{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,6,24]],"date-time":"2026-06-24T11:54:54Z","timestamp":1782302094590,"version":"3.54.5"},"reference-count":79,"publisher":"MDPI AG","issue":"8","license":[{"start":{"date-parts":[[2025,7,24]],"date-time":"2025-07-24T00:00:00Z","timestamp":1753315200000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"Fundamental Research Funds for the South-Central MinZu University","award":["YZY24019"],"award-info":[{"award-number":["YZY24019"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Biomolecules"],"abstract":"<jats:p>3-Nitropropionic acid (3-NPA) is a deadly neurotoxic nitroalkane found in numerous fungi and leguminous plants. 3-NPA, known as an antimetabolite of succinate, irreversibly inhibits succinate dehydrogenase and disrupts mitochondrial oxidative phosphorylation. Its utility in modeling Huntington\u2019s disease (HD) and oxidative stress has garnered significant research interest. Derivatives of 3-NPA, formed through esterification, have a wide range of biological activities including neurotoxic, antiviral, insecticidal, antimicrobial and antioxidant properties. This review systematically summarizes the structural characteristics, biological activities, and chemical synthesis of 3-NPA-derived compounds, providing valuable insights for further research and therapeutic applications.<\/jats:p>","DOI":"10.3390\/biom15081066","type":"journal-article","created":{"date-parts":[[2025,7,24]],"date-time":"2025-07-24T07:54:26Z","timestamp":1753343666000},"page":"1066","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":3,"title":["Progress on 3-Nitropropionic Acid Derivatives"],"prefix":"10.3390","volume":"15","author":[{"given":"Meng-Lin","family":"Feng","sequence":"first","affiliation":[{"name":"School of Pharmaceutical Sciences, South-Central Minzu University, Wuhan 430074, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1284-0288","authenticated-orcid":false,"given":"Zheng-Hui","family":"Li","sequence":"additional","affiliation":[{"name":"School of Pharmaceutical Sciences, South-Central Minzu University, Wuhan 430074, China"},{"name":"International Cooperation Base for Active Substances in Traditional Chinese Medicine in Hubei Province, School of Pharmaceutical Sciences, South-Central Minzu University, Wuhan 430074, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Bao-Bao","family":"Shi","sequence":"additional","affiliation":[{"name":"School of Pharmaceutical Sciences, South-Central Minzu University, Wuhan 430074, China"},{"name":"International Cooperation Base for Active Substances in Traditional Chinese Medicine in Hubei Province, School of Pharmaceutical Sciences, South-Central Minzu University, Wuhan 430074, China"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2025,7,24]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"3767","DOI":"10.1073\/pnas.74.9.3767","article-title":"3-Nitropropionate, the toxic substance of Indigofera, is a suicide inactivator of succinate dehydrogenase","volume":"74","author":"Alston","year":"1977","journal-title":"Proc. Natl. Acad. Sci. USA"},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"783","DOI":"10.1016\/j.phytochem.2007.09.006","article-title":"Metabolites from the endophytic fungus Phomopsis sp. PSU-D15","volume":"69","author":"Rukachaisirikul","year":"2008","journal-title":"Phytochemistry"},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"685","DOI":"10.1016\/S0021-9258(19)77741-2","article-title":"The production of beta-nitropropionic acid by a strain of Aspergillus flavus","volume":"188","author":"Bush","year":"1951","journal-title":"J. Biol. Chem."},{"key":"ref_4","first-page":"187","article-title":"Hiptagin, a New Glucoside from Hiptage medablota, gaertu","volume":"2","author":"Gorter","year":"1920","journal-title":"Bull. Jard. Bot. Buitenzorg."