Subscribe: pubmed: 0367-326X
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pubmed: 0367-326X



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Polysaccharides from the South African medicinal plant Artemisia afra: Structure and activity studies.
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Polysaccharides from the South African medicinal plant Artemisia afra: Structure and activity studies.

Fitoterapia. 2018 Jan;124:182-187

Authors: Braünlich PM, Inngjerdingen KT, Inngjerdingen M, Johnson Q, Paulsen BS, Mabusela W

Abstract
Artemisia afra (Jacq. Ex. Willd), is an indigenous plant in South Africa and other parts of the African continent, where it is used as traditional medicine mostly for respiratory conditions. The objective of this study was to investigate the structural features of the polysaccharides from the leaves of this plant, as well as the biological activities of the polysaccharide fractions against the complement assay. Leaves of Artemisia afra were extracted sequentially with organic solvents (dichloromethane and methanol), 50% aqueous ethanol, and water at 50 and 100°C respectively. The polysaccharide extracts were fractionated by ion exchange chromatography and the resulting fractions were tested for biological activity against the complement fixation assay. Active fractions were further fractionated using gel filtration. Monosaccharide compositions and linkage analyses were determined for the relevant fractions. Polysaccharides were shown to be of the pectin type, and largely contain arabinogalactan, rhamnogalacturonan and homogalacturonan structural features. The presence of arabinogalactan type II features as suggested by methylation analysis was further confirmed by the ready precipitation of the relevant polysaccharides with the Yariv reagent. An unusual feature of some of these polysaccharides was the presence of relatively high levels of xylose as one of its monosaccharide constituents. Purified polysaccharide fractions were shown to possess higher biological activity than the selected standard in the complement assay. Digestion of these polysaccharides with an endo-polygalacturonase enzyme resulted in polymers with lower molecular weights as expected, but still with biological activity which exceeded that of the standard. Thus on the basis of these studies it may be suggested that immunomodulating properties probably contribute significantly to the health-promoting effects of this medicinal plant.

PMID: 29155274 [PubMed - indexed for MEDLINE]




Naphthoquinones from the leaves of Rhinacanthus nasutus having acetylcholinesterase inhibitory and cytotoxic activities.
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Naphthoquinones from the leaves of Rhinacanthus nasutus having acetylcholinesterase inhibitory and cytotoxic activities.

Fitoterapia. 2018 Jan;124:206-210

Authors: Boonyaketgoson S, Rukachaisirikul V, Phongpaichit S, Trisuwan K

Abstract
Four new naphthoquinones (1-4), named rhinacanthins S (1), T (2), U (3) and V (4), together with 13 known naphthoquinones were isolated from the leaf extract of Rhinacanthus nasutus. The structures of isolated compounds were elucidated by spectroscopic methods, especially 1D and 2D NMR spectroscopy and mass spectrometry. Rhinacanthin S (1) exhibited acetylcholinesterase inhibition activity with a % inhibition value of 48.04±3.25. The known rhinacanthin A (5) showed cytotoxicity against a MCF-7 cell line with an IC50 value of 8.79μM, while rhinacanthin N (15) was active against the NCI-H187 cell line with an IC50=2.24μM and Vero cells (IC50=3.00μM).

PMID: 29154868 [PubMed - indexed for MEDLINE]




Monoamine oxidases inhibitors from Colvillea racemosa: Isolation, biological evaluation, and computational study.
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Monoamine oxidases inhibitors from Colvillea racemosa: Isolation, biological evaluation, and computational study.

Fitoterapia. 2018 Jan;124:217-223

Authors: Mohamed EI, Zaki MA, Chaurasiya ND, Owis AI, AbouZid S, Wang YH, Avula B, Seida AA, Tekwani BL, Ross SA

Abstract
Bioassay-guided fractionation and chemical investigation of Colvillea racemosa stems led to identification of two new α, β-dihydroxydihydrochalcones, colveol A (1) and colveol B (2) along with fifteen known compounds. The structures were elucidated via interpretation of spectroscopic data. The absolute configurations of the dihydrochalcones 1 and 2 were assigned by a combination of chemical modification and electronic circular dichroism data. The isolated compounds were evaluated for their inhibition activity toward recombinant human monoamine oxidases (rhMAO-A and -B). Compound 1 demonstrated preferential inhibition against hMAO-A isoenzyme (IC50 0.62μM, SIA/B 0.02) while S-naringenin (13) and isoliquiritigein (15) demonstrated preferential hMAO-B inhibition (IC50 0.27 and 0.51μM, SIA/B 31.77 and 44.69, respectively). Fisetin (11) showed inhibition against hMAO-A with IC50 value of 4.62μM and no inhibitory activity toward hMAO-B up to 100μM. Molecular docking studies for the most active compounds were conducted to demonstrate the putative binding modes. It suggested that 1 interacts with Gln215, Ala111, Phe352, and Phe208 amino acid residues which have a role in the orientation and stabilization of the inhibitor binding to hMAO-A, while S-naringenin (13) occupies both entrance and substrate cavities and interacts with Tyr326, a critical residue in inhibitor recognition in hMAO-B.

PMID: 29154867 [PubMed - indexed for MEDLINE]




Activation of IGF-1/IGFBP-3 signaling by berberine improves intestinal mucosal barrier of rats with acute endotoxemia.
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Activation of IGF-1/IGFBP-3 signaling by berberine improves intestinal mucosal barrier of rats with acute endotoxemia.

Fitoterapia. 2018 Jan;124:200-205

Authors: He Y, Yuan X, Zhou G, Feng A

Abstract
Insulin-like growth factor I (IGF-I) and binding protein 3 (IGFBP-3) play a role in the maintenance of gut mucosal barrier function. Nevertheless, IGF-I/IGFBP-3 and tight junction protein (TJP) expression in small intestinal mucosa are often impaired during endotoxemia. In this model of acute endotoxemia, the regulatory effect of berberine on IGF-I/IGFBP-3 and TJP expression in ileal mucosa was evaluated. The findings revealed systemic injection of lipopolysaccharide (LPS) suppressed mRNA and protein expression of IGF-I and IGFBP-3, but berberine ameliorated their production. LPS injection inhibited occludin and claudin-1 protein generation, and this inhibitory effect of LPS was abolished by berberine. Inhibition of IGF-I/IGFBP-3 signaling by AG1024 or siRNAs reduced berberine-induced occludin and claudin-1 production. Additionally, GW9662 was found to repress berberine-induced IGF-I/IGFBP-3 expression, indicating of a cross-link between PPARγ and IGF-I/IGFBP-3 axis.

