One novel alkaloid from the stems of Tinospora crispa.

The 6-methoxy-cannabisin I (1), a new alkaloid, together with five known compounds oleraisoindole A (2), cannabisin F (3), apigenin (4), syringin (5) and ethyl-syringin (6) were isolated from Tinospora crispa stems. Their structures were identified by the analysis of spectroscopic data. Compound 2 was isolated from T. crispa for the first time. Anti-inflammatory activity of compound 1 was detected against NO production in LPS-activated RAW 264.7 macrophages. However, no activity was observed.

Identification of a seven autophagy-related gene pairs signature for the diagnosis of colorectal cancer using the RankComp algorithm.

Based on the colorectal cancer microarray sets gene expression data series (GSE) GSE10972 and GSE74602 in colon cancer and 222 autophagy-related genes, the differential signature in colorectal cancer and paracancerous tissues was analyzed by RankComp algorithm, and a signature consisting of seven autophagy-related reversal gene pairs with stable relative expression orderings (REOs) was obtained. Scoring based on these gene pairs could significantly distinguish colorectal cancer samples from adjacent noncancerous samples, with an average accuracy of 97.5% in two training sets and 90.25% in four independent validation GSE21510, GSE37182, GSE33126, and GSE18105. Scoring based on these gene pairs also accurately identifies 99.85% of colorectal cancer samples in seven other independent datasets containing a total of 1406 colorectal cancer samples.

Alpinia hainanensis Rhizome Extract Ameliorates Dextran Sulfate Sodium-Induced Ulcerative Colitis: Active Ingredient Investigation and Evaluation.

Alpinia hainanensis is an important food spice and ethnic medicine in Southwest China. In this study, we found that the EtOAc-soluble fraction (AHE) of the A. hainanensis rhizome ethanol extract could ameliorate dextran sulfate sodium-induced ulcerative colitis (UC). To explore active constituents, five pairs of previously unreported enantiomers (1-5), together with nine known ones (6-14), were obtained. Structural characterization was achieved by comprehensive spectroscopic methods. Compounds 1 and 2 were new curcumin-butyrovanillone hybrids featuring a rare structural fragment of 2,3-dihyrofuran. The anti-inflammatory activities of isolates were evaluated, and the results indicated that compounds (-)-1, (-)-3, 6, 9, 11, and 12 significantly inhibited the nuclear factor-κB signaling pathway. These findings indicate the major active fraction of the A. hainanensis rhizome ethanol extract enriched with diarylheptanoids, flavonoids, phenolics, and their hybrid mixtures, which could be developed as a nutritional and dietary supplement for treating UC.

Two new monoterpenoid indole alkaloids from Mappianthus iodoides stems.

Two previously unreported monoterpenoid indole alkaloids, 19(20)E-5-carboxymethylvallesiachotamine (1) and 19(20)Z-5-carboxymethylvallesiachotamine (2), along with five known indole alkaloids (3-7) were isolated from Mappianthus iodoides stems. Their structures were characterized by extensive spectroscopic data. Among these isolates, compounds 1 and 2 were the two new Δ19(20) geometric isomers. The anti-inflammatory activities in vitro of all isolated compounds were evaluated using NO assay.[Formula: see text].

A novel pentacyclic triterpene from the canes of Uncaria sessilifructus (Rubiaceae).

One novel pentacyclic triterpene, 24-dimethoxymethyl-3ß,6ß,19α- trihydroxy -12-en-28-oic acid (1), along with six known compounds 2-7, were isolated from the canes of Uncaria sessilifructus Roxb. Their structures were determined according to spectroscopic and spectrometric analysis. The anti-inflammatory activities of the isolated compounds (1-7) were scanned against NO production in LPS-activated RAW 264.7 macrophages by MTS assay, however no activities were observed.

Development of a strategy for a quick process for separation of volatile compounds in counter-current chromatography: purification of cinnamaldehyde from Cinnamomum cassia by high performance counter-current chromatography.

It is a challenge for many researchers to separate volatile compounds. In this study, we introduce a rapid and efficient method of separating target compound from the twigs of Cinnamomum cassia by high performance counter-current chromatography. Under the bioassay guidance, the total extract exhibited a potential activity against NO production in RAW 264.7 macrophages and the total extract was further separated by high performance counter-current chromatography. Cinnamaldehyde (1) was enriched by counter-current chromatography (CCC) with reversed-phase mode using n-hexane-ethyl acetate-methanol-water (1:1:1:1,v/v/v/v) as the solvent system. Further identification was achieved by high performance liquid chromatography (HPLC).

