To study the chemical constituents of Ardisia punctata, compounds were isolated with a combination of multi-chromatography. Their structures were determined on the basis of spectral analysis and comparison to those of the known compounds. A 1,4-benzoquinone derivative and a alkylphenol were isolated from the petroleum ether extract of the roots of Ardisia punctata. Their structures were elucidated as 2-tridecyl-3-[(2-tridecyl-4-acetoxy-6-methoxy)-phenoxyl] -6-methoxy-1,4-benzoquinone (1) and 2-methoxy-4-hydroxy-6-tridecyl-phenyl acetate (2). The two compounds are both new.
Ardisia ; chemistry ; Benzoquinones ; chemistry ; isolation & purification ; Molecular Structure ; Phenylacetates ; chemistry ; isolation & purification ; Plant Roots ; chemistry ; Plants, Medicinal ; chemistry

OBJECTIVETo study the chemical constituents from the roots of Ardisia punctata.

METHODCompounds were isolated by chromatographic techniques on silica gel and Rp-HPLC column. Their structures were elucidated by chemical and spectroscopic methods.

RESULTTwelve compounds were identified as 3-hydroxy-5-tridecyl-methyl phenyl ether (1), 5-pentadecyl-1, 3-benzenediol (2), 2-methoxy-6-tridecyl-1, 4-benzoquinone (3), 2-methoxy-6-pentadecyl-1, 4-benzoquinone (4), glutinol (5), ardisicrenoside A (6), ardisiacrispin B (7), 24-ethyl-5a-cholesta-7, 22(E)-dien-3-one (8), 24-ethyl-5alpha-cholesta-7, 22(E)-dien-3beta-ol (9), daucosterol (10), vanillin acid (11), tetratriacontanoic acid (12).

CONCLUSIONAll the compounds were obtained from this plant for the first time.

Ardisia ; chemistry ; Benzoquinones ; chemistry ; isolation & purification ; Oleanolic Acid ; analogs & derivatives ; chemistry ; isolation & purification ; Plant Roots ; chemistry ; Plants, Medicinal ; chemistry ; Saponins ; chemistry ; isolation & purification ; Triterpenes ; chemistry ; isolation & purification

AIMTo study the chemical constituents of Ardisia punctata.

METHODSCompounds were separated with a combination of multi-chromatography. Their chemical structures were determined on the basis of spectral analysis and single crystal X-ray diffraction.

RESULTSThree compounds were isolated from chloroform extract of the roots of Ardisia punctata. Their structures were elucidated as 2-tridecyl-3-[(2-tridecyl-3-acetoxy-4-methoxy-6-hydroxy) -phenyl]-6-methoxy-1, 4-benzoquinone (1), 2-tridecyl-3-[(2-tridecyl-4,6-dihydroxy) -phenyl]-6-methoxy-1,4-benzoquinone (2) and 2-tridecyl-3-[(2-pentadecyl-4,6-dihydroxyl) -phenyl]-6-methoxy-,4-benzoquinone (3).

CONCLUSIONThe three compounds are new 1,4-benzoquinone derivatives.

Ardisia ; chemistry ; Benzoquinones ; chemistry ; isolation & purification ; Molecular Conformation ; Molecular Structure ; Phenols ; chemistry ; isolation & purification ; Plant Roots ; chemistry ; Plants, Medicinal ; chemistry ; Resorcinols ; chemistry ; isolation & purification

AIMTo propose a polarographic method for the determination of irisquinone.

METHODSA reduction wave of irisquinone was recorded by single sweep oscillopolarography.

RESULTSIn 8.0 x 10(-3) mol.L-1 Na2B4O7-1.6 x 10(-2) mol.L-1 KH2PO4 (pH 7.7) supporting electrolyte, a redution wave of irisquinone with peak potential -1.23 V (vs SCE) achieved high sensitivity. The 2nd-order derivative peak current of the reduction wave was proportional to irisquinone concentration in the range of 1.5 x 10(-7)-5.2 x 10(-6) mol.L-1 (gamma = 0.9992, n = 9). The detection limit was 6.0 x 10(-8) mol.L-1. Relative standard deviation (RSD) was 0.87% by performing 13 independent measurements on 2.0 x 10(-6) mol.L-1 irisquinone.

CONCLUSIONThe proposed method was sensitive, simple, rapid, and can be applied to the determination of irisquinone in raw medicine and capsule.

