Characterization of lipophilic pentasaccharides from beach morning glory (Ipomoea pes-caprae)

The hexane-soluble extract from the aerial parts of the herbal drug Ipomoea pes-caprae (beach morning-glory), through preparative-scale recycling HPLC, yielded six lipophilic glycosides, namely, five new pentasaccharides of jalapinolic acid, pescaproside A (1) and pescapreins I-IV (2-5), as well as the known stoloniferin III (6). Saponification of the crude resin glycoside mixture yielded simonic acid B (7) as the glycosidic acid component, whereas the esterifying residues of the natural oligosaccharides comprised five fatty acids: 2-methylpropanoic, (2S)-methylbutyric, n-hexanoic, n-decanoic, and n-dodecanoic acids. Pescaproside A (1), an acylated glycosidic acid methyl ester, is related structurally to the product obtained from the macrolactone hydrolysis of pescapreins I-IV (2-5). All the isolated compounds (1-6), characterized through high-field NMR spectroscopy, were found to be weakly cytotoxic to a small panel of cancer cell lines.     

Effect of Ipomoea intrapilosa Methanol Extract on the Serotonergic Response in Rat Uterus

A methanol extract (MEII) obtained from the seeds of Ipomoea intrapilosa and its isolated crude alkaloid fraction (ALKII) were tested as possible blockers of the serotonergic response in the rat uterus in vitro . The results obtained showed an unsurmountable non-selective inhibition of the contractile response induced by serotonin on isolated uterine smooth muscle.     

Hydrocotylosides I-VII, new oleanane saponins from hydrocotylesibthorpioides

Seven new oleanane-type triterpenoid saponins, hydrocotylosides I-VII (1-7), and one known saponin, udosaponin B (8), were isolated from the methanol extract of the whole plants of Hydrocotyle sibthorpioides.The structures of the new compounds were elucidated on the basis of chemical and spectroscopic evidence.     

Perennisosides I-VII, acylated triterpene saponins with antihyperlipidemic activities from the flowers of Bellis perennis

The methanolic extract and its saponin fraction (methanol-eluted fraction) of the flowers of Bellis perennis were found to suppress serum triglyceride elevation in olive oil-treated mice. From the saponin fraction, seven new triterpene saponins, perennisosides I (1), II (2), III (3), IV (4), V (5), VI (6), and VII (7), were isolated together with four known saponins, bellidioside A (8), asterbatanoside D (9), bernardioside B 2 (10), and bellissaponin BS6 (11). The stereostructures of 1- 7 were elucidated on the basis of chemical and spectroscopic evidence. Among these saponins, perennisosides I (1) and II (2) showed inhibitory effects on serum triglyceride elevation at doses of 25-50 mg/kg, po.     

Batatins I and II, ester-type dimers of acylated pentasaccharides from the resin glycosides of sweet potato

Batatins I (1) and II (2), two ester-type dimers of acylated pentasaccharides, have been isolated by recycling HPLC from the hexane-soluble extract of sweet potato (Ipomoea batatas var. batatas). The structures were elucidated by a combination of high-resolution NMR spectroscopy and mass spectrometry. Complete analysis and unambiguous assignments of the 1H and 13C NMR spectra of 1 and 2 were achieved by 2D shift correlation measurements. The glycosidic acid forming each branched pentasaccharide monomeric unit was confirmed as simonic acid B. Three different fatty acids esterify this core at the same positions in both batatins: C-2 on the second rhamnose unit and C-4 and C-2 (or C-3) on the third rhamnose moiety. The acylating residues were identified as (+)-(2S)-methylbutanoic, dodecanoic (lauric), and cinnamic acids. The site of lactonization by the aglycon in unit A was placed at C-3 of the second saccharide. The position for the ester linkage for monomeric unit B on the macrocylic unit A was identified as C-3 of the terminal rhamnose' '. Through spectroscopic simulation of these complex oligosaccharides, the chemical shifts and coupling constants were deduced for the overlapped proton resonances with a non-first-order resolution. The experimental NMR spectroscopic values registered for batatinoside I (3), a new polyacylated macroyclic pentasaccharide also isolated from this plant, were used as the starting point for spectral simulation of 1 and 2. Both polymers 1 and 2 represent dimers of compound 3.     

