Yu Shan

Two new nortriterpenoid saponins from Salicornia bigelovii Torr. and their cytotoxic activity.

Investigation of characteristic constituents of Salicornia bigelovii Torr. led to isolation of two new 30-nortriterpenoid glycosides, Bigelovii A (1), Bigelovii B (2), together with two known 30-nortriterpenoid glycosides 3-4 and three known oleanane-type triterpenoid glycosides 5-7. The structures of new compounds were elucidated by extensive 1D and 2D NMR, and MS spectroscopic analysis, and chemical evidences. All compounds were isolated for the first time from Chenopodiaceae. Thus compounds 1-4 were evaluated for their cytotoxicity and compouds 1, 3 showed moderate activity against four cell lines, HL-60 (promyelocytic leukemia), MCF-7 (breast carcinoma), HepG2 (liver carcinoma) and A549 (lung carcinoma), with IC(50) values of 6.18, 78.08, 13.64 and >100μM for 1; 31.87, >100, ~100, >100μM for 3, respectively.

Apoptosis and membrane permeabilisation induced by macranthoside B on HL-60 cells

Triterpene saponins are throught to be potential anti-tumour agents in many cell types. This study aims to evaluate the cytotoxic activity and mechanism of a triterpene saponin, macranthoside B (MB), isolated from Lonicera macranthoides Hand.-Mazz. (Caprifoliaceae). A cell viability assay showed that MB inhibited cell growth of a panel of six cancer cell lines, especially in human acute promyelocytic leukaemia HL-60 cells, with an IC50 value of 3.8u2009µmol. A hypodiploid cells assay and an annexin-V-FITC/PI double staining assay showed a significant increase of apoptosis in a dose-dependent manner on HL-60 cells both 24 and 48u2009h after MB treatment. MB-induced apoptosis was through the caspase-mediated pathway, by activation of caspase-3. Furthermore, a lactate dehydrogenase (LDH) release test suggested that an MB–cholesterol interaction led to the rearrangement of the lipid bilayer and to subsequent cell membrane impairment. Taken together, these findings demonstrate that MB may exhibit cytotoxic activity against HL-60 cells by inducing apoptosis via caspase-dependent pathways and also membrane permeabilisation.

New flavonoid-C-glycosides from Triticum aestivum

Two new flavonoid-C-glycosides named triticuside A (1a) and triticuside B (1b) were isolated from bran of Triticum aestivum L. The structures of the two new compounds were elucidated by spectral techniques including 1H NMR, 13C NMR as well as HSQC, HMBC, and COSY.

Amino-acid and mineral composition of Stellaria media

Stellaria media (L.) Vill. (Caryophyllaceae) is well known as an invasive weed in gardens, fields, and disturbed grounds in the world [1, 2], but this plant is also a Chinese traditional medicinal plant used for hundreds of years by the Chinese community, which shows very effective anti-inflammatory and antiviral activities [3]. In both Europe and North America, it also has a very long history of herbal use, which is particularly beneficial in the external treatment of kinds of itching skin conditions [4]. But not all of these uses are supported by scientific evidence. The goal of our work was to study the amino acid and mineral composition of the aerial part of S. media. Samples of raw material were collected during flowering in Nanjing Botanical Garden, Mem. Sun Yat-sen (China). We investigated the amino acid composition by using a Hitachi 835-50 mould automatic amino-acid analyzer. For this, the sample was extracted exhaustively with hot water, filtered, and evaporated to dryness in vacuo. The dry solid was treated with lithium citrate buffer (pH 2.2). Proteins were precipitated by sulfosalicylic acid solution (0.1 mL, 30%). The samples were centrifuged and analyzed. The qualitative amino-acid composition in the studied sample was determined from retention times using a standard mixture consisting of 24 amino acids as a standard. The quantitative amino acids content was calculated in mg/kg of sample. Table 1 gives the results. A total of 16 free amino acids were observed in S. media. Of these, 9 were essential (threonine, valine, methionine, isoleucine, leucine, phenylalanine, lysine, and histidine and arginine, which are not synthesized in children). Bound amino acids were determined after modified acid hydrolysis by HCI (5.7 N) at 130 C for 6 h. A total of 16 amino acids was observed in the sample. The total content of free essential amino acids in S. media was 0.85% (27.27% of the total free amino acids); that of bound essential amino acids was 7.39% (48.05% of the total bound amino acids). This indicated that proteins from the aerial part of S. media were complete. Glutamic acid dominated in the investigated sample. The macroand microelement compositions of the herb was established by inductively coupled plasma optical emission spectrometry (ICP-OES) using a Perkin–Elmer OPTIMA 4300DV spectrograph [5]. The employed method enabled the determination of 21 elements in the herb. Table 2 gives the results. The contents of toxic and potentially toxic elements decreased in the order Al > Ti > Ba > Ag > Pb, which were below the minimum acceptable concentrations [3]. The presence of essential amino acids and essential and biogenic chemical elements will determine the potential for S. media and preparations of it for treatment of many diseases that are due to their deficiency in the organism.

A New Lupane-Type Triterpenoid Saponin from Lonicera macranthoides

A new lupane-type triterpenoid saponin, named lonimacranthoside A1, was isolated from the flower buds of Lonicera macranthoides. The structure of lonimacranthoside A1 was elucidated as 3β-O-β-D-glucopyranosyl-(1u2009→u20094)-β-D-glucopyranosyl-(1u2009→u20093)-α-L-rhamnopyranosyl-(1u2009→u20092)-α-L-arabinopyranosyl-23-hydroxy-lup-20(29)-en-28-oic acid 28-O-β-D-glucopyranosyl-(1u2009→u20096)-β-D-glucopyranosyl ester (1) on the basis of spectral data and chemical evidence. This is the first reported occurrence of a lupane-type saponin in the plant.

