Beta-eudesmol induces neurite outgrowth in rat pheochromocytoma cells accompanied by an activation of mitogen-activated protein kinase.
Beta-eudesmol, a sesquiterpenoid isolated from "So-jutsu" (Atractylodis lanceae rhizomas), is known to have various unique effects on the nervous system. We examined in detail the mechanism by which beta-eudesmol modified neuronal function using rat pheochromocytoma cells (PC-12). Beta-eudesmol at concentrations of 100 and 150 microM significantly induced neurite extension in PC-12 cells, which was accompanied, at the highest concentration, by suppression of [(3)H]thymidine incorporation. Beta-eudesmol at concentrations of 100 and 150 microM also evoked a significant increase in intracellular Ca(2+) concentration ([Ca(2+)](i)) in these cells, as determined by the fura 2 assay. Much of this increase remained even after the extracellular Ca(2+) was chelated by EGTA. The [Ca(2+)](i) increase induced by beta-eudesmol was partially inhibited by the phosphoinositide-specific phospholipase C (PI-PLC) inhibitor 1-[6-[[17beta-methoxyestra-1,3,5(10)-trien-17-yl]amino]hexyl]-1H-pyrrole-2,5-dion e (U-73122) (2 microM) under extracellular Ca(2+)-free conditions. Furthermore, beta-eudesmol, in a concentration-dependent fashion, caused an accumulation of inositol phosphates. beta-Eudesmol (150 microM) promoted phosphorylation of both mitogen-activated protein kinase (MAPK) and cAMP-responsive element binding protein in a time-dependent manner. These phosphorylations were suppressed by the MAPK kinase inhibitor 2-(2'-amino-3'-methoxyphenol)-oxanaphthalen-4-one (PD98059) (50 microM), U-73122 (2 microM), the calmodulin inhibitor N-(6-aminohexyl)-5-chloro-1-naphthalenesulfonamide hydrochloride (W7) (1-10 microM), and the protein kinase A inhibitor N-[2-(4-bromocinnamylamino)ethyl]-5-isoquinoline (H89) (1-10 microM). Beta-eudesmol-induced neurite extension was significantly inhibited by both U-73122 (2 microM) and PD98059 (30 microM), suggesting the involvement of PI-PLC and MAPK in neurite outgrowth. Beta-eudesmol, being a small molecule, may therefore be a promising lead compound for potentiating neuronal function. Furthermore, the drug may be useful in helping to clarify the mechanisms underlying neuronal differentiation. (+info)
Glycosides of Atractylodes lancea.
Five sesquiterpenoid glycosides (two guaiane-type glycosides and three eudesmane-type glucosides) and a glucoside of an acetylene derivative were newly isolated from the water-soluble portion of the methanolic extract of Atractylodes lancea rhizome together with 26 known compounds. Their structures were characterized as atractyloside A 14-O-beta-D-fructofuranoside, (1S,4S,5S,7R,10S)-10,11,14-trihydroxyguai-3-one 11-O-beta-D-glucopyranoside, (5R,7R,10S)-isopterocarpolone beta-D-glucopyranoside, cis-atractyloside I, (2R,3R,5R,7R,10S)-atractyloside G 2-O-beta-D-glucopyranoside, and (2E,8E)-2,8-decadiene-4,6-diyne-1,10-diol 1-O-beta-D-glucopyranoside on the basis of chemical and spectroscopic investigation. The presence of six characteristic guaiane-type glucosides in both rhizomes of A. lancea and Atractylodes japonica suggested a close chemotaxonomic relationship between them. (+info)
Structures of new friedelane- and norfriedelane-type triterpenes and polyacylated eudesmane-type sesquiterpene from Salacia chinensis LINN. (S. prinoides DC., Hippocrateaceae) and radical scavenging activities of principal constituents.
Two new friedelane-type triterpenes, salasones D and E, a new norfriedelane-type triterpene, salaquinone B, and a new polyacylated eudesmane-type sesquiterpene, salasol B, were isolated from the stems of Salacia chinensis LINN. (S. prinoides DC., Hippocrateaceae) collected in Thailand. Their stereostructures were elucidated on the basis of chemical and physicochemical evidence. Some norfriedelane-type triterpene, lignan, and catechin constituents were found to show radical scavenging activity. (+info)
Different modes of potentiation by beta-eudesmol, a main compound from Atractylodes lancea, depending on neuromuscular blocking actions of p-phenylene-polymethylene bis-ammonium derivatives in isolated phrenic nerve-diaphragm muscles of normal and alloxan-diabetic mice.
