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China","award":["2020KJCX013"],"award-info":[{"award-number":["2020KJCX013"]}]},{"name":"Forestry Scientific Research Monitoring Project of Guangdong Province, China","award":["2021KJCX004"],"award-info":[{"award-number":["2021KJCX004"]}]},{"name":"Forestry Scientific Research Monitoring Project of Guangdong Province, China","award":["2022KJQT001"],"award-info":[{"award-number":["2022KJQT001"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Three new polycyclic phenol derivatives, 2-acetyl-4-hydroxy-6H-furo [2,3-g]chromen-6-one (1), 2-(1\u2032,2\u2032-dihydroxypropan-2\u2032-yl)-4-hydroxy-6H-furo [2,3-g][1]benzopyran-6-one (2) and 3,8,10-trihydroxy-4,9-dimethoxy-6H-benzo[c]chromen-6-one (8), along with seven known ones (3\u20137, 9 and 10) were isolated for the first time from the leaves of Spermacoce latifolia. Their structures were determined by spectroscopic analysis and comparison with literature-reported data. These compounds were tested for their in vitro antibacterial activity against four Gram-(+) bacteria: Staphyloccocus aureus (SA), methicillin-resistant Staphylococcus aureus (MRSA), Bacillus cereus (BC), Bacillus subtilis (BS), and the Gram-(\u2212) bacterium Escherichia coli. Compounds 1, 2, 5 and 8 showed antibacterial activity toward SA, BC and BS with MIC values ranging from 7.8 to 62.5 \u00b5g\/mL, but they were inactive to MRSA. Compound 4 not only showed the best antibacterial activity against SA, BC and BS, but it further displayed significant antibacterial activity against MRSA (MIC 1.95 \u00b5g\/mL) even stronger than vancomycin (MIC 3.9 \u00b5g\/mL). No compounds showed inhibitory activity toward E. coli. Further bioassay indicated that compounds 1, 4, 5, 6, 8 and 9 showed in vitro \u03b1-glucosidase inhibitory activity, among which compound 9 displayed the best \u03b1-glucosidase inhibitory activity with IC50 value (0.026 mM) about 15-fold stronger than the reference compound acarbose (IC50 0.408 mM). These results suggested that compounds 4, 8 and 9 were potentially highly valuable compounds worthy of consideration to be further developed as an effective anti-MRSA agent or effective \u03b1-glucosidase inhibitors, respectively. In addition, the obtained data also supported that S. latifolia was rich in structurally diverse bioactive compounds worthy of further investigation, at least in searching for potential antibiotics and \u03b1-glucosidase inhibitors.<\/jats:p>","DOI":"10.3390\/molecules27103334","type":"journal-article","created":{"date-parts":[[2022,5,22]],"date-time":"2022-05-22T07:13:57Z","timestamp":1653203637000},"page":"3334","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":8,"title":["Polycyclic Phenol Derivatives from the Leaves of Spermacoce latifolia and Their Antibacterial and \u03b1-Glucosidase Inhibitory Activity"],"prefix":"10.3390","volume":"27","author":[{"given":"Shao-Bo","family":"Liu","sequence":"first","affiliation":[{"name":"State Key Laboratory for Conservation and Utilization of Subtropical Agro-Bioresources\/Guangdong Key Laboratory for Innovative Development and Utilization of Forest Plant Germplasm, College of Forestry and Landscape Architecture, South China Agricultural University, Guangzhou 510642, China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Lei","family":"Zeng","sequence":"additional","affiliation":[{"name":"Guangdong Provincial Key Laboratory of Silviculture, Protection and Utilization, Guangdong Academy of Forestry, Guangzhou 510520, China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Qiao-Lin","family":"Xu","sequence":"additional","affiliation":[{"name":"Guangdong Provincial Key Laboratory of Silviculture, Protection and Utilization, Guangdong Academy of Forestry, Guangzhou 510520, China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Ying-Le","family":"Chen","sequence":"additional","affiliation":[{"name":"Guangdong Provincial Key Laboratory of Silviculture, Protection and Utilization, Guangdong Academy of Forestry, Guangzhou 510520, China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Tao","family":"Lou","sequence":"additional","affiliation":[{"name":"State Key Laboratory for Conservation and Utilization of Subtropical Agro-Bioresources\/Guangdong Key Laboratory for Innovative Development and Utilization of Forest Plant Germplasm, College of Forestry