Triterpenoid saponins from Bellis sylvestris. 2. Structures of partially deacylated saponins.

Four saponins have been isolated from the herbal parts of Bellis sylvestris and the same, together with three further compounds, from the underground parts. The structures were elucidated by electrospray ionization mass spectrometry, including tandem mass spectrometry, and by 1D and 2D homonuclear and heteronuclear NMR spectroscopy. Two of the compounds are new saponins with the structures 3-O-beta-D-glucopyranosyl-2 beta, 3 beta, 23-trihydroxyolean-12-en-28-oic acid 28-O-beta-D-glucopyranosyl (1-->3)-[alpha-L-rhamnopyranosyl (1-->2)]-beta-D- glucopyranoside and 3-O-beta-D-glucopyranosyl-2 beta, 3 beta,16 alpha, 23-tetrahydroxyolean-12-en- 28-oic acid 28-O-alpha-L-rhamnopyranosyl (1-->3)-beta-D-xylopyranosyl(1-->4)-alpha-L- rhamnopyranosyl(1-->2)-[(E)-2-butenoic acid (1-->3)]-beta-D-fucopyranoside.

1 alpha,25-dihydroxyvitamin D3 inhibits cell growth and chondrogenesis of a clonal mouse EC cell line, ATDC5.

Here we report the effects of 1 alpha,25-dihydroxyvitamin D3 [1,25(OH)2D3] in vitro on the growth and chondrogenesis of a chondroprogenitor-like clonal mouse EC cell line, 10(-10) to 10(-7) M ATDC5. 1,25(OH)2D3 inhibited [3H]thymidine incorporation in undifferentiated chondroprogenitor-like ATDC5 cells in time- and dose-dependent manners. 1,25(OH)2D3 suppressed cartilage-nodule formation and the accumulation of cartilage-specific proteoglycan in ATDC5 cells in a dose-dependent manner.

Oleanene glycosides from seeds of Trifolium alexandrinum.

From the seeds of Trifolium alexandrinum, two new oleanene-type triterpene glycosides were isolated as their methyl esters, together with five known saponins. The structures of the isolated compounds were determined by NMR and mass spectral analyses.

Reversal of daunomycin and vinblastine resistance in multidrug-resistant P388 leukemia in vitro through enhanced cytotoxicity by triterpenoids.

Examined in vitro were the effects of some triterpenoids from Panax (Araliaceae) and Glycyrrhiza (Leguminosae) spp. on the sensitivity to daunomycin (DAU) and vinblastine (VBL) of adriamycin (ADM)-resistant P388 leukemia cells (P388/ADM), which were resistant to multiple anticancer drugs. Quasipanaxatriol, 20(S)-protopanaxatriol, ginsenoside Rh2, and compound K greatly enhanced the cytotoxicity of the anti-cancer drugs in P388/ADM cells.

Antiallergic dimeric prenylbenzoquinones from Ehretia microphylla.

The ethyl acetate-soluble portion of the MeOH extract of Ehretia microphylla showed inhibitory activity on exocytosis in antigen-stimulated rat basophils. The bioassay-guided separation of this fraction afforded five biologically active compounds. By means of chemical and spectroscopic methods, the structures of these compounds, which include microphyllone, a unique dimeric prenylbenzoquinone, and its congeners, were elucidated.

Spirostanol glycosides from Peliosanthes sinica.

Three new spirostanol glycosides, peliosanthosides A--C, were isolated from the whole plants of Peliosanthes sinica, along with two known ones. Their structures were elucidated by means of chemical and spectral evidence.

Oleanane and ursane glycosides from Schefflera octophylla.

Twelve triterpene glycosides were isolated from the bark of Schefflera octophylla of Vietnamese origin. Three of them were identified as asiaticoside, cauloside D and 3 alpha-hydroxyurs-12-ene-23,28-dioic acid 28-O-alpha-L-rhamnopyranosyl (1-->4)-beta-D-glucopyranosyl(1-->6)-beta-D-glucopyranoside. The structures of nine new glycosides were elucidated by chemical and spectroscopic evidence.

Triterpenoid saponins from Bellis sylvestris, I. Structures of the major deacylsaponins.

