{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,17]],"date-time":"2026-09-17T01:25:26Z","timestamp":1789608326650,"version":"build-2803163510"},"reference-count":47,"publisher":"MDPI AG","issue":"6","license":[{"start":{"date-parts":[[2024,3,9]],"date-time":"2024-03-09T00:00:00Z","timestamp":1709942400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"Direcci\u00f3n General de Asuntos del Personal Acad\u00e9mico (DGAPA), Universidad Nacional Aut\u00f3noma de M\u00e9xico","award":["PAPIIT IG200523"],"award-info":[{"award-number":["PAPIIT IG200523"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>From the aerial parts of Salvia carranzae Zamudio and Bedolla, three new icetexane-type diterpenoids were isolated. Their structures were established through spectroscopic methods and named the following: salvicarranzanolide (1), 19-deoxo-salvicarranzanolide (2) and 19-deoxo-20-deoxy-salvicarranzanolide (3). In addition, the known icetexane-type diterpenoids, 6,7,11,14-tetrahydro-7-oxo-icetexone (4), iso-icetexone (5), 19-deoxo-iso-icetexone (6), icetexone (7), 19-deoxo-icetexone (8) and 7\u03b1-acetoxy-6,7-dihydroicetexone (9), were also isolated, along with the abietanes sessein (10) and ferruginol (11). \u03b1-Tocopherol was also identified. Compounds 5, 6 and 8 were tested for their antiproliferative activity using the sulforhodamine B assay on six cancer and one normal human cell lines. Diterpenoids 5 and 6 showed noteworthy antiproliferative activity, exhibiting an IC50 (\u03bcM) = 0.43 \u00b1 0.01 and 1.34 \u00b1 0.04, respectively, for U251 (glioblastoma), an IC50 (\u03bcM) = 0.45 \u00b1 0.01 and 1.29 \u00b1 0.06 for K5621 (myelogenous leukemia), 0.84 \u00b1 0.07 and 1.03 \u00b1 0.10 for HCT-15 (colon cancer), and 0.73 \u00b1 0.06 and 0.95 \u00b1 0.09 for SKLU-1 (lung adenocarcinoma) cell lines. On the other hand, the phytotoxicity of compounds 5\u20137 and 9\u201310 was evaluated on seed germination and root growth in some weeds such as Medicago sativa, Panicum miliaceum, Amaranthus hypochondriacus and Trifolium pratense as models. While compounds 5 and 10 exhibited a moderate inhibitory effect on the root growth of A. hypochondriacus and T. pratense at 100 ppm, the diterpenoids 6, 7 and 9 were ineffective in all the plant models. Taxonomic positions based on the chemical profiles found are also discussed.<\/jats:p>","DOI":"10.3390\/molecules29061226","type":"journal-article","created":{"date-parts":[[2024,3,11]],"date-time":"2024-03-11T04:51:12Z","timestamp":1710132672000},"page":"1226","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":5,"title":["Structure, Absolute Configuration, Antiproliferative and Phytotoxic Activities of Icetexane and Abietane Diterpenoids from Salvia carranzae and Chemotaxonomic Implications"],"prefix":"10.3390","volume":"29","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-9976-5251","authenticated-orcid":false,"given":"Celia","family":"Bustos-Brito","sequence":"first","affiliation":[{"name":"Instituto de Qu\u00edmica, Universidad Nacional Aut\u00f3noma de M\u00e9xico, Circuito Exterior, Ciudad Universitaria, Ciudad de M\u00e9xico 04510, Mexico"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0009-0008-8770-1059","authenticated-orcid":false,"given":"Juan Pablo","family":"Torres-Medicis","sequence":"additional","affiliation":[{"name":"Instituto de Qu\u00edmica, Universidad Nacional Aut\u00f3noma de M\u00e9xico, Circuito Exterior, Ciudad Universitaria, Ciudad de M\u00e9xico 04510, Mexico"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1560-1090","authenticated-orcid":false,"given":"Brenda Y.","family":"Bedolla-Garc\u00eda","sequence":"additional","affiliation":[{"name":"Instituto de Ecolog\u00eda, A. C., Centro Regional del Baj\u00edo, P. O. Box 386, P\u00e1tzcuaro 61600, Mexico"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Sergio","family":"Zamudio","sequence":"additional","affiliation":[{"name":"Independent Researcher, P. O. Box 392, P\u00e1tzcuaro 61600, Mexico"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Teresa","family":"Ram\u00edrez-Apan","sequence":"additional","affiliation":[{"name":"Instituto de Qu\u00edmica, Universidad Nacional Aut\u00f3noma de M\u00e9xico, Circuito Exterior, Ciudad Universitaria, Ciudad de M\u00e9xico 04510, Mexico"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Martha Lydia","family":"Mac\u00edas-Rubalcava","sequence":"additional","affiliation":[{"name":"Instituto de