[show abstract][hide abstract] ABSTRACT: The title compound, C(20)H(28)O(3), was isolated during our investigation into the chemical composition and pharmacological activity of Centipeda cunninghamii (DC.) A. Braun & Asch. (Asteraceae). The enanti-opure compound, a diterpene with a carbon skeleton, is composed of three six- and one five-membered rings in chair, twist-boat, half-chair and envelope conformations, respectively. Each mol-ecule makes one intra- and one inter-molecular O-H⋯O hydrogen bond in the crystal lattice, forming hydrogen-bonded chains along . The absolute configuration of the compound was assigned on the basis of optical rotation measurements.
[show abstract][hide abstract] ABSTRACT: Wheat bran has been widely recognised as a cancer preventive agent, although the mechanism of the protection is not yet fully understood. Some reports suggested that, for the protection, lipophilic phytochemicals from the bran were more important than the physiological function of bran fibre. Wheat bran lipophilic extracts were scrutinised using bioactivity-guided fractionation (HPLC) against the growth of human prostate adenocarcinoma (PC3) cells. The fractions containing unsaturated free fatty acid, phytosteroids and alkylresorcinols exerted high cytotoxic activity. Detailed research of the alkylresorcinol fraction isolated seven pure compounds, four of them with strong inhibitory properties against the growth of PC3 cells, including 5-heptadecylresorcinol (IC50 = 22.5 μg/ml), 5-(16-heneicosenyl)resorcinol (trans) (IC50 = 13.7 μg/ml), 5-(14-nonadecenyl)resorcinol (trans) (IC50 = 42.2 μg/ml) and 5-(2-oxotricosanyl)resorcinol (IC50 = 10.9 μg/ml). The alkylresorcinols in wheat bran were quantified using a Single Ion Monitoring (SIM) method developed on LC-MS. The active alkylresorcinols were found to be minor components in wheat bran, however, they exerted higher cytotoxic effects on cancer cells than the positive control chlorambucil (IC50 = 58.7 μg/ml). This research suggested that alkylresorcinols are important for the cancer preventive activity of wheat bran. Other lipophilic compounds such as some free unsaturated fatty acids and phytosteroids may also contribute to the anticancer activity.
[show abstract][hide abstract] ABSTRACT: A detailed investigation of the wood, leaf, branch and root oil of Eremophila mitchellii (Benth.) was carried out by a combination of GC-FID, GC-MS and NMR. The wood oil was composed predominantly of eremophilanes, a rare class of biologically active, bicyclic sesquiterpenoids. The root oil was also found to contain the eremophilanes together with the zizaene sesquiterpene, sesquithuriferone. 9-Hydroxy-1,7(11),9-eremophilatrien-8-one and the known 1(10),11-eremophiladien-9-one (eremophilone), 9-hydroxy-7(11),9-eremophiladien-8-one (2-hydroxyeremophilone), 8-hydroxy-11-eremophilen-9-one (santalcamphor), 8-hydroxy-10,11-eremophiladien-9-one, sesquithuriferone and 8-hydroxy-1,11-eremophiladien-9-one were purified and elucidated by NMR. Three approaches to the purification of the major eremophilanes from the wood oil are described. (+) Spathulenol, α-pinene, globulol, viridiflorene were the major constituents of the leaf oil. All of the essential oils and the eremophilanes exhibited cytotoxicity against P388D(1) mouse lymphoblast cells in-vitro.
[show abstract][hide abstract] ABSTRACT: Postprandial hyperglycaemia is a primary risk factor in the development of Type 2 diabetes. α-Glucosidase inhibitors that reduce postprandial hyperglycaemia have a key role in the treatment of Type 2 pre-diabetic states and also have the potential to reduce the progression to complications of diabetes. Epidemiological studies showed that risk for Type 2 diabetes mellitus was decreased with consumption of whole grains. The bran and germ of whole wheat are major components of whole grain consumption and are widely accepted as important ingredients in many low glycaemic index (GI) foods. In this study, the α-glucosidase inhibitory activity of wheat bran and germ was investigated. The active compounds were screened using an in vitro enzyme-inhibitory assay guided fractionation. Potent α-glucosidase inhibitory compounds from wheat germ were identified as phosphatidic acids, 1,2-dilinoleoylglycero-3-phosphate and 1-palmitoyl-2-linoleoyl-glycero-3-phosphate. The low GI property of whole grain wheat could be attributed to these α-glucosidase inhibitory phosphatidic acids, which have the potential to prevent or treat Type 2 diabetes.
