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.     

Resin glycosides from Ipomoea pes-caprae

Ipomoea pes-caprae (beach morning-glory; "ri?onina" for the herbal drug in Mexico) is prescribed by traditional healers to moderate "heat" in an infected kidney. The hexane-soluble extract from the aerial parts of this medicinal plant, through preparative-scale recycling HPLC, yielded six new lipophilic oligosaccharides of jalapinolic acid: pescaproside B (1) and pescapreins V-IX (2-6). The previously known pescaproside A (7), pescapreins I-IV (8-11), and stoloniferin III (12) were also identified in the analyzed material by means of HPLC comparison with authentic samples. The glycosidic acid structure for all pentasaccharides was confirmed as simonic acid B. Pescaproside B (1), an acylated glycosidic acid methyl ester, is structurally related to pescaprein III (10). Pescapreins V (2) and VI (3) are diasteroisomeric tetraglycosidic lactones of operculinic acid C. Both of these compounds contain (2S)-methylbutyric and n-dodecanoic acids as their esterifying residues. Pescapreins VII (4) and IX (6) are pentasaccharides that contain an n-decanoyl group as their esterifying fatty acid residue instead of the n-dodecanoyl found in pescapreins I (8) and IV (11). Pescaprein VIII (5) represents an isomer of pescaprein II (9) containing an n-dodecanoyl unit as the esterifying residue at position C-4 of the third rhamnose moiety and a 2-methylpropanoyl at C-2 of the second rhamnose. High-field NMR spectroscopy and FAB mass spectrometry were used to characterize all new isolated compounds.     

Inhibitors of bacterial multidrug efflux pumps from the resin glycosides of Ipomoea murucoides

A reinvestigation of the CHCl 3-soluble extract from flowers of the Mexican medicinal arborescent morning glory, Ipomoea murucoides, through preparative-scale recycling HPLC, yielded six new pentasaccharides, murucoidins VI-XI (1- 6), as well as the known pescaprein III (7), stoloniferin I (8), and murucoidins I-V (9- 13). Their structures were characterized through the interpretation of their NMR spectroscopic and FABMS data. Compounds 1-6 were found to be macrolactones of three known glycosidic acids identified as simonic acids A and B, and operculinic acid A, with different fatty acids esterifying the same positions, C-2 on the second rhamnose unit and C-4 on the third rhamnose moiety. The lactonization site of the aglycone was placed at C-2 or C-3 of the second saccharide unit. The esterifying residues were composed of two short-chain fatty acids, 2-methylpropanoic and (2S)-methylbutyric acids, and two long-chain fatty acids, n-dodecanoic (lauric) acid and the new (8R)-(-)-8-hydroxydodecanoic acid. For the latter residue, its absolute configuration was determined by analysis of its Mosher ester derivatives. All members of the murucoidin series exerted a potentiation effect of norfloxacin against the NorA overexpressing Staphylococcus aureus strain SA-1199B by increasing the activity 4-fold (8 microg/mL from 32 microg/mL) at concentrations of 5-25 microg/mL. Stoloniferin I (8) enhanced norfloxacin activity 8-fold when incorporated at a concentration of 5 microg/mL. Therefore, this type of amphipathic oligosaccharide could be developed further to provide more potent inhibitors of this multidrug efflux pump.     

Resin glycosides from the herbal drug jalap (Ipomoea purga)

Three new resin glycosides, purginosides I and II (1 and 2) and purgin I (3), were isolated from the aerial parts of Ipomoea purga and purified by preparative-scale recycling HPLC from a chloroform-soluble extract. Their structures were established through NMR spectroscopy and mass spectrometry. Purginosides I and II (1 and 2) are partially acylated branched pentasaccharides derived from operculinic acid A, which is composed of one D-fucose, one D-glucose, and three l-rhamnose units. The site of the aglycon macrolactonization is at C-2 of the second saccharide (rhamnose). In both compounds 1 and 2, three different esterifying residues were located at C-2 of the second rhamnose unit and at C-2 (or C-3) and C-4 on the third rhamnose moiety. The acylating residues were characterized as trans-cinnamic, n-decanoic, and either (+)-(2S)-2-methylbutanoic or n-hexanoic acid. Purgin I (3) was found to be an ester-type dimer of operculinic acid A, acylated by n-dodecanoic, (+)-(2S)-2-methylbutanoic, and trans-cinnamic acids at the same oligosaccharide core positions found in compounds 1 and 2. The site of lactonization by the aglycon in unit A was placed at C-2 of the second saccharide. The position for the ester linkage for the monomeric unit B on the macrocyclic unit A was identified as C-4 of the terminal glucose. This is the first report on the isolation, purification, and structure elucidation of intact individual resin glycoside constituents from the herbal drug jalap.     