Qu\u00edmica, Universidad Nacional Aut\u00f3noma de M\u00e9xico, Circuito Exterior, Ciudad Universitaria, Ciudad de M\u00e9xico 04510, Mexico"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4804-3013","authenticated-orcid":false,"given":"Leovigildo","family":"Quijano","sequence":"additional","affiliation":[{"name":"Instituto de Qu\u00edmica, Universidad Nacional Aut\u00f3noma de M\u00e9xico, Circuito Exterior, Ciudad Universitaria, Ciudad de M\u00e9xico 04510, Mexico"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Baldomero","family":"Esquivel","sequence":"additional","affiliation":[{"name":"Instituto de Qu\u00edmica, Universidad Nacional Aut\u00f3noma de M\u00e9xico, Circuito Exterior, Ciudad Universitaria, Ciudad de M\u00e9xico 04510, Mexico"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2024,3,9]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"767","DOI":"10.1086\/710711","article-title":"Evolution, Pollination Biology, and Species Richness of Salvia (Lamiaceae)","volume":"181","author":"Drew","year":"2020","journal-title":"Int. J. Plant Sci."},{"key":"ref_2","first-page":"1160","article-title":"Labiatae","volume":"Volume 2","author":"Bentham","year":"1876","journal-title":"Genera Plantarum"},{"key":"ref_3","unstructured":"Shahidi, F., and Ho, C. (2000). Phytochemicals and Phytopharmaceuticals, AOCS Press."},{"key":"ref_4","unstructured":"Harley, R.M., and Reynolds, T. (1992). Advances in Labiatae Science, Royal Botanic Gardens."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"573","DOI":"10.1002\/ajb2.1268","article-title":"Tracking Temporal Shifts in Area, Biomes, and Pollinators in the Radiation of Salvia (Sages) across Continents: Leveraging Anchored Hybrid Enrichment and Targeted Sequence Data","volume":"106","author":"Kriebel","year":"2019","journal-title":"Am. J. Bot."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"133","DOI":"10.12705\/661.7","article-title":"Salvia United: The Greatest Good for the Greatest Number","volume":"66","author":"Drew","year":"2017","journal-title":"Taxon"},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"33","DOI":"10.1016\/j.ympev.2016.12.041","article-title":"Time to Split Salvia s.l. (Lamiaceae)\u2014New Insights from Old World Salvia Phylogeny","volume":"109","author":"Will","year":"2017","journal-title":"Mol. Phylogenet. Evol."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"649","DOI":"10.1093\/aob\/mcy104","article-title":"Phylogeny and Staminal Evolution of Salvia (Lamiaceae, Nepetoideae) in East Asia","volume":"122","author":"Hu","year":"2018","journal-title":"Ann. Bot."},{"key":"ref_9","first-page":"559","article-title":"Cat\u00e1logo de Las Plantas Vasculares Nativas de M\u00e9xico","volume":"87","year":"2016","journal-title":"Rev. Mex. Biodivers."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"780","DOI":"10.17129\/botsci.1871","article-title":"Lamiaceae de M\u00e9xico","volume":"95","author":"Zamudio","year":"2017","journal-title":"Bot. Sci."},{"key":"ref_11","unstructured":"Calder\u00f3n de Rzedowski, G., and Rzedowski, J. (2005). Flora fanerog\u00e1mica del Valle de M\u00e9xico, Instituto de Ecolog\u00eda, A.C.\/Comisi\u00f3n Nacional para el Cono cimiento y Uso de la Biodiversidad."},{"key":"ref_12","first-page":"3","article-title":"Revisi\u00f3n Taxon\u00f3mica de Lamiceae Del Occidente de M\u00e9xico","volume":"7","year":"2016","journal-title":"Ibugana"},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"831","DOI":"10.1086\/709133","article-title":"Richness and Distribution of Salvia Subg. Calosphace (Lamiaceae)","volume":"181","author":"Harley","year":"2020","journal-title":"Int. J. Plant Sci."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"1","DOI":"10.11646\/phytotaxa.433.1.1","article-title":"Salvia huastecana (Lamiaceae), a New Species from San Luis Potos\u00ed, Mexico","volume":"433","author":"Zamudio","year":"2020","journal-title":"Phytotaxa"},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"255","DOI":"10.11646\/phytotaxa.434.3.4","article-title":"Salvia rhizomatosa (Lamiaceae) a New Species from Sierra Madre Occidental in Durango, Mexico, with a Synopsis of Salvia Sect","volume":"434","year":"2020","journal-title":"Brandegeia. Phytotaxa"},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"241","DOI":"10.11646\/phytotaxa.518.4.1","article-title":"Salvia fimbriaticalyx, a New Species of Salvia (Lamiaceae) from Oaxaca, Mexico","volume":"518","author":"Salas","year":"2021","journal-title":"Phytotaxa"},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"160","DOI":"10.11646\/phytotaxa.529.1.12","article-title":"Salvia beltraniorum (Lamiaceae), a New Species in Savannoid Vegetation from Cosal\u00e1, Sinaloa, Mexico","volume":"529","year":"2021","journal-title":"Phytotaxa"},{"key":"ref_18","first-page":"976","article-title":"Salvia gomezpompae (Lamiaceae), a New Species from Veracruz, Mexico","volume":"1","year":"2021","journal-title":"Bot. Sci."