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.     

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.     

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.     

Vanillic acid glycoside and quinic acid derivatives from Gardeniae Fructus

Bioassay-directed chromatographic fractionation of an ethyl acetate extract of Gardenia jasminoides (Gardeniae Fructus) afforded a new vanillic acid 4-O-beta-d-(6'-sinapoyl)glucopyranoside (1) and five new quinic acid derivatives, methyl 5-O-caffeoyl-3-O-sinapoylquinate (2), ethyl 5-O-caffeoyl-3-O-sinapoylquinate (3), methyl 5-O-caffeoyl-4-O-sinapoylquinate (4), ethyl 5-O-caffeoyl-4-O-sinapoylquinate (5), and methyl 3,5-di-O-caffeoyl-4-O-(3-hydroxy-3-methyl)glutaroylquinate (6), together with three known quinic acid derivatives, two flavonoids, two iridoids, and two phenolic compounds. The structures of new compounds were elucidated by the aid of spectroscopic methods. These compounds were assessed for antioxidant activity using three different cell-free bioassay systems and for HIV-1 integrase inhibitory activity. Five new quinic acid derivatives showed potent DPPH radical scavenging, superoxide anion scavenging, and lipid peroxidation inhibition activities. These new quinic acid derivatives also exhibited HIV-1 integrase inhibitory activity.     

Antiinflammatory activity of Ipomoea pes-caprae (L.) R. Br

The antiinflammatory activity of an extract from the leaves of Ipomoea pes-caprae (L.) R. Br., used as a traditional remedy for different types of inflammation, was investigated using experimental models of acute inflammation. Topical application of the extract inhibited carrageenan-induced paw oedema and ear oedema induced in rats by arachidonic acid or ethyl phenylpropiolate. In vitro prostaglandin formation was inhibited by the extract in a concentration-dependent manner, with a potency equal to that of aspirin but considerably less than that of indomethacin. This study shows that Ipomoea pes-caprae has a significant antiinflammatory activity, probably due to a reduction of prostaglandin and leukotriene formation. Thus, in addition to earlier results, this work further supports the use of Ipomoea pes-caprae as an antiinflammatory agent in traditional medicine.     

Antinociceptive properties of the methanolic extract obtained from Ipomoea pes-caprae (L.) R. Br

Ipomoea pes-caprae is a medicinal plant used in many countries for the treatment of several ailments, including inflammatory and algesic processes. The present study describes the antinociceptive effects of the methanolic extract and two fractions obtained from aerial parts of this plant. The results indicated that both methanolic extract and two fractions (ethyl acetate and aqueous) exhibited considerable antinociceptive activity against two classical models of pain in mice. Methanolic extract presented a calculated ID50 value of 33.8 mg/kg, i.p. against writhing test and also inhibited both phases of pain (neurogenic and inflammatory) of the formalin test with ID50 of 37.7 and 12.5 mg/kg, i.p. for the first and second phase, respectively. Preliminary phytochemical analysis suggested the presence of steroids, terpenoids, alkaloids and flavonoids. These findings support, at least in part, the popular use of I. pes-caprae to treat dolorous processes.     

HPLC法同时测定厚藤不同部位中8种成分

目的 建立HPLC法同时测定厚藤不同部位中新绿原酸、绿原酸、隐绿原酸、咖啡酸、异槲皮苷、异绿原酸B、异绿原酸A、异绿原酸C的含量.方法 厚藤70％甲醇提取物的分析采用InfinityLab Poroshell 120 EC-C18柱(4.6mm×250 mm,4μm);流动相乙腈-0.2％磷酸溶液,梯度洗脱;柱温25℃...     

Inhibition of ethyl phenylpropiolate-induced rat ear oedema by compounds isolated from Ipomoea pes-caprae (L.) R. Br.

The extract (IPA) of leaves from Ipomoea pes-caprae (L.) R. Br. has previously been shown to reduce the development of rat ear oedema induced by ethyl phenylpropiolate (EPP) in a dose-dependent manner. Using this bioassay to guide fractionation of the extract, two diastereomeric compounds, the actinidols 1a and 1b, were isolated (0.8% of IPA). The actinidols constitute part of the active principle of IPA. Compounds, previously isolated from IPA, with either prostaglandin synthesis inhibiting activity in vitro [2-hydroxy-4,4,7-trimethyl-1(4H)-naphthalenone, (?)-mellein and eugenol] or antispasmodic activity (E-phytol) were also assayed for inhibitory effects on the development of EPP-induced rat ear oedema. They all reduced oedema formation dose-dependently. The results suggest that IPA consists of several active compounds which interfere with the process of inflammation in different ways.     