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"322","DOI":"10.1126\/science.119.3088.322","article-title":"Hiptagenic Acid, a Toxic Component of Indigofera endecaphylla","volume":"119","author":"Morris","year":"1954","journal-title":"Science"},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"462","DOI":"10.2134\/agronj1959.00021962005100080005x","article-title":"Comparative Toxic Effects of 3-Nitropropionic Acid, Sodium Nitrite and Indigofera endecaphylla on Chicks","volume":"51","author":"Britten","year":"1959","journal-title":"Agron. J."},{"key":"ref_7","doi-asserted-by":"crossref","unstructured":"Sanberg, P.R., Nishino, H., and Borlongan, C.V. (2000). History of 3-Nitropropionic Acid. Mitochondrial Inhibitors and Neurodegenerative Disorders, Humana Press. Contemporary Neuroscience.","DOI":"10.1007\/978-1-59259-692-8"},{"key":"ref_8","first-page":"363","article-title":"Moldy Sugarcane Poisoning\u2014A Case Report with a Brief Review","volume":"33","author":"Li","year":"2008","journal-title":"J. Toxicol. Clin. Toxicol."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"492","DOI":"10.1017\/S0317167100032212","article-title":"3-Nitropropionic Acid\u2014Exogenous Animal Neurotoxin and Possible Human Striatal Toxin","volume":"18","author":"Ludolph","year":"1991","journal-title":"Can. J. Neurol. Sci."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"542","DOI":"10.1097\/00019052-199412000-00012","article-title":"Neurochemistry and Toxin Models in Huntington\u2019s Disease","volume":"7","author":"Beal","year":"1994","journal-title":"Curr. Opin. Neurol."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"63","DOI":"10.1111\/j.1476-5381.2012.01994.x","article-title":"3-Nitropropionic acid induces autophagy by forming mitochondrial permeability transition pores rather than activating the mitochondrial fission pathway","volume":"168","author":"Solesio","year":"2013","journal-title":"Br. J. Pharmacol."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"339","DOI":"10.1002\/syn.20852","article-title":"Acute and long-term response of dopamine nigrostriatal synapses to a single, low-dose episode of 3-nitropropionic acid-mediated chemical hypoxia","volume":"65","author":"Crawford","year":"2011","journal-title":"Synapse"},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"299","DOI":"10.1385\/JMN:24:2:299","article-title":"Inhibition of caspase-3 activation and apoptosis is involved in 3-nitropropionic acid-induced ischemic tolerance to transient focal cerebral ischemia in rats","volume":"24","author":"Zhu","year":"2004","journal-title":"J. Mol. Neurosci."},{"key":"ref_14","doi-asserted-by":"crossref","unstructured":"Wiprich, M.T., Altenhofen, S., Gusso, D., Vasques, R.R., Zanandrea, R., Kist, L.W., Bogo, M.R., and Bonan, C.D. (2022). Modulation of Adenosine Signaling Reverses 3-nitropropionic Acid-Induced Bradykinesia and Memory Impairment in Adult Zebrafish. Prog. Neuro-Psychopharmacol. Biol. Psychiatry, 119.","DOI":"10.1016\/j.pnpbp.2022.110602"},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"1631","DOI":"10.1007\/s11064-023-03868-1","article-title":"An Overview of the Pathophysiological Mechanisms of 3-Nitropropionic Acid (3-NPA) as a Neurotoxin in a Huntington\u2019s Disease Model and Its Relevance to Drug Discovery and Development","volume":"48","author":"Upadhayay","year":"2023","journal-title":"Neurochem. Res."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"238","DOI":"10.1002\/jctb.5000621209","article-title":"Karakin, the Glucoside of Corynocarpus levigata, and Hiptagenic Acid","volume":"62","author":"Carter","year":"2010","journal-title":"J. Chem. Technol. Biotechnol."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"343","DOI":"10.1039\/C6NP00122J","article-title":"A tale of four kingdoms\u2014Isoxazolin-5-one- and 3-nitropropanoic acid-derived natural products","volume":"34","author":"Becker","year":"2017","journal-title":"Nat. Prod. Rep."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"229","DOI":"10.1093\/ee\/6.2.229","article-title":"Toxicity of \u03b2-Nitropropionic Acid to Trichoplusia ni12","volume":"6","author":"Byers","year":"1977","journal-title":"Environ. Entomol."