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"35","DOI":"10.11646\/phytotaxa.217.1.3","article-title":"Four New Species of Salvia (Lamiaceae) from Central Mexico","volume":"217","author":"Zamudio","year":"2015","journal-title":"Phytotaxa"},{"key":"ref_20","first-page":"1","article-title":"A Revision of Salvia Subgenus Calosphace","volume":"110","author":"Epling","year":"1939","journal-title":"Feddes Repert. Specierum Nov. Regni Veg."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"3213","DOI":"10.1016\/S0040-4020(01)96672-4","article-title":"Structure of Salvigenolide, a Novel Diterpenoid with a Rearranged Neo-Clerodane Skeleton from Salvia fulgens","volume":"41","author":"Esquivel","year":"1985","journal-title":"Tetrahedron"},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"738","DOI":"10.1021\/np50052a029","article-title":"The Diterpenoid Constituents of Salvia fulgens and Salvia microphylla","volume":"50","author":"Esquivel","year":"1987","journal-title":"J. Nat. Prod."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"58","DOI":"10.1007\/s11418-005-0007-1","article-title":"Four New Diterpenoids from Salvia fulgens Cav","volume":"60","author":"Narukawa","year":"2006","journal-title":"J. Nat. Med."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"2381","DOI":"10.1016\/S0031-9422(00)81700-8","article-title":"Clerodane Diterpenoids of Salvia lineata","volume":"25","author":"Esquivel","year":"1986","journal-title":"Phytochemistry"},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"62","DOI":"10.1055\/s-2006-961827","article-title":"The Pimarane-Type Diterpenoids of Salvia microphylla Var. Neurepia","volume":"55","author":"Esquivel","year":"1989","journal-title":"Planta Med."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"3210","DOI":"10.1021\/ol401022c","article-title":"Microphyllandiolide, a New Diterpene with an Unprecedented Skeleton from Salvia microphylla","volume":"15","author":"Bautista","year":"2013","journal-title":"Org. Lett."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"1088","DOI":"10.1021\/np4009893","article-title":"5,10- Seco\u2014Neo -Clerodanes and Neo -Clerodanes from Salvia microphylla","volume":"77","author":"Bautista","year":"2014","journal-title":"J. Nat. Prod."},{"key":"ref_28","doi-asserted-by":"crossref","unstructured":"Esquivel, B., Bustos-Brito, C., S\u00e1nchez-Castellanos, M., Nieto-Camacho, A., Ram\u00edrez-Apan, T., Joseph-Nathan, P., and Quijano, L. (2017). Structure, Absolute Configuration, & Antiproliferative Activity of Abietane & Icetexane Diterpenoids from Salvia ballotiflora. Molecules, 22.","DOI":"10.20944\/preprints201709.0164.v1"},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"152748","DOI":"10.1016\/j.phymed.2018.11.009","article-title":"Leishmanicidal and Antichemotactic Activities of Icetexanes from Salvia uliginosa Benth","volume":"58","author":"Cezarotto","year":"2019","journal-title":"Phytomedicine"},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"302","DOI":"10.1016\/j.bjp.2017.01.007","article-title":"Cytotoxic Activity of the Chloroform Extract and Four Diterpenes Isolated from Salvia ballotiflora","volume":"27","year":"2017","journal-title":"Rev. Bras. Farmacogn."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"177","DOI":"10.1002\/chir.22781","article-title":"Absolute Configuration of the Diterpenoids Icetexone and Conacytone from Salvia ballotaeflora","volume":"30","author":"Esquivel","year":"2018","journal-title":"Chirality"},{"key":"ref_32","doi-asserted-by":"crossref","unstructured":"Brandt, C.W., and Neubauer, L.G. (1939). 221. Miro Resin. Part I. Ferruginol. J. Chem. Soc., 1031\u20131037.","DOI":"10.1039\/jr9390001031"},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"684","DOI":"10.1039\/C4NP00110A","article-title":"Aromatic Abietane Diterpenoids: Their Biological Activity and Synthesis","volume":"32","year":"2015","journal-title":"Nat. Prod. Rep."