Phytochemical Investigation of the Roots of Ipomoea asarifolia and Antiproliferative Activity of the Isolated Compounds against Multiple Myeloma Cells.

Ipomoea asarifolia is a herbaceous plant belonging to the family Convolvulaceae and is native to tropical regions of Africa, America, and Asia. A dichloromethane root extract showed antiproliferative activity against multiple myeloma cells (RPMI 8226). The phytochemical investigation led to the isolation of 15 compounds. Compounds 1-4, named (4S,8S)-1-(furan-3-yl)-9-hydroxy-4,8-dimethylnonane-1,6-dione, isoferulic acid hexadecyl ester, caffeic acid hexadecyl ester, and asarifolin I, respectively, are described for the first time. The structures of these molecules were established from their NMR, UV, IR spectroscopic, and MS data. 4-Hydroxycinnamic acid hexadecyl ester (5), 4-hydroxycinnamic acid octadecyl ester (6), 4-hydroxycinnamic acid eicosyl ester (7), caffeic acid octadecyl ester (8), pescapreins III, IV, XXI, XXIII, XXV, and XXVI (9-14), and stoloniferin III (15) were also isolated. All compounds were tested against a multiple myeloma cell line (RPMI 8226). When their IC50 value was lower than 10 µM, the compounds were also tested against two other multiple myeloma cell lines, MM.1S and MM.1R. Compound 3 was the most potent, with an IC50 value of 3.0 µM against RPMI 8226 cells.

Bioguided Phytochemical Study of Ipomoea cairica Extracts with Larvicidal Activity against Aedes aegypti.

Vector-borne diseases, such as those transmitted by Aedes aegypti, are a constant threat to inhabitants of tropical regions of the planet. Synthetic chemicals are commonly used as a strategy to control them; however, these products are known to persist in ecosystems and drive the appearance of resistance genes in arthropod vectors. Thus, the use of natural products has emerged as an environmentally friendly alternative in integrated vector control strategies. The present bioguided study investigated the larvicidal potential of Ipomoea cairica extracts, fractionated using thin-layer and open-column chromatography, because this species has been shown to exert larvicidal effects on the genus Aedes. The objective of this study was to evaluate the nonvolatile components in ethanolic extract of I. cairica stems as a potential natural larvicidal, and coumarins, such as 7-hydroxy-6-methoxychromen-2-one (scopoletin) and 7-hydroxychromen-2-one (umbelliferone), were identified as major compounds; however, they were not shown to be responsible for the larvicidal activity. Based on the results of the larvicidal action tests, these coumarins are not directly responsible for the larvicidal activity, but this activity might be attributed to a synergistic effect of all the compounds present in the most active secondary fraction, called F.DCM, which had an LC50 value of 30.608 mg/L. This type of study has yet not been conducted in the region; therefore, it is an important contribution to recognizing a natural and easy-to-cultivate source of vector control, such I. cairica.

Evaluation of the effects of Ipomoea staphylina on ovarian cancer cell line.

Ovarine cancer is a common woman malignancy in the world. Majority of the ovarian cancers are originated in the epithelial region which are lack of symptomps and this type of cancer is often get localized, when the tumour has spread outside the pelvis. Based on this context, the present study evaluated the effects of both aqueous and ethanolic extracts of Ipomoea staphylina leaves on ovarian cancer cell line. The SKOV-3 ovarian cancer cell line was used for evaluation of the effects of both extracts. Both extracts showed IC50 effects on ovarian cancer cell lines as sensitivity index (SI) for both extracts were recorded to above 1.iFurther, ethanol extract was more effective in the moderation of gene expressions of matrix metalloproteinase-2 (MMP-2) and matrix metalloproteinase-9 (MMP-9) in comparison to aqueous extract. Further, morphological changes of SKOV-3 cells after treatment with both extracts also confirmed the results. The study, therefore, concludes that the ethanolic extract of Ipomoea staphylina leaves is more effective against ovarian cancer cell line.

A New Glycosidic Acid, Muricatic Acid D, and Resin Glycosides, Muricatins X and XI, from the Crude Resin Glycoside Fraction of the Seeds of Ipomoea muricata.