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"1771","DOI":"10.1523\/JNEUROSCI.04-07-01771.1984","article-title":"Nerve Growth Factor-Mediated Enzyme Induction in Primary Cultures of Bovine Adrenal Chromaffin Cells: Specificity and Level of Regulation","volume":"4","author":"Acheson","year":"1984","journal-title":"J. Neurosci."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"3158","DOI":"10.1021\/acs.orglett.4c00758","article-title":"How Fungi Biosynthesize 3-Nitropropanoic Acid: The Simplest Yet Lethal Mycotoxin","volume":"26","author":"Johnson","year":"2024","journal-title":"Org. Lett."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"409","DOI":"10.1016\/S0031-9422(00)85490-4","article-title":"Hiptagin and Other Aliphatic Nitro Esters in Lotus pedunculatus","volume":"25","author":"Gnanasunderam","year":"1986","journal-title":"Phytochemistry"},{"key":"ref_22","unstructured":"Shaw, P., Mead, R., Higginbottom, A., and Barber, S. (2011). Therapeutics for Neurological Disorders. (US20110251230A1), U.S. Patent."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1016\/S0008-6215(00)85470-1","article-title":"Assessment of Carbon-13 Shift Parameters in Di- and Tri-(3-nitropropanoyl)-D-glucopyranoses","volume":"73","author":"Pfeffer","year":"1979","journal-title":"Carbohydr. Res."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"375","DOI":"10.1016\/0031-9422(77)80068-X","article-title":"Corollin, Coronillin and Coronarian: Three New 3-Nitropropanoyl-D-glucopyranoses from Coronilla varia","volume":"16","author":"Moyer","year":"1977","journal-title":"Phytochemistry"},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"95","DOI":"10.1021\/bk-1986-0296.ch008","article-title":"3-Nitropropionate in Crownvetch: A Natural Deterrent to Insects?","volume":"296","author":"Byers","year":"1986","journal-title":"ACS Symp. Ser."},{"key":"ref_26","first-page":"141","article-title":"Pharmacological Evaluation of the Cardiac Glycoside Coronillin","volume":"5","author":"Kigel","year":"1964","journal-title":"Serd. Sosud. Patol."},{"key":"ref_27","first-page":"16","article-title":"Pharmacodynamics of the Cardiac Glycoside Coronillin","volume":"27","author":"Kigel","year":"1964","journal-title":"Farmakol. Toksikol."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"2393","DOI":"10.1016\/0031-9422(92)83284-6","article-title":"Three Nitropropanoyl Esters of Glucose from Indigofera linnaei","volume":"31","author":"Benn","year":"1992","journal-title":"Phytochemistry"},{"key":"ref_29","unstructured":"Hempstead, B.L. (2010). Small Molecule Modulators of proNGF Uptake. (WO2010042728A1), World Patent."},{"key":"ref_30","first-page":"543","article-title":"2,3,4,6-Tetra-O-(3-nitropropanoyl)-O-\u03b2-D-glucopyranoside, a New Antibacterial from the Roots of Heteropteris aphrodisiaca","volume":"24","author":"Vilegas","year":"2005","journal-title":"Lat. Am. J. Pharm."},{"key":"ref_31","unstructured":"De Mello, J.C.P., Cardoso, M.L.C., and Nakamura, C.V. (2005). Process to Obtain and Isolate a New Compound with Anti-Viral, Fungicide and Antibacterial Properties. (BR PI0302921-6), Brazil Patent."},{"key":"ref_32","first-page":"1448","article-title":"New 3-Nitropropionyl-D-glucopyranoses in Root of Indigofera kirilowii","volume":"38","author":"Yang","year":"2007","journal-title":"Zhong Cao Yao"},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"451","DOI":"10.1016\/j.fitote.2008.04.006","article-title":"Six New Glucose Esters of 3-Nitropropanoic Acid from Indigofera kirilowii","volume":"79","author":"Su","year":"2008","journal-title":"Fitoterapia"},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"1785","DOI":"10.1021\/np050268+","article-title":"Acryloylated Glucose 3-Nitropropanoates from Indigofera kirilowii","volume":"68","author":"Su","year":"2005","journal-title":"J. Nat. Prod."