Their structures were elucidated by means of UV, IR, HR-ESI-MS, 1D NMR and 2D NMR spectroscopic data.

The total synthesis of hypodematine.

Hypodematine, isolated from Hypodematium sinense Iwatsuki as an alkaloid with a new skeleton, was synthesized via nine reaction steps, in which the synthesis of 2-aryl-1-benzazocines via Beckmann rearrangement of 5H-benzocyclohepten-5-one oxime mesylate in dry toluene is discussed.

Bioactive carboxylic acids from Lysimachia clethroides.

Six new carboxylic acids (1-6), together with 11 known ones (7-17), were isolated from the aerial parts of Lysimachia clethroides. Their structures were elucidated on the basis of spectroscopic analysis and chemical evidence. Five new carboxylic acids (1 and 3-6) were evaluated for their in vitro inhibitory activity against aldose reductase.

Hepatoprotective iridoid glycosides from the roots of Rehmannia glutinosa.

Eleven new iridoid glycosides, rehmaglutosides A-K (1-11), together with 20 known analogues were isolated from the air-dried roots of Rehmannia glutinosa. The structures of these compounds were elucidated on the basis of spectroscopic data analysis and chemical evidence. Furthermore, in in vitro assays, compounds 3, 7, and 9-11 (10 µM) exhibited moderate hepatoprotective activities against D-galactosamine-induced HL-7702 cell damage.

Bioactive sesquiterpenoids from the rhizomes of Acorus calamus.

Eight new sesquiterpenes (1-8) and one new norsesquiterpene (9) named calamusins A-I were isolated from the ethanol extract of Acorus calamus rhizomes. The absolute configuration of compound 8 was determined by comparing its experimental and calculated ECD spectra. The absolute configurations of the other compounds were determined from their CD spectra. Furthermore, in in vitro assays, compounds 3, 4, 7, and 9 (10 µM) exhibited weak hepatoprotective activities against APAP-induced HepG2 cell damage.

Four new N-contained iridoid glycosides from flower buds of Lonicera japonica.

Four new N-contained iridoid glycosides, lonijapospiroside A (1), L-phenylalaninosecologanin B (2), L-phenylalaninosecologanin C (3), and dehydroprolinoylloganin A (4), were isolated from the flower buds of Lonicera japonica Thunb. Their structures were established on the basis of UV, IR, MS, and NMR spectral data.

Four new flavonoids from Morus australis.

Four new flavonoids, benzokuwanon E (1), hydroxymorusin (2), dicyclokuwanon EA (3), and dicyclokuwanon EB (4), were isolated from Morus australis. Their structures were elucidated on the basis of UV, IR, MS, NMR, and CD spectral data.

Steroidal alkaloids from the bulbs of Fritillaria unibracteata.

Two new steroidal alkaloids peimisine-3-O-ß-D-glucopyranoside (1) and puqiedinone-3-O-ß-D-glucopyranoside (3), together with three known compounds peimisine (2), puqiedinone (4), and puqiedine (5), were isolated and characterized from the bulbs of Fritillaria unibracteata. Their structures were fully elucidated by spectroscopic and chemical methods. Compound 1 showed moderate protection effect on neurotoxicity of PC12 cell lines induced by rotenone.

Cytotoxic triterpenoid saponins from Lysimachia clethroides.

Seven oleanane-type triterpenoid saponins, named clethroidosides A-G (1-7), an ursane-type triterpenoid saponin, clethroidoside H (8), and six known saponins were isolated from the aerial parts of Lysimachia clethroides. The structures of the saponins were elucidated on the basis of physical data analysis (1D and 2D NMR, HR-ESIMS) and chemical evidence. The cytotoxic activities of compounds 1-14 were evaluated against five human tumor cell lines (HT-29, HePG2, BGC-823, A549, and A375). Compounds 3, 4, 6, and 11-13 exhibited moderate cytotoxic activity, with IC50 values of 0.75-2.62 µM, while compound 5 showed selective cytotoxic activity.

Chemical constituents of the stem bark of Morus cathayana.

Phytochemical investigation of the stem bark of Morus cathayana led to the isolation and identification of six new compounds, cathayanons F-J (1-5) and cathayanin A (6), and two known compounds, cathayanins B-C (7-8). Their structures were elucidated by spectroscopic methods. Compounds 1, 2, 3, 5, and 7 exhibited weak activities against five human cancer cell lines, with IC(50) values ranging from 4.7 to 9.8 microg/ml.

Three new Diels-Alder type adducts from the stem bark of Morus cathayana.

Three new Diels-Alder type adducts cathayanons C (1), D (2), and E (3), together with one known compound sanggenon C (4), were isolated from the stem bark of Morus cathayana. Their structures were fully elucidated by spectroscopic and chemical methods. Compound 2 showed good anti-oxidation activity with the inhibitory rate of malondialdehyde being 88% at a concentration of 10(- 6) mol/l.

2-Arylbenzofuran Derivatives from Morus cathayana.

Four new 2-arylbenzofuran derivatives, cathafurans A (1), B (2), C (3), and D (4), were isolated from the stem bark of Morus cathayana. Their structures were determined by spectroscopic methods. Compounds 2 and 3 exhibited moderate activities against five human cancer cell lines, with IC(50) values ranging from 6.17 to 9.60 microg/mL.

Two new dimeric stilbenes from the stem bark of Morus australis.

Two new dimeric stilbenes austrafuran B and austrafuran C were isolated from the bark of Morus australis. Their structures were elucidated on the basis of spectroscopic methods.