Antineoplastic Agents, Phytogenic ; administration & dosage ; analysis ; chemistry ; Benzoquinones ; administration & dosage ; analysis ; chemistry ; isolation & purification ; Capsules ; Electrochemistry ; Iris ; chemistry ; Plants, Medicinal ; chemistry ; Polarography ; Seeds ; chemistry

The present study was designed to determine the chemical constituents of the stems and hooks of Uncaria rhynchophylla. The chemical constituents were isolated and purified from CH2Cl2 fraction by chromatography. Their structures were elucidated by spectroscopic analyses. Their cytotoxicity was tested using MTT method. Two new ortho benzoquinones, 3-diethylamino-5-methoxy-1, 2-benzoquinone (1) and 3-ethylamino-5-methoxy-1, 2-benzoquinone (2), together with a known compound isorhynchophyllic acid (3) were isolated from U. rhynchophylla. These compounds were evaluated for their cytotoxicity against cancer cells A549, HepG2 and A2780. Compounds 1 and 2 were new ortho benzoquinones and showed weak antiproliferative activities on A549, HepG2 and A2780 cells. Compound 3 significantly inhibited the proliferation of A549, HepG2 and A2780 cells with IC50 values being 5.8, 12.8 and 11.8 µmol·L(-1), respectively.
A549 Cells ; Antineoplastic Agents, Phytogenic ; chemistry ; pharmacology ; Benzoquinones ; isolation & purification ; pharmacology ; Drug Screening Assays, Antitumor ; Hep G2 Cells ; Humans ; Plant Extracts ; chemistry ; pharmacology ; Uncaria ; chemistry

AIMTo study the active constituents for the treatment of rheumatoid arthritis from the ethyl acetate extracts of the roots of Lasianthus acuminatissimus Merr.

METHODSVarious chromatographic techniques were used to separate and purify the constituents. Their structures were established on the basis of 1D, 2D NMR and HRMS spectroscopic analyses and their preliminary evaluation of anti-inflammation effect on the release of beta-glucuronidase was carried out.

RESULTSEight compounds were isolated and identified as lasianthuslactone A (1), codonolactone (2), 2,5-dimethoxy-1, 4-benzoquinone (3), uncargenin A (4), nonadecyl alcohol (5), 13-docosenoic acid (6), tetracosanoic acid (7) and beta-sitosterol (8). Compound 3 showed a significant inhibitory effect on release of beta-glucuronidase rat polymorphous nuclear leukocytes activated by platelet activating factor (PAF).

CONCLUSIONCompound 1 is a new one, the others were isolated from the plant for the first time and 3 is one of active anti-inflammation compound in the plant.

Animals ; Anti-Inflammatory Agents, Non-Steroidal ; chemistry ; isolation & purification ; pharmacology ; Benzoquinones ; chemistry ; isolation & purification ; pharmacology ; Glucuronidase ; metabolism ; Molecular Conformation ; Molecular Structure ; Neutrophils ; metabolism ; Plant Roots ; chemistry ; Plants, Medicinal ; chemistry ; Rats ; Rubiaceae ; chemistry ; Sesquiterpenes ; chemistry ; isolation & purification ; pharmacology

To identify the anti-bacterial compound(s) from Streptomyces hygroscopicus 17997, a geldanamycin producer, silica gel thin layer chromatography (TLC) TLC was used to separate the secondary metabolites of S. hygroscopicus 17997. Compound(s) from the silica gel TLC with anti-Gram positive bacteria activity and becoming red upon color reaction by 2.0 mol/L NaOH was analyzed by HPLC. The UV absorption profile and the retention time of a peak of HPLC were identical to those of authentic elaiophylin. A conserved region of dTDP-glucose-4,6-dehydratase (Tgd) gene was amplified by PCR from the genomic DNA of Streptomyces hygroscopicus 17997. DNA sequence analysis of the amplified DNA fragment indicated that it should be the tgd gene of elaiophylin biosynthetic gene cluster. These results implied that the compound in the peak of HPLC was elaiophylin, a macrodiolide antibiotic. The compound was then confirmed to be elaiophylin by LC-(+)-ESI-MS, which revealed that Streptomyces hygroscopicus 17997 was an elaiophylin producer. At the same time, a fast procedure, which consisted of silica gel TLC, color reaction, HPLC, PCR detection and DNA sequence analysis of tgd gene, and LC-(+)-ESI-MS, was established for rapid identification of elaiophylin and its producer.
Benzoquinones ; metabolism ; Chromatography, Liquid ; methods ; DNA, Bacterial ; genetics ; Hydro-Lyases ; genetics ; Lactams, Macrocyclic ; metabolism ; Macrolides ; analysis ; isolation & purification ; metabolism ; Mass Spectrometry ; methods ; Sequence Analysis, DNA ; Streptomyces ; genetics ; isolation & purification ; metabolism