New coumarin glucoside from Angelica dahurica

A new linear furanocoumarin glycoside named dahurin B (1) was isolated from the fresh roots and rhizomes of Angelica dahurica. The structure of the new compound was elucidated by spectral techniques including 1H NMR, 13C NMR, as well as HSQC, HMBC, and COSY.

Macranthoside B Induces Apoptosis and Autophagy Via Reactive Oxygen Species Accumulation in Human Ovarian Cancer A2780 Cells

ABSTRACT Macranthoside B (MB), a saponin compound in Lonicera macranthoides, can block cell proliferation and induce cell death in several types of cancer cells; however, the precise mechanisms by which MB exerts its anticancer effects remain poorly understood. MB blocked A2780 human ovarian carcinoma cell proliferation both dose- and time-dependently. MB induced apoptosis, with increased poly (ADP-ribose) polymerase (PARP) and caspase-3/9 cleavage. MB also caused autophagy in A2780 cells, with light chain 3 (LC3)-II elevation. Inhibiting MB-induced autophagy with the autophagy inhibitor 3-methyladenine (3-MA) significantly decreased apoptosis, with a reduction of growth inhibition; inhibiting MB-induced apoptosis with the pan-caspase inhibitor Z-VAD-FMK did not decrease autophagy but elevated LC3-II levels, indicating that MB-induced autophagy is cytotoxic and may be upstream of apoptosis. Furthermore, MB increased intracellular reactive oxygen species (ROS) levels, with activated 5′ adenosine monophosphate-activated protein kinase (AMPK), decreased mammalian target of rapamycin (mTOR) and P70S6 kinase phosphorylation, and increased PARP and caspase-3/9 cleavage, and LC3-II elevation; treatment with the ROS scavenger N-acetyl cysteine and the AMPK inhibitor Compound C diminished this effect. Therefore, the ROS/AMPK/mTOR pathway mediates the effect of MB on induction of apoptosis via autophagy in human ovarian carcinoma cells.

Triterpenoids from the Herbs of Salicornia bigelovii.

A new nortriterpene saponin, 3-O-β-d-glucuronopyranosyl-30-norolean-12,20(29)-dien-23-oxo-28-oic acid, namely bigelovii D (11), was isolated from the hydroalcoholic extract of herbs of Salicornia bigelovii along with 10 known saponins (1–10). Their chemical structures were identified on the basis of spectroscopic analyses including two-dimensional NMR and a comparison with literature data. Some of these compounds showed potent antifungal activities in vitro. Compounds 3, 4, 5, 6, 7, 10 and 11 demonstrated potent inhibitory activities against Colletotrichum gloeosporioides and compound 11 displayed broad-spectrum inhibitory activity against Alternaria alternata, A. solani, Botrytis cinerea, C. gloeosporioides, Fusarium graminearum, F. verticilloides, Thanatephorus cucumeris and Sclerotinia sclerotiorum, with EC50 values ranging from 13.6 to 36.3 μg/mL.

Bigelovii A induces apoptosis of HL‑60 human acute promyelocytic leukaemia cells.

In the present study, the antitumor effects of the nor‑Oleanane type triterpene saponin, Bigeloviixa0A, isolated from Salicornia bigelovii Torr, were examined. Bigeloviixa0A was demonstrated to inhibit HL‑60 human acute promyelocytic leukaemia cell growth with an IC50 value of 2.15xa0µg/ml. In addition, Bigeloviixa0A promoted apoptosis in HL‑60 cells, as shown by apoptotic morphological changes and the hypodiploid cell assay. Apoptotic induction by Bigeloviixa0A was associated with the downregulation of Bcl‑2, the upregulation of Bax and the activation of caspase‑3, as demonstrated by RT‑PCR and western blot analysis. In addition, a lactate dehydrogenase release test indicated that Bigeloviixa0A may exhibit cytotoxic activity by the induction of cell membrane impairment. This study is the first to identify that Bigeloviixa0A exhibits potential antitumor activity and induces marked apoptosis and membrane permeabilisation in HL‑60 cells. Bigeloviixa0A may be a novel candidate for future cancer therapy.

Purification and characterization of a novel anti-HSV-2 protein with antiproliferative and peroxidase activities from Stellaria media

A novel antiviral protein, designated as Stellarmedin A, was purified from Stellaria media (L.) Vill. (Caryophyllaceae) by using ammonium sulfate precipitation, cation-exchange chromatography system. Gel electrophoresis analysis showed that Stellarmedin A is a highly basic glycoprotein with a molecular weight of 35.1 kDa and an isoelectric point of ∼8.7. The N-terminal 14-amino acid sequence, MGNTGVLTGERNDR, is similar to those of other plant peroxidases. This protein inhibited herpes simplex virus type 2 (HSV-2) replication in vitro with an IC50 of 13.18 µg/ml and a therapeutic index exceeding 75.9. It was demonstrated that Stellarmedin A affects the initial stage of HSV-2 infection and is able to inhibit the proliferation of promyelocytic leukemia HL-60 and colon carcinoma LoVo cells with an IC50 of 9.09 and 12.32 µM, respectively. Moreover, Stellarmedin A has a peroxidase activity of 36.6 µmol/min/mg protein, when guaiacol was used as substrate. To our knowledge, this is the first report about an anti-HSV-2 protein with antiproliferative and peroxidase activities from S. media.