The synthesis of analogs of shuangkangsu, a novel natural cycloperoxide glucoside from Lonicera japonica Thunb.

Four novel optically pure cycloperoxide glucosides 9a, 9b, 10a, and 10b, analogs of shuangkangsu--a natural product with unusual skeleton and antivirus activity from the buds of Lonicera japonica Thunb, were firstly synthesized by employing peroxidation and glucosidation reactions from phthalaldehyde or 4,5-dichloro phthalaldehyde and glucose.

Four new alkaloids from Polyalthia nemoralis (Annonaceae).

Four new alkaloids, polynemoralines A (1), B (2), C (3), and D (4), were isolated from the branches and leaves of Polyalthia nemoralis A DC. The structures of 1-4 were elucidated mainly on the basis of spectroscopic methods. The structure of 4 was confirmed by X-ray diffraction analysis.

Evaluation of enantiopure N-(ferrocenylmethyl)azetidin-2-yl(diphenyl)methanol for catalytic asymmetric addition of organozinc reagents to aldehydes.

A facile and practical approach to preparation of enantiopure N-(ferrocenylmethyl)azetidin-2-yl(diphenyl)methanol was developed from cheap and easily available l-(+)-methionine. Synthetic highlights include the three-step, one-pot construction of the chiral azetidine ring and the development of an improved one-step procedure for the synthesis of the key intermediate l-2-amino-4-bromobutanoic acid. Enantiopure N-(ferrocenylmethyl)azetidin-2-yl(diphenyl)methanol was evaluated for catalytic asymmetric addition of organozinc reagents to aldehydes. The asymmetric ethylation, methylation, arylation, and alkynylation of aldehydes achieved enantioselectivity of up to 98.4%, 94.1%, 99.0%, and 84.6% ee, respectively, in the presence of a catalytic amount of chiral N-(ferrocenylmethyl)azetidin-2-yl(diphenyl)methanol. Our results demonstrated further that the four-membered heterocycle-based backbone was a good potential chiral unit for the catalytic asymmetric induction reaction, and the hindrance of the bulky ferrocenyl group, compared to a phenyl group, played an important role in the enantioselectivities. A possible transition for the catalytic asymmetric addition has been proposed on the basis of the crystal structure of the chiral ligand 3b including two HOAc molecules and previous studies.

Three new cytotoxic Diels-Alder-type adducts from Morus australis.

Three new natural products, australisines A-C (1-3, resp.), were isolated from the stem bark of Morus australis, together with eight related compounds, including mulberrofurans E-G, J, and Q, mongolicin C, chalcomoracin, and kuwanon G. Their structures were fully characterized by spectroscopic methods. Compounds 1-3, mulberrofuran G, mongolicin C, and chalcomoracin showed moderate cytotoxic activities against five human cancer cell lines, with IC50 values ranging from 4.6-9.2 microg/ml, as determined by MTT assay.

Presence and integration of HBV DNA in mouse oocytes.

AIM: Hepatitis B is a worldwide public health problem. To explore the feasibility of hepatitis B virus (HBV) vertical transmission via oocytes, the presence and integration of HBV DNA in mouse oocytes were studied. METHODS: Genomic DNA was isolated and metaphases were prepared, respectively from mouse oocytes cocultured with pBR322-HBV DNA plasmids. PCR, Southern blot, dot hybridization and fluorescence in situ hybridization (FISH) were performed to explore the existence and integration of HBV DNA in oocytes. RESULTS: PCR detected positive bands in the tested samples, and then Southern blot revealed clear hybridization signals in PCR products. Final washing solutions were collected for dot hybridization and no signal for HBV DNA was observed, which excluded the possibility that contamination of washing solutions gave rise to positive results of PCR and Southern blot. FISH demonstrated that 36 of 1,000 metaphases presented positive signals. CONCLUSION: HBV DNA sequences are able to pass through the zona and oolemma to enter into oocytes and to integrate into their chromosomes. HBV DNA sequences might be brought into embryo via oocytes as vectors when they are fertilized with normal spermatozoa.

Effect of dynein inhibitor on mouse oocyte in vitro maturation and its cyclin B1 mRNA level.

OBJECTIVE: To evaluate the effect of dynein inhibitor on mouse oocyte in vitro maturation and its cyclin B1 transcription level. METHODS: Immature mouse oocytes were cultured in vitro with a known dynein ATPase activity inhibitor-sodium orthovanadate (SOV) to detect the changes of maturation rate, and semi-quantitative RT-PCR and single cell RT-PCR were performed to detect the changes of cyclin B1 mRNA level. RESULTS: In dose-dependent experiments, the maturation rates of oocytes were significantly different between 5 micromol/L SOV and control groups (P < 0.05), and decreased with SOV increasing doses. However, the elevation of cyclin B1 mRNA level of immatured oocytes cultured for 12 h depended on SOV concentrations ranging from 50 to 500 micromol/L. In incontinuity exposed SOV experiments, the maturation rates of oocytes markedly reduced after the first incubation with 400 micromol/L SOV at least for 1 h and were first cultured in SOV-free medium for 4 h or 8 h before exposure to SOV (P < 0.05). In time-course experiment, the opposite changes of cyclin B1 mRNA level in oocytes between SOV and control groups were observed. CONCLUSION: Dynein inhibitor might delay oocytes meiosis process, and cause ectopic expression of cyclin B1 in oocytes. Most Oocytes incubated with SOV blocked at germinal vesicles (GV) stage or M I to anaphase transition due to dynein dysfunction and ectopic transcription level of cyclin B1.