Pentasaccharide Glycosides from the Roots of Ipomoea murucoides

Leon, Ismael; Enríquez, Raúl G.; Nieto, D.; Alonso, Daniel F.; Reynolds, William F.; Aranda, Eduardo; Villa, Josué

doi:10.1021/np050075m

Cited by 16 publications

(18 citation statements)

References 4 publications

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“…Infusions of the leaves, bark and flowers to treat inflamations and against scorpion bites (León et al, 2005).…”

Section: Murucoidesmentioning

confidence: 99%

“…Murucin 1 (64) presents marginal activity (ED50 5.0 μg/mL) against ovarian carcinoma (OVCAR-5) cells, but was inactive (ED50 >20.0 μg/mL) against colon carcinoma (HCT-15) and cervical carcinoma (UISO-SQC-1) cells. Murucins 2-5 were inactive against all three of these cell lines (León et al, 2005). From flowers of Ipomoea murucoides were isolated five lipophilic tetrasaccharide called murucoidins XII-XVI.…”

Section: Ipomoea Murucoides Roem and Schultmentioning

confidence: 99%

See 1 more Smart Citation

Review of the genus Ipomoea: traditional uses, chemistry and biological activities

Meira¹,

Silva²,

David³

et al. 2012

Rev. bras. farmacogn.

170

120

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Approximately 600-700 species of Ipomoea, Convolvulaceae, are found throughout tropical and subtropical regions of the world. Several of those species have been used as ornamental plants, food, medicines or in religious ritual. The present work reviews the traditional uses, chemistry and biological activities of Ipomoea species and illustrates the potential of the genus as a source of therapeutic agents. These species are used in different parts of the world for the treatment of several diseases, such as, diabetes, hypertension, dysentery, constipation, fatigue, arthritis, rheumatism, hydrocephaly, meningitis, kidney ailments and infl ammations. Some of these species showed antimicrobial, analgesic, spasmolitic, spasmogenic, hypoglycemic, hypotensive, anticoagulant, anti-infl ammatory, psychotomimetic and anticancer activities. Alkaloids, phenolics compounds and glycolipids are the most common biologically active constituents from these plant extracts.

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“…Infusions of the leaves, bark and flowers to treat inflamations and against scorpion bites (León et al, 2005).…”

Section: Murucoidesmentioning

confidence: 99%

Section: Ipomoea Murucoides Roem and Schultmentioning

confidence: 99%

Review of the genus Ipomoea: traditional uses, chemistry and biological activities

Meira¹,

Silva²,

David³

et al. 2012

Rev. bras. farmacogn.

170

120

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“…In particular, Ipomea species (morning glory species), which have extensive traditional uses in Mexican folk medicine, are prolific producers of such compounds, which are trivially known as "resin glycosides". 20 Some of the resin glycosides reported from Ipomea species include turpethinic acids A-E (I. turpethum), 21,22 murucins 1-5 and murucoidins I-V (I. murucoides), 23,24 operculinic acid, operculins (I. leptophylla), 25 stoloniferins I-XII (I. stolonifera), 26 scammomins I-VIII (ConVolVulus scammonia), 27,28,29 cuscutic acids A-D (Cuscuta chinensis), 30 cuscutic acids A 1 -A 3 (Cuscuta australis), 31 and soldanelline A (Calystegia soldanella). 32 These compounds mostly incorporate a linear tetra-or pentaglycosidic oligosaccharide unit attached to a secondary hydroxyl function of a fatty acid.…”

Section: Resultsmentioning

confidence: 99%

Crypthophilic Acids A, B, and C: Resin Glycosides from Aerial Parts of Scrophularia crypthophila

