{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,7,30]],"date-time":"2025-07-30T09:43:28Z","timestamp":1753868608460,"version":"3.41.2"},"reference-count":61,"publisher":"Wiley","issue":"6","license":[{"start":{"date-parts":[[2025,6,2]],"date-time":"2025-06-02T00:00:00Z","timestamp":1748822400000},"content-version":"vor","delay-in-days":1,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/501100002383","name":"King Saud University","doi-asserted-by":"publisher","award":["ORF\u20102025\u2010380"],"award-info":[{"award-number":["ORF\u20102025\u2010380"]}],"id":[{"id":"10.13039\/501100002383","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Chirality"],"published-print":{"date-parts":[[2025,6]]},"abstract":"<jats:title>ABSTRACT<\/jats:title><jats:p>The present study reports the chemical investigation on the aerial parts of <jats:italic>Cleome droserifolia<\/jats:italic> yielding the related eudesmane sesquiterpene solyraterpenoid A (<jats:bold>1<\/jats:bold>) and the novel cledrone A (<jats:bold>2<\/jats:bold>) from the acetonitrile fraction of the dichloromethane extract. These compounds were separated by column chromatography, centrifugal thin layer chromatography (CTLC) followed by semipreparative reversed\u2010phase high performance liquid chromatography (RP\u2010HPLC). The chemical structure of these compounds was determined by mono and bidimensional NMR techniques, IR spectroscopy, and HRESIMS, while the absolute configuration was established by computational analysis of ECD spectra. Furthermore, the structure and absolute configuration of both <jats:bold>1<\/jats:bold> and <jats:bold>2<\/jats:bold> were unambiguously confirmed via single crystal X\u2010ray diffraction (scXRD). Both compounds showed antibacterial activity against <jats:styled-content style=\"fixed-case\"><jats:italic>Escherichia coli<\/jats:italic><\/jats:styled-content> and <jats:styled-content style=\"fixed-case\"><jats:italic>Pseudomonas aeruginosa<\/jats:italic><\/jats:styled-content> strains, with compound <jats:bold>2<\/jats:bold> being more active.<\/jats:p>","DOI":"10.1002\/chir.70038","type":"journal-article","created":{"date-parts":[[2025,6,3]],"date-time":"2025-06-03T04:44:41Z","timestamp":1748925881000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["Stereoisomers of Eudesmane Sesquiterpene From <i>Cleome droserifolia<\/i>"],"prefix":"10.1002","volume":"37","author":[{"given":"Sarfaraz","family":"Ahmed","sequence":"first","affiliation":[{"name":"Department of Pharmacognosy, College of Pharmacy King Saud University  Riyadh Saudi Arabia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Mohammad","family":"Nur\u2010e\u2010Alam","sequence":"additional","affiliation":[{"name":"Department of Pharmacognosy, College of Pharmacy King Saud University  Riyadh Saudi Arabia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Umberto","family":"Calice","sequence":"additional","affiliation":[{"name":"Department of Basic and Applied Sciences University of Basilicata  Potenza Italy"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Patrizia","family":"Scafato","sequence":"additional","affiliation":[{"name":"Department of Basic and Applied Sciences University of Basilicata  Potenza Italy"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"James\u00a0B.","family":"Orton","sequence":"additional","affiliation":[{"name":"UK National Crystallography Service, School of Chemistry University of Southampton  Southampton UK"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Maria\u00a0Grazia","family":"Bonomo","sequence":"additional","affiliation":[{"name":"Department of Health Sciences University of Basilicata  Potenza Italy"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Hattan\u00a0A.","family":"Alharbi","sequence":"additional","affiliation":[{"name":"Department of Pharmacognosy, College of Pharmacy King Saud University  Riyadh Saudi Arabia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0262-7101","authenticated-orcid":false,"given":"Omer\u00a0I.","family":"Fantoukh","sequence":"additional","affiliation":[{"name":"Department of Pharmacognosy, College of