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"212","DOI":"10.1016\/j.jep.2018.02.012","article-title":"Sessein and Isosessein with Anti-Inflammatory, Antibacterial and Antioxidant Activity Isolated from Salvia sessei Benth","volume":"217","author":"Zamilpa","year":"2018","journal-title":"J. Ethnopharmacol."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"243","DOI":"10.1021\/np50056a008","article-title":"A New Royleanone-Type Diterpene from Salvia sessei","volume":"51","author":"Jimenez","year":"1988","journal-title":"J. Nat. Prod."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"3297","DOI":"10.1016\/S0031-9422(00)82491-7","article-title":"Diterpenoid Abietane Quinones Isolated from Salvia regla","volume":"26","author":"Esquivel","year":"1987","journal-title":"Phytochemistry"},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"931","DOI":"10.1016\/0031-9422(95)00083-J","article-title":"Abietane and Clerodane Diterpenes from Salvia regla","volume":"39","author":"Ortega","year":"1995","journal-title":"Phytochemistry"},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"87","DOI":"10.1080\/10575639708043720","article-title":"Abietane and Icetexane Diterpenoids from Salvia pubescens","volume":"10","author":"Esquivel","year":"1997","journal-title":"Nat. Prod. Lett."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"43","DOI":"10.1007\/s00606-017-1445-4","article-title":"Phylogeny of the Neotropical Sages (Salvia Subg. Calosphace; Lamiaceae) and Insights into Pollinator and Area Shifts","volume":"304","author":"Salazar","year":"2018","journal-title":"Plant Syst. Evol."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"483","DOI":"10.1007\/s10265-012-0543-1","article-title":"Phylogeny of New World Salvia Subgenus Calosphace (Lamiaceae) Based on CpDNA (PsbA-TrnH) and NrDNA (ITS) Sequence Data","volume":"126","author":"Jenks","year":"2013","journal-title":"J. Plant Res."},{"key":"ref_41","doi-asserted-by":"crossref","unstructured":"Forzato, C., and Nitti, P. (2022). New Diterpenes with Potential Antitumoral Activity Isolated from Plants in the Years 2017\u20132022. Plants, 11.","DOI":"10.3390\/plants11172240"},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"1434","DOI":"10.1016\/j.cropro.2010.08.002","article-title":"Phytotoxicity of Salvia spp. Exudates","volume":"29","author":"Bisio","year":"2010","journal-title":"Crop Prot."},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"243","DOI":"10.1002\/chir.22138","article-title":"SpecDis: Quantifying the Comparison of Claculated and Experimental Electronic Circular Dichroism Spectra","volume":"25","author":"Gerhard","year":"2013","journal-title":"Chirality"},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"130367","DOI":"10.1016\/j.molstruc.2021.130367","article-title":"Clerodane and 5 10-Seco-Clerodane-Type Diterpenoids from Salvia involucrata","volume":"1237","author":"Zamudio","year":"2021","journal-title":"J. Mol. Struct."},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"757","DOI":"10.1093\/jnci\/83.11.757","article-title":"Feasibility of a High-Flux Anticancer Drug Screen Using a Diverse Panel of Cultured Human Tumor Cell Lines","volume":"83","author":"Monks","year":"1991","journal-title":"JNCI J. Natl. Cancer Inst."},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"3553","DOI":"10.1021\/jf500965k","article-title":"Naphthoquinone Spiroketals and Organic Extracts from the Endophytic Fungus Edenia gomezpompae as Potential Herbicides","volume":"62","year":"2014","journal-title":"J. Agric. Food Chem."},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"4255","DOI":"10.1021\/acs.jafc.6b01111","article-title":"Phytotoxic Potential of Secondary Metabolites and Semisynthetic Compounds from Endophytic Fungus Xylaria feejeensis Strain SM3e-1b Isolated from Sapium macrocarpum","volume":"64","year":"2016","journal-title":"J. Agric. Food Chem."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/29\/6\/1226\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,10]],"date-time":"2025-10-10T14:11:16Z","timestamp":1760105476000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/29\/6\/1226"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2024,3,9]]},"references-count":47,"journal-issue":{"issue":"6","published-online":{"date-parts":[[2024,3]]}},"alternative-id":["molecules29061226"],"URL":"https:\/\/doi.org\/10.3390\/molecules29061226","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2024,3,9]]}}}