Resin glycosides from the roots of Ipomoea tyrianthina and their biological activity

Seven new tetrasaccharide glycosides, tyrianthins 1-7 (1-7), along with six known glycolipids were isolated from the roots of Ipomoea tyrianthina, and their structures were elucidated by spectroscopic and chemical methods. The content of resin glycosides in samples collected in three different regions was analyzed and compared, and the results showed that the flowering or dry season did not have any effect on the chemical composition for the same locality, but the growing location itself did affect the chemical composition of resin glycosides. Intraperitoneal administration to mice of tyrianthin 6 (6) resulted in antidepressant activity. Tyrianthin 6 (6), scammonin 1 (8), and scammonin 2 (9) exhibited dose-dependent protective effects against pentylenetetrazole-induced seizures. Also, tyrianthin 6 (6) and scammonin 2 (9) produced relaxant effects on spontaneous contractions in the isolated rat ileum.     

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.     

Flavonol glycosides from the flowers of Aconitum paniculatum

Three new acetylated flavonol glycosides-kaempferol 3-O-beta-(2' '-acetyl)galactopyranoside (1), kaempferol 3-O-beta-(2' '-acetyl)galactopyranoside-7-O-alpha-arabinopyranoside (2), and quercetin 3-O-beta-(2' '-acetyl)galactopyranoside-7-O-alpha-arabinopyranoside (3)-were isolated from the flowers of Aconitum paniculatum. Their structures were elucidated by 1D and 2D NMR studies ((1)H-(1)H COSY, HSQC, HMBC) as well as by HPLC-MS.     

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.     

Sedative activity of two flavonol glycosides isolated from the flowers of Albizzia julibrissin Durazz

The flowers of Albizzia julibrissin are used as a sedative in oriental traditional medicine. The phytochemical study of this plant allowed the isolation of two flavonol glycosides, quercitrin (1) and isoquercitrin (2). The sedative activity of these compounds was evaluated, and both compounds 1 and 2 increased pentobarbital-induced sleeping time in dose-dependent manner in mice. These results support the use of the flowers of this plant as a sedative agent.     

Isolation and characterization of five new tetrasaccharide glycosides from the roots of Ipomoea stans and their cytotoxic activity

Five new tetrasaccharide glycosides, stansins 1-5, were isolated from the roots of Ipomoea stans, and their structures were elucidated using spectroscopic and chemical methods. Preliminary testing showed the cytotoxicity of 5 toward the OVCAR and UISO-SQC-1 cancer cell lines.     

Isolation and characterization of free radical scavenging flavonoid glycosides from the flowers of Spartium junceum by activity-guided fractionation

Spartium junceum L. (Fabaceae) flowers are used for the treatment of peptic ulcers in Turkish folk medicine. The possible superoxide dismutase-like activity of the extracts, fractions and constituents obtained through activity-guided fractionation were studied by using in vitro electron spin resonance spectrometry, in order to explain the role of antioxidant principles in the potent antiulcerogenic activity of the extract. Despite the fact that the triterpene, spartitrioside, which was previously reported as the active antiulcerogenic constituent of the flowers was found almost inactive, the flavonoid-rich fractions showed potent antioxidant activity. Five flavonoid glycosides bearing catechol structure in ring B were isolated from the butanol extract and their structures were elucidated using 1H- and 13C-NMR techniques as isoquercitrin (quercetin 3beta-glucoside) (1,); luteolin 4'beta-glucoside (2); quercetin 3, 4'-diglucoside (3); azaleatin 3beta-glucoside (quercetin 5-methylether 3beta-glucoside) (4), quercetin 4'beta-glucoside (5). Flavonoids (2) and (4) showed the highest in vitro antioxidant activity with 22.59 and 19.08 U/ml, respectively.     

Bioassay-guided isolation of anti-inflammatory, antinociceptive and wound healer glycosides from the flowers of Verbascum mucronatum Lam.