Quinic acid esters from Pluchea indica with collagenase, MMP-2 and MMP-9 inhibitory activities

Investigation of collagenase inhibitory natural components afforded two quinic acid esters (1 and 2) and quercetin (3) from the leaves of Pluchea indica (Compositae). Of these, compounds 1 and 2 exhibited collagenase inhibitory activity (IC(50)) at a concentration of less than 10 microm, and 1 showed matrix metalloproteinase (MMP)-2 and -9 inhibitory activity (IC(50)) at 2.5 and 6.4 microm, respectively.     

Antioxidant activity of caffeoyl quinic acid derivatives from the roots of Dipsacus asper Wall

The methanol extract from Dipsacus asper Wall (Dipsacaceae) was found to show antioxidant activity against free radical and Cu(2+)-mediated LDL oxidation. In further study, to identify active constituents from the plant, six caffeoyl quinic acid derivatives: 3,4-di-O-caffeoylquinic acid (1), methyl 3,4-di-O-caffeoyl quinate (2), 3,5-di-O-caffeoylquinic acid (3), methyl 3,5-di-O-caffeoyl quinate (4), 4,5-di-O-caffeoylquinic acid (5) and methyl 4,5-di-O-caffeoyl quinate (6) were isolated. Their structures were identified by spectroscopic methods including 2D-NMR. The isolated compounds, 1-6, were found to be potent scavengers of the free radical 1,1-diphenyl-2-picrylhydrazyl (DPPH), and are more potent than butylated hydroxyl toluene (BHT) used as a positive control. The compounds 1-6 also inhibited Cu(2+)-mediated low-density lipoprotein (LDL) oxidation. They increased the lag time of conjugated dienes formation and inhibited the generation of thiobarbituric acid reactive substances (TBARS) in a dose-dependent manner. These results suggested that Dipsacus asper due to its antioxidant constituents, 1-6, may have a role to play in preventing the development and progression of atherosclerotic disease.     

Caffeic acid esters and lignans from Piper sanguineispicum

Three new caffeic acid esters (1-3), four new lignans (4-7), and the known compounds (7'S)-parabenzlactone (8), dihydrocubebin (9), and justiflorinol (10) have been isolated from leaves of Piper sanguineispicum. Their structures were determined by spectroscopic methods, including 1D and 2D NMR, HRCIMS, CD experiments, and chemical methods. Compounds 1-10 were assessed for their antileishmanial potential against axenic amastigote forms of Leishmania amazonensis. Caffeic acid esters 1 and 3 exhibited the best antileishmanial activity (IC(50) 2.0 and 1.8 μM, respectively) with moderate cytotoxicity on murine macrophages.     

Cinnamic ester derivatives from Oxalis pes-caprae (Bermuda buttercup)

Seven new cinnamic ester derivatives ( 1- 7) were isolated from a methanol extract of the fresh leaves and twigs of Oxalis pes-caprae (Bermuda buttercup). The structures of these new compounds were determined by spectroscopic data interpretation. The effects of compounds 1- 7 on the germination and growth of Lactuca sativa (lettuce) were studied.     

Tyrosinase inhibitory p-coumaric acid from ginseng leaves.

By bioassay-guided fractionation using mushroom tyrosinase, p-coumaric acid was characterized as the principal tyrosinase inhibitor from the fresh leaves of Panax ginseng (Araliaceae). It inhibited the oxidation of L-tyrosine more strongly than that of L-3, 4-dihydroxyphenylalanine (L-DOPA) by this enzyme. On the basis of this finding, various related phenylpropanoid analogues were also tested in order to gain new insights into their structural criteria.     

Neutralization of toxic effects of different crude jellyfish venoms by an extract of Ipomoea pes-caprae (L.) R. Br.

