{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,5,9]],"date-time":"2026-05-09T17:59:45Z","timestamp":1778349585181,"version":"3.51.4"},"reference-count":34,"publisher":"MDPI AG","issue":"5","license":[{"start":{"date-parts":[[2023,2,24]],"date-time":"2023-02-24T00:00:00Z","timestamp":1677196800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"National Natural Science Foundation of China","award":["32170401"],"award-info":[{"award-number":["32170401"]}]},{"name":"National Natural Science Foundation of China","award":["31270406"],"award-info":[{"award-number":["31270406"]}]},{"name":"National Natural Science Foundation of China","award":["2023A1515012805"],"award-info":[{"award-number":["2023A1515012805"]}]},{"name":"National Natural Science Foundation of China","award":["2019A1515011236"],"award-info":[{"award-number":["2019A1515011236"]}]},{"name":"National Natural Science Foundation of China","award":["2020KJCX013"],"award-info":[{"award-number":["2020KJCX013"]}]},{"name":"National Natural Science Foundation of China","award":["2021-KJXM-14"],"award-info":[{"award-number":["2021-KJXM-14"]}]},{"name":"National Natural Science Foundation of China","award":["2021-KYXM-01"],"award-info":[{"award-number":["2021-KYXM-01"]}]},{"name":"Guangdong Basic and Applied Basic Research Foundation, China","award":["32170401"],"award-info":[{"award-number":["32170401"]}]},{"name":"Guangdong Basic and Applied Basic Research Foundation, China","award":["31270406"],"award-info":[{"award-number":["31270406"]}]},{"name":"Guangdong Basic and Applied Basic Research Foundation, China","award":["2023A1515012805"],"award-info":[{"award-number":["2023A1515012805"]}]},{"name":"Guangdong Basic and Applied Basic Research Foundation, China","award":["2019A1515011236"],"award-info":[{"award-number":["2019A1515011236"]}]},{"name":"Guangdong Basic and Applied Basic Research Foundation, China","award":["2020KJCX013"],"award-info":[{"award-number":["2020KJCX013"]}]},{"name":"Guangdong Basic and Applied Basic Research Foundation, China","award":["2021-KJXM-14"],"award-info":[{"award-number":["2021-KJXM-14"]}]},{"name":"Guangdong Basic and Applied Basic Research Foundation, China","award":["2021-KYXM-01"],"award-info":[{"award-number":["2021-KYXM-01"]}]},{"name":"Forestry Science and Technology Innovation Project of Guangdong Province, China","award":["32170401"],"award-info":[{"award-number":["32170401"]}]},{"name":"Forestry Science and Technology Innovation Project of Guangdong Province, China","award":["31270406"],"award-info":[{"award-number":["31270406"]}]},{"name":"Forestry Science and Technology Innovation Project of Guangdong Province, China","award":["2023A1515012805"],"award-info":[{"award-number":["2023A1515012805"]}]},{"name":"Forestry Science and Technology Innovation Project of Guangdong Province, China","award":["2019A1515011236"],"award-info":[{"award-number":["2019A1515011236"]}]},{"name":"Forestry Science and Technology Innovation Project of Guangdong Province, China","award":["2020KJCX013"],"award-info":[{"award-number":["2020KJCX013"]}]},{"name":"Forestry Science and Technology Innovation Project of Guangdong Province, China","award":["2021-KJXM-14"],"award-info":[{"award-number":["2021-KJXM-14"]}]},{"name":"Forestry Science and Technology Innovation Project of Guangdong Province, China","award":["2021-KYXM-01"],"award-info":[{"award-number":["2021-KYXM-01"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Four new germacrane sesquiterpene dilactones, 2\u03b2-hydroxyl-11\u03b2,13-dihydrodeoxymikanolide (1), 3\u03b2-hydroxyl-11\u03b2,13-dihydrodeoxymikanolide (2), 1\u03b1,3\u03b2-dihydroxy-4,9-germacradiene-12,8:15,6-diolide (3), and (11\u03b2,13-dihydrodeoxymikanolide-13-yl)-adenine (4), together with five known ones (5\u20139) were isolated from the aerial parts of Mikania micrantha. Their structures were elucidated on the basis of extensive spectroscopic