Alkaline hydrolysis of crude resin glycoside fraction of the seeds of Ipomoea muricata (L.) Jacq. (Convolvulaceae) yielded a new glycosidic acid, muricatic acid D; three known glycosidic acids, namely, muricatic acids A, B, and C; and three known organic acids, namely, isobutyric, 2S-methylbutyric, and 2S-methyl-3S-hydroxybutyric acid. Two new genuine resin glycosides with macrolactone structures (jalapins), muricatins X and XI, were also isolated from the fraction. Their structures were determined using spectroscopic data and chemical evidence.

Nitrogen-doped carbon dots for dual-wavelength excitation fluorimetric assay for ratiometric determination of phosalone.

N-doped carbon dots (N-CDs) were fabricated in a simple procedure by hydrothermal treatment of cellobiose and urea. When excited at 235 nm or 327 nm, only one emission peak at around 420 nm has been observed. With the addition of phosalone, the excitation band at 235 nm was efficiently quenched within 1 min, while the excitation band at 327 nm showed little change. Accordingly, the fluorescence of the N-CDs-phosalone mixture showed quenching under 254-nm UV light, while nearly no fluorescence quenching could be observed under 365-nm UV light. This phenomenon provides a novel anti-false-positive mechanism for phosalone identification. Therefore, the label-free ratiometric sensor for rapid, naked-eye, and anti-false-positive detection of phosalone was proposed for the first time based on the intrinsic dual-excitation N-CDs. Under the optimum experimental conditions, the linear ranges of the excitation-based ratiometric assay were 0.08~4.0 µg/mL and 4.0~14.0 µg/mL; the limit of detection was 28.5 ng/mL. The as-constructed sensor was applied to detect phosalone residue in actual samples, and results were compared with the standard gas chromatographic (GC) method. The recoveries of the established sensor were between 90.0% and 110.0% with RSD lower than 6.6%, while that for the GC method was between 92.5% and 113.0% with RSD lower than 5.8%. Results reveal that the accuracy (recovery) and precision (RSD) of the as-constructed method are comparable to the standard GC method. In this paper, dual-excitation N-doped carbon dots (N-CDs) were synthesized by a simply one-step hydrothermal method for the first time. The novel dual-excitation ratiometric sensor based on the sole intrinsic N-CDs was constructed for phosalone sensing.

Ipomoea staphylina Attenuates Potassium Dichromate-Induced Nephrotoxicity in Wistar Rats via Antioxidant and Antiapoptotic Effects.

Occupational and environmental exposure to chromium compounds leads to nephrotoxicity to humans and animals due to the overproduction of ROS. Our study was aimed to demonstrate the shielding effect of hydroethanolic extract of Ipomoea staphylina (HEIS) bark on male Wistar rats challenged with potassium dichromate (K2Cr2O7). Division of animals was done in 4 groups' viz., normal control, K2Cr2O7 control, K2Cr2O7+HEIS (100 mg/kg), and K2Cr2O7+HEIS (200 mg/kg). Except for the normal control group, other groups were challenged with a single dose (subcutaneous) of K2Cr2O7 (15 mg/kg) and then treated with HEIS (100 and 200 mg/kg) for 1 week. It was observed that animals treated with K2Cr2O7 showed a notable increase in serum creatinine, blood urea, and BUN and dwindles in protein level. These changes were significantly reversed after a 1-week treatment with HEIS (100 and 200 mg/kg). Moreover, HEIS (100 and 200 mg/kg) showed a remarkable improvement in the activity of antioxidant enzymes (GPx, CAT, and SOD) and decreased the levels of TNF-α and IL-1ß in the kidney. Furthermore, treatment with HEIS (100 and 200 mg/kg) notably decreased the activity of caspase-3 and improved the level of HO-1 especially in the K2Cr2O7+ HEIS (200 mg/kg) group. Also, the histopathological study of the kidney supported the protective effects of HEIS. Hence, HEIS bark holds a notable protective effect against K2Cr2O7-induced nephrotoxicity in rats.

Relationship between the amount and composition of epicuticular wax and tolerance of Ipomoea biotypes to glyphosate.