Two major saponins from Bellis sylvestris have been isolated and their structures determined, mainly by high-field nmr spectroscopy. One of these [2] was identical with bellissaponin BS1 from Bellis perennis, while the second is a new triterpenoid saponin [1], named besysaponin C12, and identified as 3-O-alpha-L-rhamnopyranosyl-2 beta,3 beta,16 alpha,23-tetrahydroxyolean-12-en-28-oic acid 28-O-beta-D-xylopyranosyl(1-->4)-alpha-L-rhamnopyranosyl(1-->2)-beta-D- fucopyranoside.

Dolabellane diterpene glucosides from Chrozophora obliqua.

Three novel dolabellane diterpene glucosides and one new dolabellane diterpenoid have been isolated from Chrozophora obliqua. Their structures were elucidated by various NMR and mass spectral techniques.

A sterol with an unusual side chain from Anoectochilus koshunensis.

A new sterol with a non-conventional side chain has been isolated from the whole plant of Anoectochilus koshunensis, together with four known sterols, a megastigmane glucoside and 2'-deoxyadenosine. The structure of the new sterol was elucidated as 26-methylstigmasta-5,22,25, (27)-trien-3 beta-ol based on chemical and detailed spectroscopic evidence.

Production and characterization of an antibody against the human bone GLA protein (BGP/osteocalcin) propeptide and its use in immunocytochemistry of bone cells.

We have generated and characterized an antibody that recognizes the C-terminal sequence of the propeptide of human bone GLA protein (BGP/osteocalcin)(amino acid -26 to -1, with +1 being the amino terminus of the mature protein). The range of sensitivity of the antibody, as determined by enzyme-linked immunosorbent assay (ELISA), was 0.5-250 ng/ml.

Inhibitory effect of some triterpenoid saponins on glucose transport in tumor cells and its application to in vitro cytotoxic and antiviral activities.

The effects of some triterpenoid saponins on glucose transport in Ehrlich ascites tumor (EAT) cells were examined by measuring 2-deoxy-D-glucose (2-DG) uptake. The correlation of the effects with those on the growth of a human T-cell line (MT-4) and the replication of human immunodeficiency virus in MT-4 cells was also studied. Chikusetsusaponin Ia isolated from rhizomes of Panax japonicus C.

Inhibitory effects of cucurbitane triterpenoids on Epstein-Barr virus activation and two-stage carcinogenesis of skin tumors.

To search for possible anti-tumor-promoters, we carried out a primary screening of 21 cucurbitane triterpenoids using an in vitro assay system. Of these triterpenoids, scandenoside R6 (6), 23,24-dihydrocucurbitacin F (14), 25-acetyl-23,24-dihydrocucurbitacin F (15), 2-O-beta-D-glucopyranosyl-23,24-dihydrocucurbitacin F (17) and cucurbitacin F (18) exhibited significant inhibitory effects on Epstein-Barr virus (EBV) activation induced by the tumor promoter, 12-O-tetradecanoyl-phorbol-13-acetate (TPA). Further, compounds 14 and 17 exhibited remarkable anti-tumor-promotion effects on mouse skin tumor promotion in an in vivo two-stage carcinogenesis test.

Interactions of ginseng extract, ginseng separated fractions, and some triterpenoid saponins with glucose transporters in sheep erythrocytes.

The effects of Panax ginseng extract, ginseng saponins, and some other triterpenoid saponins on glucose uptake were examined by using sheep erythrocytes. Initial rates of glucose transport were determined by measurements of 2-deoxy-D-glucose (2-DG) uptake. From kinetic analysis apparent Km and Vmax values of facilitated glucose transport in sheep erythrocytes were calculated as 2.

Effective intervention of low peak bone mass and bone modeling in the spontaneous murine model of senile osteoporosis, SAM-P/6, by Ca supplement and hormone treatment.

SAM-P/6 is a recently developed strain of osteoporotic mice. In this study we tried to determine whether calcium, vitamin D3, parathyroid hormone (PTH), and estrogen modified the peak bone mass of young SAM-P/6 mice, and whether the effect of these medications persisted after treatment had been discontinued. Calcium supplement, PTH, and estrogen treatment increased the peak bone mass of SAM-P/6 mice.

Ultrastructural study of the A-W GC-bone interface after long-term implantation in rat and human bone.