and Landscape Architecture, South China Agricultural University, Guangzhou 510642, China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Shan-Xuan","family":"Zhang","sequence":"additional","affiliation":[{"name":"State Key Laboratory for Conservation and Utilization of Subtropical Agro-Bioresources\/Guangdong Key Laboratory for Innovative Development and Utilization of Forest Plant Germplasm, College of Forestry and Landscape Architecture, South China Agricultural University, Guangzhou 510642, China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Jian-Wen","family":"Tan","sequence":"additional","affiliation":[{"name":"State Key Laboratory for Conservation and Utilization of Subtropical Agro-Bioresources\/Guangdong Key Laboratory for Innovative Development and Utilization of Forest Plant Germplasm, College of Forestry and Landscape Architecture, South China Agricultural University, Guangzhou 510642, China"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2022,5,22]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"231","DOI":"10.3417\/1055-3177(2006)16[231:ANHSSR]2.0.CO;2","article-title":"A new heterophyllous Spermacoce species (Rubiaceae) from the Marungu highlands (D.R.Congo)","volume":"16","author":"Dessein","year":"2006","journal-title":"Novon"},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"46","DOI":"10.4103\/0973-7847.95866","article-title":"Borreria and Spermacoce species (Rubiaceae): A review of their ethnomedicinal properties, chemical constituents, and biological activities","volume":"6","author":"Conserva","year":"2012","journal-title":"Pharmacogn Rev."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"229","DOI":"10.1016\/0378-8741(92)90021-I","article-title":"Medicinal plants used in some rural populations of Oaxaca, Puebla and Veracruz, Mexico","volume":"35","author":"Pola","year":"1992","journal-title":"J. Ethnopharmacol."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"119","DOI":"10.1021\/ol990811b","article-title":"Iridoids from Borreria verticillata","volume":"1","author":"Vieira","year":"1999","journal-title":"Org. Lett."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"1751","DOI":"10.1002\/hlca.200900457","article-title":"New chemical constituents from Borreria verticillata (Rubiaceae)","volume":"93","author":"Moreira","year":"2010","journal-title":"Helv. Chim. Acta."},{"key":"ref_6","first-page":"501","article-title":"On species diversity, niche breath and interspecies association in communities invaded by Spermacoce latifolia Zhejiang province","volume":"26","author":"Hong","year":"2008","journal-title":"J. Wuhan Bot. Res."},{"key":"ref_7","first-page":"1","article-title":"Research progress on the exotic plant species Borreria latifolia","volume":"37","author":"Zhang","year":"2019","journal-title":"Weed Sci."},{"key":"ref_8","first-page":"231","article-title":"An inventory of some vegetable drug resources of Makawanpur district Nepal","volume":"66","author":"Manandlar","year":"1995","journal-title":"Fitoterapia"},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"207","DOI":"10.1590\/S0102-33062006000100020","article-title":"da Reserva Florestal Mata do Para\u00edso, Vi\u00e7osa, MG, Brasil","volume":"20","author":"Pereira","year":"2006","journal-title":"Acta. Bot. Bras."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"537","DOI":"10.3987\/COM-01-S(K)45","article-title":"Studies on the constituents of Indonesian Borreria latifolia","volume":"56","author":"Kohei","year":"2002","journal-title":"Heterocycles"},{"key":"ref_11","first-page":"25","article-title":"Antibiotics and bacterial resistance in the 21st century","volume":"6","author":"Fair","year":"2014","journal-title":"Perspect. Med. Chem."},{"key":"ref_12","doi-asserted-by":"crossref","unstructured":"Oboh, M., Govender, L., Siwela, M., and Mkhwanazi, B.N. (2021). Anti-diabetic potential of plant-based pentacyclic triterpene derivatives: Progress made to improve efficacy and bioavailability. Molecules, 26.","DOI":"10.3390\/molecules26237243"},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"308","DOI":"10.1016\/j.foodchem.2011.03.021","article-title":"a-Glucosidase inhibitors from the bulb of Eleutherine americana","volume":"128","author":"Ieyama","year":"2011","journal-title":"Food Chem."