{ "document_id": 13701, "page": 19, "width_pt": 612, "height_pt": 792, "rotation": 0, "pipeline_version": "paddleocr-vl-1.6+paul-48", "engine": "paddleocr_vl", "source_run_id": 13812, "item_count": 83, "counts_by_type": { "figure": 1, "form_field": 1, "formula": 22, "header": 3, "heading": 1, "table": 1, "table_cell": 18, "text": 36 }, "build_ms": 10, "items": [ { "id": "p19.1", "order": 1, "type": "header", "bbox": { "l": 53.76, "t": 765.6, "r": 70.56, "b": 757.44 }, "text": "522", "attrs": { "block_label": "number" }, "level": 2 }, { "id": "p19.2", "order": 2, "type": "header", "bbox": { "l": 75.6, "t": 766.08, "r": 264.24, "b": 756.24 }, "text": "Journal of Natural Products, 1999, Vol. 62, No. 3", "attrs": { "block_label": "header" }, "level": 2 }, { "id": "p19.3", "order": 3, "type": "header", "bbox": { "l": 501.36, "t": 765.84, "r": 559.68, "b": 756 }, "text": "Invited Review", "attrs": { "block_label": "header" }, "level": 2 }, { "id": "p19.4", "order": 4, "type": "heading", "bbox": { "l": 53.28, "t": 746.16, "r": 142.8, "b": 736.32 }, "text": "Table 4. (Continued)", "attrs": { "block_label": "paragraph_title" }, "level": 3 }, { "id": "p19.5", "order": 5, "type": "text", "bbox": { "l": 237.12, "t": 732.96, "r": 373.92, "b": 723.36 }, "text": "Mono-THF Acetogenins (Continued)" }, { "id": "p19.6", "order": 6, "type": "text", "bbox": { "l": 69.12, "t": 722.88, "r": 205.44, "b": 712.56 }, "text": "50. mosin[p19.6.1] ([p19.6.2], MW594) Mono-THF Acetogenins (Continued)", "children": [ { "id": "p19.6.1", "order": 7, "type": "formula", "bbox": { "l": 69.12, "t": 722.88, "r": 205.44, "b": 712.56 }, "text": "\\textbf{50. mosin } \\textbf{C}^{105} \\, (\\mathrm{C}_{35}\\mathrm{H}_{62}\\mathrm{O}_{7}, \\mathrm{MW}\\,594)", "attrs": { "latex": "\\textbf{50. mosin } \\textbf{C}^{105} \\, (\\mathrm{C}_{35}\\mathrm{H}_{62}\\mathrm{O}_{7}, \\mathrm{MW}\\,594)", "inline": true, "text_offset": 9, "text_span": 9, "bbox_estimated": true, "alt": "textbf 50. mosin textbf C to the power of 105, C sub 35 H sub 62 O sub 7, MW, 594", "notation": "latex", "mathml": "50. mosin C105(C35H62O7,MW594)" } }, { "id": "p19.6.2", "order": 8, "type": "text", "bbox": { "l": 69.12, "t": 722.88, "r": 205.44, "b": 712.56 }, "text": "C₃₅H₆₂O₇", "attrs": { "inline": true, "text_offset": 20, "text_span": 9, "bbox_estimated": true } } ] }, { "id": "p19.7", "order": 9, "type": "formula", "bbox": { "l": 156.96, "t": 712.8, "r": 452.88, "b": 663.36 }, "text": "", "attrs": { "block_label": "image", "alt": "Skeletal structure of an annonaceous acetogenin: butenolide ring, THF ring, hydroxyl groups at C4, C15, C20, and a ketone at…", "source": "vision" } }, { "id": "p19.8", "order": 10, "type": "table", "bbox": { "l": 157.44, "t": 653.04, "r": 358.8, "b": 617.76 }, "text": "", "attrs": { "block_label": "table", "n_rows": 3, "n_cols": 6, "integrity": { "skipped": "no_text_layer" } }, "children": [ { "id": "p19.8.1", "order": 11, "type": "table_cell", "bbox": { "l": 157.44, "t": 653.04, "r": 191, "b": 641.28 }, "text": "Position", "attrs": { "row": 0, "col": 0, "rowspan": 1, "colspan": 1, "column_header": true, "header_source": "heuristic" } }, { "id": "p19.8.2", "order": 12, "type": "table_cell", "bbox": { "l": 191, "t": 653.04, "r": 224.56, "b": 641.28 }, "text": "9", "attrs": { "row": 0, "col": 1, "rowspan": 1, "colspan": 1, "column_header": true, "header_source": "heuristic" } }, { "id": "p19.8.3", "order": 13, "type": "table_cell", "bbox": { "l": 224.56, "t": 653.04, "r": 258.12, "b": 641.28 }, "text": "15", "attrs": { "row": 0, "col": 2, "rowspan": 1, "colspan": 1, "column_header": true, "header_source": "heuristic" } }, { "id": "p19.8.4", "order": 14, "type": "table_cell", "bbox": { "l": 258.12, "t": 653.04, "r": 291.68, "b": 641.28 }, "text": "16", "attrs": { "row": 0, "col": 3, "rowspan": 1, "colspan": 1, "column_header": true, "header_source": "heuristic" } }, { "id": "p19.8.5", "order": 15, "type": "table_cell", "bbox": { "l": 291.68, "t": 653.04, "r": 325.24, "b": 641.28 }, "text": "19", "attrs": { "row": 0, "col": 4, "rowspan": 1, "colspan": 1, "column_header": true, "header_source": "heuristic" } }, { "id": "p19.8.6", "order": 16, "type": "table_cell", "bbox": { "l": 325.24, "t": 653.04, "r": 358.8, "b": 641.28 }, "text": "20", "attrs": { "row": 0, "col": 5, "rowspan": 1, "colspan": 1, "column_header": true, "header_source": "heuristic" } }, { "id": "p19.8.7", "order": 17, "type": "table_cell", "bbox": { "l": 157.44, "t": 641.28, "r": 191, "b": 629.52 }, "text": "¹H ( δ)", "attrs": { "row": 1, "col": 0, "rowspan": 1, "colspan": 1 } }, { "id": "p19.8.8", "order": 18, "type": "table_cell", "bbox": { "l": 191, "t": 641.28, "r": 224.56, "b": 629.52 }, "text": "---", "attrs": { "row": 1, "col": 1, "rowspan": 1, "colspan": 1 } }, { "id": "p19.8.9", "order": 19, "type": "table_cell", "bbox": { "l": 224.56, "t": 641.28, "r": 258.12, "b": 629.52 }, "text": "3.42 m", "attrs": { "row": 1, "col": 2, "rowspan": 1, "colspan": 1 } }, { "id": "p19.8.10", "order": 20, "type": "table_cell", "bbox": { "l": 258.12, "t": 641.28, "r": 291.68, "b": 629.52 }, "text": "3.81 m", "attrs": { "row": 1, "col": 3, "rowspan": 1, "colspan": 1 } }, { "id": "p19.8.11", "order": 21, "type": "table_cell", "bbox": { "l": 291.68, "t": 641.28, "r": 325.24, "b": 629.52 }, "text": "3.81 m", "attrs": { "row": 1, "col": 4, "rowspan": 1, "colspan": 1 } }, { "id": "p19.8.12", "order": 22, "type": "table_cell", "bbox": { "l": 325.24, "t": 641.28, "r": 358.8, "b": 629.52 }, "text": "3.42 m", "attrs": { "row": 1, "col": 5, "rowspan": 1, "colspan": 