Species from Pavonia genus (Malvaceae) are traditionally used as antioxidant, n anti inflammatory and antimicrobial remedies. Previous studies have revealed their diversity of specialized metabolites widely used in the development of new medicines. This is the first study on Pavonia glazioviana Gurke, a Brazilian species known as “Malva da Chapada”. The research led to identify fifteen compounds: 132 (S) hydroxy pheophytin a; and 132(S) hydroxy 173 ethoxyphaeophorbide, n decanol, cycloart 23Z ene 3β,25 diol, cycloart 24S 25 ene 3β,24 diol, sitosterol 3 O β D glucopyranoside, stigmasterol 3 O β D glucopyranoside, quercetin, acacetin, kaempferol, tiliroside, 5 hydroxy 3,7,8,4’ tetramethoxyflavone, 5,7 dihydroxy 3,8,4’ trimethoxyflavone, 5,7 dihydroxy 4’ methoxyflavone, 5,7,4’ trihydroxy 3,8 dimethoxyflavone and 5,7,4’ trihydroxy 3 methoxyflavone. The major flavonoids were tested for their antimicrobial activity, and the compound 5,7 dihydroxy 3,8,4’ trimethoxyflavone showed strong activity against Escherichia coli (MIC = 512 μg mL1), Pseudomonas aeruginosa (MIC = 512 μg mL1), Candida albicans (MIC = 512 μg mL1), Candida tropicalis (MIC = 512 μg mL1), Candida parapsilosis (MIC = 512 μg mL1), Aspergillus flavus (MIC = 512 μg mL1) and A. fumigantus (MIC = 512 μg mL1). The total phenolic content, flavonoid content, and radical scavenging potential were determined showing its great production of phenolics and flavonoids, along with interesting radical scavenging potential (DPPH EC50 = 6.36 ± 0.029 mg mL 1). Our findings contributed to characterize P. glazioviana as a source of methoxylated flavonoids with antimicrobial potential. Malvaceae (Malvaceae antioxidant remedies medicines Gurke Malva Chapada. Chapada . Chapada” compounds 13 S (S 132S 132(S 17 ethoxyphaeophorbide decanol Z 3β25 3β 3β,2 diol 2 3β24 24 glucopyranoside quercetin acacetin kaempferol tiliroside 3,7,8,4 3784 7 8 4 tetramethoxyflavone 57 5, 3,8,4 384 methoxyflavone 5,7,4 574 38 3, MIC 51 mL1, mL1 , A mL1. content DPPH EC EC5 636 6 36 6.3 0029 0 029 0.02 1. 1 1) P 3β2 3β, 3,7,8, 378 3,8, 5,7, 63 6. 002 02 0.0 3,7,8 37 00 0. 3,7, 3,7

Considering the relevance of natural products to the development of new drugs, this study focuses on the species Sida rhombifolia (L.), Malvaceae, widely used as a traditional remedy in several countries. The species is used to treat several diseases such as fevers, skin diseases, stomach pain, diarrhea, gum infection, conjunctivitis, urinary infections and inflammation. Many researchers around the word have investigated its pharmacological potential, and many uses have been confirmed. In spite of that, the phytochemical composition of its extracts is still poorly investigated. This research aims to make advances on the understanding of the constituents of S. rhombifolia identifying its alkaloidal compounds using ultra-high performance liquid chromatography coupled to mass spectrometry (UPLC-QTOF-MS/MS). By analyzing its alkaloidal fraction, it was possible to identify: 11-cryptolepine carboxylic acid (1), cryptolepine (2), quindoline (3), 11 methoxyquidoline (4), quindolinone (5), cryptolepinone (6), and 11-quindoline methyl ester (7). The alkaloids 1 and 7 are being reported for the first time from Sida genus. Based on the antimicrobial potential of cryptolepinone-type alkaloids, we prepared by semi-synthesis two cryptolepinone derivatives: 10-methylcryptolepinone (8) and the unreported compound 10-ethylcryptolepinone (9). Both derivatives were tested against fungal and bacterial strains and 10-methylcryptolepinone (8) showed strong activity against Cryptococcus neoformans, Candida albicans, Candida tropicalis, Aspergillus fumigatus and Aspergillus flavus. drugs L., L L. , (L.) Malvaceae countries fevers pain diarrhea infection conjunctivitis inflammation confirmed that S ultrahigh ultra high UPLCQTOFMS/MS. UPLCQTOFMSMS UPLC QTOF MS/MS . MS (UPLC-QTOF-MS/MS) fraction identify 11cryptolepine 1, (1) 2, 2 (2) 3, 3 (3) 4, 4 (4) 5, 5 (5) 6, 6 (6) 11quindoline 7. (7) genus cryptolepinonetype type semisynthesis semi synthesis 10methylcryptolepinone methylcryptolepinone 10 8 (8 10ethylcryptolepinone ethylcryptolepinone 9. 9 (9) neoformans albicans tropicalis flavus (L. UPLCQTOFMS UPLCQTOFMS/MS MSMS (UPLC-QTOF-MS/MS (1 (2 (3 (4 (5 (6 (7 ( (9 (L