},{"key":"ref_14","doi-asserted-by":"crossref","unstructured":"Gao, Y., Bian, W., Fang, Y., Du, P., Liu, X., Zhao, X., and Li, F. (2022). \u03b1-Glucosidase inhibitory activity of fermented okara broth started with the strain Bacillus amyloliquefaciens SY07. Molecules, 27.","DOI":"10.3390\/molecules27031127"},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"242","DOI":"10.1016\/j.phytochem.2010.11.025","article-title":"Bio-assay guided isolation and identification of \u03b1-glucosidase inhibitors from the leaves of Aquilaria sinensis","volume":"72","author":"Feng","year":"2011","journal-title":"Phytochemistry"},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"127","DOI":"10.1016\/j.phytol.2014.12.005","article-title":"A new ursane and a new oleanane triterpene acids from the whole plant of Spermacoce latifolia","volume":"11","author":"Luo","year":"2015","journal-title":"Phytochem. Lett."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"869","DOI":"10.1080\/10286020.2017.1279609","article-title":"A new anthraquinone and a new naphthoquinone from the whole plant of Spermacoce latifolia","volume":"19","author":"Luo","year":"2017","journal-title":"J. Asian Nat. Prod. Res."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"3865","DOI":"10.1016\/j.bmc.2006.01.046","article-title":"Synthesis of 8-geranyloxypsoralen analogues and their evaluation as inhibitors of CYP3A4","volume":"14","author":"Row","year":"2006","journal-title":"Bioorganic Med. Chem."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"11668","DOI":"10.1021\/jf802152z","article-title":"Active compounds from Lagerstroemia speciosa, insulin-like glucose uptake-stimulatory\/inhibitory and adipocyte differentiation-inhibitory activities in 3T3-L1 cells","volume":"56","author":"Bai","year":"2008","journal-title":"J. Agric. Food Chem."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"819","DOI":"10.1016\/0031-9422(93)85365-X","article-title":"Coumarins and coumarin giucosides from the fruits of Ammi-Majus","volume":"34","author":"Shalaby","year":"1993","journal-title":"Phytochemistry"},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"215","DOI":"10.1016\/j.fitote.2014.08.014","article-title":"Mangostanaxanthones I and II, new xanthones from the pericarp of Garcinia mangostana","volume":"98","author":"Mohamed","year":"2014","journal-title":"Fitoterapia"},{"key":"ref_22","first-page":"15","article-title":"Study on the chemical constituents of Ipomoea Pescaprae (L.) Sweet (I)","volume":"25","author":"Wang","year":"2006","journal-title":"Chin. J. Mar. Drugs"},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"195","DOI":"10.1002\/hlca.201000306","article-title":"New approach for the construction of the coumarin frame and application in the total synthesis of natural products","volume":"94","author":"Jerezano","year":"2011","journal-title":"Helv. Chim. Acta"},{"key":"ref_24","first-page":"517","article-title":"Coumarins in Horse chestnut flowers: Isolation and quantification by UPLC method","volume":"70","year":"2013","journal-title":"Acta Pol. Pharm."},{"key":"ref_25","first-page":"1109","article-title":"Chemical Constituents from Origanum vulgare","volume":"47","author":"Guo","year":"2012","journal-title":"Chin. Pharm. J."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"240","DOI":"10.1002\/hlca.201100286","article-title":"Identification of three new flavonoids from the peels of Citrus unshiu","volume":"95","author":"Shin","year":"2012","journal-title":"Helv. Chim. Acta"},{"key":"ref_27","doi-asserted-by":"crossref","unstructured":"Yang, R., Li, P., Li, N., Zhang, Q., Bai, X., Wang, L., Xiao, Y., Sun, L., Yang, Q., and Yan, J. (2017). Xanthones from the pericarp of Garcinia mangostana. Molecules, 22.","DOI":"10.3390\/molecules22050683"},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"336","DOI":"10.1038\/nature17042","article-title":"Antibacterial drug discovery in the resistance era","volume":"529","author":"Brown","year":"2016","journal-title":"Nature"},{"key":"ref_29","doi-asserted-by":"crossref","unstructured":"Piasecki, B., Biernasiuk, A., Skiba, A., Skalicka-Wo\u2019zniak, K., and Ludwiczuk, A. (2021). Composition, Anti-MRSA Activity and Toxicity of Essential Oils from Cymbopogon Species. Molecules, 26.","DOI":"10.3390\/molecules26247542"},{"key":"ref_30","first-page":"356","article-title":"Advances on mechanism of drug-resistance to MRSA and test method of molecular biology","volume":"17","author":"Yang","year":"2007","journal-title":"Chin. J. Nosocomiol."