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"14970","DOI":"10.3390\/molecules200814970","article-title":"Fast Identification of Radical Scavengers from Securigera varia by Combining 13C-NMR-Based Dereplication to Bioactivity-Guided Fractionation","volume":"20","author":"Sientzoff","year":"2015","journal-title":"Molecules"},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"353","DOI":"10.1002\/jps.2600570233","article-title":"Structure of Hiptagin as 1,2,4,6-Tetra-O-(3-nitropropanoyl)-\u03b2-D-glucopyranoside, Its Identity with Endecaphyllin X, and the Synthesis of Its Methyl Ether","volume":"57","author":"Finnegan","year":"1968","journal-title":"J. Pharm. Sci."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"901","DOI":"10.1016\/S0031-9422(00)90635-6","article-title":"Additional Esters of 3-Nitropropanoic Acid and Glucose from Fruit of the New Zealand Karaka Tree, Corynocarpus laevigatus","volume":"35","author":"Majak","year":"1994","journal-title":"Phytochemistry"},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"191","DOI":"10.1303\/aez.2002.191","article-title":"Adult Secretions of Four Japanese Chrysomelinae (Coleoptera: Chrysomelidae)","volume":"37","author":"Sugeno","year":"2002","journal-title":"Appl. Entomol. Zool."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"29","DOI":"10.1111\/j.1365-3032.1986.tb00388.x","article-title":"Chemical defense in chrysomelid eggs and neonate larvae","volume":"11","author":"Pasteels","year":"1986","journal-title":"Physiol. Entomol."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"1891","DOI":"10.1016\/0040-4020(82)80038-0","article-title":"Chemical defence in chrysomelid larvae and adults","volume":"38","author":"Pasteels","year":"1982","journal-title":"Tetrahedron"},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"54","DOI":"10.1002\/jsfa.2740020203","article-title":"The constitution of karakin","volume":"2","author":"Carter","year":"1951","journal-title":"J. Sci. Food Agric."},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"146","DOI":"10.2460\/javma.1981.178.02.146","article-title":"Syndromes of Astragalus poisoning in livestock","volume":"178","author":"James","year":"1981","journal-title":"J. Am. Vet. Med. Assoc."},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"1629","DOI":"10.1016\/0031-9422(95)00482-M","article-title":"Aliphatic nitro-compounds in Astragalus canadensis","volume":"40","author":"Benn","year":"1995","journal-title":"Phytochemistry"},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"1107","DOI":"10.2527\/jas1977.4461107x","article-title":"Ruminal metabolism of 3-nitropropanoyl-D-glucopyranoses from crownvetch","volume":"44","author":"Gustine","year":"1977","journal-title":"J. Anim. Sci."},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"15","DOI":"10.1016\/j.fitote.2005.06.015","article-title":"New aliphatic nitro-compounds from Indigofera carlesii","volume":"77","author":"Zhang","year":"2006","journal-title":"Fitoterapia"},{"key":"ref_46","first-page":"330","article-title":"Preparation of tert-butyl 3-nitropropionate","volume":"36","author":"Zhang","year":"2005","journal-title":"Chin. J. Pharm."},{"key":"ref_47","unstructured":"Cheng, W., Zhu, L., Chang, Y., Shang, M., Meng, H., and Chen, G. (2017). Process for preparation of tert-butyl 3-amino-5-bromo-4-oxo-pentanoate. (CN106831463A), Chinese Patent."},{"key":"ref_48","unstructured":"Aja, T., Ching, B.W., and Gladstone, P.L. (2002). Anti-Apoptotic Agents or Interleukin 1\u03b2 Converting Enzyme (ICE\/CED-3) Inhibitors for Preserving Antigenicity of Markers Associated with Diseases. (WO2002070544A2), World Patent."},{"key":"ref_49","unstructured":"Fritz, L.C., and Tomaselli, K.J. (1998). Inhibition of Apoptosis Using Interleukin-1\u03b2-Converting Enzyme (ICE)\/CED-3 Family Inhibitors. (WO9810778A1), World Patent."},{"key":"ref_50","unstructured":"Lawrence, F.C., Tomaselli, K.J., Karanewsky, D.S., Linton, S.D., and Bai, X. (2002). Treatment of Infectious Disease Using Interleukin-1\u03b2-Converting Enzyme (ICE)\/CED-3 Family Inhibitors. (US20020128306A1), U.S. Patent."