analysis. Compound 4 is featured with an adenine moiety in the molecule, which is the first nitrogen-containing sesquiterpenoid so far isolated from this plant species. These compounds were evaluated for their in vitro antibacterial activity against four Gram-(+) bacteria of Staphyloccocus aureus (SA), methicillin-resistant Staphylococcus aureus (MRSA), Bacillus cereus (BC) and Curtobacterium. flaccumfaciens (CF), and three Gram-(\u2013) bacteria of Escherichia coli (EC), Salmonella. typhimurium (SA), and Pseudomonas Solanacearum (PS). Compounds 4 and 7\u20139 were found to show strong in vitro antibacterial activity toward all the tested bacteria with the MIC values ranging from 1.56 to 12.5 \u00b5g\/mL. Notably, compounds 4 and 9 showed significant antibacterial activity against the drug-resistant bacterium of MRSA with MIC value 6.25 \u00b5g\/mL, which was close to reference compound vancomycin (MIC 3.125 \u00b5g\/mL). Compounds 4 and 7\u20139 were further revealed to show in vitro cytotoxic activity toward human tumor A549, HepG2, MCF-7, and HeLa cell lines, with IC50 values ranging from 8.97 to 27.39 \u03bcM. No antibacterial and cytotoxic activity were displayed for the other compounds. The present research provided new data to support that M. micrantha is rich in structurally diverse bioactive compounds worthy of further development for pharmaceutical applications and for crop protection in agricultural fields.<\/jats:p>","DOI":"10.3390\/molecules28052119","type":"journal-article","created":{"date-parts":[[2023,2,27]],"date-time":"2023-02-27T02:04:11Z","timestamp":1677463451000},"page":"2119","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":8,"title":["Germacrane Sesquiterpene Dilactones from Mikania micrantha and Their Antibacterial and Cytotoxic Activity"],"prefix":"10.3390","volume":"28","author":[{"given":"Li-Mei","family":"Dong","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"},{"name":"Guangdong Eco-Engineering Polytechnic, Guangzhou 510520, China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9437-4828","authenticated-orcid":false,"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":"Shao-Bo","family":"Liu","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":"Meng-Fei","family":"Liu","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":"Jin-Long","family":"Duan","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":"Jin-Kui","family":"Ouyang","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":"Jia-Tao","family":"Hu","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":"Fen-Yu","family":"Fu","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":[[2023,2,24]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"42","DOI":"10.1111\/j.1365-3180.2003.00371.x","article-title":"Mikania micrantha H.B.K. in China\u2014An overview","volume":"44","author":"Zhang","year":"2004","journal-title":"Weed Res."},{"key":"ref_2","unstructured":"Lowe, S., Browne, M., and Boudjelas, S. (2001). 100 of the World\u2019s Worst Invasive Alien Species, a Selection from the Global Invasive Species Database, IUCN\/SSC Invasive Species Specialist Group (ISSG)."},{"key":"ref_3","first-page":"263","article-title":"The distribution and harmful effect of Mikania micrantha in Guangdong","volume":"10","author":"Feng","year":"2002","journal-title":"J. Trop. Subtrop. Bot."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"1384","DOI":"10.1590\/S0102-695X2012005000099","article-title":"Genus Mikania: Chemical composition and phytotherapeutical activity","volume":"22","author":"Rufatto","year":"2012","journal-title":"Braz. J. Pharmacogn."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"1455","DOI":"10.1211\/0022357991777119","article-title":"Investigation of plants used in Jamaican folk medicine for anti-bacterial activity","volume":"51","author":"Facey","year":"1999","journal-title":"J. Pharm. Pharmacol."