Preparation and analysis of photochromic behavior of carboxymethyl chitin derivatives containing spiropyran moieties.

1'-(2-Acryloxyethyl)-3,3'-dimethyl-6-nitrospiro[2 H-1-benzopyran-2,2'-indoline] (SPA) was synthesized and grafted onto a water-soluble carboxymethyl chitin (CMCH) macromolecule to prepare a photochromic copolymer (CMCH-g-SPA). The structure of CMCH-g-SPA was characterized by Fourier-transform infrared (FT-IR) spectroscopy, thermogravimetric (TG) analysis, X-ray diffraction (XRD) analysis, water-solubility evaluation, and UV-vis spectroscopy. XRD patterns of CMCH-g-SPA revealed that grafting copolymerization disrupts the CMCH semicrystalline structure, thus improving water solubility. UV-vis spectroscopy results supported the negative photochromic behavior of the merocyanine (MC) form of CMCH-g-SPA (CMCH-g-MCA) present in a water solution of the target copolymer. In addition to high solvent polarity, the intermolecular and intramolecular electrostatic attraction between the indolenine cation and the COO- anion were found to be influencing factors, which stabilize these MC form of spiropyran groups grafted onto CMCH. In a water solution, visible light bleaching was completed over a short period (8 minutes) under artificial visible light irradiation and the thermal coloration reaction, whose rate constant at 25 °C was 4.64 × 10-4 s-1, which fit the first-order reaction equation. After ten photochromic cycles in water solution, the relative absorption intensity of CMCH-g-MCA decreased by 7.92%.

Cyclized 9,11-secosterol enol-ethers from the gorgonian Pseudopterogorgia americana.

Chemical investigation of the MeOH extract from the gorgonian Pseudopterogorgia americana afforded two rare sterols, ameristerenol A (1) and B (2), both 9,11-secosterols possesses a seven-membered cyclic enol-ether in ring C, and ameristerol A (3) is the first example of a naturally occurring 9,11-secosterol containing a gorgosterol side chain with a C-24(28) double bond. Ameristerenol A (1) was converted to the sterol derivatives 4-6 to provide additional chemical diversity and comparison for biological screening. The structures of compounds 1-6, along with three related known analogues 7-9, were determined on the basis of extensive spectroscopic analysis and by comparison with literature data. Compound 6 exhibited slight cytotoxicity activity against human breast cancer cell line MDA-MB-231.

Liver X receptor and peroxisome proliferator-activated receptor agonist from Cornus alternifolia.

BACKGROUND: Peroxisome proliferator-activated receptors (PPARs) belong to the nuclear receptors superfamily and are transcription factors activated by specific ligands. Liver X receptors (LXR) belong to the nuclear hormone receptors and have been shown to play an important role in cholesterol homeostasis. From the previous screening of several medicinal plants for potential partial PPARγ agonists, the extracts of Cornus alternifolia were found to exhibit promising bioactivity. In this paper, we report the isolation and structural elucidation of four new compounds and their potential as ligands for PPAR. METHODS: The new compounds were extracted from the leaves of C. alternifolia and fractionated by high-performance liquid chromatography. Their structures were elucidated on the basis of spectroscopic evidence and analysis of their hydrolysis products. RESULTS: Three new iridoid glycosides including an iridolactone, alternosides A-C (1-3), a new megastigmane glycoside, cornalternoside (4) and 10 known compounds, were obtained from the leaves of C. alternifolia. Kaempferol-3-O-ß-glucopyranoside (5) exhibited potent agonistic activities for PPARα, PPARγ and LXR with EC50 values of 0.62, 3.0 and 1.8 µM, respectively. CONCLUSIONS: We isolated four new and ten known compounds from C. alternifolia, and one known compound showed agonistic activities for PPARα, PPARγ and LXR. GENERAL SIGNIFICANCE: Compound 1 is the first example of a naturally occurring iridoid glycoside containing a ß-glucopyranoside moiety at C-6.