},{"key":"ref_51","unstructured":"Fritz, L.C., Tomaselli, K.J., and Karanewsky, D.S. (2003). Preparation of 2-Indolecarbonyl Amino Acid Amides for Inhibition of Inflammation Using Interleukin-1\u03b2-Converting Enzyme (ICE)\/CED-3 Family Inhibitors. (6,531,467), U.S. Patent."},{"key":"ref_52","unstructured":"Karanewsky, D.S., and Bai, X. (1998). Preparation of N-Substituted-2-Indolyl Dipeptides as Inhibitors of the ICE\/Ced-3 Family of Cysteine Proteases. (WO1998011129A1), World Patent."},{"key":"ref_53","unstructured":"Karanewsky, D.S., and Bai, X. (2001). Preparation of C-Terminal Modified N-Substituted 2-Indolylcarbonyl Dipeptides as Inhibitors of the ICE\/Ced-3 Family of Cysteine Proteases. (WO2001000658A1), World Patent."},{"key":"ref_54","unstructured":"Roesch, F., Waldron, B.P., and Parker, D. (2014). Bifunctional Chelating Agents Based on the 1,4-Diazepine Scaffold (DAZA) for Non-Invasive Molecular Imaging. (WO2014198478A1), World Patent."},{"key":"ref_55","unstructured":"Xu, X.L. (2018). A Kind of Method that Enzyme Process Prepares Aliskiren Key Intermediate. (CN108192933A), Chinese Patent."},{"key":"ref_56","doi-asserted-by":"crossref","first-page":"138","DOI":"10.1055\/s-1982-29718","article-title":"Titanate-mediated transesterifications with functionalized substrates","volume":"1982","author":"Seebach","year":"1982","journal-title":"Synthesis"},{"key":"ref_57","doi-asserted-by":"crossref","first-page":"595","DOI":"10.1081\/SCC-100000587","article-title":"An Expeditious Synthesis of 3-Nitropropionic Acid and Its Ethyl and Methyl Esters","volume":"31","author":"Silva","year":"2001","journal-title":"Synth. Commun."},{"key":"ref_58","first-page":"1626","article-title":"Chemical Constituents in Roots of Indigofera kirilowii","volume":"39","author":"Su","year":"2008","journal-title":"Zhongcaoyao"},{"key":"ref_59","doi-asserted-by":"crossref","first-page":"1136","DOI":"10.1002\/jps.2600540809","article-title":"Chemical examination of a toxic extract of Indigofera endecaphylla: The Endecaphyllins","volume":"54","author":"Finnegan","year":"1965","journal-title":"J. Pharm. Sci."},{"key":"ref_60","first-page":"240","article-title":"Gas Chromatograph-Mass Spectrometer Analysis and Acute Oral Toxicity of Cinnamomum burmannii Ness ex Bl. Essential Oil","volume":"9","author":"Herdwiani","year":"2016","journal-title":"Asian J. Pharm. Clin. Res."},{"key":"ref_61","unstructured":"Ma, G., Wang, J., and Yang, F. (2023). Method for Reducing Byproduct Succinic Acid During Lactic Acid Fermentation by Adding Isocitrate Lyase Inhibitor. (CN116622785A), Chinese Patent."},{"key":"ref_62","first-page":"101","article-title":"Nitropropanoic acid from five Astragalus species","volume":"21","author":"Somanthan","year":"1990","journal-title":"Rev. Latinoam. Quim."},{"key":"ref_63","doi-asserted-by":"crossref","first-page":"36","DOI":"10.1007\/s42452-020-04101-2","article-title":"GC\u2013MS Analysis of Phytocompounds and Antihyperglycemic Property of Hydrocotyle sibthorpioides Lam","volume":"3","author":"Swargiary","year":"2021","journal-title":"SN Appl. Sci."},{"key":"ref_64","unstructured":"Marom, E., Mizhiritskii, M., and Rubnov, S. (2012). Intermediate Compounds and Process for the Preparation of Fingolimod. (WO2012056458A2), World Patent."},{"key":"ref_65","unstructured":"Jin, Y.-H., Zhang, Q.-H., Liu, T.-L., Zhang, W.-Q., Huang, S., and Wang, K.-C. (2024). Preparation of 1,3-Diazidopropan-2-yl 3-Nitropropanoate Use as Energetic Plasticizer. (CN117567316A), Chinese Patent."},{"key":"ref_66","doi-asserted-by":"crossref","first-page":"89","DOI":"10.1016\/0031-9422(95)00346-9","article-title":"Nitroaliphatic compounds in Hippocrepis comosa and other legumes in the European flora","volume":"40","author":"Salem","year":"1995","journal-title":"Phytochemistry"},{"key":"ref_67","doi-asserted-by":"crossref","first-page":"6274","DOI":"10.1039\/C6OB00899B","article-title":"Biosynthesis of isoxazolin-5-one and 3-nitropropanoic acid containing glucosides in juvenile Chrysomelina","volume":"14","author":"Becker","year":"2016","journal-title":"Org. Biomol. Chem."