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"919","DOI":"10.1016\/S0367-326X(01)00318-5","article-title":"Analgesic sesquiterpene dilactone from Mikania cordata","volume":"72","author":"Ahmed","year":"2001","journal-title":"Fitoterapia"},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"107","DOI":"10.1007\/s10616-013-9543-9","article-title":"The anti-tumor activity of Mikania micrantha aqueous extract in vitro and in vivo","volume":"66","author":"Dou","year":"2014","journal-title":"Cytotechnology"},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"259","DOI":"10.1007\/s11418-007-0216-x","article-title":"Antibacterial activity of some medicinal plant extracts","volume":"62","author":"Ghosh","year":"2008","journal-title":"J. Nat. Med."},{"key":"ref_9","first-page":"121","article-title":"In vitro evaluation of antiprotozoal and antiviral activities of extracts from Argentinean Mikania species","volume":"12","author":"Laurella","year":"2012","journal-title":"Sci. World J."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"517","DOI":"10.1007\/s10535-009-0093-0","article-title":"Responses of photosynthetic parameters of Mikania micrantha and Chromolaena odorata to contrasting irradiance and soil moisture","volume":"53","author":"Zhang","year":"2009","journal-title":"Biol. Plant."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"155","DOI":"10.1016\/j.fitote.2014.02.006","article-title":"Sesquiterpene lactones from Mikania micrantha and Mikania cordifolia and their cytotoxic and anti-inflammatory evaluation","volume":"94","author":"Torres","year":"2014","journal-title":"Fitoterapia"},{"key":"ref_12","first-page":"293","article-title":"Active antifungal components of Mikania micrantha H. B. K","volume":"36","author":"Zhuang","year":"2010","journal-title":"J. Zhejiang Univ."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"e1","DOI":"10.3732\/ajb.1000387","article-title":"Development and characterization of EST-SSRs in an invasive weed Mikania micrantha","volume":"98","author":"Yan","year":"2011","journal-title":"Am. J. Bot."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"2409","DOI":"10.5897\/AJMR2013.5451","article-title":"Antimicrobial potential and chemical constituent of Mikania micrantha H. B. K","volume":"7","author":"Li","year":"2013","journal-title":"Afr. J. Microbiol. Res."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"105","DOI":"10.1055\/s-2006-962638","article-title":"Germacra-1,10Z,4E-dien-12,8\u03b1-olides from Mikania micrantha","volume":"53","author":"Boeker","year":"1987","journal-title":"Planta Med."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"925","DOI":"10.1021\/np800542t","article-title":"Antiviral constituents against respiratory viruses from Mikania micrantha","volume":"72","author":"But","year":"2009","journal-title":"J. Nat. Prod."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"625","DOI":"10.1021\/np50057a040","article-title":"Sesquiterpene lactones from Mikania micrantha","volume":"51","author":"Cuenca","year":"1988","journal-title":"J. Nat. Prod."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"233","DOI":"10.1016\/0031-9422(75)85045-X","article-title":"Mikanokryptin, a new guianolide from Mikania","volume":"14","author":"Herz","year":"1975","journal-title":"Phytochemistry"},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"734","DOI":"10.1021\/np034027i","article-title":"New sesquiterpene lactones from Mikania micrantha","volume":"67","author":"Huang","year":"2004","journal-title":"J. Nat. Prod."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"2587","DOI":"10.1016\/0031-9422(81)83102-0","article-title":"Allelopathic potential of sesquiterpene lactones and phenolic constituents from Mikania micrantha H. B. K","volume":"20","author":"Nicollier","year":"1981","journal-title":"Phytochemistry"},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"1091","DOI":"10.1016\/j.bse.2004.04.013","article-title":"Phenolic constituents from Mikania micrantha","volume":"32","author":"Wei","year":"2004","journal-title":"Biochem. Syst. Ecol."