Pharmacy King Saud University  Riyadh Saudi Arabia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7265-1625","authenticated-orcid":false,"given":"Stefano","family":"Superchi","sequence":"additional","affiliation":[{"name":"Department of Basic and Applied Sciences University of Basilicata  Potenza Italy"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0009-0008-2538-908X","authenticated-orcid":false,"given":"Adnan\u00a0J.","family":"Al\u2010Rehaily","sequence":"additional","affiliation":[{"name":"Department of Pharmacognosy, College of Pharmacy King Saud University  Riyadh Saudi Arabia"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2025,6,2]]},"reference":[{"key":"e_1_2_6_2_1","doi-asserted-by":"publisher","DOI":"10.1007\/s00606-008-0026-y"},{"key":"e_1_2_6_3_1","doi-asserted-by":"publisher","DOI":"10.1590\/2317-1545v36n31013"},{"volume-title":"Flora of Java (Spermatophytes Only). Vol. II; Angiospermae, families 111\u2010190","year":"1965","author":"Backer C. A.","key":"e_1_2_6_4_1"},{"key":"e_1_2_6_5_1","doi-asserted-by":"publisher","DOI":"10.1093\/aob\/mcq239"},{"key":"e_1_2_6_6_1","doi-asserted-by":"publisher","DOI":"10.1515\/znc-2012-5-605"},{"key":"e_1_2_6_7_1","doi-asserted-by":"publisher","DOI":"10.1248\/cpb.57.620"},{"key":"e_1_2_6_8_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.clnesp.2020.07.016"},{"key":"e_1_2_6_9_1","unstructured":"S.Collenette \u201cWild Flowers of Saudi Arabia \u201d (1999):109\u2013113."},{"key":"e_1_2_6_10_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0944-7113(11)80059-0"},{"key":"e_1_2_6_11_1","doi-asserted-by":"publisher","DOI":"10.21608\/ejhm.2002.18766"},{"key":"e_1_2_6_12_1","doi-asserted-by":"publisher","DOI":"10.2754\/avb200574030347"},{"key":"e_1_2_6_13_1","doi-asserted-by":"publisher","DOI":"10.21608\/ejhm.2004.18217"},{"key":"e_1_2_6_14_1","doi-asserted-by":"publisher","DOI":"10.5530\/pj.2014.5.4"},{"issue":"9","key":"e_1_2_6_15_1","first-page":"507","article-title":"Role of the Hypoglycemic Plant Extract Cleome droserifolia in Improving Glucose and Lipid Metabolism and Its Relation to Insulin Resistance in Fatty Liver","volume":"135","author":"Nicola W. G.","year":"1996","journal-title":"Bollettino Chimico Farmaceutico"},{"key":"e_1_2_6_16_1","doi-asserted-by":"publisher","DOI":"10.1016\/0378-8741(94)90106-6"},{"key":"e_1_2_6_17_1","doi-asserted-by":"publisher","DOI":"10.1590\/S0036-46652006000400010"},{"key":"e_1_2_6_18_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.sajb.2015.03.184"},{"key":"e_1_2_6_19_1","doi-asserted-by":"publisher","DOI":"10.3390\/10080971"},{"key":"e_1_2_6_20_1","first-page":"76","article-title":"Sesquiterpene From Cleome droserifolia","volume":"49","author":"Hussein N. S.","year":"1994","journal-title":"Pharmazie"},{"key":"e_1_2_6_21_1","doi-asserted-by":"publisher","DOI":"10.1177\/1934578X0800300915"},{"key":"e_1_2_6_22_1","first-page":"107","article-title":"Potential Antioxidant Activity of Flavonoids From Hypericum triquetrifolium Turra and Cleome droserifoila (Forssk) Del","volume":"41","author":"Nassar M. I.","year":"2003","journal-title":"Bulletin of Faculty of Pharmacy, Cairo University"},{"key":"e_1_2_6_23_1","first-page":"313","article-title":"Flavonoids From Cleome droserifolia (Forssk) Del. Growing in Egypt","volume":"28","author":"Seif El\u2010Din A. A.","year":"1987","journal-title":"Egyptian Journal of Pharmaceutical Sciences"},{"key":"e_1_2_6_24_1","first-page":"231","article-title":"Flavonoids of Cleome droserifolia","volume":"55","author":"Seif El\u2010Nasr M. M.","year":"1984","journal-title":"Fitoterapia"},{"key":"e_1_2_6_25_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0305-1978(96)00099-3"},{"key":"e_1_2_6_26_1","doi-asserted-by":"publisher","DOI":"10.1016\/0305-1978(92)90084-Q"},{"key":"e_1_2_6_27_1","doi-asserted-by":"publisher","DOI":"10.1055\/s-1999-14084"},{"issue":"1","key":"e_1_2_6_28_1","first-page":"443","article-title":"Flavonoids of Cleome droserifolia","volume":"31","author":"Yang S. S.","year":"1990","journal-title":"Egyptian Journal of Pharmaceutical Sciences"},{"key":"e_1_2_6_29_1","unstructured":"L. I.Diab \u201cPharmacognostical Study of CertainCleomeSpecies Growing in Egypt. M.Sc. Thesis AL\u2010Azhar University Egypt \u201d (1992)."