PMID: 29154866 [PubMed - indexed for MEDLINE]




Hydroxycinnamoylmalated flavone C-glycosides from Lemna japonica.
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Hydroxycinnamoylmalated flavone C-glycosides from Lemna japonica.

Fitoterapia. 2018 Jan;124:211-216

Authors: Bai HH, Wang NN, Mi J, Yang T, Fang DM, Wu LW, Zhao H, Li GY

Abstract
Three previously undescribed flavone C-glycosides (1-3), along with seven known ones (4-10), were isolated and characterized from the smallest flowering aquatic plant, Lemna japonica. On the basis of spectroscopic analysis and alkaline hydrolysis, compounds 1-3 were identified to be luteolin 6-C-(2″-O-trans-caffeoyl-d-malate)-β-glucoside (1), apigenin 6-C-(2″-O-trans-caffeoyl-d-malate)-β-glucoside (2), and luteolin 6-C-(2″-O-trans-coumaroyl-d-malate)-β-glucoside (3). Compounds 1-3 are characteristic of a trans-coumaroyl-d-malate or trans-caffeoyl-d-malate linked to C-2″ of the glucose, which was reported for the first time. Compounds 1-3 exhibited weak cytotoxicity against HepG-2, SW-620, and A-549 cell lines, with IC50 values between 42.5 and 19.2μg/ml, and moderate antioxidant activity. Meanwhile compound 3 displayed moderate nematocidal activity with an EC50 value of 1.56mg/ml.

PMID: 29154864 [PubMed - indexed for MEDLINE]




Development of a selective HPLC-DAD/ELSD method for the qualitative and quantitative assessment of commercially available Eurycoma longifolia products and plant extracts.
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Development of a selective HPLC-DAD/ELSD method for the qualitative and quantitative assessment of commercially available Eurycoma longifolia products and plant extracts.

Fitoterapia. 2018 Jan;124:188-192

Authors: Mutschlechner B, Schwaiger S, Tran TVA, Stuppner H

Abstract
Aqueous extracts of the roots of Eurycoma longifolia are traditionally used to improve sexual performance, to treat infertility and other sexual dysfunctions but also to increase muscle strength. Nowadays, many different products are commercially available which are promoted as E. longifolia extracts and claim to possess beneficial aphrodisiac effects. Since such herbal aphrodisiac preparations have been recently the target of fraudulent product counterfeiting and because eurycomanone, one of the main quassinoids of E. longifolia, is suspected to possess toxic effects at higher concentrations, a highly selective HPLC-DAD/ELSD method has been established to analyze commercially available products and extracts of plant material. The presented method was established by the use of a mixture of 27 reference compounds for qualitative issues and fully validated according to the ICH guidelines for the quantification of three quassinoides: laurycolactone A, longilactone, and eurycomanone. The calibration curves of these showed a linearity over a range of 0.05 to 1.0mg/ml, with a regression coefficient not lower than R2=0.9969. The inter-day and intra-day precision (indicated as relative standard deviation) of the developed method was <2.9%. The recovery ranged from -3.3% to +6.0%. Eight randomly purchased products have been analyzed with this method, but only five of them contained E. longifolia compounds in detectable amounts. The concentration of eurycomanone in these products varied from 0.22±0.002mg eurycomanone per capsule to 1.84±0.08mg corresponding to a maximal recommended daily intake of 0.76±0.02 to 31.90±0.21mg.

PMID: 29154863 [PubMed - indexed for MEDLINE]




C21-steroidal glycosides and sesquiterpenes from the roots of Cynanchum bungei and their inhibitory activities against the proliferation of B and T lymphocytes.
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C21-steroidal glycosides and sesquiterpenes from the roots of Cynanchum bungei and their inhibitory activities against the proliferation of B and T lymphocytes.

Fitoterapia. 2018 Jan;124:193-199

Authors: Qin JJ, Chen X, Lin ZM, Xu YS, Li YM, Zuo JP, Zhao WM

Abstract
Phytochemical investigation of the roots of Cynanchum bungei Decne (Asclepiadaceae) led to the elucidation of seven C21-steroidal glycosides (1-7) including three new compounds (1-3), named cynabungosides A-C, one new eudesmane-type sesquiterpene (8), named cynabungone, and one new humulane-type sesquiterpene (9), named cynabungolide. Their structures were elucidated on the basis of extensive spectroscopic analysis. The absolute configurations of 8 and 9 were defined unequivocally by ECD analysis and X-ray crystallography, respectively. A putative biosynthetic pathway of humulane-type sesquiterpenes 9 and 10 is proposed.

PMID: 29154862 [PubMed - indexed for MEDLINE]




Identification of tagitinin C from Tithonia diversifolia as antitrypanosomal compound using bioactivity-guided fractionation.
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Identification of tagitinin C from Tithonia diversifolia as antitrypanosomal compound using bioactivity-guided fractionation.

Fitoterapia. 2018 Jan;124:145-151

Authors: Sut S, Dall'Acqua S, Baldan V, Ngahang Kamte SL, Ranjbarian F, Biapa Nya PC, Vittori S, Benelli G, Maggi F, Cappellacci L, Hofer A, Petrelli R

Abstract
Tithonia diversifolia (Asteraceae), is used as traditional medicine in tropical countries for the treatment of various diseases, including malaria. Although numerous studies have assessed the antimalarial properties, nothing is known about the effect of T. diversifolia extracts on trypanosomiasis. In this study extracts of T. diversifolia aerial parts were evaluated for their bioactivity against Trypanosoma brucei. The activity was studied against bloodstream forms of T. brucei (TC221), as well as against mammalian cells (BALB/3T3 mouse fibroblasts), as a counter-screen for toxicity. Both methanolic and aqueous extracts showed significant effects with IC50 values of 1.1 and 2.2μg/mL against T. brucei (TC221) and 5.2 and 3.7μg/mL against BALB/3T3 cells, respectively. A bioassay-guided fractionation on the methanolic extract yielded in identification of active fractions (F8 and F9) with IC50 values of 0.41 and 0.43μg/mL, respectively, against T. brucei (TC221) and 1.4 and 1.5μg/mL, respectively, against BALB/3T3 cells,. The phytochemical composition of the extracts and the purified fractions were investigated using HPLC-ESI-MS/MS and 1D and 2D NMR spectra showing the presence of sesquiterpene lactones that in turn were subjected to the isolation procedure. Tagitinin A and C were rather active but the latter presented a very strong inhibition on T. brucei (TC221) with an IC50 value of 0.0042μg/mL. This activity was 4.5 times better than that of the reference drug suramin. The results of this study shed light on the antitrypanosomal effects of T. diversifolia extracts and highlighted tagitinin C as one of the possible responsible for this effect. Further structure activity relationships studies on tagitinins are needed to consider this sesquiterpenes as lead compounds for the development of new antitrypanosomal drugs.

