Rogelio Pereda‐Miranda

Universidad Nacional Autónoma de México

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Mabel Fragoso‐Serrano

Universidad Nacional Autónoma de México

Jhon Castañeda-Gómez

South Colombian University

Rachel Mata

Universidad Nacional Autónoma de México

Carlos M. Cerda-Garcı́a-Rojas

Instituto Politécnico Nacional

Daniel Rosas-Ramírez

Universidad Nacional Autónoma de México

Suzana Guimarães Leitão

Universidade Federal do Rio de Janeiro

Guillermo Delgado

Universitario Francisco de Asís

Gabriela Figueroa‐González

Universidad Nacional Autónoma de México

Moustapha Bah

Autonomous University of Queretaro

Robert Bye

Universidad Nacional Autónoma de México

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Universidad Nacional Autónoma de México

105

Universidade Federal do Rio de Janeiro

Universidad Autónoma del Estado de Morelos

Instituto Politécnico Nacional

University of Illinois Chicago

Center for Research and Advanced Studies of the National Polytechnic Institute

University of Ottawa

University of London

Universidad Autónoma de la Ciudad de México

Rede de Química e Tecnologia

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Amarissinin F and its 16-epimer, two neo-clerodane diterpenoids from Salvia amarissima containing a 5-hydroxy-furan-2(5H)-one with MDR modulatory activity in cancer cells

Journal of Molecular Structure (2024)

Jennifer Alexis Rojas-Morales Mabel Fragoso‐Serrano Rubén A. Toscano Verenice I. Merlin-Lucas Ángel G. Alpuche‐Solís

Amarissinin F (1) and its 16-epimer (2) are two neo-clerodane diterpenoids isolated from the leaves and flowers of Salvia amarissima that occur as an unresolved epimeric mixture by chromatographic methods. The molecular structures of these compounds were deduced by the extensive analyses of their HRESIMS and their 1D/2D NMR data. Both compounds co-exist in the solid state as confirmed by single-crystal X-ray diffraction. In solution, both isolates appeared as the major compounds, which was corroborated by derivatization with Mosher reagents. However, the 1H and 13C NMR spectra demonstrated evidence for epimerization at C-20 and the possible interconversion of the 16-hydroxy-15,16-furanone to a 15-hydroxy-16,15-furanone, which was supported by a variable temperature 1H NMR analysis. The absolute configuration of compounds 1 and 2 was established by single-crystal X-ray diffraction and NMR. The cytotoxic effects of the isolated epimeric mixture (1 and 2) against a set of human cancer cells and the MDR modulatory activity in resistant MCF-7 breast cancer cells were explored.

Epimer

Furan

Salvia

10.1016/j.molstruc.2024.139132

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CCDC 627307: Experimental Crystal Structure Determination

The Cambridge Structural Database (2007)

Mabel Fragoso‐Serrano Rogelio Pereda‐Miranda Carlos M. Cerda-Garcı́a-Rojas

An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.

10.5517/ccp1rq5

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Batatinosides II−VI, Acylated Lipooligosaccharides from the Resin Glycosides of Sweet Potato

Journal of Agricultural and Food Chemistry (2008)

Edgar Escalante-Sánchez Daniel Rosas-Ramírez Edelmira Linares Robert Bye Rogelio Pereda‐Miranda

Sweet potato (Ipomoea batatas) belongs to the Convolvulaceae (morning glory family) and is native to Mexico and Central America. Its edible tuberous roots have been much appreciated since pre-Hispanic times in Mesoamerica and now play an important role as a basic diet staple and a medicinal plant worldwide. The hexane-soluble extract from roots, through preparative-scale recycling HPLC, yielded five new lipophilic oligosaccharides of jalapinolic acid, batatinosides II−VI (1−5), as well as the known pescapreins I (6) and VII (7) and murucoidin I (8), which are part of the purgative resin glycoside mixture. NMR spectroscopy and FAB mass spectrometry were used to characterize their structures. Compounds 1 and 2 are tetraglycosidic lactones of operculinic acid C. The pentasaccharide structures for compounds 3 and 4 were confirmed to be macrolactones of simonic acid B, and that characterized for 5 was derived from operculinic acid A. The lactonization site of the aglycone was placed at C-3 of the second saccharide unit in all compounds except 4, where it was placed at C-2. All compounds contain an esterifying residue that is composed of a long-chain fatty acid, n-decanoic acid (capric) or n-dodecanoic acid (lauric). In compound 3, an additional short-chain fatty acid, (2S)-methylbutyric acid, was also identified.