1 } }, { "id": "p19.8.13", "order": 23, "type": "table_cell", "bbox": { "l": 157.44, "t": 629.52, "r": 191, "b": 617.76 }, "text": "¹³C ( δ)", "attrs": { "row": 2, "col": 0, "rowspan": 1, "colspan": 1 } }, { "id": "p19.8.14", "order": 24, "type": "table_cell", "bbox": { "l": 191, "t": 629.52, "r": 224.56, "b": 617.76 }, "text": "211.50", "attrs": { "row": 2, "col": 1, "rowspan": 1, "colspan": 1 } }, { "id": "p19.8.15", "order": 25, "type": "table_cell", "bbox": { "l": 224.56, "t": 629.52, "r": 258.12, "b": 617.76 }, "text": "74.38", "attrs": { "row": 2, "col": 2, "rowspan": 1, "colspan": 1 } }, { "id": "p19.8.16", "order": 26, "type": "table_cell", "bbox": { "l": 258.12, "t": 629.52, "r": 291.68, "b": 617.76 }, "text": "82.66", "attrs": { "row": 2, "col": 3, "rowspan": 1, "colspan": 1 } }, { "id": "p19.8.17", "order": 27, "type": "table_cell", "bbox": { "l": 291.68, "t": 629.52, "r": 325.24, "b": 617.76 }, "text": "82.66", "attrs": { "row": 2, "col": 4, "rowspan": 1, "colspan": 1 } }, { "id": "p19.8.18", "order": 28, "type": "table_cell", "bbox": { "l": 325.24, "t": 629.52, "r": 358.8, "b": 617.76 }, "text": "74.28", "attrs": { "row": 2, "col": 5, "rowspan": 1, "colspan": 1 } } ] }, { "id": "p19.9", "order": 29, "type": "text", "bbox": { "l": 71.52, "t": 617.04, "r": 540.48, "b": 576 }, "text": "White waxy solid.[p19.9.2]:[p19.9.3] (c 0.007, CH_{2}Cl_{2}). UV ([p19.9.4], MeOH, nm): 216 (log[p19.9.5] 3.56). MS: EIMS m/z 325, 307, 289, 225, 207. NMR: ^{1}H NMR (500MHz, CDCl_{3}), ^{13}C NMR (125 MHz, CDCl_{3}). Derivatives: per-MTPA esters (^{1}H NMR). Biological activities ( [p19.9.6]g/mL): BST LC_{50} 1.5[p19.9.7] 10^{-1}, A-549ED_{50} 6.0[p19.9.8] 10^{-1}, MCF-7 ED_{50} >1, HT-29ED_{50} >1, A-498ED_{50} >1, PC-3ED_{50} >1, PACA-2ED_{50} 1.2[p19.9.9] 10^{-4}. Source: Annona squamosa, bark stem.", "children": [ { "id": "p19.9.1", "order": 30, "type": "form_field", "bbox": { "l": 110.12, "t": 617.04, "r": 122.12, "b": 605.04 }, "text": "", "attrs": { "field_kind": "radio", "label": "(c 0.007, CH_{2}Cl_{2}). UV ( $ \\lambda_{max} $, MeOH, nm):…", "source": "glyph_estimate", "bbox_estimated": true, "text_offset": 37, "text_span": 0 } }, { "id": "p19.9.2", "order": 31, "type": "formula", "bbox": { "l": 71.52, "t": 617.04, "r": 540.48, "b": 576 }, "text": "[\\alpha]_{D}", "attrs": { "latex": "[\\alpha]_{D}", "inline": true, "text_offset": 17, "text_span": 9, "bbox_estimated": true, "notation": "latex", "alt": "alpha sub D", "mathml": "[α]D" } }, { "id": "p19.9.3", "order": 32, "type": "formula", "bbox": { "l": 71.52, "t": 617.04, "r": 540.48, "b": 576 }, "text": "-2.7^{\\circ}", "attrs": { "latex": "-2.7^{\\circ}", "inline": true, "text_offset": 27, "text_span": 9, "bbox_estimated": true, "notation": "latex", "alt": "minus 2.7 to the power of