PMID: 29146170 [PubMed - indexed for MEDLINE]




Prepubertal chrysin exposure upregulates either AR in male ventral prostate or AR and ERα in Skene's paraurethral gland of pubertal and adult gerbils.
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Prepubertal chrysin exposure upregulates either AR in male ventral prostate or AR and ERα in Skene's paraurethral gland of pubertal and adult gerbils.

Fitoterapia. 2018 Jan;124:137-144

Authors: Ribeiro NCS, Campos MS, Santos MB, Ayusso GM, Vilamaior PSL, Regasini LO, Taboga SR, Biancardi MF, Perez APS, Santos FCA

Abstract
Chrysin is a plant-derived polyphenol that has the potential to increase endogenous testosterone levels both by inhibiting the aromatase enzyme and by stimulating testicular steroidogenesis. The effects of chrysin on the prostate are unknown, especially during its development and functional maturation. Thus, the aim of this study was to evaluate the effects of chrysin prepubertal exposure on the male and female prostates of both pubertal and adult gerbils. To evaluate the possible androgenic responses of chrysin, gerbils were also exposed to testosterone. Male and female gerbils were exposed to chrysin or to testosterone cypionate from postnatal day 15 to 42. Male and female gerbils were euthanized at either 43days or 90days age. The prostates were collected for biometrical, morphological and immunohistochemical analysis. The results showed that prepubertal exposure to chrysin had differential effects on the prostate of both pubertal and adult animals. The prostates of male and female pubertal gerbils showed no histological alterations, although there was increased frequency of androgen receptor (AR) in males and females, and estrogen receptor alpha (ERα) in females. Adult males and females presented developed prostate glands, with higher cell proliferative rate. In addition, AR and ERα frequency remained high in the prostate of adult animals. These results demonstrated that prepubertal exposure to chrysin disrupts steroid receptors regulation in the prostate, potentiating the response of this gland to the biological effects of endogenous steroids. In this context, excessive consumption of phytoestrogens during the critical stages of development should be considered with caution.

PMID: 29132837 [PubMed - indexed for MEDLINE]




Isolation, modification and cytotoxic evaluation of stilbenoids from Acanthopanax leucorrhizus.
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Isolation, modification and cytotoxic evaluation of stilbenoids from Acanthopanax leucorrhizus.

Fitoterapia. 2018 Jan;124:167-176

Authors: Hu HB, Liang HP, Li HM, Yuan RN, Sun J, Zhang LL, Han MH, Wu Y

Abstract
Twenty natural stilbenoids (1-20), including seven new stilbenoids (2, 4-7, 19, 20) and thirteen known stilbenoids (1, 3, 8-18), were isolated from the stem barks of Acanthopanax leucorrhizus, and six modified stilbenoid derivatives (1a, 2a, 4a, 4b, 7a and 17a) were obtained via methylation, demethylation and isopentenylation of the corresponding isolates (1, 2, 4, 7 and 17). These stilbenoids were structurally characterized by comprehensive analysis of their spectroscopic data and comparison with literature information, and evaluated for their cytotoxic activities against three human tumor cell lines (leukemia HL-60, hepatoma SMMC-7721 and breast carcinoma MCF-7) in vitro by MTT assay. The results showed that compounds 1a, 4a and 4b showed potent selective cytotoxicity against SMMC-7721 (IC50=10.16±1.95μM and 9.76±1.32μM) and MCF-7 (IC50=10.72±2.78μM) cell lines. The cytotoxic evaluation of these structurally modified stilbenoid derivatives have led to the establishment of a structure-activity relationship.

PMID: 29128601 [PubMed - indexed for MEDLINE]




Monoterpenoid indole alkaloids from Gardneria multiflora.
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Monoterpenoid indole alkaloids from Gardneria multiflora.

Fitoterapia. 2018 Jan;124:8-11

Authors: Yang WX, Chen YF, Yang J, Huang T, Wu LL, Xiao N, Hao XJ, Zhang YH

Abstract
Six new monoterpenoid indole alkaloids, 19(E)-9-demethoxy-16-dehydroxylchitosenine-17-O- β-d-glucopyranoside (1), 19(E)-9,10-didemethoxy-16-dehydroxylchitosenine-17-O-β-d-gluco-pyranoside (2), 19(E)-9,10-didemethoxy-16-dehydroxyl-11-methoxychitosenine (3), 19(E)-9,10-didemethoxy-16-dehydroxyl-11-methoxychitosenine-17-O-β-d-glucopyranoside (4), 19(Z)-18-carboxylgardneramine (5), and 19(E)-18-demethoxygardneramine-N (4)-oxide (6), along with four known alkaloids, were isolated from Gardneria multiflora, and their structures were elucidated by spectroscopic analysis. Compounds 1, 2 and 4 are the first example of Gardneria alkaloids whose glucose units were attached to C-17. None of the compounds were cytotoxic to any of five human cancer cell lines.

PMID: 29128600 [PubMed - indexed for MEDLINE]




3-Arylisoindolinone and sesquiterpene derivatives from the mangrove endophytic fungi Aspergillus versicolor SYSU-SKS025.
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3-Arylisoindolinone and sesquiterpene derivatives from the mangrove endophytic fungi Aspergillus versicolor SYSU-SKS025.

Fitoterapia. 2018 Jan;124:177-181

Authors: Cui H, Liu Y, Li T, Zhang Z, Ding M, Long Y, She Z

Abstract
A pair of 3-arylisoindolinone enantiomers: (+)-asperglactam A (1), (-)-asperglactam A (1) and a pair of nor-bisabolane enantiomers: (+)-1-hydroxyboivinianic acid (2), (-)-1-hydroxyboivinianic acid (2), along with seven known compounds (3-8) were obtained from the mangrove endophytic fungus Aspergillus versicolor SYSU-SKS025. Their structures were determined on the basis of HRESIMS and NMR spectroscopic data, and X-ray diffraction. (+)-Asperglactam A (1) and (-)-asperglactam A (1) are the first optically pure examples in the 3-arylisoindolinone family, which are rarely found in natural sources. All isolated compounds were evaluated for α-glucosidase inhibitory activity. The enantiomers of 1-3 showed moderate inhibitory activity against α-glucosidase with IC50 values ranging from 50 to 190μM. Compound 7 exhibited significant inhibitory activity against α-glucosidase with IC50 value of 7.5μM. In addition, compound 7 was found to inhibit nitric oxide production in RAW 264.7 macrophages with IC50 value of 12.5μM.