},{"key":"e_1_2_6_30_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0367-326X(02)00061-8"},{"key":"e_1_2_6_31_1","doi-asserted-by":"publisher","DOI":"10.1080\/14786419.2021.2019734"},{"key":"e_1_2_6_32_1","unstructured":"Rigaku Oxford Diffraction (2018)."},{"key":"e_1_2_6_33_1","doi-asserted-by":"publisher","DOI":"10.1107\/S0021889808042726"},{"key":"e_1_2_6_34_1","doi-asserted-by":"publisher","DOI":"10.1107\/S2053229614024218"},{"key":"e_1_2_6_35_1","doi-asserted-by":"publisher","DOI":"10.1107\/S2053273314026370"},{"key":"e_1_2_6_36_1","unstructured":"SPARTAN'02: Wavefunction Inc \u201cIrvine CA\u201d http:\/\/www.wavefunction.com."},{"volume-title":"GAUSSIAN 09, Revision A.02","year":"2009","author":"Frisch M. J.","key":"e_1_2_6_37_1"},{"key":"e_1_2_6_38_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr9904009"},{"key":"e_1_2_6_39_1","doi-asserted-by":"publisher","DOI":"10.1002\/chir.22138"},{"key":"e_1_2_6_40_1","doi-asserted-by":"publisher","DOI":"10.2174\/1570180816666181108114115"},{"key":"e_1_2_6_41_1","doi-asserted-by":"publisher","DOI":"10.3390\/antibiotics10121466"},{"key":"e_1_2_6_42_1","doi-asserted-by":"publisher","DOI":"10.1071\/CH9960707"},{"key":"e_1_2_6_43_1","doi-asserted-by":"publisher","DOI":"10.1039\/a803993c"},{"key":"e_1_2_6_44_1","doi-asserted-by":"publisher","DOI":"10.1515\/chem-2018-0051"},{"key":"e_1_2_6_45_1","doi-asserted-by":"publisher","DOI":"10.1021\/np030222l"},{"key":"e_1_2_6_46_1","first-page":"593","volume-title":"Comprehensive Chiroptical Spectroscopy","author":"Autschbach J.","year":"2012"},{"key":"e_1_2_6_47_1","doi-asserted-by":"publisher","DOI":"10.1002\/9781118120392.ch12"},{"key":"e_1_2_6_48_1","doi-asserted-by":"publisher","DOI":"10.2174\/0929867324666170310112009"},{"key":"e_1_2_6_49_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2014.08.038"},{"key":"e_1_2_6_50_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.jep.2017.05.019"},{"key":"e_1_2_6_51_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.fitote.2018.06.013"},{"key":"e_1_2_6_52_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jnatprod.0c00182"},{"key":"e_1_2_6_53_1","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.201200459"},{"key":"e_1_2_6_54_1","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.201800553"},{"key":"e_1_2_6_55_1","doi-asserted-by":"publisher","DOI":"10.1002\/9781118120392.ch2"},{"key":"e_1_2_6_56_1","doi-asserted-by":"publisher","DOI":"10.1039\/j39680002941"},{"key":"e_1_2_6_57_1","doi-asserted-by":"publisher","DOI":"10.1002\/chir.23013"},{"key":"e_1_2_6_58_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.202002163"},{"key":"e_1_2_6_59_1","doi-asserted-by":"publisher","DOI":"10.1039\/b606168k"},{"key":"e_1_2_6_60_1","doi-asserted-by":"publisher","DOI":"10.1002\/jlac.198619860502"},{"key":"e_1_2_6_61_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0031-9422(96)00521-3"},{"key":"e_1_2_6_62_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0031-9422(97)00029-0"}],"container-title":["Chirality"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chir.70038","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,6,17]],"date-time":"2025-06-17T03:11:15Z","timestamp":1750129875000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/chir.70038"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2025,6]]},"references-count":61,"journal-issue":{"issue":"6","published-print":{"date-parts":[[2025,6]]}},"alternative-id":["10.1002\/chir.70038"],"URL":"https:\/\/doi.org\/10.1002\/chir.70038","archive":["Portico"],"relation":{},"ISSN":["0899-0042","1520-636X"],"issn-type":[{"type":"print","value":"0899-0042"},{"type":"electronic","value":"1520-636X"}],"subject":[],"published":{"date-parts":[[2025,6]]},"assertion":[{"value":"2025-04-26","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2025-05-19","order":2,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication History"}},{"value":"2025-06-02","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e70038"}}