Ethnopharmacological relevance

The leaves, flowers and whole aerial parts of Verbascum L. species have been used to treat respiratory problems, haemorrhoids and other types of inflammatory conditions in traditional Turkish medicine.

Aim of the study

In order to evaluate this traditional information, the anti-inflammatory, antinociceptive and wound healing activities of Verbascum mucronatum Lam. which is used as haemostatic in Turkish folk medicine were investigated.

Materials and methods

In vivo inhibitory effect of the extracts on the carrageenan-induced hind paw edema model in mice was studied for the assessment of anti-inflammatory activity. Moreover, the wound healing potential of the plant were evaluated by using in vivo wound healing experimental models, i.e. incision and excision models on mice and rats, were comparatively assessed with a reference ointment Madecassol^®. Skin samples were also evaluated histopathologically.

Results

The results of these experimental studies exhibited that Verbascum mucronatum displays anti-inflammatory, antinociceptive and wound healing activities. Through bioassay-guided fractionation and isolation procedures four iridoid glucosides, ajugol (1), aucubin (2), lasianthoside I (3), catalpol (4), two saponins, ilwensisaponin A (5) and C (6) and a phenylethanoid glycoside, verbascoside (7) were isolated and their structures were elucidated by spectral techniques. Verbascoside (7) was found to possess significant wound healing activity as well as antinociceptive and anti-inflammatory potentials, per os without inducing any apparent acute toxicity or gastric damage.

Conclusion

The experimental study revealed that Verbascum mucronatum displays remarkable antinociceptive, anti-inflammatory and wound healing activities.     

Ipomotaosides A-D, resin glycosides from the aerial parts of Ipomoea batatas and their inhibitory activity against COX-1 and COX-2

Four new resin glycosides, namely, ipomotaosides A-D (1-4), were isolated from the dried aerial parts of Ipomoea batatas. The structures of 1-4 were elucidated by analysis of their spectroscopic data and by chemical derivatization and were tested for their anti-inflammatory activity against cyclooxygenase (COX)-1 and -2.     

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。     

Diterpenoids from the flowers of Rhododendron molle

Five new grayanane-type diterpenoids, rhodomolleins IX (1), X (2), XI (3), XII (4), and XIII (5), a new kalmane-type diterpenoid, rhodomollein XIV (6), and seven known diterpenoids, grayanotoxin II, rhodomolleins I and XIX, rhodojaponins II, III, and VI (7), and kalmanol, were isolated from the flowers of Rhododendron molle. The structures of 1-6 were elucidated by spectroscopic methods, including 1D and 2D NMR experiments.     

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.     

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。     

Cytotoxic withanolides from the flowers of Datura metel

Chemical investigation of a methanol extract of the flowers of Datura metel has led to the isolation of 10 new withanolides, withametelins I-P (1-8), 1,10-seco-withametelin B (9), and 12beta-hydroxy-1,10-seco-withametelin B (10), together with seven known withanolides. The structures of 1-10 were elucidated by means of spectroscopic methods, and the absolute stereochemistry of 1 was confirmed by single-crystal X-ray analysis. Compounds 1, 3, 4, and 6 exhibited cytotoxic activities against A549 (lung), BGC-823 (gastric), and K562 (leukemia) cancer cell lines, with IC50 values ranging from 0.05 to 3.5 microM.     

石榴花化学成分的研究

目的研究石榴Punica granatum L.花的化学成分。方法石榴花60%乙醇提取物采用硅胶、Sephadex LH-20、ODS、半制备液相、重结晶等进行分离纯化,根据理化性质及波谱数据鉴定所得化合物的结构。结果从中分离得到12个化合物,分别鉴定为β-1,4,6-三-O-没食子酰基葡萄糖(1)、butylbrevifolin carboxylate(2)、短叶苏木酚酸甲酯(3)、短叶苏木酚(4)、β-1,6-二-O-没食子酰基葡萄糖(5)、鞣花酸(6)、鹰嘴豆芽素A(7)、retusin-8-methylether(8)、蒲公英赛醇(9)、谷甾醇(10)、β-谷甾醇棕榈酸酯(11)、 crispin A(12)。结论化合物1～3、7～12为首次从石榴属植物中分离得到,化合物1～4、7～12为首次从该植物中分离得到。