[Preparation of brazilein from Caesalpinia sappan by high performance countercurrent chromatography].

Brazilein is among the main chemical constituents of Caesalpinia sappan. It has diverse pharmacological activities. Modern pharmacological studies have shown that the compound has antitumor, anti-inflammatory, antibacterial, antioxidant, immunomodulatory, and other pharmacological activities. Brazilein is often used as a stain in various industries. The separation of brazilein by traditional column chromatography will not only result in contamination of the chromatographic column materials, but also lead to loss of the active ingredient. Countercurrent chromatography is an advanced liquid-liquid chromatographic separation technique. It has been widely used for natural product separation and isolation as it offers several advantages, such as low solvent consumption, a highly selective solvent system, and high recoveries. Typical countercurrent chromatography techniques include centrifugal partition chromatography (CPC), high-speed countercurrent chromatography (HSCCC), and high performance countercurrent chromatography (HPCCC). It is well known that choosing a suitable solvent system is vital in countercurrent separation. Therefore, two methods were introduced for choosing a suitable solvent system. One is the generally useful estimation of solvent systems (GUESS) method, which employs thin-layer chromatography (TLC) to identify a suitable solvent system with minimal labor for the rapid purification of target compounds, and another is the Shake-Flash method. The solvent system could be determined by observing the distribution of the sample in the upper and lower phases. Two kinds of solvent systems were screened using the TLC-GUESS and Shake-Flash methods, and tested through the analysis mode of the HPCCC instrument. The results showed that chloroform-methanol-water (4:3:2, v/v/v) was the optimal solvent system for HPCCC separation. A total of 15.2 mg of brazilein and 5.7 mg of caesappanin C were obtained from an ethyl acetate extract with high purities (95.6% and 89.0%, analyzed by HPLC) in one step using the preparation mode of HPCCC, the reversed-phase liquid chromatography mode with the apparatus rotated at 1600 r/min, a flow rate of 10 mL/min, separation temperature of 25℃, and detection wavelength of 285 nm. Their structures were determined by spectroscopic and spectrometric analyses. Brazilein stained the solid packing material in the column and was difficult to elute. The results showed that the use of HPCCC for the separation of brazilein can not only prevent the loss of target active ingredients in Caesalpinia sappan, but also shorten the separation and purification times and improve the operating efficiency. Therefore, HPCCC can be used for the separation and preparation of other pigment compounds in Caesalpinia sappan and other dye plants.

Two new steroidal saponins from Neolamarckia cadamba.

Two new steroidal saponins, ß-sitosterol-3-O-α-l-glucopyranoside (3) and ß-sitosterol-3-O-ß-d-glucopyranosyl-(1→6)-ß-d-glucopyranoside (4), were isolated and identified from the bark of Neolamarckia cadamba, along with 13 known compounds. Their structures were established on the basis of spectral data.

Countercurrent separation assisted identification of two mammalian steroid hormones in Vitex negundo.

Countercurrent separation (CCS) has been widely used for the separation of high abundance compounds. However, the identification of low abundance compounds, such as mammalian steroid hormones, from natural sources is still a challenging task. A mixture of 14 human steroid hormone reference compounds was prepared for the development of a CCS enrichment strategy. The TLC-based GUESS (Generally Useful Estimate of Solvent Systems) method along with partitioning experiments were implemented to develop a process for the enrichment of these low abundance compounds with CCS. The application of CCS to the steroid hormone enrichment of Vitex negundo extracts was demonstrated by the identification of progesterone and estriol. This method provides a CCS-driven strategy to mine plant sources for low abundance compounds.

Chemical constituents and anti-inflammatory activities of Maqian (Zanthoxylum myriacanthum var. pubescens) bark extracts.

In this study, 44 compounds in the petroleum ether extract of Maqian (Zanthoxylum myriacanthum var. pubescens) bark, a traditional Dai herbal medicine, were identified by GC-MS. Major components included 3(2H)-benzofuranone, asarinin and (dimethoxymethyl)-3-methoxy-benzene. A total of 18 compounds were isolated from the ethyl acetate extracts of Maqian bark by column chromatography and identified by chemical and spectral analyses. Rhoifoline B, zanthoxyline dimethoxy derivative, N-nortidine, nitidine, decarine are the major alkaloids. Both the petroleum ether and ethyl acetate extracts showed significant inhibition on NO production, which imply anti-inflammatory activity, in lipopolysaccharide-induced RAW 264.7 cells without cell toxicity. Decarine is the major anti-inflammatory constituent with NO IC50 values of 48.43 µM on RAW264.7 cells. The petroleum ether extract, the ethyl acetate extract and decarine showed anti-inflammatory activities through inhibiting TNF-α and IL-1ß production in lipopolysaccharide-stimulated THP-1 cells without cell toxicity too. Decarine showed anti-inflammatory activity on human colon cells by reducing IL-6 and IL-8 production in TNF-α+IL-1ß-induced Caco-2 cells. These results support the use of Maqian bark as a remedy for enteritis and colitis recorded by Dai medicine in China, and elucidate the major pharmacological compounds in Maqian bark.

