Geranylated or prenylated flavonoids from Cajanus volubilis.

Five new flavonoid derivatives, cajavolubones A-E (1-5), along with six known analogues (6-11) were isolated from Cajanus volubilis, and their structures were elucidated by spectroscopic analysis and quantum chemical calculations. Cajavolubones A and B (1 and 2) were identified as two geranylated chalcones. Cajavolubone C (3) was a prenylated flavone, while cajavolubones D and E (4 and 5) were two prenylated isoflavanones. Compounds 3, 8, 9 and 11 displayed cytotoxicity against HCT-116 cancer cell line.

Five new terpenoids from Viburnum odoratissimum var. sessiliflorum.

Five new terpenoids, including two vibsane-type diterpenoids (1, 2) and three iridoid allosides (3-5), together with eight known ones, were isolated from the leaves and twigs of Viburnum odoratissimum var.sessiliflorum. Their planar structures and relative configurations were determined by spectroscopic methods, especially 2D NMR techniques. The sugar moieties of the iridoids were confirmed as ß-D-allose by GC analysis after acid hydrolysis and acetylation. The absolute configurations of neovibsanin Q (1) and dehydrovibsanol B (2) were determined by quantum chemical calculation of their theoretical electronic circular dichroism (ECD) spectra and Rh2(OCOCF3)4-induced ECD analysis. The anti-inflammatory activities of compounds 1, 3, 4, and 5 were evaluated using an LPS-induced RAW264.7 cell model. Compounds 3suppressed the release of NO in a dose-dependent manner, with an IC50 value of 55.64 µmol·L-1. The cytotoxicities of compounds 1-5 on HCT-116 cells were assessed and the results showed that compounds 2 and 3 exhibited moderate inhibitory activities with IC50 values of 13.8 and 12.3 µmol·L-1, respectively.

Geranyl phenyl ethers from Illicium micranthum and their anti-HBV activity.

Fourteen new geranyl phenyl ethers (1-14) along with three known compounds (15-17) were isolated from Illicium micranthum, and their structures were elucidated by comprehensive spectroscopic methods. Illimicranins A-H (1-8) were characterized as geranyl vanillin ethers, while 9 and 10 were dimethyl acetal derivatives. Illimicranins I and J (11 and 12) were rare geranyl isoeugenol ethers. Illimicranins K and L (13 and 14) represented the first example of geranyl guaiacylacetone ether and geranyl zingerone ether, respectively. Compounds 1, 2 and 15 exhibited anti-HBV (hepatitis B virus) activity against HBsAg (hepatitis B surface antigen) and HBeAg (hepatitis B e antigen) secretion, and HBV DNA replication.

Lignans and Neolignans with Antioxidant and Human Cancer Cell Proliferation Inhibitory Activities from Cinnamomum bejolghota Confirm Its Functional Food Property.

In the aim to evaluate the functional food property of Cinnamomum bejolghota, seven new lignans and neolignans, bejolghotins A-G (1-4 and 9-11), along with 14 known ones (5-8 and 12-21), were isolated and their structures including absolute configurations were elucidated by extensive spectroscopic data and electronic circular dichroism (ECD) analyses. All of the isolates were tested for antioxidant and human cancer cell proliferation inhibitory activities. Twenty compounds showed comparable antioxidant activity to the positive controls, and three significantly inhibited the growth of three cancer cell lines HCT-116, A549, and MDA-MB-231 with IC50 values of 0.78-2.93 µM, which confirmed its health benefits.

Anti-hepatitis B virus activity of swertisin isolated from Iris tectorum Maxim.

ETHNOPHARMACOLOGICAL RELEVANCE: Iris tectorum Maxim (I. tectorum, Yuan Wei in Chinese) is a common and traditional Chinese medicinal herb that be used to treat liver-related diseases. However, the anti-HBV activity of I. tectorum and its isolates has not been systemically studied. AIM OF THE STUDY: To screen the active part of I. tectorum and systemically evaluate their anti-HBV activity. MATERIALS AND METHODS: In this study, a series of compounds from I. tectorum were evaluated for their ability to inhibit HBV replication. Swertisin showed a significant inhibitory function on HBV replication. Then, the suppression effect of different concentrations of swertisin in HBsAg, HBeAg and HBV DNA level in HepG2.2.15 cells and HBV-infected HepG2-NTCP cells were comprehensive evaluated, respectively. Moreover, the anti-HBV effects of swertisin were confirmed in HBV transgenic mice model. RESULTS: Among these compounds, swertisin strongly inhibited the HBsAg, HBeAg and HBV DNA level in a dose-dependent manner in HepG2.2.15 cells and HBV-infected HepG2-NTCP cells. Furthermore, swertisin showed a significant inhibition role on HBV replication in HBV transgenic mice model, the inhibition effect of which was enhanced when combined with ETV. CONCLUSIONS: We have identified that swertisin can inhibit HBeAg and HBsAg production, as well as HBV DNA in vitro and in vivo. This study show that we may found a novel compound isolated from traditional Chinese medicines with potent anti-HBV function.