Surgery remains the preferred treatment for hydatid cyst (cystic echinococcosis, CE). Various scolicidal agents have been used for inactivation of protoscolices during surgery, but most of them are associated with adverse side effects. The present study aimed to evaluate the in vitro scolicidal effect of Nigella sativa (Ranunculaceae) essential oil and also its active principle, thymoquinone, against protoscolices of hydatid cysts. Protoscolices were aseptically aspirated from sheep livers having hydatid cysts. Various concentrations of the essential oil (0.01-10 mg/ml) and thymoquinone (0.125-1.0 mg/ml) were used for 5 to 60 min. Viability of protoscolices was confirmed by 0.1% eosin staining. Furthermore, the components of the N. sativa essential oil were identified by gas chromatography/mass spectroscopy (GC/MS). Our study revealed that the essential oil of N. sativa at the concentration of 10 mg/ml and its main component, thymoquinone, at the concentration of 1 mg/ml had potent scolicidal activities against protoscolices of Echinococcus granulosus after 10 min exposure. Moreover, thymoquinone (42.4%), p-cymene (14.1%), carvacrol (10.3%), and longifolene (6.1%) were found to be the major components of N. sativa essential oil by GC/MS analysis. The results of this study indicated the potential of N. sativa as a natural source for production of a new scolicidal agent for use in hydatid cyst surgery. However, further studies will be needed to confirm these results by checking the essential oil and its active component in in vivo models.
Animals ; Anthelmintics/isolation & purification/*pharmacology ; Benzoquinones/isolation & purification/*pharmacology ; Biological Assay ; Echinococcosis/parasitology/veterinary ; Echinococcus granulosus/*drug effects/isolation & purification ; Gas Chromatography-Mass Spectrometry ; Nigella sativa/*chemistry ; Oils, Volatile/chemistry/isolation & purification/*pharmacology ; Seeds/chemistry ; Sheep ; Sheep Diseases/parasitology ; Survival Analysis ; Time Factors

Recent studies reported that thymoquinone (TQ), a component derived from the medicinal spice Nigella sativa (also called black cumin), exhibited inhibitory effects on cell proliferation of many cancer cell lines. This study was performed to investigate the anti-metastatic effect of thymoquinone on the pancreatic cancer in vitro and in vivo. The results showed that thymoquinone suppressed the migration and invasion of Panc-1 cells in a does-dependent manner. To investigate the possible mechanisms involved in these events, Western blotting analysis was performed, and found that thymoquinone significantly down-regulates NF-kappaB and MMP-9 in Panc-1 cells. In addition, metastatic model simulating human pancreatic cancer was established by orthotropic implantation of histologically intact pancreatic tumor tissue into the pancreatic wall of nude mice. And administration of thymoquinone significantly reduced tumor metastasis compared to untreated control. Furthermore, the expression of NF-kappaB and MMP-9 in tumor tissues was also suppressed after treatment with thymoquinone. Taken together, the results indicate that thymoquinone exerts anti-metastatic activity on pancreatic cancer both in vitro and in vivo, which may be related to down-regulation of NF-kappaB and its regulated molecules such as MMP-9 protein. Consequently, these results provide important insights into thymoquinone as an antimetastatic agent for the treatment of human pancreatic cancer.
Animals ; Antigens, CD34 ; metabolism ; Antineoplastic Agents, Phytogenic ; administration & dosage ; isolation & purification ; pharmacology ; Benzoquinones ; administration & dosage ; isolation & purification ; pharmacology ; Cell Line, Tumor ; Cell Movement ; drug effects ; Dose-Response Relationship, Drug ; Down-Regulation ; Female ; Humans ; Matrix Metalloproteinase 9 ; metabolism ; Mice ; Mice, Inbred BALB C ; Mice, Nude ; NF-kappa B ; metabolism ; Neoplasm Invasiveness ; Neoplasm Metastasis ; Neoplasm Transplantation ; Nigella sativa ; chemistry ; Pancreatic Neoplasms ; metabolism ; pathology ; Plants, Medicinal ; chemistry

OBJECTIVETo discuss the effect of the association of Shiquandabutang with Hetaokun on the protection to liver and immunity of tumor mouse S180.

METHODThrough the comparison between tumor transplanted and tumor cultured completely out of cell body, the effect was investigated, with Hetaokun singly used and Shiquandabutang associated with Hetaokun, on the level of SGPT, licking up function of monocyte macrophage, thymus index, spleen index and transform percentage of lymphocyte of the mouse S180. The scanning electron micrographs indicated the protective function of the association of Shiquandabutang with Hetaokun for liver.

RESULT12.5 mg x kg(-1) Hetaokun could obviously restrain the tumor when it was singly used at 73.1%, but it increased SGPT at the same time. The association of Shiquandabutang with Hetaokun could protect liver of the mouse S180. SGPT (P > 0.05) was compared with the common ones and the result showed that the association of shiquandabutang with Hetaokun could make K value increase (P > 0.01). Through the scanning electron micrographs, association of two medicines was found to change liver cells little and expansion of rough Neizhiwang was not found. Compared with the control group, the immunity of the two tumor mouse groups taking the medicine mentioned above was promoted obviously.

CONCLUSIONThe association of Shiquandabutang with Hetaokun can enhance the efficiency and decrease poison of them to body. With the promotion of immunity of the body, the efficiency is enhanced on the whole.

Animals ; Antineoplastic Agents, Phytogenic ; pharmacology ; Benzoquinones ; isolation & purification ; pharmacology ; Drug Combinations ; Drugs, Chinese Herbal ; isolation & purification ; pharmacology ; Fruit ; chemistry ; Juglans ; chemistry ; Liver ; pathology ; Lymphocyte Activation ; drug effects ; Macrophages ; immunology ; Male ; Mice ; Mitochondria, Liver ; drug effects ; Mitochondrial Swelling ; drug effects ; Phagocytosis ; drug effects ; Plants, Medicinal ; chemistry ; Sarcoma 180 ; immunology ; pathology