Phenyl glycosides from the leaves of Flacourtia indica (Burm. f.) Merr (Salicaceae).

Thirteen phenolic glycosides, together with fourteen various known compounds, were isolated from the methanolic extract of leaves of Flacourtia indica. Twelve of these were composed of gentisyl or salicyl alcohols, glycosylated on the phenol and acylated on the primary alcohol with various more or less oxidized forms of pyrocatechuic acid. A number of positions on the glucose or on the acid were further acylated by benzoic or cinnamic acid. In addition to these, a glucoside of a phenyl propanoid was also isolated. The gross structures were elucidated by spectroscopic means including 1D and 2D NMR experiments and HR-ESI-MS analyses. Several of these structures, for example, xylosmin, were previously described but it proved extremely difficult to conclude on their exact identity with the absence of clear data on absolute configuration in the literature.

A new hopane derivative from the lichen Dirinaria applanata.

Chemical investigation of the lichen Dirinaria applanata led to isolate nine compounds including a new hopane derivative, 1ß-acetoxy-21α-hopane-3ß,22-diol (1) together with six phenolic compounds naming divaricatinic acid (2), methyl divaricatinate (3), methyl-ß-orcinolcarboxylate (4), methyl haematommate (5), divarinol (6), ramalinic acid A (7), and two xanthones namely lichenxanthone (8), 4,5-dichlorolichenxanthone (9). Their structures were elucidated by spectroscopic data in combination with published literature. Except compound 2, all compounds were isolated from this species for the first time.

Developmental toxicity of Clerodendrum cyrtophyllum turcz ethanol extract in zebrafish embryo.

ETHNOPHARMACOLOGICAL RELEVANCE: Clerodendrum cyrtophyllum Turcz has been used in traditional medicine for the treatment of various diseases. In spite of its therapeutic applications, research on its toxicity and teratogenicity is still limited. AIM OF THE STUDY: The study aimed to investigate the developmental toxicity of the ethanol extract of C. cyrtophyllum (EE) in zebrafish embryo model. MATERIAL AND METHODS: Major compounds from crude ethanol extract of Clerodendron cyrtophyllum Turcz leaves were determined using HPLC-DAD-Orbitrap-MS analysis. The developmental toxicity of EE were investigated using zebrafish embryo model. Zebrafish embryos at 6 h post-fertilization (hpf) were treated with EE at different concentrations. Egg coagulation, mortality, hatching, yolk sac edema, pericardial edema and teratogenicity were recorded each day for during a 5-day exposure. At time point 120 hpf, body length, pericardial area, heartbeat and yolk sac area were assessed. In order to elucidate molecular mechanisms for the developmental toxicity of EE, we further evaluated the effects of the EE on the expression of genes involved on signaling pathways affecting fish embryo's development such as heart development (gata5, myl7, myh6, has2, hand2, nkx 2.5), oxidative stress (cat, sod1, gpx4, gstp2), wnt pathway (ß-catenin, wnt3a, wnt5, wnt8a, wnt11), or cell apoptosis (p53, bax, bcl2, casp3, casp8, casp9, apaf-1, gadd45bb) using qRT-PCR analysis. RESULTS: Our results demonstrated that three major components including acteoside, cirsilineol and cirsilineol-4'-O-ß-D-glucopyranoside were identified from EE. EE exposure during 6-96 h post-fertilization (hpf) at doses ranging from 80 to 200 µg/mL increased embryo mortality and reduced hatching rate. EE exposure at 20 and 40 µg/mL until 72-120 hpf induced a series of malformations, including yolk sac edema, pericardial edema, spine deformation, shorter body length. Based on two prediction models using a teratogenic index (TI), a 25% lethality concentration (LD25) and the no observed-adverse-effect level (NOAEL), EE is considered as teratogenic for zebrafish embryos with TI (LC50/EC50) and LD25/NOAEC values at 96 hpf reaching 3.87 and 15.73 respectively. The mRNA expression levels of p53, casp8, bax/bcl2, gstp2, nkx2.5, wnt3a, wnt11, gadd45bb and gata5 were significantly upregulated by EE exposure at 20 and 40 µg/mL while the expression of wnt5, hand2 and bcl2 were downregulated. CONCLUSIONS: These results provide evidence for toxicity effects of EE to embryo stages and provide an insight into the potential toxicity mechanisms on embryonic development.

Anti-radical flavonol glycosides from the aerial parts of Cleome chelidonii L.f.

Eleven previously undescribed flavonoid glycosides, named cleomesides C-M, along with five known compounds, were isolated from the aerial parts of Cleome chelidonii L.f. (Cleomaceae). All flavonol glycosides were esterified derivatives of 3,7-O-diglycosides of quercetin or kaempferol. Their structures were elucidated by analysis of the 1D and 2D NMR spectra, HR-ESI-MS data, UV spectra, optical rotation and by comparison with literature data. The DPPH radical scavenging properties of the flavonoid glycosides were studied in order to appreciate the effect of the glycoside parts and of the ester groups on this activity compared with the quercetin and kaempferol aglycones. An acetate at position 3 of rhamnose linked to C-7 of flavonol, gave compounds with the strongest antiradical activity. An aromatic ester group at position 6 of terminal glucose of diglycoside chain linked to C-3 of flavonol did not seem to influence the antiradical activity.