(±)-Meliviticines A and B: Rearranged prenylated acetophenone derivatives from Melicope viticina and their antimicrobial activity.

Two new prenylated acetophenone derivatives racemates, meliviticines A (1) and B (2) with unprecedented rearranged skeletons, were isolated from Melicope viticina. Subsequent chiral resolution led to the separation of two pairs of enantiomers, (±)-meliviticines A (1a/1b) and (±)-meliviticines B (2a/2b). Their structures including absolute configurations were elucidated by extensive spectroscopic data, electronic circular dichroism analysis, and X-ray crystallography. A plausible biosynthetic pathway of 1 and 2, involving ring cleavage and rearrangement of the prenylated acetophenone backbone was proposed. All the isolates showed moderate antimicrobial activities with MIC values of 25-50 µg/mL against several bacterial and fungal strains.

Cytotoxic arylalkenyl α,ß-unsaturated δ-lactones from Cryptocarya brachythyrsa.

Three new arylalkenyl α,ß-unsaturated δ-lactones, cryptobrachytones A-C (1-3), together with one known analogue kurzilactone (4), were isolated from the leaves and twigs of Cryptocarya brachythyrsa. Their structures were elucidated based on extensive spectroscopic data and electronic circular dichroism (ECD) analysis. All the isolates were evaluated in vitro for anti-proliferative activity against a panel of five human cancer cell lines and one human normal cell, respectively, and the results showed 1, 2 and 4 possessing significant selective cytotoxicity toward the human cancer cell lines with IC50 values from 5.41 to 15.43 µM. This is the first study for C. brachythyrsa.

Two spiroketal derivatives with an unprecedented amino group and their cytotoxicity evaluation from the endophytic fungus Pestalotiopsis flavidula.

Two new spiroketal derivatives with an unprecedented amino group, 2'-aminodechloromaldoxin (1) and 2'-aminodechlorogeodoxin (2), along with one known analogue dechloromaldoxin (3), were isolated from the plant endophytic fungus Pestalotiopsis flavidula. Their structures were elucidated on the basis of extensive spectroscopic analysis. The purification was cytotoxicity-guided which indicated the extract, fractions and compounds were evaluated in vitro for anti-proliferative activity against a panel of human cancer cell lines. The results showed compounds 1 and 2 with moderate cytotoxicity while 3 was inactive, which suggested -NH2 group might play a very important role for their cytotoxicity. This is the first study for P. flavidula and the first time to report the spiroketal derivatives as alkaloids from the Pestalotiopsis genus.

Sesquiterpenoid Lactones in Tanacetum huronense Inhibit Human Glioblastoma Cell Proliferation.

Tanacetum huronense (Lake Huron tansy), which is native to the upper Midwest region of USA and Canada, was examined for the presence of anticancer compounds using an in vitro human tumor cell proliferation inhibition assay, with glioblastoma derived cell line U-87 MG. Bioassay-directed purification of the ethyl acetate extract of the aerial portion of this plant identified six active sesquiterpenoid lactones (1-6). Among these, compounds 5 and 6 are new structural analogs. One of the most abundant isolates, tanacin (4), exhibited the greatest inhibition with an IC50 value of 4.5 µg/mL.

Phenanthrenes in Chinese Yam Peel Exhibit Antiinflammatory Activity, as Shown by Strong in Vitro Cyclooxygenase Enzyme Inhibition.

Chinese yam (Dioscorea opposita), peeled or whole, is a popular food item that is considered to be healthy. Often, the yam is peeled before cooking. However, it is also consumed with peel. Therefore, in this study, the peel of this yam was extracted sequentially with n-hexane, ethyl acetate and methanol, and studied for its health-benefits, using in vitro bioassays. Bioactivity-guided purifications of extracts of the peel afforded phenanthrenes (1-4), as characterized- by spectroscopic methods. Phenanthrene I is a novel analogue. The extracts and isolates were tested for antiinflammatory activity using cyclooxygenase enzyme (COX- I and -2) inhibitory assays. All phenanthrenes isolated from the yam peel showed higher inhibition of COX enzymes than the over-the-counter nonsteroidal anti-inflammatory drugs (NSAIDs) aspirin, ibuprofen and naproxen.