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"425","DOI":"10.1016\/j.phytol.2013.05.007","article-title":"Two new ent-kaurene diterpene glucosides from the roots of Mikania micrantha","volume":"6","author":"Xu","year":"2013","journal-title":"Phytochem. Lett."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"7309","DOI":"10.1021\/jf4017652","article-title":"Phenolic constituents from the roots of Mikania micrantha and their allelopathic effects","volume":"61","author":"Xu","year":"2013","journal-title":"J. Agric. Food Chem."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"49","DOI":"10.1016\/j.phytol.2020.09.011","article-title":"New Germacrane-sesquiterpenoids from the leaves of Mikania micrantha Kunth","volume":"40","author":"Ma","year":"2020","journal-title":"Phytochem. Lett."},{"key":"ref_25","doi-asserted-by":"crossref","unstructured":"Dong, L.-M., Jia, X.-C., Luo, Q.-W., Zhang, Q., Luo, B., Liu, W.-B., Zhang, X., Xu, Q.-L., and Tan, J.-W. (2017). Phenolics from Mikania micrantha and their antioxidant activity. Molecules, 22.","DOI":"10.3390\/molecules22071140"},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"155","DOI":"10.1016\/j.phytol.2017.04.029","article-title":"Four new ent-kaurene diterpene glucosides from Mikania micrantha","volume":"20","author":"Dong","year":"2017","journal-title":"Phytochem. Lett."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"674","DOI":"10.1007\/s10600-019-02776-7","article-title":"Two new sesquiterpene lactones from Ixeris sonchifolia","volume":"55","author":"Cai","year":"2019","journal-title":"Chem. Nat. Compd."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"1441","DOI":"10.1016\/0031-9422(94)00864-P","article-title":"Germacranolides of Mikania cordata","volume":"38","author":"Aguinaldo","year":"1995","journal-title":"Phytochemistry"},{"key":"ref_29","doi-asserted-by":"crossref","unstructured":"Liu, S.-B., Zeng, L., Xu, Q.-L., Chen, Y.-L., Lou, T., Zhang, S.-X., and Tan, J.-W. (2022). Polycyclic phenol derivatives from the leaves of Spermacoce latifolia and their antibacterial and \u03b1-glucosidase inhibitory activity. Molecules, 27.","DOI":"10.3390\/molecules27103334"},{"key":"ref_30","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_31","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_32","doi-asserted-by":"crossref","first-page":"5755","DOI":"10.1039\/D0RA08885D","article-title":"Thymol derivatives with antibacterial and cytotoxic activity from the aerial parts of Ageratina adenophora","volume":"11","author":"Zhang","year":"2021","journal-title":"RSC Adv."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"2927","DOI":"10.1016\/j.bmc.2007.02.005","article-title":"Quantitative structure\u2013activity relationship of sesquiterpene lactones with cytotoxic activity","volume":"15","author":"Scotti","year":"2007","journal-title":"Bioorgan. Med. Chem."},{"key":"ref_34","doi-asserted-by":"crossref","unstructured":"Dong, L.-M., Huang, L.-L., Dai, H., Xu, Q.-L., Ouyang, J.-K., Jia, X.-C., Gu, W.-X., and Tan, J.-W. (2018). Anti-MRSA sesquiterpenes from the semi-mangrove Plant Myoporum Bontioides A. Gray. Marine Drugs, 16.","DOI":"10.3390\/md16110438"}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/28\/5\/2119\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,10]],"date-time":"2025-10-10T18:41:33Z","timestamp":1760121693000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/28\/5\/2119"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2023,2,24]]},"references-count":34,"journal-issue":{"issue":"5","published-online":{"date-parts":[[2023,3]]}},"alternative-id":["molecules28052119"],"URL":"https:\/\/doi.org\/10.3390\/molecules28052119","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2023,2,24]]}}}