An extract (IPA) of the plant Ipomoea pes-caprae (L.) R. Br., previously shown to be clinically effective toward dermatitis caused by venomous jellyfishes, was studied as to its ability to neutralize toxic activities of jellyfish venoms. Different venoms exhibited different degrees of activity. When IPA was incubated with active venoms, it inhibited the actions of all jellyfish venoms tested, with IC50 values in the range of 0.3-0.8 mgIPA/mg venom for proteolytic action, and with about 10 times lower IC50 values for the neutralization of haemolytic action. These activities of IPA support the previously reported effectiveness in the treatment of dermatitis caused by jellyfish sting.     

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.     

Antioxidant metabolism induced by quinic acid. Increased urinary excretion of tryptophan and nicotinamide

For over 50 years, hippuric/quinic acids were believed to have no biological efficacy. Here data are presented to support the hypothesis that quinic acid is not responsible for any efficacy, but rather that quinic acid nutritionally supports the synthesis of tryptophan and nicotinamide in the gastrointestinal (GI) tract, and that this in turn leads to DNA repair enhancement and NF-kB inhibition via increased nicotinamide and tryptophan production.Moreover, it is shown that quinic acid is a normal constituent of our diet, capable of conversion to tryptophan and nicotinamide via the GI tract microflora, thus providing an in situ physiological source of these essential metabolic ingredients to humans. The concentrations of quinic and hippuric acids in the diet were dependent on each other when analysed in urine, as was evidenced by a significant linear regression analysis that included unsupplemented control subjects (n = 45, p < 0.001). Thus, these ingredients were identified as major dietary components, and not simply originating from environmental pollution as previously had been thought.     

An active ingredient of Cat's Claw water extracts identification and efficacy of quinic acid

Historic medicinal practice has defined Cat's Claw, also known as Una de Gato or Uncaria tomentosa, as an effective treatment for several health disorders including chronic inflammation, gastrointestinal dysfunction such as ulcers, tumors and infections. The efficacy of Cat's Claw was originally believed, as early as the 1960s, to be due to the presence of oxindole alkaloids. However, more recently water-soluble Cat's Claw extracts were shown not to contain significant amounts of alkaloids (<0.05%), and yet still were shown to be very efficacious. Here we characterize the active ingredients of a water-soluble Cat's Claw extract called C-Med-100 as inhibiting cell growth without cell death thus providing enhanced opportunities for DNA repair, and the consequences thereof, such as immune stimulation, anti-inflammation and cancer prevention. The active ingredients were chemically defined as quinic acid esters and could also be shown to be bioactive in vivo as quinic acid.     

Four aristolochic acid esters of rearranged ent-elemane sesquiterpenes from aristolochia heterophylla

Four aristolochic acid esters of ent-elemane type sesquiterpene having a new carbon skeleton, aristophyllides A (1), B (2), C (3), and D (4), were isolated from the stems and roots of Aristolochia heterophylla. The esters were characterized by NMR and MS methods and included is a study of absolute configurations using the CD exciton chirality method.     

Lupeol long-chain fatty acid esters with antimalarial activity from Holarrhena floribunda

An ethnopharmacological investigation was conducted among the Baka pygmies of Dja biosphere reserve (Cameroon) to collect information on the antimalarial plants used in their daily life. Holarrhena floribunda is one of those plants. Extracts of the stem barks of H. floribunda showed remarkable inhibitory activity against drug-resistant strains of Plasmodium falciparum at doses of 1.02-18.53 microg/mL when tested in vitro against two parasite clones designated as Indochina (W-2) and Sierra Leone (D-6). The aqueous extract was the most active against Indochina (W-2), with IC50 values of 1.02 microg/mL, while the ethanolic extract appeared to be the most active against Sierra Leone (D-6), with an IC50 of 4.33 microg/mL. The bioassay-guided fractionation of the neutral fraction of the crude extract led to the isolation of lupeol (1) and its three new long-chain fatty acid ester derivatives, namely, 3-O-(3'-hydroxyeicosanoyl)lupeol (2), 3-O-[(2'-(tetracosyloxy)acetyl]lupeol (3), and 3-O-[(1' '-hydroxyoctadecyloxy)-2'-hydroxypropanoyl]lupeol (4). These new compounds displayed some in vitro inhibition activity against the chloroquine-resistant strain FCR-3 isolated from Gambia and the chloroquine-sensitive standard strain 3D7. The hydroxy group of the fatty acid side chain appears to decrease the observed activity.