PMID: 29126957 [PubMed - indexed for MEDLINE]




Iridoids and sfingolipids from Hedyotis diffusa.
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Iridoids and sfingolipids from Hedyotis diffusa.

Fitoterapia. 2018 Jan;124:152-159

Authors: Wang C, Xin P, Wang Y, Zhou X, Wei D, Deng C, Sun S

Abstract
Seven new compounds were isolated from the aerial part of Hedyotis diffusa, including three iridoid glycosides, hedyoiridoidside A - C (1-3), two cerebrosides, hedyocerenoside F (4) and G (5), and two new ceramides, hedyoceramide A (6) and B (7). And six known iridoid glycosides (8-13) were also obtained. Their structures were established by their physico-chemical constants and spectroscopic analysis. The cytotoxicity of all compounds against tumor cell lines of human cervical cancer HeLa, human leukemia HL-60, human lung cancer A459, human hepatoma HepG2, human gastric gland carcinoma BCG-823, human nasopharyngeal cancer CNE-2, human colon cancer HCT15, and human prostate cancer PC-3 were also evaluated in vitro. As a result, new compound 1 exhibited evident cytotoxicity to all tumor cell lines, and the IC50 values are from 9.5μM to 28.2μM, while new compound 2 exhibited evident cytotoxicity to Hela, HL-60, A459, HepG2, BGC-823, CNE-2, and HCT15, and the IC50 values are from 15.8μM to 26.2μM. Known compound 11 also exhibited evident cytotoxicity to HL-60, A459, HepG2, BGC-823, CNE-2, and HCT15, and the IC50 values are from 16.5μM to 40.4μM. New compounds 4-7 and known compounds 12 and 13 showed moderate cytotoxicity to some tumor cell lines.

PMID: 29122633 [PubMed - indexed for MEDLINE]




New C16-noriridals and formyl-monocycloiridals from the rhizomes of Iris pseudoacorus.
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New C16-noriridals and formyl-monocycloiridals from the rhizomes of Iris pseudoacorus.

Fitoterapia. 2018 Jan;124:160-166

Authors: Chen X, Zhang X, Geng C, Li T, Chen J

Abstract
Four new C16-noriridals (1-4) and two reported C16-noriridals (5-6), together with two new formyl-monocycloiridals (7-8) and three known monocycloiridals (9-11) were isolated from the rhizomes of Iris pseudoacorus. Irispseudoacorins A-D (1-4) and iridojaponals A-B (5-6) were C16-noriridals which shared a 6/5/7 tricyclic ring system (1-2, 5-6) or 6/5 tricyclic ring system (3-4). The formyl-monocycloiridals (7-8) were detected in the crude extracts of I. pseudoacorus by LC-MS analysis which suggested they were originated from natural sources rather than artificial products during the isolation. Their structures were determined by UV, IR, extensive NMR spectra and X-ray diffraction analyses. The known monocycloiridals 9-10 displayed pronounced cytotoxic effects against five human tumor cell lines. The IC50 values of 9 were ranging from 12.63 to 24.69μM.

PMID: 29122632 [PubMed - indexed for MEDLINE]




3-Hydroxy-3-methylglutaryl flavone glycosides from the leaves of Turpinia arguta.
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3-Hydroxy-3-methylglutaryl flavone glycosides from the leaves of Turpinia arguta.

Fitoterapia. 2018 Jan;124:80-85

Authors: Ma SG, Yuan SP, Liu YB, Qu J, Li Y, Wang XJ, Wang RB, Xu S, Hou Q, Yu SS

Abstract
Three new 3-hydroxy-3-methylglutaryl (HMG) flavone 7-O-diglycosides, argutosides A-C (1-3); two new flavone 7-O-triglycosides, argutosides D-E (4-5); and one known apigenin 7-O-triglycoside (6), were isolated from the leaves of Turpinia arguta. The structures of these compounds were elucidated by spectroscopic and chemical techniques. The NO inhibitory activities of compounds 1-6 were evaluated using lipopolysaccharide-induced RAW264.7 cells. Only compound 2 showed a moderate inhibitory effect on NO production with an IC50 value of 25.74μM. Compounds 1-6 were not cytotoxic to RAW264.7 cells at 10μM.

PMID: 29111165 [PubMed - indexed for MEDLINE]




Isolation and identification of a tribenzylisoquinoline alkaloid from Nelumbo nucifera Gaertn, a novel potential smooth muscle relaxant.
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Isolation and identification of a tribenzylisoquinoline alkaloid from Nelumbo nucifera Gaertn, a novel potential smooth muscle relaxant.

Fitoterapia. 2018 Jan;124:58-65

Authors: Yang GM, Sun J, Pan Y, Zhang JL, Xiao M, Zhu MS

Abstract
A new skeleton benzylisoquinoline (BI) named neoliensinine (1) was isolated from embryos of lotus seed (Nelumbo nucifera Gaertn.), a traditional Chinese herb. The tribenzylisoquinoline (TBI) structure of 1 was confirmed by interpreting spectroscopic data of UV, IR, MS, 1D and 2D NMR. The stereo-configurations of the new compound, together with two known bisbenzylisoquinolines (BBI), neferine and isoliensinine were established by analyzing 1H NMR and 13C NMR spectra. The relaxation of 1, neferine, isoliensinine and liensinine in isolated mesenteric vascular smooth muscle (VSM) was evaluated. All the four BIs could efficiently inhibit MVSM contraction induced by 124mM KCl, with IC50 values of 2.407μM (1), 1.169μM (neferine), 3.504μM (isoliensinine) and 3.583μM (liensinine), respectively, suggesting that they were all potential relaxants for abnormal smooth muscle contractions. Interestingly, VSM treated by the three BBIs could re-contract when being stimulated by KCl after the drugs were removed, while VSM dealt with the TBI couldn't. It indicated that 1 has much high affinity with the molecular targets on relaxation of VSM contraction, which may relate to the unique skeleton with three BI groups.

PMID: 29108933 [PubMed - indexed for MEDLINE]




Azacoccones A-E, five new aza-epicoccone derivatives from Aspergillus flavipes.
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Azacoccones A-E, five new aza-epicoccone derivatives from Aspergillus flavipes.