Ipomoea species are troublesome weeds in crop systems through Brazil. Drought stress typically reduces glyphosate efficacy by reducing the foliar uptake of herbicides and their translocation. Using both glyphosate tolerant (GT) and sensitive (GS) plants from Ipomoea grandifolia, I. indivisa and I. purpurea species, this research aimed to (a) correlate amounts of epicuticular wax and tolerance to glyphosate in plants and (b) determine the effect of drought stress (DStress) on changes in the quantity and chemical composition of plant epicuticular waxes. The dose that causes 50% inhibition of growth (GR50) of the biotypes varied between 62 and 1208 (I. grandifolia), 159 and 913 (I. indivisa), and 389 and 1925 g a.e. ha-1 of glyphosate (I. purpurea). There was low inverse correlation (-0.46) between the amount of epicuticular wax and the sensitivity to glyphosate. GT biotypes of the species presented greater plastic capacities than GS biotypes for increasing the amount of epicuticular wax under DStress. The three Ipomoea species exhibited different chemical profiles of waxes supported by IR spectra, which allows for their differentiation. For I. grandifolia and I. purpurea, there was an increase in the polar components in the state without DStress, while for the species I. indivisa, no differences in infrared spectra were detected between the two water conditions.

Decreased Root-Knot Nematode Gall Formation in Roots of the Morning Glory Ipomoea tricolor Symbiotic with Ergot Alkaloid-Producing Fungal Periglandula Sp.

Many species of morning glories (Convolvulaceae) form symbioses with seed-transmitted Periglandula fungal endosymbionts, which produce ergot alkaloids and may contribute to defensive mutualism. Allocation of seed-borne ergot alkaloids to various tissues of several Ipomoea species has been demonstrated, including roots of I. tricolor. The goal of this study was to determine if infection of I. tricolor by the Periglandula sp. endosymbiont affects Southern root-knot nematode (Meloidogyne incognita) gall formation and host plant biomass. We hypothesized that I. tricolor plants infected by Periglandula (E+) would develop fewer nematode-induced galls compared to non-symbiotic plants (E-). E+ or E- status of plant lines was confirmed by testing methanol extracts from individual seeds for endosymbiont-produced ergot alkaloids. To test the effects of Periglandula on nematode colonization, E+ and E- I. tricolor seedlings were grown in soil infested with high densities of M. incognita nematodes (N+) or no nematodes (N-) for four weeks in the greenhouse before harvesting. After harvest, nematode colonization of roots was visualized microscopically, and total gall number and plant biomass were quantified. Four ergot alkaloids were detected in roots of E+ plants, but no alkaloids were found in E- plants. Gall formation was reduced by 50% in E+ plants compared to E- plants, independent of root biomass. Both N+ plants and E+ plants had significantly reduced biomass compared to N- and E- plants, respectively. These results demonstrate Periglandula's defensive role against biotic enemies, albeit with a potential trade-off with host plant growth.

Ipomeolides A and B, Resin Glycosides from Ipomoea pes-caprae and Combination Therapy of Ipomeolide A with Doxorubicin.

Two new resin glycosides, ipomeolides A (1) and B (2), both with an unusual nonlinear heteropentasaccharide core, along with five known compounds were isolated from the n-hexane/CHCl3 (1:1) extract of the aerial parts of Ipomoea pes-caprae. Ipomeolides A (1) and B (2) are macrolactone analogues of the rare (11 R)-jalapinolic acid, and macrolactonization occurred at C-2 of the second saccharide moiety. Compounds 1 and 2 show structural variation even in the pentasaccharide core. The structures of 1 and 2 were established by a combination of spectroscopic techniques as well as chemical modifications such as acetyl and acetonide derivatives as well as hydrolysis products. The new glycosidic acid was named ipomeic acid (1c). Compounds 1, 1b, and 2b were evaluated for cytotoxicity against human tumor cell lines. Compounds 1b and 2b were not effective on epithelial cells, but affected survival of K-562, which is of hematopoietic origin. A sublethal concentration of compound 1 (4 µM) when used in combination with 1 µM doxorubicin, an anticancer agent, significantly enhanced cytotoxicity to tumor cells. Such combined synergistic potency against leukemia cells and the absence of effects on epithelial cells may be beneficial for chemotherapy with minimal side effects to treat CML (chronic myeloid leukemia) malignancies.

Residue behavior and dietary risk assessment of chlorothalonil and its metabolite SDS-3701 in water spinach to propose maximum residue limit (MRL).