et al. 2007

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The water-soluble part of the methanolic extract from the aerial parts of Scrophularia crypthophila, through chromatographic methods, yielded three new resin glycosides, crypthophilic acids A-C (1-3). Compounds 1-3 are tetraglycosides of (+)-3S,12S-dihydroxypalmitic acid. The structures of these and 10 known compounds were elucidated by spectroscopic and chemical means. All natural resin glycosides known so far have been obtained from Convolvulaceae plants; this is the first report of such glycosides from another, taxonomically unrelated family (Scrophulariaceae).In the flora of Turkey, the genus Scrophularia is represented by 59 species, 23 of which are endemic. 1 Some Scrophularia species, especially S. nodosa, are used in folk medicine as a diuretic and for the treatment of wounds and hemorrhoids. Previous studies performed on Scrophularia species resulted in the isolation of iridoids, phenylethanoid glycosides and triterpene saponins. 2-8 Here, we report the isolation and structural elucidation of three new resin glycosides, 1-3, and 10 known compounds. Resin glycosides 1-3 are being reported for the first time from a family (Scrophulariaceae) other than Convolvulaceae. Results and DiscussionChromatographic studies performed on the above-ground parts of Scrophularia cryptophila Boiss. & Heldr. (Scrophulariaceae) afforded three new resin glycosides, crypthophilic acids A (1), B (2), and C (3). The known compounds catalpol, 9 aucubin, 10 methylcatalpol, 5,8 harpagide, 11 acetylharpagide, 11 chlorogenic acid, 12 tryptophan, 13 acteoside ()verbascoside), 14 angoroside C, 3 and buddlejasaponin III 15 were also isolated. The structures of the known compounds were based on their spectroscopic data (UV, IR, 1 H NMR, 13 C NMR, and MS).Compound 1 was isolated as a colorless, amorphous powder. The IR spectrum showed absorption bands for OH (3415 cm -1 ), CH (2920 cm -1 ), and C-O-C (1137 cm -1 ). Na + ). In the 1 H NMR spectrum of 1, all proton resonances were observed between δ 5.30 and 3.00 and between δ 2.50 and 0.90 (Table 1). COSY experiments revealed the presence of five spin systems. Four of these were attributed to two hexose and two 6-deoxyhexose (methylpentose) units, and four anomeric protons were observed at δ H 5.21 (d, J ) 1.7 Hz), 4.71 (d, J ) 1.7 Hz), 4.91 (d, J ) 7.7 Hz), and 4. 33 (d, J ) 7.4 Hz). These indicated the presence of a tetraglycosidic structure. The 13 C NMR spectrum showed 40 carbon resonances, of which 24 were assigned to the tetraglycosidic moiety. An HSQC experiment made clear the assignments of each carbon resonance involved in the five spin systems. The coupling constants of the protons and the corresponding carbon resonances together with two secondary methyl signals at δ H 1.25 and 1.27 (each d, J ) 6.3 Hz) indicated that 1 was a tetraglycoside composed of two glucose and two rhamnose moieties. The anomeric configurations were assigned as for the glucopyranosyl and R for the rhamnopyranosyl groups from their coupling constants (Table 1). The sugar sequence was determined on the bas...

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“…In case of scorpion bite the decoction of this medicinal plant complex is drunk, and for alleviating tootache gargles are recommended . Besides the cytotoxic activity of murucins, some murucoidins from flowers of I. murucoides showed antimicrobial activity against SA‐1199B a norfloxacin‐resistant strain that over‐expresses the NorA MDR efflux pump . Murucoidins have also shown effects on the growth of Spodoptera frugiperda .…”

Section: Introductionmentioning

confidence: 99%

“…Murucoidins have also shown effects on the growth of Spodoptera frugiperda . The glycolipids isolated from the root and flowers of I. murucoides consist of a pentasaccharide or tetrasaccharide unit bonded to an 11‐hydroxyhexadecanoic acid forming a macrolactone …”

Section: Introductionmentioning

confidence: 99%

Hepta‐, hexa‐, penta‐, tetra‐, and trisaccharide resin glycosides from three species of Ipomoea and their antiproliferative activity on two glioma cell lines

León‐Rivera

Rı́o-Portilla

Enríquez

et al. 2016

Magnetic Reson in Chemistry

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Six new partially acylated resin glycosides were isolated from convolvulin of Ipomoea purga, Ipomoea stans, and Ipomoea murucoides (Convolvulaceae). The structures of compounds 1-6 were elucidated by a combination of NMR spectroscopy and mass spectrometry. The structure of jalapinoside B (1) consists of a hexasaccharide core bonded to an 11-hydroxytetradecanoic (convolvulinic) acid forming a macrolactone acylated by a 2-methylbutanoyl, a 3-hydroxy-2-methylbutanoyl, and a quamoclinic acid B units. Purginoic acid A (2) contains a hexasaccharide core bonded to a convolvulinic acid acylated by a 3-hydroxy-2-methylbutanoyl unit. Stansin A (4) is an ester-type heterodimer, and consists of two stansoic acid A (3) units, acylated by 2-methylbutanoic and 3-hydroxy-2-methylbutanoic acids. The site of lactonization was located at C-3 of Rhamnose, and the position for the ester linkage of the monomeric unit B on the macrolactone unit A was established as C-4 of the terminal rhamnose. Compounds 5 and 6 are glycosidic acids. Murucinic acid II (5) is composed of a pentasaccharide core bonded to an 11-hydroxyhexadecanoic (jalapinolic) acid, acylated by an acetyl unit. Stansinic acid I (6) is a tetrasaccharide core bonded to a jalapinolic acid, acylated by 2-methylbutanoyl and 3-hydroxy-2-methylbutanoyl units. Preliminary testing showed the cytotoxicity of compounds 1-6 toward OVCAR and UISO-SQC-1 cancer cell lines. In addition, compound 1 showed an antiproliferative activity on glioma C6 and RG2 tumor cell lines. Copyright © 2016 John Wiley & Sons, Ltd.

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Pentasaccharide Glycosides from the Roots of Ipomoea murucoides

Cited by 16 publications

References 4 publications

Review of the genus Ipomoea: traditional uses, chemistry and biological activities

Review of the genus Ipomoea: traditional uses, chemistry and biological activities

Crypthophilic Acids A, B, and C: Resin Glycosides from Aerial Parts of Scrophularia crypthophila

Hepta‐, hexa‐, penta‐, tetra‐, and trisaccharide resin glycosides from three species of Ipomoea and their antiproliferative activity on two glioma cell lines

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