Resin glycosides from the flowers of Ipomoea murucoides

The CHCl(3)-soluble extract from the flowers of the Mexican medicinal plant Ipomoea murucoides, through preparative-scale recycling HPLC, yielded murucoidins I-V (1-5), which are new pentasaccharides of jalapinolic acid, as well as the known stoloniferin I (6). Saponification of the crude resin glycoside mixture yielded two glycosidic acids, simonic acid B (9) and operculinic acid A (10), and their esterifying residues were composed of the two short-chain fatty acids, 2-methylpropanoic and (2S)-methylbutyric acids. All the isolated compounds (1-6) were characterized through high-field NMR spectroscopy. Compound 4 exhibited marginal cytotoxicity against Hep-2 cells (ED(50) 4 microg/mL).     

Pentasaccharide glycosides from the roots of Ipomoea murucoides

Five pentasaccharide glycosides, murucins 1-5 (1-5), were isolated from the roots of the arboreal species Ipomoea murucoides, and their structures were elucidated by spectroscopic and chemical methods. Compounds 1-5 were evaluated for cytotoxicity against a small panel of cancer cell lines.     

甘薯的化学成分

目的：对甘薯（lpomoea batatas）的化学成分进行研究。方法：运用多种层析方法进行分离纯化，通过渡谱和化学方法确定化合物的结构。结果：分离鉴定了5个化合物，即乙酰-β-香树醇（1）、表木栓醇（2）、咖啡酸乙酯（3）、咖啡酸（4）、simonin Ⅳ（5）。结论：5个化合物为首次从该植物中分离得到，其中simonin Ⅳ（5）为首次从甘薯中分离得到的树脂糖苷类化合物。     

番薯块根化学成分研究

目的:研究番薯块根的化学成分。方法:95%乙醇提取回收溶剂后以氯仿萃取,萃取部位经多种层析方法分离;结合理化性质和波谱方法进行结构鉴定。结果:分离并鉴定了6个化合物,分别为:Batatinoside I(1)、枸橼苦素(2)、咖啡酸十八烷酯(3)、乙酰-β-香树醇(4)、咖啡酸(5)、东莨菪素(6)。结论:其中,化合物1为结构新颖的树脂糖苷类化合物,并首次从番薯中分离得到。     

Sedative, vasorelaxant, and cytotoxic effects of convolvulin from Ipomoea tyrianthina

Aim of the study

Ipomoea tyrianthina has been used in Mexican traditional medicine as a mild purgative, for the treatment of nervous disorders, and against tumors. In this study, the effect of convolvulin (an ether-insoluble resin glycoside) from the root of Ipomoea tyrianthina on: Central Nervous System; as spasmolytic and vasodilator; cytotoxic against cancer cell lines is evaluated.

Materials and methods

Convolvulin isolated from the root of Ipomoea tyrianthina (IT-EM) was tested on pentylentetrazole induced seizures, pentobarbital-induced hypnosis, release of GABA and glutamic acid, isolated rat aorta and ileum rings, and against Caco-2 and KB cell lines.

Results

IT-EM increased the hypnotic effect induced by pentobarbital and the release of GABA in brain cortex of mice, but did not protect mice against pentylenetetrazole-induced convulsions. IT-EM produced a significant vasodilator effect in concentration- and endothelium-dependent manners on isolated rat aorta, but did not inhibit significantly contractions on rat ileum, colon, and jejune rings. IT-EM showed cytotoxic activity against nasopharyngeal carcinoma KB cell line.