The essential moieties in p-phenylene-polymethylene bis-ammonium (PMBA) derivatives, C6H4[X(CH2)nN+R3]2, on the potentiating effects by beta-eudesmol, a main component of Atractylodes lancea, of their neuromuscular blockades were investigated in isolated phrenic nerve-diaphragm muscle preparations of normal and alloxan-diabetic mice. PMBA derivatives were separated into the following three groups based on the patterns of the potentiating effects: group I: PMBA-23 (n = 6, R = Me) and PMBA-24 (n = 6, R = Et); group II: PMBA-1 (n = 4, R = Me), PMBA-21 (n = 4, R = Et) and PMBA-2 (X = O, n = 3, R = Me); and group III: PMBA-31 (X = S, n = 3, R = Me), PMBA-3 (X = CO, n = 3, R = Me) and PMBA-4 (X = CHOH, n = 3, R = Me). The pretreatment with 80 microM beta-eudesmol for 60 min did not affect group I-induced neuromuscular blocking action, and it potentiated group II- and group III-induced ones. The potentiating effect of beta-eudesmol on group III was greater in diabetic muscles than in normal one and that on group II was to the same extent in both muscles. These results suggest that the four-methylene length of the side chains in normal muscles and the hydrophilic moieties adjacent to a phenylene ring in diabetic muscles are related to the potentiating effect by beta-eudesmol on PMBA derivatives. (+info)
Beta-eudesmol, a new sesquiterpene component in intact and organized root of chamomile (Chamomilla recutita).
Gas chromatography (GC) and GC-mass spectrometry are used to identify a new sesqiterpene, beta-eudesmol, which seems to be a characteristic essential oil component of the intact and in vitro organized root of chamomile [Chamomilla recutita (L.) Rauschert]. It is identified on three types of stationary phases by GC. The confirmation of identity is carried out by comparison of mass spectra with those reported in the literature and measured from a reference compound. The percentage evaluation of the oil component is made by area normalization, on the basis of three parallel measurements. Among the cultivated and wild chamomile species examined, the wild species from the areas of Szeghalom contain the highest quantity of beta-eudesmol (9.25% in the total essential oil). (+info)
Induction of apoptosis by yomogin in human promyelocytic leukemic HL-60 cells.
Yomogin is an active compound isolated from Artemisia princep, a traditional Oriental medicinal herb, which has been shown to inhibit tumor cell proliferation. In this study, we investigated the effects of yomogin on the cytotoxicity, induction of apoptosis, and putative pathways of its actions in human promyelocytic leukemia cells. Yomogin-treated HL-60 cells displayed several features of apoptosis, including DNA fragmentation, formation of DNA ladders in agarose gel electrophoresis, and externalization of annexin-V targeted phosphatidylserine residues. We observed that yomogin caused activation of caspase-8, caspase-9, and caspase-3. A general caspase inhibitor (z-VAD-fmk), caspase-8 inhibitor (z-IETD-fmk) and caspase-3 inhibitor (z-DEVD-fmk), almost completely suppressed the yomogin-induced DNA fragmentation. We further demonstrated that yomogin induced Bid cleavage, mitochondrial translocation of Bax from the cytosol, and cytochrome c release from mitochondria in a caspase-8-dependent manner. Taken together, our data indicate that yomogin is a potent inducer of apoptosis and facilitates its activity via caspase-8 activation, Bid cleavage, Bax translocation to mitochondria, and subsequent release of cytochrome c into the cytoplasm, providing a potential mechanism for the anticancer activity of yomogin. (+info)
Eudesmane sesquiterpenes from the aquatic fungus Beltrania rhombica.
From the ethyl acetate extract of the culture broth of Beltrania rhombica, two new eudesmane sesquiterpenes, named rhombidiol (1) and rhombitriol (2), were isolated and characterized along with five enantiomers of known sesquiterpenes: (-)-beta-eudesmol, (-)-pterocarpol, (-)-chrysanthemol, (-)-longilobol and (-)-5beta-hydroxy-beta-eudesmol. Their structures were determined by analysis of 1D and 2D NMR data and comparison of spectral data and physical data with those previously reported. (+info)
Two new sesquiterpene lactones with the sulfonic acid group from Saussurea lappa.
Two new sesquiterpene lactones with the unusual sulfonic acid group, 13-sulfo-dihydrosantamarine (1) and 13-sulfo-dihydroreynosin (2), have been isolated from the roots of Saussurea lappa C. Their structures, including the absolute configurations, were elucidated by spectroscopic methods. (+info)