Two new lignans from Saururus chinensis.

Two new lignans, (Z)-14-bis(3',4'-dimethoxyphenyl)-2,3-dimethylbut-2-ene-1,4-dione (1), threo-2-methyl-3-oxo-1-(3',4',5'-trimethoxyphenyl)butyl-3″,4″-dimethoxybenzoate (2), together with 15 known derivatives (3-17) were isolated from Saururus chinensis. Their structures were determined on the basis of spectral data, including 1D and 2D NMR experiments and HREIMS spectra. The antitumour activity was screened by MTT assay, compounds 1, 2, 3, 5, 9-11 and 13-15 showed no cytotoxic activity against HL-60, SMMC-7721, A549, MCF-7 and SW480 cell lines.

Quick method for separating target compounds from the bark of Maqian (Zanthoxylum myriacanthum var. pubescens) by high-performance countercurrent chromatography.

Choosing a suitable solvent system for a countercurrent chromatography separation presents a challenge for many researchers. In this study, we introduce a quick method of separating a target compound from the bark of Zanthoxylum myriacanthum var. pubescens by countercurrent chromatography. This method relies on the thin-layer chromatography based generally useful estimation of solvent systems. This paper will present how to quickly choose a suitable solvent system with a thin-layer chromatography based generally useful estimation of solvent systems working chart. O-Methyltembamide (1) was enriched by countercurrent chromatography using n-hexane/ethyl acetate/methanol/water (6:4:6:4) as the solvent system. Further purification was achieved by high-performance liquid chromatography with purities of 98.2% from Z. myriacanthum var. pubescens bark.

A new isoflavone glycoside from Pueraria alopecuroides.

A new isoflavone glycoside, (-)-tuberosin-3-O-ß-D-glucopyranoside (1), along with 10 known compounds 1a-10, was isolated from Pueraria alopecuroides. Their structures were determined on the basis of spectral data including 1D and 2D NMR and HREIMS. These compounds were isolated from this plant for the first time.

One new flavonoid from Oroxylum indicum.

One new flavonoid, 5,6,7-trimethoxyflavone-8-O-ß-D-glucopyranoside (1), along with six known compounds 2-7, was isolated from Oroxylum indicum. Their structures were determined on the basis of spectral data. The antibacterial activities of compounds 1-4 were studied. Compounds 1 and 3 showed medium antibacterial activity against Staphylococcus aureus with MIC/MBC at 32-128 µg/ml.

Flavonoids from twigs of Millettia pubinervis.

A new flavone, 3-methoxy-5-hydroxy-[2",3":7,8] furanoflavone, pubinerone (1), was isolated from the twigs of Millettia pubinervis Kurz, together with ten known flavonoids, karanjin (2), kanjone (3), 3,6-dimethoxy-[2",3":7,8] furanoflavone (4), pongaglabrone (5), pongapin (6), pongaflavone (7), 3,6-dimethoxy- 6",6"-dimethylchromene-[2",3":7,8] flavone (8), pongachromene (9), 3,6-dimethoxy-3',4'-methylenedioxy-6",6"-dimethylchromene-[2",3":7,8] flavone (10) and demethoxykanugin (11). This is the first phytochemical investigation of this plant. The structure of compound 1 was elucidated on the basis of spectroscopic data interpretation, including 1D and 2D NMR and HREIMS analysis. The cytotoxicity of 1 against five human cancer cell lines; HL-60, SMMC-7721, A-549, MCF-7 and SW480, was evaluated, but it was inactive (IC50 > 40 µM).

Two new triterpenoid glycosides from the leaves of Anthocephalus chinensis.