Antioxidant and Antiinflammatory Compounds in Nutmeg (Myristicafragrans) Pericarp as Determined by in vitro Assays.

Nutmeg, Myristicafragrans, is known for its culinary and medicinal values. The nutmeg pericarp, abundant during the production of the seed, is also used in food and beverage preparations. In this study, the pericarp of M. fragrans was evaluated for its bioactive components using in vitro antioxidant and antiinflammatory assays. The hexane, ethyl acetate and methanolic extracts inhibited lipid peroxidation (LPO) by 82.5, 70.1 and 73.2%, and cyclooxygenase enzymes COX-1 by 44, 44 and 42% and COX-2 by 47, 41 and 36%, respectively, at 100 microg/mL. The bioassay-guided purifications of extracts yielded 20 compounds belonged to neolignans (0.13%), phenylpropanoids (0.28%), phenolic aldehyde (0.35%), triterpenoids (0.06%), triglycerides (0.20%), sugars (10.2%) and steroids (0.49%). Pure isolates 1-5 inhibited LPO by 70-99% and 3-12 inhibited COX-1 and -2 enzymes by 37-49%. This is the first report on the bioassay-guided characterization of constituents in nutmeg pericarp. Our results support the medicinal claims of nutmeg pericarp.

Evaluation of coriander spice as a functional food by using in vitro bioassays.

Coriander leaves and seeds are widely used as a condiment and spice. The use of roasted coriander seeds in food and beverage is very common. In this study, we investigated raw and roasted coriander seeds for their functional food quality using antioxidant, anti-inflammatory and human tumour cell proliferation inhibitory assays. The hexane and methanolic extracts of raw and roasted coriander seeds showed identical chromatographic and bioassay profiles. Chromatographic purification of the roasted seed extracts afforded tripetroselinin as the predominant component. Other isolates were petroselinic acid, 1,3-dipetroselinin, 2-C-methyl-d-erythritol, 2-C-methyl-d-erythritol 4-O-ß-d-glucopyranoside and linalool. Hexane and methanolic extracts of both raw and roasted seeds and pure isolates from them showed comparable antioxidant and anti-inflammatory activities to the positive controls used in the assays, and inhibited the growth of human tumour cells AGS (gastric carcinoma), DU-145 and LNCaP (prostate carcinoma), HCT-116 (colon carcinoma), MCF-7 (breast carcinoma) and NCI-H460 (lung carcinoma) by 4-34%, respectively.

Major constituents of Boswellia carteri resin exhibit cyclooxygenase enzyme inhibition and antiproliferative activity.

Aromatic gum from Boswellia carteri (olibanum oleogum) has long been used in Egyptian traditional medicine. Cyclooxygenase-1 (COX-1) enzyme inhibitory assay guided purification of the extracts of this resin resulted in five bioactive compounds, 3alpha-O-acetyl-8,24-dien-tirucallic acid (1), verticilla-4(20),7,11-triene (2), cembrene A (3), incensole acetate (4), and incensole (5). The pure isolates were investigated for their inhibitory effects on COX-1 and -2 enzymes and human tumor cell lines Hep-G2, MCF-7 and RAW 264.7. Compounds 1-5 inhibited COX-2 enzyme by 39.0, 32.7, 60.0, 46.3, and 49.8%, respectively. Furthermore, compound 2 showed an inhibitory concentration of 50% (IC50) at 9 microg/mL against Hep-G2 tumor cell line. This is the first report of COX-1 and -2 enzyme and tumor cell proliferation inhibitory effects of compounds 1 and 2.

Antioxidant and anti-inflammatory assays confirm bioactive compounds in Ajwa date fruit.

Ajwa, a variety of date palm Phoenix dactylifera L., produces the most expensive date fruits. Percentages of seed, moisture, fructose, glucose, soluble protein, and fiber in Ajwa dates were 13.24, 6.21, 39.06, 26.35, 1.33, and 11.01, respectively. The ethyl acetate, methanolic, and water extracts of Ajwa dates, active at 250 µg/mL in the MTT assay, inhibited lipid peroxidation (LPO) by 88, 70, and 91% at 250 µg/mL and cyclooxygenase enzymes COX-1 by 30, 31, and 32% and COX-2 by 59, 48, and 45% at 100 µg/mL, respectively. Bioactivity-guided purifications afforded compounds 1-7, in addition to phthalates and fatty acids. Compounds 1-3 showed activity at 100 µg/mL in the MTT assay; inhibited COX-1 enzyme by 59, 48, amd 50% and COX-2 enzyme by 60, 40, amd 39% at 50 µg/mL; and inhibited LPO by 95, 58, amd 66% at 100 µg/mL, respectively. The soluble protein fraction was also very active in both antioxidant and anti-inflammatory assays.