Dietary risk assessment generally combines food consumption data and the concentration of pesticide by using the risk quotient (RQ) method. Chlorothalonil is the second popular fungicide in the world, and its residue and risk assessment in water spinach remain unknown. In this paper, the field trials of chlorothalonil in water spinach were operated under good agricultural practice (GAP) in China to human health protective. The dissipation experiments demonstrated that chlorothalonil was rapidly degraded in water spinach, with the half-lives of 1.8-3.2 days, and the amount of its metabolite SDS-3701 (4-hydroxy-2,5,6-trichloroisophthalonitrile) taken up through the water spinach roots from the soil was minor. The terminal experiments disclosed that the average residues of chlorothalonil and SDS-3701 in water spinach were below 6.59 mg/kg and 0.01 mg/kg, respectively. The results suggested the chronic dietary risk probability of chlorothalonil was 51.95-59.15% in terms of all registered crops, and the acute dietary risk probability of chlorothalonil was 12.30%-63.01% in water spinach, highlighting that the dietary risk of chlorothalonil in water spinach under GAP was acceptable. MRL of chlorothalonil was proposed as 7 mg/kg for water spinach and 5 days was recommended as a safe pre-harvest interval (PHI) for chlorothalonil application in water spinach field.

Tremorgenic Indole Diterpenes from Ipomoea asarifolia and Ipomoea muelleri and the Identification of 6,7-Dehydro-11-hydroxy-12,13-epoxyterpendole A.

Indole diterpene alkaloids have been isolated from Ipomoea asarifolia and I. muelleri and are associated with a tremorgenic syndrome in livestock. To better characterize the tremorgenic activity of the major indole diterpene alkaloids in these two plants, terpendole K (1), 6,7-dehydroterpendole A (2), 11-hydroxy-12,13-epoxyterpendole K (3), terpendole C (5), paxilline (6), and a new compound, 6,7-dehydro-11-hydroxy-12,13-epoxyterpendole A (4), were isolated and evaluated for tremorgenic activity in a mouse model. Compounds 1, 2, 5, and 6 all showed similar and significant signs of tremorgenic activity. In contrast, the 11-hydroxy-12,13-epoxy compounds, 3 and 4, showed no significant tremorgenic activity.

Ergot Alkaloids and their Hallucinogenic Potential in Morning Glories.

Naturally occurring and semisynthetic ergot alkaloids play a role in health care or as recreational drugs in Western and indigenous Mexican societies. Evidence is summarized that ergot alkaloids present in Central American Convolvulaceae like Turbina corymbosa, Ipomoea violacea, and Ipomoea asarifolia are colonized by different species of a newly described clavicipitaceous fungal genus named Periglandula. The fungi are associated with peltate glandular trichomes on the adaxial leaf surface of its host plants. The Periglandula fungi are not yet culturable in vitro but were demonstrated to have the capacity to synthesize ergot alkaloids. The alkaloids do not remain in the fungal mycelium but are translocated via the glandular trichomes into their plant host. Both fungi and host benefit from a symbiotic lifestyle. In evolutionary terms the alkaloid biosynthetic gene cluster in the Periglandula/Ipomoea symbiosis is likely to have a conserved (basic) structure while biosynthetic ergot gene clusters within the genera Claviceps and Epichloe were under ecological selection for alkaloid diversification.

Effect of inoculation with arbuscular mycorrhizal fungi and blanching on the bioaccessibility of heavy metals in water spinach (Ipomoea aquatica Forsk.).

A plant's tolerance to heavy metals (HMs) and its detoxification mechanisms are associated with the subcellular distribution of HMs and their chemical forms. In this study, water spinach (Ipomoea aquatica Forsk.) was grown in two soils contaminated with a single HM (cadmium, Cd) or combined HMs (Cd and nickel, Ni). Inoculation of arbuscular mycorrizal fungi (AMF) was conducted to increase the accumulation of phosphorus (P) in plants. One major exception was to decrease the migration and accumulation of HMs in edible parts by the formation of P-HM complexes. The effects of blanching and simulated digestion on bioaccessibility were also assessed. The experimental results showed that the water spinach species used in this study had a high capacity to accumulate HMs. AMF treatment improved water spinach growth and decreased the accumulation of Ni but not that of Cd. Soluble and inorganic Cd and Ni were the major subcellular fractions and chemical forms in water spinach; these two HMs also exhibited higher migration capacities in comparison to chromium (Cr). Relative to raw tissues, 45-84% of Cd, Cr, and Ni were leached after blanching. Approximately 32-55%, 16-50%, and 27-40% of Cd, Cr, and Ni, respectively, were bioaccessible and could be metabolized by in vitro digestive fluids.