Fitoterapia. 2018 Jan;124:127-131

Authors: Zou S, Wang Z, Wang J, Wei G, Wang W, Zang Y, Zeng F, Chen K, Liu J, Wang J, Luo Z, Xue Y, Zhu H, Yin C, Chen C, Zhang Y

Abstract
Azacoccones A-E (1-5), five new aza-epicoccone derivatives, were isolated from the culture of Aspergillus flavipes. Their structures were determined by extensive NMR spectroscopic analyses and the absolute configuration of 5 was determined by electronic circular dichroism (ECD) calculation. Compounds 1-5 are proposed to be generated via a Pictet-Spengler reaction-based biosynthetic route starting from the precursor flavipin. Pictet-Spengler reaction is rarely found in the fungal kingdom, which indicated the distinctive nature of 1-5. Compounds 3 and 5 exhibit significant free radical scavenging activities with IC50 values of 4.0 and 2.4μg/mL, respectively, which are better than the positive control trolox (4.55μg/mL).

PMID: 29106995 [PubMed - indexed for MEDLINE]




Induction of new metabolites from the endophytic fungus Bionectria sp. through bacterial co-culture.
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Induction of new metabolites from the endophytic fungus Bionectria sp. through bacterial co-culture.

Fitoterapia. 2018 Jan;124:132-136

Authors: Kamdem RST, Wang H, Wafo P, Ebrahim W, Özkaya FC, Makhloufi G, Janiak C, Sureechatchaiyan P, Kassack MU, Lin W, Liu Z, Proksch P

Abstract
A new alkaloid, 1,2-dihydrophenopyrrozin (1), along with five known compounds (2-6) was isolated from an axenic culture of the endophytic fungus, Bionectria sp., obtained from seeds of the tropical plant Raphia taedigera. Co-cultivation of this fungus either with Bacillus subtilis or with Streptomyces lividans resulted in the production of two new o-aminobenzoic acid derivatives, bionectriamines A and B (7 and 8) as well as of two additional known compounds (9 and 10). None of the latter compounds (7-10) were detected in axenic cultures of the fungus or of the bacteria indicating activation of silent biogenetic gene clusters through co-cultivation with bacteria. The structures of the new compounds were unambiguously determined based on detailed NMR and MS spectroscopic analysis and by comparison with the literature. The crystal structure of agathic acid (6) is reported here for the first time. Penicolinate A (4) exhibited potent cytotoxic activity against the human ovarian cancer cell line A2780 with an IC50 value of 4.1μM.

PMID: 29106994 [PubMed - indexed for MEDLINE]




Isobenzofuranones from the aerial parts of Leontopodium leontopodioides (Wild.) Beauv.
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Isobenzofuranones from the aerial parts of Leontopodium leontopodioides (Wild.) Beauv.

Fitoterapia. 2018 Jan;124:66-72

Authors: Zhang Y, Yang Y, Ruan J, Chen Q, Li J, Guo Y, Han L, Wang T

Abstract
A phytochemical investigation to obtain new triglyceride (TG) accumulation inhibitors resulted in the isolation of six new isobenzofuranones, leontopodiols A (1), B (2), leontopodiosides C (3), D (4), E (5), F (6), together with three known ones (7-9) from the aerial parts of Leontopodium leontopodioides (Willd.) Beauv. The structures of these isolates were identified by routine NMR experiments, optical rotation determination, electronic circular dichroism (ECD) calculation, along with chemical reaction. Moreover, compounds 1, 2, 5, and 7-9 displayed TG accumulation inhibitory effects on HepG2 cells.

PMID: 29074227 [PubMed - indexed for MEDLINE]




Monoterpenoid indole alkaloids from the leaves of Alstonia scholaris and their NF-κB inhibitory activity.
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Monoterpenoid indole alkaloids from the leaves of Alstonia scholaris and their NF-κB inhibitory activity.

Fitoterapia. 2018 Jan;124:73-79

Authors: Yang J, Fu J, Liu X, Jiang ZH, Zhu GY

Abstract
Four new monoterpenoid indole alkaloids (MIAs), scholarisines P-S (1-4), and 14 known MIAs (5-18) were isolated from the leaves of Alstonia scholaris (L) R. Br. (Apocynaceae). Their structures were elucidated by analyzing their HRESIMS data and NMR spectroscopic data. All of the isolated MIAs were evaluated for their Nuclear Factor-kappa B (NF-κB) inhibitory activity in HepG2-NF-κB-Luc cells. Among them, five compounds (4, 7, 8, 13 and 16) exhibited significant NF-κB inhibitory activity.

PMID: 29074226 [PubMed - indexed for MEDLINE]




Phenylisotertronic acids from the TCM endophytic fungus Phyllosticta sp.
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Phenylisotertronic acids from the TCM endophytic fungus Phyllosticta sp.

Fitoterapia. 2018 Jan;124:86-91

Authors: Yang HG, Li JJ, Chen SM, Mou LM, Zou J, Wang CX, Chen GD, Qin SY, Yao XS, Gao H

Abstract
Four new phenylisotertronic acids (1a/1b, 2a, and 3a) were isolated from a TCM endophytic fungal strain Phyllosticta sp. J13-2-12Y obtained from the leaves of Acorus tatarinowii, along with two known ones (2b and 3b). Compounds 1-3 all existed as mixtures of enantiomers, and their corresponding optically pure enantiomers were successfully isolated by chiral HPLC. The structures of isolated compounds were determined by comprehensive spectroscopic analyses and X-ray diffraction. Their absolute configurations were determined by ECD experiments and quantum chemical calculations. In addition, the antimicrobial activities and the cytotoxicities of these three pairs of optically pure enantiomers (1a/1b, 2a/2b, and 3a/3b) had been evaluated.

PMID: 29074225 [PubMed - indexed for MEDLINE]




Phochrodines A-D, first naturally occurring new chromenopyridines from mangrove entophytic fungus Phomopsis sp. 33.
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Phochrodines A-D, first naturally occurring new chromenopyridines from mangrove entophytic fungus Phomopsis sp. 33.

Fitoterapia. 2018 Jan;124:103-107

Authors: Chen H, Huang M, Li X, Liu L, Chen B, Wang J, Lin Y

Abstract
Four new chromenopyridine derivatives, phochrodines A-D (1-4), were identified from mangrove entophytic fungus Phomopsis sp. 33# by means of various modern chromatographic, spectroscopic and single crystal X-ray diffraction techniques. Compounds 1-4 with an unusual 5H-chromeno[4,3-b]pyridine skeleton were the first naturally occurring chromenopyridines. Their anti-inflammatory, antioxidant and cytotoxic activities were evaluated. 3 and 4 showed moderate inhibition of nitric oxide production with IC50 values of 49.0 as well as 51.0μM, respectively. 4 had well ability to scavenge DPPH radical with IC50 value of 34.0μM. The four had no cytotoxic activity for MDA-MB-435 breast cancer cells.