},{"key":"ref_68","doi-asserted-by":"crossref","first-page":"12779","DOI":"10.1021\/jo4023155","article-title":"Synthesis of Isoxazolin-5-one Glucosides by a Cascade Reaction","volume":"78","author":"Becker","year":"2013","journal-title":"J. Org. Chem."},{"key":"ref_69","unstructured":"Luo, S. (2016). Method for Producing Polydienes and Polydiene Copolymers with Reduced Cold Flow. (WO2016057388A1), World Patent."},{"key":"ref_70","doi-asserted-by":"crossref","first-page":"6406","DOI":"10.1021\/ol202710g","article-title":"Diastereoselective Synthesis of 1,3,5-Trisubstituted 4-Nitropyrrolidin-2-ones via a Nitro-Mannich\/Lactamization Cascade","volume":"13","author":"Pelletier","year":"2011","journal-title":"Org. Lett."},{"key":"ref_71","doi-asserted-by":"crossref","first-page":"24","DOI":"10.1080\/14786419.2021.1946536","article-title":"Two New Farnesyl Hydroquinones from Pestalotiopsis diploclisia (BCC 35283), the Fungus Associated with Algae","volume":"37","author":"Bunyapaiboonsri","year":"2023","journal-title":"Nat. Prod. Res."},{"key":"ref_72","doi-asserted-by":"crossref","first-page":"246","DOI":"10.1016\/j.phytol.2017.05.008","article-title":"Spiroarthrinols A and B, Two Novel Meroterpenoids Isolated from the Sponge-Derived Fungus Arthrinium sp.","volume":"20","author":"Elissawy","year":"2017","journal-title":"Phytochem. Lett."},{"key":"ref_73","doi-asserted-by":"crossref","first-page":"738","DOI":"10.1016\/j.phytol.2012.08.003","article-title":"Anthraquinone Derivatives from the Mangrove-Derived Fungus Phomopsis sp. PSU-MA214","volume":"5","author":"Klaiklay","year":"2012","journal-title":"Phytochem. Lett."},{"key":"ref_74","doi-asserted-by":"crossref","first-page":"125","DOI":"10.2298\/JSC200815002I","article-title":"Molecular Docking Study on Biomolecules Isolated from Endophytic Fungi","volume":"86","author":"Krmar","year":"2021","journal-title":"J. Serb. Chem. Soc."},{"key":"ref_75","doi-asserted-by":"crossref","first-page":"368","DOI":"10.1016\/j.phytol.2013.04.010","article-title":"Two New Flavonols, Including One Flavan Dimer, from the Roots of Indigofera stachyodes","volume":"6","author":"Qiu","year":"2013","journal-title":"Phytochem. Lett."},{"key":"ref_76","unstructured":"Hao, X.-Y., He, H.-P., Qiu, L., Hao, X.-J., Liang, Y., Liu, L., and Yao, C.-F. (2013). 3-Nitropropionyl Containing Flavanol, Its Medicinal Composition and Application in Pharmaceuticals Industry. (CN102942551), Chinese Patent."},{"key":"ref_77","doi-asserted-by":"crossref","first-page":"2851","DOI":"10.1021\/acs.jmedchem.8b00147","article-title":"Nitro-Group-Containing Drugs","volume":"62","author":"Nepali","year":"2019","journal-title":"J. Med. Chem."},{"key":"ref_78","doi-asserted-by":"crossref","unstructured":"Fan, T., Sun, G., Zhao, L., Cui, X., and Zhong, R. (2018). QSAR and Classification Study on Prediction of Acute Oral Toxicity of N-Nitroso Compounds. Int. J. Mol. Sci., 19.","DOI":"10.3390\/ijms19103015"},{"key":"ref_79","doi-asserted-by":"crossref","first-page":"11","DOI":"10.22606\/mocr.2018.31002","article-title":"Toward the Toxicology of Some Nitro-Compounds","volume":"3","author":"Tan","year":"2018","journal-title":"Mod. Org. Chem. Res."}],"container-title":["Biomolecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/2218-273X\/15\/8\/1066\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,9]],"date-time":"2025-10-09T18:15:03Z","timestamp":1760033703000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/2218-273X\/15\/8\/1066"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2025,7,24]]},"references-count":79,"journal-issue":{"issue":"8","published-online":{"date-parts":[[2025,8]]}},"alternative-id":["biom15081066"],"URL":"https:\/\/doi.org\/10.3390\/biom15081066","relation":{},"ISSN":["2218-273X"],"issn-type":[{"value":"2218-273X","type":"electronic"}],"subject":[],"published":{"date-parts":[[2025,7,24]]}}}