Conclusions

Convolvulin (IT-EM) from Ipomoea tyrianthina has sedative effect, vasorelaxant effect in concentration- and endothelium-dependent manners, and cytotoxic activity against nasopharyngeal carcinoma KB cell line.     

Ipomoeassins A-E, cytotoxic macrocyclic glycoresins from the leaves of Ipomoea squamosa from the Suriname rainforest

The new glycoresins, ipomoeassins A-E (1-5), have been isolated from the leaves of Ipomoea squamosa. The structures were elucidated by spectroscopic analyses and chemical transformations. The absolute configurations of C-5 (ipomoeassins 3-5) and C-11 (ipomoeassins 1 and 2) were determined by their derivatives with (R)- and (S)-MPA. All the isolates were active in the A2780 human ovarian cancer cell line assay, and 4 showed the highest activity with an IC(50) value of 35 nM.     

Antinociceptive effect from Ipomoea cairica extract

Ipomoea cairica L. Sweet (Convolvulaceae) is used in Brazilian folk medicine for the treatment of rheumatism and inflammations. Ipomoea cairica ethanolic extract (100, 300, 1000 and 3000 mg/kg; per os) induced dose-dependent reduction of response in the formalin test inflammatory phase in mice. The same dose range did not modify neurogenic pain in formalin test, tail-flick reflex latency, carrageenan-induced paw edema, and Rota-Rod test motor performance. From the bio-active fraction 3,5-di-O-caffeoylquinic acid and 4,5-di-O-caffeoylquinic acid were obtained. These compounds have been previously reported to have analgesic and antioxidative effects. A possible explanation for the antinociception is that somehow the compounds present in the extract reduced the release of pro-nociceptive mediators unrelated to carrageenan-induced edema, such as histamine. Interestingly, caffeoylquinic acid derivatives have been reported to inhibit histamine release on in vitro models. The isolated caffeoylquinic acids could explain, at least in part, the antinociceptive effect of Ipomoea cairica polar extract.     

Pentasaccharide resin glycosides from Ipomoea pes-caprae

Pescapreins XXI-XXX (1-10), pentasaccharide resin glycosides, together with the known pescapreins I-IV and stoloniferin III were isolated from the aerial parts of Ipomoea pes-caprae (beach morning-glory). The pescapreins are macrolactones of simonic acid B, partially esterified with different fatty acids. The lactonization site of the aglycone, jalapinolic acid, was located at C-2 or C-3 of the second saccharide moiety. Their structures were established by a combination of spectroscopic and chemical methods. Compounds 1-10 were evaluated for their potential to modulate multidrug resistance in the human breast cancer cell line MCF-7/ADR. The combined use of these new compounds at a concentration of 5 μg/mL increased the cytotoxicity of doxorubicin by 1.5-3.7-fold.     

五爪金龙的化学成分研究

目的:为阐明五爪金龙的有效成分,对其地上部分进行了化学成分研究。方法:五爪金龙地上部分乙醇回流提取,提取物用石油醚、氯仿、乙酸乙酯和正丁醇萃取,氯仿萃取部位经反复硅胶柱层析。化合物结构鉴定通过理化常数和波谱数据进行确定。结果:分离得到4个化合物,经光谱方法和物理方法鉴定分别为槲皮素-4′,7-二甲醚(Ⅰ),山奈素-4′,7-二甲醚(Ⅱ),β-胡萝卜苷(Ⅲ),β-谷甾醇(Ⅳ)。结论:以上化合物全部为首次从该植物中分离得到,其中化合物Ⅱ为首次从该属中分离得到。     

Characterization of pentasaccharide glycosides from the roots of Ipomoea arborescens

Ten new pentasaccharide glycosides, arboresins 1-6 (1-6) and murucins 6-9 (8-11), along with five known glycolipids, were isolated from the roots of Ipomoea arborescens, and their structures were elucidated by spectroscopic and chemical methods. Compounds 1-6 and 8-11 were evaluated for cytotoxicity against a small panel of cancer cell lines.     