PMID: 29074224 [PubMed - indexed for MEDLINE]




β-elemene attenuates macrophage activation and proinflammatory factor production via crosstalk with Wnt/β-catenin signaling pathway.
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β-elemene attenuates macrophage activation and proinflammatory factor production via crosstalk with Wnt/β-catenin signaling pathway.

Fitoterapia. 2018 Jan;124:92-102

Authors: Fang Y, Kang Y, Zou H, Cheng X, Xie T, Shi L, Zhang H

Abstract
β-elemene, extracted from Rhizoma zedoariae, has been widely used as a traditional medicine for its antitumor activity against a broad range of cancers. However, the effect of β-elemene in inflammation disorders has yet to be determined. The present study was designed to investigate the anti-inflammatory effects and potential molecular mechanisms of β-elemene in lipopolysaccharide (LPS)-induced murine macrophage cells RAW264.7. We found that the production of pro-inflammatory mediators, including interleukin-6(IL-6), tumor necrosis factor-α (TNF-α) and interleukin-1β (IL-1β), induced by LPS was significantly suppressed by β-elemene in a dose-dependent manner in RAW264.7 macrophage cell line. Also, β-elemene inhibited LPS-induced nitric oxide synthase (iNOS) and interleukin-10 (IL-10) expression by RAW264.7, which was related to the down-regulation of Wnt/β-catenin signaling pathway. Importantly, this study demonstrates that β-catenin was significantly inhibited by β-elemene, which appeared to be largely responsible for the down-regulation of Wnt/β-catenin signaling pathway. Accordingly, the deletion of β-catenin in primary macrophages reversed β-catenin-elicited inhibition of immune response. Furthermore, β-catenin expression and Wnt/β-catenin signaling pathway induced by LPS in RAW264.7 was also significantly inhibited by α-humulene, one isomeric sesquiterpene of β-elemene. α-humulene was also found to significantly inhibit LPS-induced production of proinflammatory cytokines. However, α-humulene showed more cytotoxic ability than β-elemene. Collectively, our data illustrated that β-elemene exerted a potent inhibitory effect on pro-inflammatory meditator and cytokines production via the inactivation of β-catenin, and also demonstrated the protective functions of β-elemene in endotoxin-induced inflammation. β-elemene may serve as potential nontoxic modulatory agents for the prevention and treatment of inflammatory diseases.

PMID: 29066299 [PubMed - indexed for MEDLINE]




Sulfur-containing compounds from the roots of Ferula latisecta and their cytotoxic activities.
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Sulfur-containing compounds from the roots of Ferula latisecta and their cytotoxic activities.

Fitoterapia. 2018 Jan;124:108-112

Authors: Soltani S, Amin GR, Salehi-Sourmaghi MH, Schneider B, Lorenz S, Iranshahi M

Abstract
Five new sulfur-containing compounds, with a new geometry (cis) of the propenyl moiety, and five known compounds were isolated from the roots of Ferula latisecta. The structures of these compounds, were elucidated on the basis of spectroscopic data including 1D and 2D NMR experiments and HRMS. All of the isolated compounds were tested against A2780, A549, HeLa, and HCT116 human cancer cell lines and some of them showed moderate cytotoxic activities.

PMID: 29066298 [PubMed - indexed for MEDLINE]




Medicinal Mascarene Aloes: An audit of their phytotherapeutic potential.
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Medicinal Mascarene Aloes: An audit of their phytotherapeutic potential.

Fitoterapia. 2018 Jan;124:120-126

Authors: Lobine D, Cummins I, Govinden-Soulange J, Ranghoo-Sanmukhiya M, Lindsey K, Chazot PL, Ambler CA, Grellscheid S, Sharples G, Lall N, Lambrechts IA, Lavergne C, Howes MR

Abstract
A phytochemical and biological investigation of the endemic Mascarene Aloes (Aloe spp.), including A. tormentorii (Marais) L.E.Newton & G.D.Rowley, A. purpurea Lam, A. macra Haw., A. lomatophylloides Balf.f and A. vera (synonym A. barbadensis Mill.), which are used in the traditional folk medicine of the Mascarene Islands, was initiated. Methanolic extracts of the Aloes under study were analysed using high resolution LC-UV-MS/MS and compounds belonging to the class of anthraquinones, anthrones, chromones and flavone C-glycosides were detected. The Mascarene Aloes could be distinguished from A. vera by the absence of 2″-O-feruloylaloesin and 7-O-methylaloeresin. GC-MS analysis of monosaccharides revealed the presence of arabinose, fucose, xylose, mannose and galactose in all the Mascarene Aloes and in A. vera. The crude extracts of all Aloes analysed displayed antimicrobial activity against Bacillus cereus, Staphylococcus aureus, Escherichia coli and Pseudomonas aeruginosa. Only extracts of A. macra were active against P. aeruginosa and Klebsiella pneumoniae, while none of the Aloe extracts inhibited Propionibacterium acnes. A. macra displayed anti-tyrosinase activity, exhibiting 50% inhibition at 0.95mg/mL, and extracts of A. purpurea (Mauritius) and A. vera displayed activity in a wound healing-scratch assay. In vitro cytotoxicity screening of crude methanolic extracts of the Aloes, using the MTT (3-(4, 5-dimethylthiazolyl-2)-2, 5-diphenyltetrazolium bromide) showed that only A. purpurea (Réunion) elicited a modest toxic effect against HL60 cells, with a percentage toxicity of 8.2% (A. purpurea-Réunion) and none of the Aloe extracts elicited a toxic effect against MRC 5 fibroblast cells at a concentration of 0.1mg/mL. Mascarene Aloe species possess noteworthy pharmacological attributes associated with their rich phytochemical profiles.

PMID: 29066297 [PubMed - indexed for MEDLINE]




Two novel bioactive sulfated guaiane sesquiterpenoid salt alkaloids from the aerial parts of Scorzonera divaricata.
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Two novel bioactive sulfated guaiane sesquiterpenoid salt alkaloids from the aerial parts of Scorzonera divaricata.

