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Compared with raw garlic, black garlic has a higher content of PPs and S-allyl cysteine (SAC), a key OSC due to its bioactivities. The objective of the present work was to optimize by chemometric tools a green microwave-assisted extraction (MAE) of SAC and PPs present in black Chiloe\u2019s giant garlic to detect and identify novel bioactive molecules with antioxidant and\/or inhibitory activities over cyclooxygenase, \u03b1-glucosidase, and acetylcholinesterase enzymes. The MAE factors were optimized using a central composite design, establishing optimal PP and SAC yields at 67 \u00b0C, 0% ethanol, 12 min and 30 \u00b0C, 40% ethanol, 3 min, respectively. PP and SAC values were 9.19 \u00b1 0.18 mg GAE\/g DW and 2.55 \u00b1 0.10 mg SAC\/g DW. Applying effect-directed analysis using high-performance thin layer chromatography-bioassay and mass spectrometry, the bioactive molecules present in the MAE extract with antioxidant and inhibitory activities over cyclooxygenase, \u03b1-glucosidase, and acetylcholinesterase enzymes were identified as N-fructosyl-glutamyl-S-(1-propenyl)cysteine, N-fructosyl-glutamylphenylalanine, and Harmane.<\/jats:p>","DOI":"10.3390\/antiox14080913","type":"journal-article","created":{"date-parts":[[2025,7,25]],"date-time":"2025-07-25T11:38:41Z","timestamp":1753443521000},"page":"913","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":2,"title":["Identification of Novel Bioactive Molecules in Black Chiloe\u2019s Giant Garlic (Allium ampeloprasum L.) by Green Microwave-Assisted Extraction and Effect-Directed Analysis Using High-Performance Thin Layer Chromatography-Bioassay and Mass Spectrometry"],"prefix":"10.3390","volume":"14","author":[{"given":"Joaqu\u00edn","family":"Fern\u00e1ndez-Mart\u00ednez","sequence":"first","affiliation":[{"name":"Laboratory of Food and Drug Research, Faculty of Chemistry and Pharmacy, Pontificia Universidad Cat\u00f3lica de Chile, Santiago 7820436, Chile"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1267-6676","authenticated-orcid":false,"given":"David","family":"Arr\u00e1ez-Rom\u00e1n","sequence":"additional","affiliation":[{"name":"Department of Analytical Chemistry, Universidad de Granada, 18071 Granada, Spain"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1782-085X","authenticated-orcid":false,"given":"Darlene","family":"Peterssen","sequence":"additional","affiliation":[{"name":"Department of Biological and Chemical Sciences, Faculty of Sciences, Universidad San Sebasti\u00e1n, Concepci\u00f3n 4090762, Chile"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8090-1153","authenticated-orcid":false,"given":"Gerald","family":"Zapata","sequence":"additional","affiliation":[{"name":"Center of Molecular Modelling, Biophysics and Bioinformatics, Faculty of Chemistry and Pharmaceutical Sciences, Universidad de Chile, Santiago 8380544, Chile"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Karem","family":"Henr\u00edquez-Aedo","sequence":"additional","affiliation":[{"name":"Laboratory of Food Biotechnology and Genetics, Department of Basic Sciences, Faculty of Sciences, Universidad del B\u00edo-B\u00edo, Chill\u00e1n 3810189, Chile"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7846-9149","authenticated-orcid":false,"given":"Mario","family":"Aranda","sequence":"additional","affiliation":[{"name":"Laboratory of Food and Drug Research, Faculty of Chemistry and Pharmacy, Pontificia Universidad Cat\u00f3lica de Chile, Santiago 7820436, Chile"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2025,7,25]]},"reference":[{"key":"ref_1","unstructured":"WHO (2022). 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