circ", "mathml": "−2.7∘" } }, { "id": "p19.9.4", "order": 33, "type": "formula", "bbox": { "l": 71.52, "t": 617.04, "r": 540.48, "b": 576 }, "text": "\\lambda_{max}", "attrs": { "latex": "\\lambda_{max}", "inline": true, "text_offset": 66, "text_span": 9, "bbox_estimated": true, "notation": "latex", "alt": "lambda sub max", "mathml": "λmax" } }, { "id": "p19.9.5", "order": 34, "type": "text", "bbox": { "l": 71.52, "t": 617.04, "r": 540.48, "b": 576 }, "text": "ε", "attrs": { "inline": true, "text_offset": 96, "text_span": 9, "bbox_estimated": true } }, { "id": "p19.9.6", "order": 35, "type": "formula", "bbox": { "l": 71.52, "t": 617.04, "r": 540.48, "b": 576 }, "text": "\\text{White waxy solid. } [\\alpha]_D: -2.7^\\circ (c\\,0.007, \\text{CH}_2\\text{Cl}_2). \\text{UV } (\\lambda_{\\max}, \\text{MeOH, nm}): 216 (\\log \\epsilon\\, 3.56). \\text{MS: EIMS } m/z\\ 325, 307, 289, 225, 207. \\text{NMR: } {}^{1}\\text{H NMR (500 MHz, CDCl}_3), {}^{13}\\text{C NMR (125 MHz, CDCl}_3). \\text{Derivatives: per-MTPA esters (}{}^{1}\\text{H NMR). Biological activities } (\\mu\\text{g/mL}): \\text{BST } LC_{50}\\ 1.5 \\times 10^{-1}, \\text{A-549 } ED_{50}\\ 6.0 \\times 10^{-1}, \\text{MCF-7 } ED_{50} > 1, \\text{HT-29 } ED_{50} > 1, \\text{A-498 } ED_{50} > 1, \\text{PC-3 } ED_{50} > 1, \\text{PACA-2 } ED_{50}\\ 1.2 \\times 10^{-4}. \\text{Source: } \\textit{Annona squamosa}, \\text{bark stem.} \\\\ \\textbf{51. } \\textit{\\textbf{cis}-solamin}^{*115} (\\text{C}_{35}\\text{H}_{65}\\text{O}_5, \\text{MW } 564)", "attrs": { "latex": "\\text{White waxy solid. } [\\alpha]_D: -2.7^\\circ (c\\,0.007, \\text{CH}_2\\text{Cl}_2). \\text{UV } (\\lambda_{\\max}, \\text{MeOH, nm}): 216 (\\log \\epsilon\\, 3.56). \\text{MS: EIMS } m/z\\ 325, 307, 289, 225, 207. \\text{NMR: } {}^{1}\\text{H NMR (500 MHz, CDCl}_3), {}^{13}\\text{C NMR (125 MHz, CDCl}_3). \\text{Derivatives: per-MTPA esters (}{}^{1}\\text{H NMR). Biological activities } (\\mu\\text{g/mL}): \\text{BST } LC_{50}\\ 1.5 \\times 10^{-1}, \\text{A-549 } ED_{50}\\ 6.0 \\times 10^{-1}, \\text{MCF-7 } ED_{50} > 1, \\text{HT-29 } ED_{50} > 1, \\text{A-498 } ED_{50} > 1, \\text{PC-3 } ED_{50} > 1, \\text{PACA-2 } ED_{50}\\ 1.2 \\times 10^{-4}. \\text{Source: } \\textit{Annona squamosa}, \\text{bark stem.} \\\\ \\textbf{51. } \\textit{\\textbf{cis}-solamin}^{*115} (\\text{C}_{35}\\text{H}_{65}\\text{O}_5, \\text{MW } 564)", "inline": true, "text_offset": 284, "text_span": 9, "bbox_estimated": true, "alt": "White waxy solid. alpha sub D : minus 2.7 to the power of circ of c, 0.007, CH sub 2 Cl sub 2 . UV of lambda sub max, MeOH, nm : 216 times log epsilon, 3.56 . MS: EIMS m over z 325, 307, 289, 225, 207. NMR: to the power of 1 H NMR of 500 MHz, CDCl sub 3, to the power of 13 C NMR of 125 MHz, CDCl sub 3 . Derivatives: per minus MTPA esters of to the power of 1 H NMR . Biological activities of mu g over mL : BST LC sub 50 1.5 times 10 to the power of minus 1, A minus 549 ED sub 50 6.0 times 10 to the power of minus 1, MCF minus 7 ED sub 50 is greater than 1, HT minus 29 ED sub 50 is greater than 1, A minus 498 ED sub 50 is greater than 1, PC minus 3 ED sub 50 is greater than 1, PACA minus 2 ED sub 50 1.2 times 10 to the power of minus 4 . Source: textit Annona squamosa, bark stem. textbf 51. textit textbf cis minus solamin to the power of *115 times C sub 35 H sub 65 O sub 5, MW 564", "notation": "latex", "mathml": "White waxy solid. [α]D:−2.7∘(c0.007,CH2Cl2).UV (λmax,MeOH, nm):216(logϵ3.56).MS: EIMS m/z 325,307,289,225,207.NMR: 1H NMR (500 MHz, CDCl3),13C NMR (125 MHz, CDCl3).Derivatives: per-MTPA esters (1H NMR). Biological activities (μg/mL):BST LC50 1.5×10−1,A-549 ED50 6.0×10−1,MCF-7 ED50>1,HT-29 ED50>1,A-498 ED50>1,PC-3 ED50>1,PACA-2 ED50 1.2×10−4.Source: Annona squamosa,bark stem.51. \\textbf{cis−solamin}*115(C35H65O5,MW 564)" } }, { "id": "p19.9.7", "order": 36, "type": "text", "bbox": { "l": 71.52, "t": 617.04, "r": 540.48, "b": 576 }, "text": "×", "attrs": { "inline": true, "text_offset": 315, "text_span": 9, "bbox_estimated": true } }, { "id": "p19.9.8", "order": 37, "type": "text", "bbox": { "l": 71.52, "t": 617.04, "r": 540.48, "b": 576 }, "text": "×", "attrs": { "inline": true, "text_offset": 350, "text_span": 9, "bbox_estimated": true } }, { "id": "p19.9.9", "order": 38, "type": "text", "bbox": { "l": 71.52, "t": 617.04, "r": 540.48, "b": 576 }, "text": "×", "attrs": { "inline": true, "text_offset": 454, "text_span": 9, "bbox_estimated": true } } ] }, { "id": "p19.10", "order": 39, "type": "text", "bbox": { "l": 69.6, "t": 579.6, "r": 223.2, "b": 568.56 }, "text": "51. cis-solamin[p19.10.1] (C [p19.10.2]H [p19.10.3]O[p19.10.4], MW564)", "children": [ { "id": "p19.10.1", "order": 40, "type": "formula", "bbox": { "l": 69.6, "t": 579.6, "r": 223.2, "b": 568.56 }, "text": "^{*115}", "attrs": { "latex": "^{*115}", "inline": true, "text_offset": 15, "text_span": 10, "bbox_estimated": true, "notation": "latex", "alt": "to the power of *115", "mathml": "*115" } }, { "id": "p19.10.2", "order": 41, "type": "formula", "bbox": { "l": 69.6, "t": 579.6, "r": 223.2, "b": 568.56 }, "text": "₃₅", "attrs": { "latex": "_{35}", "inline": true, "text_offset": 29, "text_span": 10, "bbox_estimated": true, "alt": "sub 35", "mathml": "35" } }, { "id": "p19.10.3", "order": 42, "type": "text", "bbox": { "l": 69.6, "t": 579.6, "r": 223.2, "b": 568.56 }, "text": "₆₅", "attrs": { "inline": true, "text_offset": 41, "text_span": 10, "bbox_estimated": true } }, { "id": "p19.10.4", "order": 43, "type": "formula", "bbox": { "l": 69.6, "t": 579.6, "r": 223.2, "b": 