Fitoterapia. 2018 Jan;124:113-119

Authors: Wu QX, He XF, Jiang CX, Zhang W, Shi ZN, Li HF, Zhu Y

Abstract
Extracts of the aerial parts of Scorzonera divaricata afforded sulfoscorzonin D (1) and sulfoscorzonin E (2), two novel pyrrolidine inner salt alkaloids with a sulfated guaiane sesquiterpene lactone nucleus, along with 22 known compounds. Especially, sulfoscorzonin D containing a unusual monoterpene moiety is very rare. The structures of new compounds were established using spectroscopic analysis including one- and two-dimensional NMR and HRESIMS. The cytotoxicities of compounds 1-4 and 10 against three tumor cell lines (K562, Hela, and HepG2) were evaluated using the MTT assay. Compounds 2 and 10 exhibited moderate cytotoxic activity. The biological properties of 1-3, 5-8, 10-14, and 16-24, were screened against nine different gram-positive and gram-negative bacteria. Compounds 1, 5-8, 10, and 18, showed potent antibacterial activities.
CHEMICAL COMPOUNDS STUDIED IN THIS ARTICLE: Glucozaluzanin C (PubChem CID: 442320); 1β,4α-dihydroxy-5α,6β,7α,11βH-eudermn-12; 6-olide (CID: 11119093); oleanolic acid (CID: 10494); lup-20(29)-ene-3β,28-diol (CID: 72326); (22E)-5α,8α-epidioxyergosta-6,22-dien-3β-ol (CID: 5469431); ergosta-3β,5α, 6β-trialcohol (CID: 44558918); stigma-5-en-3-O-β-glucoside (CID: 5742590); vomifoliol (CID: 12444927); trans-caffeic acid (CID: 689043); trans-p-hydroxy coumaric acid (CID: 637542); 4-hydroxy-3-methoxyphenyl ferulate (CID: 11500646); 7,3',4'-trihydroxyflavonol (CID: 5281614); tricin (ID: 5281702); luteolin (CID: 5280445); diosmetin (CID: 5281612); 5,7-dihydroxy-8-methoxyflavone (CID: 5281703); 5,7-dihydroxy-6-methoxyflavone (CID: 5320315); methyl-3,4-dihydroxy benzoate (CID: 287064); m-hydroxy benzoic acid (CID: 7420); 7-hydroxy-coumarin (CID: 5281426); and scopoletin (CID: 5280460).

PMID: 29066296 [PubMed - indexed for MEDLINE]




Polyphenolic profile and biological activities of black carrot crude extract (Daucus carota L. ssp. sativus var. atrorubens Alef.).
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Polyphenolic profile and biological activities of black carrot crude extract (Daucus carota L. ssp. sativus var. atrorubens Alef.).

Fitoterapia. 2018 Jan;124:49-57

Authors: Smeriglio A, Denaro M, Barreca D, D'Angelo V, Germanò MP, Trombetta D

Abstract
Black carrot (Daucus carota L. ssp. sativus var. atrorubens Alef.) is a valuable source of carbohydrates, minerals and vitamins and contains also high amounts of anthocyanins giving the characteristic deep-purple color. These latter compounds are known as natural dyes used in the food and pharmaceutical industry that have recently attracted much attention for their healthful properties. The aim of this work was to investigate for the first time the polyphenolic profile and biological properties of a black carrot crude extract (BCCE) through an in-depth analysis of the main polyphenolic classes evaluating its antioxidant, cytoprotective and anti-angiogenic properties. Twenty five polyphenols were quantified by LC-DAD-FLD-MS/MS analysis (anthocyanins 78.06%, phenolic acids 17.89% and other flavonoids 4.06%) with polyglycosylated cyanidins as major components. In addition, BCCE showed a strong antioxidant and free radical scavenging activity particularly in the hydrogen transfer-based assays (ORAC and β-carotene bleaching) and a significant increase in the cell viability. Furthermore, BCCE exhibited a strong anti-angiogenic activity at the highest concentration assayed on the chick chorioallantoic membrane (50μg/egg). In conclusion, the obtained results demonstrated the antioxidant, cytoprotective and anti-angiogenic properties of BCCE, which highlight that the higher biological activity of BCCE is probably due to the synergic effects exerted by various polyphenolic classes.

PMID: 29050970 [PubMed - indexed for MEDLINE]




Resolution and identification of scalemic caged xanthones from the leaf extract of Garcinia propinqua having potent cytotoxicities against colon cancer cells.
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Resolution and identification of scalemic caged xanthones from the leaf extract of Garcinia propinqua having potent cytotoxicities against colon cancer cells.

Fitoterapia. 2018 Jan;124:34-41

Authors: Sriyatep T, Tantapakul C, Andersen RJ, Patrick BO, Pyne SG, Muanprasat C, Seemakhan S, Borwornpinyo S, Laphookhieo S

Abstract
A new scalemic 8,8a-dihydro caged xanthone (1) was isolated from the leaf extract of Garcinia propinqua. Five other known natural products, the three caged xanthones (2, 5 and 6) and the two neocaged xanthones, (3 and 4) were also isolated as scalemic mixtures. Their structures were characterized by spectroscopic methods. The enantiomeric ratios (er) of compounds 1-6 ranged from 1:0.7 to 1:0.9. These compounds were also resolved by semipreparative chiral HPLC. The absolute configurations of (+)-2 and (+)-3 were determined by single-crystal X-ray diffraction analysis using Cu Kα radiation while the absolute configurations of the other compounds were determined by comparisons of their ECD spectra. Compounds (-)-4, (+)-4, (-)-5, (+)-5, and (-)-6 showed potent cytotoxicities against a colon cancer cell line HCT116 with IC50 values of 2.60, 7.02, 1.47, 3.37, and 4.14μM, respectively, which were better than the standard control doxorubicin (IC50 9.74μM).

PMID: 29031558 [PubMed - indexed for MEDLINE]




Silybin counteracts doxorubicin resistance by inhibiting GLUT1 expression.
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Silybin counteracts doxorubicin resistance by inhibiting GLUT1 expression.

Fitoterapia. 2018 Jan;124:42-48

Authors: Catanzaro D, Gabbia D, Cocetta V, Biagi M, Ragazzi E, Montopoli M, Carrara M

Abstract
Despite significant advances in the diagnosis and treatment of cancer, the development of drug resistance still remains one of the principal causes that hampers the effectiveness of the therapy. Emerging evidences support the idea that the dysregulated metabolism could be related to drug resistance. The major goal of this study was to target cancer metabolic pathways using new pharmacological approaches coming from natural sources in order to possibly prevent or overcome this phenomenon. Firstly, the metabolic profile of human colorectal adenocarcinoma cells sensitive (LoVo WT) and resistant to doxorubicin (LoVo DOX) was delineated demonstrating that resistant cells remodel their metabolism toward a glycolytic phenotype. In particular it was observed that doxorubicin-resistant cancer cells exhibit an increased dependency from glucose for their survival, associated with overexpression of the glycolytic pathway. Moreover, both GLUT1 mRNA and protein expression significantly increased in LoVo DOX cells. Given the results about the metabolic profile, silybin, modulator of GLUTs, was selected as potential candidate to overcome doxorubicin resistance and, intriguingly, data revealed not only that silybin is more active in resistant cells than in wild type cells, but also that the combined treatment with doxorubicin and silybin presents a synergistic effect in LoVo DOX cells. Although many unanswered questions still remain about the molecular mechanism of silybin, these data suggest that targeting GLUTs may be a good strategy to restore doxorubicin sensitivity and elude drug resistance.