Antioxidant and anti-inflammatory compounds in the popular landscape plant Berberis thunbergii var. atropurpurea.

Berberis thunbergii var, atropurpurea. DC is one of the popular landscape plants in the USA, but until now lacked report on its chemical composition and biological properties. In this study, the antioxidant and anti-inflammatory activities of the methanolic extract and pure isolates of B. thunbergii var. atropurpurea, Crimson Pygmy, roots were evaluated using established bioassay procedures. The methanolic extract gave an absorbance value of 0.44 at 250 microg/mL concentration in the MTT assay. In addition, the extract inhibited lipid peroxidation (LPO) by 93% and the cyclooxygenase enzymes, COX-1 by 54 and COX-2 by 34%, at 100 microg/mL concentration. Therefore, a bioactivity-guided purification was carried out yielding pure isolates, out of which compounds 3-6 inhibited LPO by 34-66% at 100 microg/mL concentration. Similarly, compounds 1-6 inhibited COX-1 and -2 by 24-65 and 23-43% at 25 microg/mL concentration, respectively. This is the first report of the chemical constituents and biological activities of this plant.

Fluevirosines A-C: a biogenesis inspired example in the discovery of new bioactive scaffolds from Flueggea virosa.

Biogenesis inspired chemical investigation of a Chinese folk medicine, Flueggea virosa, returned three unprecedented C,C-linked trimeric Securinega alkaloids, fluevirosines A-C (1-3). Their absolute structures were characterized on the basis of spectroscopic data and computational analysis. Compounds 2 and 3 showed inhibition against the splicing of XBP1 mRNA.

Sesquiterpenes from Dysoxylum oliganthum and Dysoxylum excelsum.

Three new sesquiterpenes (1-3), (6R,7S,11R,10S)-15-hydroxy-sesquisabinene hydrate (1), (6R,7R,11S,10S)-15-hydroxy-sesquisabinene hydrate (2), and (6R,7R,10S)-15-hydroxy-zingiberenol (3), along with three known compounds, were isolated from the stems of Dysoxylum oliganthum; and three new isodaucane (salvionane) sesquiterpenes, namely isodauc-6-ene-10ß,14-diol (4), 4-epi-isodauc-6-ene-10ß,14-diol (5), and 4-epi-6α,10ß-dihydroxy-artabotrol (6) together with 15 known compounds were isolated from the twigs and leaves of D. excelsum. Their structures were established on the basis of extensive spectroscopic analysis and chemical shifts. The absolute configuration of C-10 in compounds 1-3 of a rare class was determined by using Snatzke's method.

Daphnane-type diterpenoids from Trigonostemon howii.

Nine new daphnane-type diterpenoids (1-9), named trigohownins A-I, and four known analogues were isolated from Trigonostemon howii. Their structures were elucidated on the basis of extensive NMR and MS analyses. Trigohownins A (1) and D (4) exhibited moderate cytotoxic activity against the HL-60 tumor cell line, with IC50 values of 17.0 and 9.3 µM, respectively.

Limonoids and Diterpenoids from Toona ciliata Roem. var. yunnanensis.

Three new limonoids (toonaciliatins N-P, 1-3)and four new pimaradiene-type diterpenoids(toonacilidins A-D, 4-7) were isolated from the leaves and twigs of Toona ciliata Roem. var. yunnanensis.Their structures were elucidated on the basis of spectroscopic methods. Toonacilidin B(5)showed moderate inhibitory activity against H. pylori-SS1 with an MIC of 50 µg/mL.

Onoceranoid-type triterpenoids from Lansium domesticum.

A rare class of onoceranoid-type triterpenoids, represented by lamesticumin A (1), the ethanolysis product of lamesticumin A (2), lamesticumins B-F (3-7), lansic acid 3-ethyl ester (8), and ethyl lansiolate (9), along with four known analogues were isolated from the twigs of Lansium domesticum. Their structures were elucidated on the basis of extensive spectroscopic analysis, and the absolute configuration of C-21 in compound 7 was assigned by using Snatzke's method. Compounds 1-9 exhibited moderate antibacterial activity against Gram-positive bacteria.