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"295","DOI":"10.1016\/j.jgar.2017.05.019","article-title":"Future trends in the treatment of methicillin-resistant Staphylococcus aureus (MRSA) infection: An in-depth review of newer antibiotics active against an enduring pathogen","volume":"10","author":"Bal","year":"2017","journal-title":"J. Glob. Antimicrob. Resist."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"603","DOI":"10.1128\/CMR.00134-14","article-title":"Staphylococcus aureus infections: Epidemiology, pathophysiology, clinical manifestations, and management","volume":"28","author":"Tong","year":"2015","journal-title":"Clin. Microbiol. Rev."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"2346","DOI":"10.1093\/jac\/dks255","article-title":"Reduced vancomycin susceptibility and Staphylococcal cassette chromosome mec (SCCmec) type distribution in methicillin-resistant Staphylococcus aureus bacteraemia","volume":"67","author":"Han","year":"2012","journal-title":"J. Antimicrob. Chemoth."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"211","DOI":"10.1186\/s13054-017-1801-3","article-title":"Incidence, prevalence, and management of MRSA bacteremia across patient populationsda review of recent developments in MRSA management and treatment","volume":"21","author":"Hassoun","year":"2017","journal-title":"Crit. Care"},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"1192","DOI":"10.1128\/AAC.02192-12","article-title":"Multicenter evaluation of the clinical outcomes of daptomycin with and without concomitant b-lactams in patients with Staphylococcus aureus bacteremia and mild to moderate renal impairment. Antimicrob","volume":"57","author":"Moise","year":"2013","journal-title":"Agents Chemother."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"51","DOI":"10.1093\/cid\/cir764","article-title":"Daptomycin versus vancomycin for bloodstream infections due to methicillin resistant Staphylococcus aureus with a high vancomycin minimum inhibitory concentration: A case-control study","volume":"54","author":"Moore","year":"2012","journal-title":"Clin. Infect. Dis."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"351","DOI":"10.1016\/j.jiac.2016.02.012","article-title":"Empirical therapy in methicillin-resistant Staphylococcus aureus infections: An up-to-date approach","volume":"22","author":"Vaneperen","year":"2016","journal-title":"J. Infect. Chemother."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"19","DOI":"10.4103\/0973-7847.79096","article-title":"\u03b1-Glucosidase inhibitors from plants: A natural approach to treat diabetes","volume":"5","author":"Kumar","year":"2011","journal-title":"Pharmacogn. Rev."},{"key":"ref_39","doi-asserted-by":"crossref","unstructured":"Shehadeh, M.B., Suaifan, G.A.R.Y., and Abu-Odeh, A.M. (2021). Plants secondary metabolites as blood glucose-lowering molecules. Molecules, 26.","DOI":"10.3390\/molecules26144333"},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"1601","DOI":"10.1016\/j.phytochem.2005.05.001","article-title":"A benzoisofuranone derivative and carbazole alkaloids from Murraya koenigii and their antimicrobial activity","volume":"66","author":"Rahman","year":"2005","journal-title":"Phytochemistry"},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"4301","DOI":"10.3390\/molecules19044301","article-title":"Bioactive 30-Noroleanane Triterpenes from the Pericarps of Akebia trifoliata","volume":"19","author":"Wang","year":"2014","journal-title":"Molecules"},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"1755","DOI":"10.1021\/np900237a","article-title":"Triterpenoid saponins from Rubus ellipticus var","volume":"72","author":"Li","year":"2009","journal-title":"obcordatus. J. Nat. Prod."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/27\/10\/3334\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,10]],"date-time":"2025-10-10T23:16:31Z","timestamp":1760138191000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/27\/10\/3334"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2022,5,22]]},"references-count":42,"journal-issue":{"issue":"10","published-online":{"date-parts":[[2022,5]]}},"alternative-id":["molecules27103334"],"URL":"https:\/\/doi.org\/10.3390\/molecules27103334","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2022,5,22]]}}}