PMID: 29031537 [PubMed - indexed for MEDLINE]




Identification of berberrubine metabolites in rats by using ultra-high performance liquid chromatography coupled with quadrupole time-of-flight mass spectrometry.
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Identification of berberrubine metabolites in rats by using ultra-high performance liquid chromatography coupled with quadrupole time-of-flight mass spectrometry.

Fitoterapia. 2018 Jan;124:23-33

Authors: Wang K, Qiao M, Chai L, Cao S, Feng X, Ding L, Qiu F

Abstract
Berberrubine, an isoquinoline alkaloid isolated from many medicinal plants, possesses diverse pharmacological activities, including glucose-lowering, lipid-lowering, anti-inflammatory, and anti-tumor effects. This study aimed to investigate the metabolic profile of berberrubine in vivo. Therefore, a rapid and reliable method using the ultra-high performance liquid chromatography coupled with quadrupole time-of-flight mass spectrometry (UPLC-Q-TOF-MS) and metabolynx™ software with mass defect filter (MDF) technique was developed. Plasma, bile, urine and feces samples were collected from rats after oral administration of berberrubine with a dose of 30.0mg/kg and analyzed to characterize the metabolites of berberrubine in vivo for the first time. A total of 57 metabolites were identified, including 54 metabolites in urine, 39 metabolites in plasma, 28 metabolites in bile and 18 metabolites in feces. The results indicated that demethylenation, reduction, hydroxylation, demethylation, glucuronidation, and sulfation were the major metabolic pathways of berberrubine in vivo.

PMID: 28993283 [PubMed - indexed for MEDLINE]




seco-Tiaminic acids B and C: Identification of two novel 3,4-seco-tirucallane triterpenoids isolated from the root of Entandrophragma congoënse (Meliaceae).
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seco-Tiaminic acids B and C: Identification of two novel 3,4-seco-tirucallane triterpenoids isolated from the root of Entandrophragma congoënse (Meliaceae).

Fitoterapia. 2018 Jan;124:17-22

Authors: Happi GM, Talontsi FM, Laatsch H, Zühlke S, Ngadjui BT, Spiteller M, Kouam SF

Abstract
Chemical investigation of the roots of Entandrophragma congoënse (Meliaceae) led to the isolation of two new 3,4-seco-tirucallane triterpenes, namely seco-tiaminic acids B and C (1 and 2) together with nine known compounds: 3,4-secotirucalla-21-formyl-23-oxo-4(28),7,24-trien-3-oic acid (3), methyl angolensate (4), molucensin N (5), molucensin O (6), piscidinol A (7), 7α,20(S)-dihydroxy-4,24(28)-ergostadien-3-one (8), 24-methylene-cholest-5-en-3β,7α-diol (9), entilin A (10), and entilin B (11). Their structures were determined using extensive spectroscopic methods including 1D and 2D NMR, HRMS, and CD analyses; new results were compared to existing data in the literature. The two newly identified seco-tiaminic acids showed moderate antiplasmodial and cytotoxic activities against a chloroquine-sensitive strain of the malaria parasite (Plasmodium falciparum NF54) and were cytotoxic toward an L6 rat skeletal myoblast cell line, respectively.

PMID: 28987553 [PubMed - indexed for MEDLINE]




Sulfated neo-clerodane diterpenoids and triterpenoid saponins from Sheareria nana S. Moore.
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Sulfated neo-clerodane diterpenoids and triterpenoid saponins from Sheareria nana S. Moore.

Fitoterapia. 2018 Jan;124:12-16

Authors: Tang Z, Shen J, Zhang F, Liang J, Xia Z

Abstract
Three novel neo-clerodane diterpenoids Sheareria A-C (1-3) together with three known triterpenoid saponins were isolated from the whole herb of Sheareria nana S. Moore. Their structures were established by spectroscopic and chemical method. This is the first natural sulfated neo-clerodane diterpenoids. This is the first report of all these compounds from this plant. These neo-clerodane diterpenoids and triterpenoid saponins from S. nana S. Moore may be considered as chemotaxonomic markers for the genus. The compounds isolated were evaluated for their cytotoxic effects against three cancer cell lines, the test substances demonstrated selectivity toward the cancer cells. To date, this is the first report on the phytochemical and biological activity of secondary metabolites from S. nana S. Moore.

PMID: 28986264 [PubMed - indexed for MEDLINE]




Four new diterpenes from the mangrove Ceriops tagal and structure revision of four dolabranes with a 4,18-epoxy group.
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Four new diterpenes from the mangrove Ceriops tagal and structure revision of four dolabranes with a 4,18-epoxy group.

Fitoterapia. 2018 Jan;124:1-7

Authors: Zhang X, Li W, Shen L, Wu J

Abstract
Four new diterpenes named tagalons A-D (1-4), comprising an isopimarane (1), two 16-nor-pimaranes (2-3), and a dolabrane (4), were isolated from the Chinese mangrove, Ceriops tagal, together with four known dolabranes containing a 4,18-epoxy group, viz. tagalene I (5), 4-epitagalene I (6), tagalsin A (7), and tagalsin B (8). The structures of these compounds were unambiguously established by HR-ESIMS and NMR spectroscopic data. Based on the new criteria of NOE interactions between H2-18/H3-19 and H2-18/H3-20, previously reported relative configurations of the above four known dolabranes were correctly revised as their C-4 epimers, respectively. The relative configuration of tagalon B (2) and the absolute configuration of tagalene I (5) were established by single-crystal X-ray diffraction analyses, conducted with Cu Kα radiation. Most notably, tagalons C (3) and D (4) exhibited selective cytotoxicities against the human breast cancer cell line MT-1 with IC50 values of 3.75 and 8.07μM, respectively; whereas tagalene I (5) displayed potent cytotoxic effects against four human breast cancer cell lines MDA-MB-453, MDA-MB-231, SK-BR-3, and MT-1 with IC50 values of 8.97, 8.97, 4.62, and 3.93μM, respectively.

PMID: 28964872 [PubMed - indexed for MEDLINE]