[show abstract][hide abstract] ABSTRACT: Bioactivity-guided fractionation of an ethanolic extract of the rhizome of Pleuranthodium racemigerum, a tropical Zingiberaceae species from Northeastern Australia, resulted in the isolation and structural elucidation of 1-(4''-methoxyphenyl)-7-(4'-hydroxyphenyl)-(E)-hept-2-ene (1), a new diarylheptanoid related to curcumin. Compound 1 was a fairly potent inhibitor of prostaglandin E(2) production in 3T3 murine fibroblasts (IC(50) approximately 34 microM) and also displayed moderate cytotoxicity against this cell line (IC(50) = 52.8 microM). The compound also demonstrated cytotoxic activity against the P388D1 murine lymphoblast cell line (IC(50) = 117.0 microM) and four human cell lines: Caco-2 colonic adenocarcinoma (IC(50) = 44.8 microM), PC3 prostate adenocarcinoma (IC(50) = 23.6 microM), HepG2 hepatocyte carcinoma (IC(50) = 40.6 microM), and MCF7 mammary adenocarcinoma (IC(50) = 56.9 microM). The cytotoxicity of compound 1 closely resembled that of curcumin, in terms of both IC(50) values and dose-response curves.
Journal of Natural Products 03/2010; 73(4):743-6. · 3.29 Impact Factor
[show abstract][hide abstract] ABSTRACT: Eleven new bisresorcinols including four mixtures each of two isomers and one resorcinol/phloroglucinol derivative, together with five known resorcinols have been isolated from the ethyl acetate extract of stems of Grevillea whiteana. The new compounds were identified as 4-(3-hydroxy-3-methylbutyl)grebustol-B (10a), 4'-(3-hydroxy-3-methylbutyl)grebustol-B (10b), 4-(4-hydroxy-3-methylbutyl)grebustol-B (2a) and 4'-(4-hydroxy-3-methylbutyl) rebustol-B (2b), 2,2-dimethyldihydropyrano grebustol-B (11a) and iso-2,2-dimethyldihydropyranogrebustol-B (11b), 2,2-dimethyl-3xi-hydroxydihydropyranogrebustol-B (7a) and iso-2,2-dimethyl-3xi-hydroxydihydropyranogrebustol-B (7b), 15-(2-(4-hydroxy-3-methylbutyl)-resorcinol-5-yl)-1-(phloroglucinolyl)-9(Z)pentadecen-one (whiteanone) (4), 5,5'-(hexadecan-diyl)bisresorcinol (12) and 2-methyl-5,5'-(8(Z)-hexadecen-1,16-diyl)bisresorcinol (9). This is the first record of pyranobisresorcinols in the genus and the first report of a phloroglucinol terminal phenolic unit in any Grevillea species.
[show abstract][hide abstract] ABSTRACT: Seven new bisresorcinol derivatives, together with four known resorcinols, have been isolated from the ethyl acetate extract of the stems of Grevillea floribunda. Five of the new compounds (floribol A–E) were characterized as bisnorstriatol derivatives substituted at C-2 of both resorcinol units with variously modified prenyl (3-methylbut-2-enyl) units. The remaining two new compounds are similarly substituted derivatived of grebustol-B.