Nine compounds were isolated from the leaves of Anthocephalus chinensis by column chromatography on silica gel and Sephadex LH-20, and their structures were elucidated by spectroscopic techniques as clethric acid-28-O-ß-d-glucopyranosyl ester (1), mussaendoside T (2), ß-stigmasterol (3), hederagenin (4), ursolic acid (5), clethric acid (6), 3ß,6ß,19α,24-tetrahydroxyurs-12-en-28-oic acid (7), mussaendoside I (8), and cadambine (9). Compounds 1 and 2, and 7 and 8 were isolated from the plants of this genus for the first time, and compounds 1 and 2 were new triterpenoid glycosides.

Responses of the pollinating wasp Ceratosolen solmsi marchali to odor variation between two floral stages of Ficus hispida.

During development of figs on Ficus hispida, only the female floral stage is receptive to its pollinator Ceratosolen solmsi marchali. After this stage, the quantity of fig odor decreases. The effects of F. hispida volatiles from receptive figs (figs at the female floral stage, when they are pollinated) and interfloral figs (between the female floral and male floral stages) on their pollinator were studied, together with responses to compounds present in the odor. Odors emitted by both receptive and interfloral figs were attractive to the pollinator. However, wasps preferred the odor of receptive figs to that of interfloral figs even though the quantity of interfloral volatiles increased. Three monoterpenes that included linalool (major constitutent) and two minor compounds limonene and beta-pinene from the receptive fig volatiles were used to test the pollinator responses. The levoisomer and racemic mixtures of linalool were attractive to the pollinator at high doses, but the dextroisomer was neutral. (+/-)-Limonene and (-)-beta-pinene at high doses were even less attractive to the pollinator than clean air and were neutral at low doses, while (R)-(+)-, (S)-(-)-limonene were neutral at all doses. In blend tests, all four mixtures of (+/-)-linalool or (S)-(-)-linalool combined with (+/-)-limonene or (-)-beta-pinene attracted C. solmsi marchali when administered at high doses. (R)-(+)-linalool and (-)-beta-pinene enhanced the attractiveness of (S)-(-)-linalool to the pollinator, while enantiomers of limonene did not. These results suggest that both quality and quantity of fig volatiles regulate C. solmsi marchali response and that quality is the main host-finding and floral stage-distinguishing cue for the pollinator. Synergistic effects of some compounds may play a role in enhancing attractiveness of the active compounds.

Antimicrobial anthraquinones from Morinda angustifolia.

Investigation on Morinda angustifolia resulted in the isolation of a new anthraquinone, 1,8-dihydroxy-2-methyl-3,7-dimethoxyanthraquinone (1), along with five known analogues, lucidin 3-O-beta-primeveroside (2), 1,3-dihydroxy-2-methylanthraquinone (3), lucidin- omega -ethyl ether (4), lucidin-omega-butyl ether (5) and damnacanthol (6). The new compound demonstrated significant antimicrobial activity against Bacillus subtilis, Escherichia coli, Micrococcus luteus, Sarcina lutea, Candida albicans and Saccharomyces sake.

Anticancer activity of tirucallane triterpenoids from Amoora dasyclada.

A new tetranortriterpene 3alpha-acetoxy-24,25,26,27-tetranortirucalla-7-ene-23(21)-lactone (3), and eleven other compounds were isolated from the twigs of Amoora dasyclada. The structure of compound 3 was identified on the basis of spectroscopic data, and the bioactive experiments of 1 and 3-5 against AGZY 83-a (human lung cancer cells) and SMMC-7721 (human liver cancer cells) are documented. Among them, compound 5 exhibited a strong activity against SMMC-7721.

Four new prenylated isoflavonoids in Tadehagi triquetrum.

Investigation on the anthelminthic bioactive compounds of the ethanol extract of Tadehagi triquetrum resulted in the isolation of three new prenylated isoflavones, triquetrumones A (1), B (2), and C (3), and one new prenylated biisoflavanone, (R)-triquetrumone D (4), along with 16 known compounds, cyclokievitone (5), yukovanol (6), aromadendrin (7), kaempferol (8), astragalin (9), 2-O-methyl-l-chiro-inositol (10), galactitol (11), p-hydroxycinnamic acid (12), ursolic acid (13), betulinic acid (14), beta-sitosterol (15), daucosterol (16), stigmasterol (17), stigmasta-5,22-dien-3-O-beta-d-glucopyranoside (18), saccharose (19), and docosanoic acid (20). The structures of 1-4 were elucidated on the basis of spectroscopic and spectrometric methods. Compounds 1-3 displayed mild anthelminthic bioactivity, and compound 3 showed a significant binding ability to the estrogen receptor.