Identification of some Bioactive Metabolites in a Fractionated Methanol Extract from Ipomoea aquatica (Aerial Parts) through TLC, HPLC, UPLC-ESI-QTOF-MS and LC-SPE-NMR Fingerprints Analyses.

INTRODUCTION: The plant species Ipomoea aquatica contains various bioactive constituents, e.g. phenols and flavonoids, which have several medical uses. All previous studies were executed in Asia; however, no reports are available from Africa, and the secondary metabolites of this plant species from Africa are still unknown. OBJECTIVE: The present study aims finding suitable conditions to identify the bioactive compounds from different fractions. METHODOLOGY: Chromatographic fingerprint profiles of different fractions were developed using high-performance liquid chromatography (HPLC) and then these conditions were transferred to thin-layer chromatography (TLC). Subsequently, the chemical structure of some bioactive compounds was elucidated using ultra-performance liquid chromatography-quadrupole time of flight-tandem mass spectrometry (UPLC-QTOF-MS) and liquid chromatography-solid phase extraction-nuclear magnetic resonance (LC-SPE-NMR) spectroscopy. RESULTS: The HPLC fingerprints, developed on two coupled Chromolith RP-18e columns, using a gradient mobile phase (methanol/water/trifluoroacetic acid, 5:95:0.05, v/v/v), showed more peaks than the TLC profile. The TLC fingerprint allows the identification of the types of chemical constituents, e.g. flavonoids. Two flavonoids (nicotiflorin and ramnazin-3-O-rutinoside) and two phenolic compounds (dihydroxybenzoic acid pentoside and di-pentoside) were tentatively identified by QTOF-MS, while NMR confirmed the structure of rutin and nicotiflorin. CONCLUSION: The HPLC and TLC results showed that HPLC fingerprints give more and better separated peaks, but TLC helped in determining the class of the active compounds in some fractions. Bioactive constituents were identified as well using MS and NMR analyses. Two flavonoids and two phenolic compounds were tentatively identified in this species for the first time, to the best of our knowledge. Copyright © 2017 John Wiley & Sons, Ltd.

Intestinal Anti-Inflammatory Activity of the Aqueous Extract from Ipomoea asarifolia in DNBS-Induced Colitis in Rats.

Inflammatory bowel disease is triggered by an uncontrolled immune response associated with genetic, environmental, and intestinal microbiota imbalance. Ipomoea asarifolia (IA), popularly known as "salsa" or "brave salsa", belongs to the Convolvulaceae family. The aim of this approach was to study the preventive effect of IA aqueous extract in 2,4-dinitrobenzene sulfonic acid (DNBS)-induced colitis in rats. Rats pretreated with IA extract or sulfasalazine (SSZ) received intracolonic instillation of DNBS in 50% ethanol (v/v). IA extract presented a protective effect against intestinal inflammation, with improvement in the disease activity index and macroscopic damage. IA or SSZ significantly reduced myeloperoxidase activity, and also down-regulation of the gene expression of JNK1, NF-κß-p65, STAT3, and decreased levels of TNFα, IL-1ß, and increased IL-10, associated with a significant improvement of oxidative stress, in addition to a reduction in MDA and an increase of glutathione in colonic tissue. The protective effect of the extract was also confirmed in histological evaluation, showing preservation of the colonic cytoarchitecture. Immunohistochemical analysis revealed down-regulation of NF-κß-p65, iNOS, IL-17, and up-regulation of SOCs-1 and MUC-2. IA extract presents antioxidant and anti-inflammatory intestinal properties, and proved to be a potential application for preventing damage induced by DNBS.

Wound healing effect of ethanolic extract from Morning Glory (Ipomoea carnea Jacq.) leaves by using different models in rats.