Centre for Phytochemistry and Pharmacology Papers. 01/2009;
[show abstract][hide abstract] ABSTRACT: Here, 45 Chinese herbs that regulate blood circulation were analyzed for antioxidant activity using the oxygen radical absorbance capacity (ORAC) assay. A recent publication by Ou et al. identified a close relationship between in vitro antioxidant activity and classification of Chinese herbs as yin or yang. The 45 Chinese herbs in this study could be assigned the traditional characteristics of natures (cold, cool, hot and warm), flavors (pungent, sweet, sour, bitter and salty) and functions (arresting bleeding, promoting blood flow to relieve stasis, nourishing blood and clearing away heat from blood). These characteristics are generalized according to the theory of yin and yang. We identified a broad range, 40-1990 micromol Trolox Equivalent/g herbs, of antioxidant activity in water extracts. There was no significant correlation between ORAC values and natures or functions of the herbs. There was a significant relationship between flavors and ORAC values. Bitter and/or sour herbs had the highest ORAC values, pungent and/or sweet herbs the lowest. Other flavors had intermediate values. Flavors also correspond with the yin/yang relationship and our results are supportive of the earlier publication. We reported for the first time antioxidant properties of many Chinese herbs. High antioxidant herbs were identified as Spatholobus suberectus vine (1990 micromol TE/g), Sanguisorba officinalis root (1940 micromol TE/g), Agrimonia pilosa herb (1440 micromol TE/g), Artemisia anomala herb (1400 micromol TE/g), Salvia miltiorrhiza root (1320 micromol TE/g) and Nelembo nucifera leaf (1300 micromol TE/g). Antioxidant capacity appears to correlate with the flavors of herbs identified within the formal TCM classification system and may be a useful guide in describing their utility and biochemical mechanism of action.
Evidence-based Complementary and Alternative Medicine 01/2009; 5(4):429-34. · 1.72 Impact Factor
[show abstract][hide abstract] ABSTRACT: To investigate the effects of 50% ethyl alcohol (EtOH) extracts from Danzhi Xiaoyao Pill (, DXP) on the proliferation of MCF-7 human breast cancer cells and potential mechanisms.
ATP-Lite assay was performed to test the proliferation of the MCF-7 breast cancer cell line; and antioxidant activity was measured by the oxygen radical absorbance capacity (ORAC). The effects of DXP on nitric oxide (NO) production were tested by lipopolysaccharide (LPS)-stimulated RAW 264.7 murine macrophages using the Griess reaction.
The 50% EtOH DXP extracts displayed a cytotoxic response on MCF-7 cells at 0.10, 0.25 and 0.50 mg/mL dose-dependently with the proliferation inhibited by more than 85%. The ORAC value of the DXP was 820 micro moL Trolox equivalent/g, about 40% of the vitamin C value. DXP extracts had significant inhibitory effect on NO production at the concentration from 0.0625 mg/mL to 0.5 mg/mL (P<0.05, P<0.01).
The extracts of DXP could significantly inhibit the proliferation of MCF-7 cells, with the effect possibly related to its antioxidant activity and the inhibition of NO production.
Chinese Journal of Integrative Medicine 07/2008; 14(2):128-31. · 1.06 Impact Factor
[show abstract][hide abstract] ABSTRACT: The effects of Echinacea and several of its phytochemical components on NFkappaB expression by Jurkat cells (a human T-cell line) were investigated in vitro. In the absence of stimulation, Echinacea and its components exerted no significant effect on basal NFkappaB expression levels. In the presence of endotoxin (LPS), NFkappaB expression was decreased. However, this decrease was significantly reversed by treatment with cichoric acid, an Echinacea root extract (prepared from both Echinacea angustifolia and Echinacea purpurea) and the alkylamide fraction derived from this combination. For the phorbol myristate acetate stimulation of Jurkat cells, effects on NFkappaB expression were mixed. Depending on the concentration, cichoric acid and a 2,4-diene alkylamide significantly induced NFkappaB levels, whereas a 2-ene alkylamide caused a significant inhibition. In contrast, both the Echinacea and the mixed alkylamide fraction exerted no effect. The alkylamide results indicate that the two basic forms of these compounds present in Echinacea may have opposing effects. These opposing effects demonstrate the importance of a knowledge, not only of the phytochemical make-up of a herbal preparation, but also of the actions of each component and the consequences of differing relative amounts in the preparation being investigated.