巴西甘薯叶化学成分研究

目的:研究巴西甘薯叶的化学成分。方法:巴西甘薯叶乙醇提取物经石油醚、乙酸乙酯、正丁醇萃取,其中乙酸乙酯、正丁醇萃取部位用硅胶柱色谱、Sephadex LH-20凝胶柱色谱等方法,分离得到4个化合物,经理化性质和波谱数据鉴定结构。结果:从巴西甘薯叶中分离鉴定4个化合物,分别为枸橼苦素(1)、咖啡酸(2)、3,4-二咖啡酰基奎宁酸(3)、1,2,3,4-四氢-β-咔啉-3-羧酸(4)。结论:化合物1~4均为首次从该植物中分离得到。     

Orizabins V-VIII, tetrasaccharide glycolipids from the Mexican scammony root (Ipomoea orizabensis).

An extensive investigation of the so-called jalapin resinoid obtained from roots of the Mexican scammony, Ipomoea orizabensis, using high field NMR spectroscopy led to the characterization of six glycosides, including the known scammonins I (1) and II (2) and four new tetrasaccharides of jalapinolic acid, orizabins V-VIII (3-6). All the isolates (1-6) were found to be weakly cytotoxic toward human oral epidermoid carcinoma (KB).     

Additional toxic, bitter saponins from the seeds of Chenopodium quinoa

Quinoa (Chenopodium quinoa) is an important Native American food grain. Prior to consumption, the seeds must be washed with H2O to remove bitterness and improve nutritive value. From the warm-H2O extract of quinoa seeds from Mexico, saponins 1-4 were isolated by monitoring the fractionation with brine shrimp lethality and a taste test for bitterness. By chemical, spectral, and enzymatic methods, 1-4 were identified as glycosides of oleanolic acid. Saponin 4, 3-O-[(beta-D-xylopyranosyl)(1----3)]-beta-D-glucuronopyranosyl-6-O -methyl ester]-oleanolic acid, is a new natural compound.     

Moluccensins R-Y, limonoids from the seeds of a mangrove, Xylocarpus moluccensis

Eight limonoids, named moluccensins R-Y (1, 2, 5-10), and six known compounds, including 6-hydroxymexicanolide (3), were isolated from the seeds of an Indian mangrove, Xylocarpus moluccensis, collected in the estuaries of Andhra Pradesh. The absolute configuration of moluccensin V (7) was confirmed by means of single-crystal X-ray diffraction analysis. The (1)H and (13)C NMR data for 6-hydroxymexicanolide (3) was assigned for the first time, and the 6R absolute configuration established by single-crystal X-ray diffraction analysis. Moluccensin R (1), 6R-hydroxymexicanolide (3), and 2-hydroxyfissinolide (4) exhibited marked antifeedant activity against the third-instar larvae of Brontispa longissima at a concentration of 1 mg/mL. The most potent compound tested was 2-hydroxyfissinolide (4), with an AFC(50) (concentration for 50% antifeedant activity) value of 94 μg/mL at 24 h.     

Anticonvulsant Effect of Aqueous,Hydroalcohol and Chloroform Extracts from Ipomoea stans Root in the Rat

The anticonvulsant activity of aqueous (AQ), ethanol (E-OH) and chloroform (CHL) extracts of Ipomoea stans root was demonstrated in adult male Wistar rats following ad libitum ingestion of the aqueous extract over 7 days, or a single oral dose of 100 mg/kg ethanol or chloroform extract. Maximal electroshock seizure inducing test (MES) and subcutaneously injected metrazole (METsc) were the experimental epilepsy models used. Maximum protection exhibited to MES were 80%, 36% and 57%; and in the case of METsc, 15%, 41% and 50% when AQ, E-OH or CHL extract was administered, respectively.