Current study aims to evaluate the wound healing effect with apparent mechanism and determination of flavonoid (quercetin) from ethanol extract of Ipomea carnea jacq. leaves, family Convolvulaceae. The wound healing effect of ethanol extract from I. carnea jacq. leaves screened by excision and incision wound methods in rats. Five groups (Negative control, vehicle control, 2.5%w/w, 5% w/w ethanol extract ointment and 5%w/w Reference Ointment Povidone-iodine group) of rats (n-6) were experimentally wounded at dorsal portion of rats. The 5% w/w ointment of ethanol extract found significant wound contraction at 18-20th days, greater tensile strength, and biochemical parameters. Ethyl acetate fraction of ethanolic extract was analysed by RP-HPLC and retention time was found 3.042 min. The percentage of quercetin was found in I. carnea leaves as 0.842%. The results were supported by histopathological studies which showed augment in terms of collagen fibers, fibroblast and new blood vessels. The results were evidently exhibited the traditional uses of I. carnea leaves for wound healing effects. The healing effect may be attributed by presence of flavonoid and other compounds present in the leaves with free radical scavenging mechanism.

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

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.

Four Pentasaccharide Resin Glycosides from Argyreia acuta.

Four pentasaccharide resin glycosides, acutacoside F-I (1-4), were isolated from the aerial parts of Argyreia acuta. These compounds were characterized as a group of macrolactones of operculinic acid A, and their lactonization site of 11S-hydroxyhexadecanoic acid was esterified at the second saccharide moiety (Rhamnose) at C-2. The absolute configuration of the aglycone was S. Their structures were elucidated by established spectroscopic and chemical methods.

Identification and determination of ergot alkaloids in Morning Glory cultivars.

Seeds of plants from Ipomoea genera contain numerous ergot alkaloids, including psychoactive ergine and ergometrine, and are often abused as so-called "legal highs." In this work, an analytical method for determination of ergine and ergometrine, and identification of other alkaloids was developed, optimized, and validated. Three extraction techniques, ultrasound-assisted extraction in bath, or with sonotrode, and microwave-assisted extraction were evaluated, and it was concluded that ultrasonic bath is the most suitable technique for extraction of ergot alkaloids. The extraction method was later optimized using a Doehlert experimental design with response surface methodology and used together with the optimized LC-Q-TOF-MS method. The analytical procedure was validated in terms of recovery and matrix effect, repeatability, and intermediate precision. Limits of detection and quantification were 1.0 and 3.0 ng mL(-1), respectively, and were sufficient for determination of ergot alkaloids in Ipomoea seeds. The analysis revealed that from five kinds of seeds purchased from different vendors, only three contained ergot alkaloids. Concentration of alkaloids and their relative abundance was similar in samples representative for whole seeds packs; however, when single seeds were analyzed, significant discrepancies in ergine and ergometrine concentrations were detected.

Resin Glycosides from Ipomoea alba Seeds as Potential Chemosensitizers in Breast Carcinoma Cells.

Multidrug resistance is the expression of one or more efflux pumps, such as P-glycoprotein, and is a major obstacle in cancer therapy. The use of new potent and noncytotoxic efflux pump modulators, coadministered with antineoplastic agents, is an alternative approach for increasing the success rate of therapy regimes with different drug combinations. This report describes the isolation and structure elucidation of six new resin glycosides from moon vine seeds (Ipomoea alba) as potential mammalian multidrug-resistance-modifying agents. Albinosides IV-IX (1-6), along with the known albinosides I-III (7-9), were purified from the CHCl3-soluble extract. Degradative chemical reactions in combination with NMR spectroscopy and mass spectrometry were used for their structural elucidation. Four new glycosidic acids, albinosinic acids D-G (10-13), were released by saponification of natural products 3-6. They were characterized as tetrasaccharides of either convolvulinolic (11S-hydroxytetradecanoic) or jalapinolic (11S-hydroxyhexadecanoic) acids. The potentiation of vinblastine susceptibility in multidrug-resistant human breast carcinoma cells of albinosides 1-6 was evaluated by modulation assays. The noncytotoxic albinosides VII (4) and VIII (5), at a concentration of 25 µg/mL, exerted the strongest potentiation of vinblastine susceptibility, with a reversal factor (RFMCF-7/Vin+) of 201- and >2517-fold, respectively.