[show abstract][hide abstract] ABSTRACT: Danzhixiaoyao Wan (DW) is a common 10 herbs formulation in China for regulating several clinical conditions affecting women. This research tried to explain one of DW's functions, purging heat, using in vitro pharmacological analyses. The whole formulation and each single herb of DW were compared based on antioxidant activity with the oxygen radical absorbance capacity (ORAC) assay, and for their inhibitory effect (IE) on nitric oxide (NO) production by lipopolysaccharide (LPS)-activated RAW 264.7 macrophages with the Griess assay. The results showed that DW as a whole formulation had both antioxidant activity and an IE on NO production, while the individual herb component of DW varied in their ORAC values and inhibition of NO production. The ORAC value of the whole DW was 450 mumol TE g(-1). The order of antioxidant (ORAC) activity of the single herbs was: Mentha haplocalyx (1352 mumol TE g(-1)) > Glycyrrhiza uralensis (1184 mumol TE g(-1)) > Gardenia jasminoides (1129 mumol TE g(-1)) > Paeonia suffruticosa (465 mumol TE g(-1)), with the contributions being additive rather than synergistic. The production of nitrite by stimulated RAW 264.7 murine macrophages (unstimulated: 0.5 +/- 0.1 muM versus LPS: 38.9 +/- 2.3 muM) was significantly inhibited (P < 0.05) by M. haplocalyx, G. jasminoides, Bupleurum chinense and Paeonia lactiflora. DW as a whole had an IE on NO production, but this was not significant. The single herb M. haplocalyx had the highest ORAC value and the highest IE on NO production, followed by G. jasminoides. Both of these herbs have the 'purging heat' property in the theory of traditional Chinese medicine and this property of the samples may be correlated with the antioxidant activity and IE on NO production.
Evidence-based Complementary and Alternative Medicine 01/2008; 4(4):425-30. · 1.72 Impact Factor
[show abstract][hide abstract] ABSTRACT: The ability of Echinacea and its components to alter the immune response was examined in vitro in a macrophage cell line under either basal or immunostimulated conditions. Potential immunostimulatory and inflammatory activity was determined using a nuclear transcription factor (NFkappaB) expression, tumour necrosis factor alpha (TNFalpha) and nitric oxide (NO) production as biomarkers. In the absence of alternate stimulation, the only significant effects seen were a decrease in NFkappaB expression by a 2-ene alkylamide ((2E)-N-isobutylundeca-2-ene-8,10-diynamide (1)) and a decrease in TNFalpha levels by cichoric acid and an Echinacea alkylamide fraction (EPL AA). When the cells were stimulated by lipopolysaccharide (LPS), inhibition of the increased NFkappaB expression levels was caused by cichoric acid, an Echinacea preparation (EPL), EPL AA and a 2,4-diene ((2E,4E,8Z,10Z)-N-isobutyldodeca-2,4,8,10-tetraenamide (2)). Increases in TNFalpha levels were inhibited by cichoric acid, EPL and EPL AA but enhanced by 1 in the presence of LPS, while only EPL AA was able to inhibit the stimulated increases in NO. When using phorbol myristate acetate to stimulate the cells, NFkappaB and NO levels were unaffected by Echinacea or its components while only cichoric acid and 2 inhibited TNFalpha levels. Although cichoric acid was found to have an effect, it is probably not an important contributor to the Echinacea modulation of the immune response in vivo, as it is not bioavailable. Echinacea appears to attenuate the response of macrophages to an immune stimulus and its combination of phytochemicals exhibits different pharmacological properties to one or more of the isolated major individual components.
[show abstract][hide abstract] ABSTRACT: Exhaustive hydro-distillation of the leaves of Piper aduncum and fruits of Piper gibbilimbum (Piperaceae) afforded colorless and pale orange colored oils in 0.35 and 0.30 % yields, respectively. Detailed chemical analysis by GC/MS indicated the volatile constituents of Piper aduncum to be composed of dill apiole (43.3%), beta-caryophyllene (8.2%), piperitione (6.7%) and alpha-humulene (5.1%), whilst the oil of P. gibbilimbum is dominated by the gibbilimbols A-D (74.2%), with the remaining major constituents being the terpenes camphene (13.6%) and alpha-pinene (6.5%).
[show abstract][hide abstract] ABSTRACT: Exhaustive hydro-distillation of the bark, heartwood and fruits of Cryptocarya massoy (Lauraceae) afforded pale yellow-coloured oils in 0.7, 1.2 and 1.0 % yields, respectively. Detailed chemical evaluation of these distillates using GC/MS revealed the major components in the bark and the heartwood oils to be the C-10 (5,6-dihydro-6-pentyl-2H-pyran-2-one) and C-12 (5,6-dihydro-6-heptyl-2H-pyran-2-one) massoia lactones, while the major fruit oil constituent was benzyl benzoate (68.3 %). The heartwood also contained trace amounts of the C-14 (5,6-dihydro-6-nonyl-2H-pyran-2-one) massoia lactone (1.4 %) and the saturated C-10 derivative delta-decalactone (2.5 %).