The interface between apatite- and wollastonite-containing glass-ceramic (A-W GC) and bone after long-term implantation was studied by scanning and transmission electron microscopy (SEM and TEM) using rat and human specimens. First, particles of A-W GC (100-220 microns in diameter) were implanted into rat tibiae, and specimens were prepared for observation at 24, 48, 72, and 96 weeks after the operation. These long-term specimens showed an A-W GC-bone interface different from that at an earlier stage, which was investigated in our previous studies.

Modification of strain-specific femoral bone density by bone marrow-derived factors administered neonatally: a study on the spontaneously osteoporotic mouse, SAMP6.

SAMP6 is a recently developed strain of osteoporotic mice, and SAMP2 is a control for SAMP6 and has a higher peak bone mass. The bone mass of SAMP6 was increased until 2 months of age when a lysate of cells derived from the bone marrow of SAMP2 was injected at 1 or 4 days of age, but it was not increased when the lysate was injected at 21 days of age. No effect on bone mass was observed when lysates of other cells, bovine serum albumin or heat-inactivated lysate of bone marrow-derived cells of SAMP2, were injected.

Saponins from Vietnamese ginseng, Panax vietnamensis Ha et Grushv. collected in central Vietnam. III.

Five new dammarane saponins derived from four new aglycones were isolated from the rhizomes and roots of Panax vietnamensis Ha et Grushv. On the basis of physicochemical and spectral evidence, the structures of these compounds were established as 6-O-beta-D-glucopyranosyl 20(S),25-epoxydammarane-3 beta,6 alpha,12 beta,24 alpha-tetrol (1), 6-O-beta-D-xylopyranosyl-(1-->2)-beta-D-glucopyranosyl 20(S),25-epoxydammarane-3 beta,6 alpha,12 beta,24 alpha-tetrol (2), 6-O-beta-D-glucopyranosyl dammarane-3 beta,6 alpha,12 beta,20(S),24 xi,25-hexol (5), 3-O-[beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranosyl]-20-O-beta-D- glucopyranosyl dammarane-3 beta,12 beta,20(S),24 xi,25-pentol (8) and 6-O-beta-D-xylopyranosyl-(1-->2)-beta-D-glucopyranosyl 20(S),24(S)-epoxydammarane-3 beta,6 alpha,12 beta,25 xi,26-pentol (10). The trivial names, vina-ginsenoside-R10, -R11, -R12, -R13 and -R14, respectively, were assigned to the new saponins.

Saponins from Vietnamese Ginseng, Panax vietnamensis HA et Grushv. Collected in central Vietnam. II.

Further investigation on the saponin composition of rhizomes and roots of Panax vietnamensis HA et GRUSHV. has resulted in the isolation and structural elucidation of seven new dammarane saponins named vina-ginsenosides-R3 (12), -R4 (11), -R5 (16), -R6 (17), -R7 (6), -R8 (20), -R9 (22), together with the identification of six known saponins including 20-gluco-ginsenoside-Rf (10), ginsenoside-Rc (4), notoginsenoside-R6 (9), quinquenoside-R1 (5), gypenoside XVII (2) and majoroside F1 (21). The structures of the novel saponins were established on the basis of chemical and spectral evidence.

Diterpenoid glycosyl esters from Phlomis younghusbandii and P. medicinalis roots.

From the roots of Phlomis younghusbandii collected in Tibet, new furanolabdane-type diterpenoid glycosides named phlomisosides III and IV were isolated together with a known sweet furanolabdane-type diterpenoid glycoside, phlomisoside I. The structure of the common aglycone of phlomisosides III and IV, which we have named phlomisoic acid, was established as 15,16-epoxy-8,13(16),14-labdatrien-19-oic acid by MS and NMR spectroscopy. Phlomisosides III and IV are tasteless and the structures of these were determined to be the beta-D-xylopyranosyl(1-->2)-beta-D-glucopyranosyl and the alpha-L-rhamnopyranosyl(1-->2)-beta-D-glucopyranosyl ester of phlomisoic acid by chemical and spectroscopic methods, respectively.

Screening of plant constituents for effect on glucose transport activity in Ehrlich ascites tumour cells.

The effect of plant extracts on D-glucose uptake by Ehrlich ascites tumour cells was examined. Among the 23 extracts of medicinal plants, five samples inhibited, and six samples activated, the uptake significantly. From one of the active plants, Lagerstroemia speciosa, two triterpenoids, colosolic acid and maslinic acid were isolated.