Honatisine, a novel diterpenoid alkaloid, and six known alkaloids from Delphinium honanense and their cytotoxic activity.

A novel diterpene alkaloid named honatisine (1) has been isolated from the whole plants of Delphinium honanense, along with six known alkaloids, siwanine E (2), isoatisine (3), atisine (4), delcorinine (5), uraphine (6), and nordhagenine A (7). Their structures were deduced on the basis of their spectral data. All of them were evaluated by a SRB assay for their cytotoxicity, and compound 1 showed a significant cytotoxic activity (IC(50) =3.16 µM) against the MCF-7 cell line.

Diterpenoid alkaloids from a Tibetan medicinal plant Aconitum richardsonianum var. pseudosessiliflorum and their cytotoxic activity.

The chemical constituents from Aconitum richardsonianum var. pseudosessiliflorum were investigated. The roots of this plant were extracted three times with 90% EtOH at the room temperature. The ethanol extracts were combined and concentrated under reduced pressure to yield residue, which was suspended in water and successively partitioned with chloroform. The chloroform extraction was isolated and purified by silica gel and Sephadex LH-20 column chromatography. Six compounds were isolated and elucidated as delelatine (1), isodelpheline (2), 3-acetylaconitine (3), isoatisine (4), nordhagenine A (5) and yunaconitine (6). Compounds 1-5 were obtained from Aconitum Brunneum for the first time. Compound (1) showed significant cytotoxic activities (IC50= 4.36 µM) against the human tumor cell line P388.

Chemical constituents from Delphinium chrysotrichum and their biological activity.

A new diterpene alkaloid named delphatisine C (1) has been isolated from aerial parts of Delphinium chrysotrichum along with three known norditerpenoid alkaloids delpheline (2), delbrunine (3), and delectinine (4). Their structures were characterized on the basis of their spectral data. All of them were determined by SRB assay for their cytotoxicity, and compound (1) showed significant cytotoxic activities (IC(50)=2.36 µmol/L) against the A549 cell line.

A new norditerpenoid alkaloid from Aconitum taipaicum.

To investigate the chemical constituents of the roots of Aconitum taipaicum, silica gel column chromatography was used for the isolation and purification of compounds. A new norditerpenoid alkaloid, isodelelatine (1), along with five known alkaloids, atisine (2), delfissinol (3), liangshanine (4), hypaconitine (5) and delelatine (6) were isolated and identified. The structure of the new compound was elucidated on the basis of spectral data.

[Study on chemical constituents from Delphinium honanense var. piliteram].

OBJECTIVE: To study the chemical constituents from Delphinium honanense var. piliteram. METHOD: The constituents were isolated and purified with chromatographic methods, identified by NMR, MS and IR. RESULT: Six compounds were isolated and elucidated as siwanine E (1), isoatisine (2), 12-epi-napelline (3), acontine (4), ajadelphinine (5) and beta-sitosterol (6). CONCLUSION: Compounds 1-6 are all isolated from the plant for the first time.

[Studies on chemical constituents of Clerodendrum bungei].

OBJECTIVE: To study the constituents from Clerodendrum bungei. METHOD: The constituents were isolated and purified with chromatographic methods, and identified by NMR, MS and IR. RESULT: Five compounds were isolated, beta-sitosterol (1), taraxerol (2), glochidone (3), glochidonol (4), glochidiol (5). CONCLUSION: Compounds (3), (4) and (5) were isolated for the first time from C. bungei.

[Studies on chemical constituents in leafs of Clerodendron fragrans].

OBJECTIVE: To separate and identify the constituents from Clerodendron fragrans. METHOD: The constituents were isolated and purified with chromatographic methods, identified by NMR, MS, IR. RESULT: Beta-sitosterol (1), clerosterol (2), daucosterol (3), caffeic acid (4), kaempferol (5), 5,4'-dihydroxy-kaempferol-7-O-beta-rutinoside (6), acteoside (7) and leucoseceptoside A (8), were isolated and identified. CONCLUSION: Compound 7 and 8 were identified for the first time from Clerodendron fragrans.