Capric Acid

Convolvulaceae

Decanoic acid

Ipomoea

Stearic acid

Pharbitis nil

10.1021/jf801973m

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Citations (23)

Flavonoids from Salvia nicolsoniana

Journal of Natural Products (1986)

Rogelio Pereda‐Miranda Guillermo Delgado

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTFlavonoids from Salvia nicolsonianaRogelio Pereda-Miranda and Guillermo DelgadoCite this: J. Nat. Prod. 1986, 49, 6, 1160–1161Publication Date (Print):November 1, 1986Publication History Published online1 July 2004Published inissue 1 November 1986https://pubs.acs.org/doi/10.1021/np50048a050https://doi.org/10.1021/np50048a050research-articleACS PublicationsRequest reuse permissionsArticle Views136Altmetric-Citations8LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InRedditEmail Other access optionsGet e-Alertsclose Get e-Alerts

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10.1021/np50048a050

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Methyl 4-Hydroxy-3-(3‘-methyl-2‘-butenyl)benzoate, Major Insecticidal Principle from Piper guanacastensis

Journal of Natural Products (1997)

Rogelio Pereda‐Miranda Claude B. Bernard Tony Durst John T. Arnason Pablo Sánchez-Vindas

The CHCl3-soluble extract of Piper guanacastensis (Piperaceae) was found to have noteworthy insecticidal activity to Aedes atropalpus mosquito larvae (LC50 80.5 μg/mL). Bioassay-guided fractionation afforded methyl 4-hydroxy-3-(3'-methyl-2'-butenyl)benzoate (1) as the major bioactive constituent (LC50 20.5 μg/mL). The separation of compound 1 from its transesterification artifact (2), ethyl 4-hydroxy-3-(3'-methyl-2'-butenyl)benzoate, was achieved by recycling reversed-phase HPLC. The flavonoids acacetin, chrysin, and pinostrobin were also isolated from the active fraction but did not display insecticidal properties.

Piperaceae

Acacetin

Methyl benzoate

Benzyl benzoate

Chrysin

10.1021/np960601x

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Citations (36)

Hepatotoxic pyrrolizidine alkaloids in the Mexican medicinal plant Packera candidissima (Asteraceae: Senecioneae)

Journal of Ethnopharmacology (1994)

Moustapha Bah Robert Bye Rogelio Pereda‐Miranda

Boraginaceae

Senecioneae

Dry weight

10.1016/0378-8741(94)90112-0

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Citations (50)

Use of in vitro assays to assess the potential antigenotoxic and cytotoxic effects of saffron (Crocus sativus L.)

Toxicology in Vitro (2003)

Fikrat Abdullaev Leticia Riverón‐Negrete Heriberto Caballero-Ortega J. M. Hernández Israel Pérez‐López

Safranal

HeLa

Ames test

10.1016/s0887-2333(03)00098-5

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Citations (160)

Reversal of multidrug resistance by amphiphilic morning glory resin glycosides in bacterial pathogens and human cancer cells

Phytochemistry Reviews (2019)

Jesús Lira-Ricárdez Rogelio Pereda‐Miranda

Efflux

Convolvulaceae

10.1007/s11101-019-09631-1

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Citations (19)

Antifungal Phenylpropanoid Glycosides from Lippia rubella

Journal of Natural Products (2019)

Gabriel R. Martins Thamirys Silva da Fonseca Lucero Martínez-Fructuoso Rosineide C. Simas Fabio T. Silva

Lippia species share various pharmacological activities and are used in traditional cooking and medicine worldwide. Combined chromatographic techniques such as column chromatography, high-performance liquid chromatography, and countercurrent chromatography led to the purification of two new antifungal phenylpropanoid glycosides, lippiarubelloside A (1) and lippiarubelloside B (2), by bioactivity-directed fractionation of an ethanol-soluble extract from Lippia rubella, in addition to the known active related compounds forsythoside A (3), verbascoside (4), isoverbascoside (5), and poliumoside (6). The structures of compounds 1 and 2 were determined by comparison of their NMR spectroscopic data with the prototype active compound 4. Cryptococcus neoformans, which causes opportunistic lung infections, was sensitive to compounds 1–6 in the concentration range of 15–125 μg/mL. A synergistic effect (FICindex = 0.5) between 3 and amphotericin B was demonstrated. The glycosylated flavonoids pectolinarin (7), linarin (8), and siparunoside (9) were also isolated.

Verbascoside

Lippia

Phenylpropanoid

10.1021/acs.jnatprod.8b00975

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Citations (22)

Glycosidic Acid Content from the Roots of Operculina hamiltonii (Brazilian Jalap) and Some of Their Phytopharmaceuticals with Purgative Activity

Revista Brasileira de Farmacognosia (2021)

María Emma Montiel-Ayala Nadia Rosalina Jiménez-Bárcenas Jhon Castañeda-Gómez Armando Moreno-Velasco Jesús Lira-Ricárdez

Tetrasaccharide

Glycosidic bond

10.1007/s43450-021-00190-1

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Citations (6)