568.56 }, "text": "₅", "attrs": { "latex": "_{5}", "inline": true, "text_offset": 52, "text_span": 10, "bbox_estimated": true, "alt": "sub 5", "mathml": "5" } } ] }, { "id": "p19.11", "order": 44, "type": "formula", "bbox": { "l": 159.36, "t": 564, "r": 452.88, "b": 520.8 }, "text": "", "attrs": { "block_label": "image", "alt": "Skeletal structure of an annonaceous acetogenin: bis-tetrahydrofuran with two hydroxyls, long alkyl chains, and a butenolide…", "source": "vision" } }, { "id": "p19.12", "order": 45, "type": "text", "bbox": { "l": 159.12, "t": 510, "r": 318.96, "b": 500.88 }, "text": "Position 15 16 19 20" }, { "id": "p19.13", "order": 46, "type": "text", "bbox": { "l": 158.88, "t": 496.56, "r": 322.8, "b": 474.96 }, "text": "[p19.13.1]H (δ) 3.41 m 3.81 m 3.81 m 3.41 m\n [p19.13.2]C (δ) 74.3 82.8 82.8 74.3", "children": [ { "id": "p19.13.1", "order": 47, "type": "formula", "bbox": { "l": 158.88, "t": 496.56, "r": 322.8, "b": 474.96 }, "text": "¹", "attrs": { "latex": "^{1}", "inline": true, "text_offset": 0, "text_span": 10, "bbox_estimated": true, "alt": "to the power of 1", "mathml": "1" } }, { "id": "p19.13.2", "order": 48, "type": "formula", "bbox": { "l": 158.88, "t": 496.56, "r": 322.8, "b": 474.96 }, "text": "¹³", "attrs": { "latex": "^{13}", "inline": true, "text_offset": 45, "text_span": 10, "bbox_estimated": true, "alt": "to the power of 13", "mathml": "13" } } ] }, { "id": "p19.14", "order": 49, "type": "text", "bbox": { "l": 71.52, "t": 472.32, "r": 532.56, "b": 443.76 }, "text": "White powder. Mp: 63–66°C. [α]D: +22° (c O.55, MeOH). UV (λmax, MeOH, nm): 217.2 (log ε 3.61). IR (νmax, film, cm⁻¹): 3420, 2916, 2840, 1759, 1471, 1321, 1114, 1080, 1033, 962, 845, 751, 717. MS: EIMS m/z 347, 295, 251, 199, 111, 97. NMR: ¹H NMR (400 MHz, CDCl₃), ¹³C NMR (50 MHz, CDCl₃). Source: Annona muricata, roots." }, { "id": "p19.15", "order": 50, "type": "text", "bbox": { "l": 70.08, "t": 444.72, "r": 233.52, "b": 434.16 }, "text": "52. cis-panatellin[p19.15.1] (C [p19.15.2]H [p19.15.3]O[p19.15.4], MW564)", "children": [ { "id": "p19.15.1", "order": 51, "type": "formula", "bbox": { "l": 70.08, "t": 444.72, "r": 233.52, "b": 434.16 }, "text": "^{*115}", "attrs": { "latex": "^{*115}", "inline": true, "text_offset": 18, "text_span": 10, "bbox_estimated": true, "notation": "latex", "alt": "to the power of *115", "mathml": "*115" } }, { "id": "p19.15.2", "order": 52, "type": "text", "bbox": { "l": 70.08, "t": 444.72, "r": 233.52, "b": 434.16 }, "text": "₃₅", "attrs": { "inline": true, "text_offset": 32, "text_span": 10, "bbox_estimated": true } }, { "id": "p19.15.3", "order": 53, "type": "text", "bbox": { "l": 70.08, "t": 444.72, "r": 233.52, "b": 434.16 }, "text": "₆₅", "attrs": { "inline": true, "text_offset": 44, "text_span": 10, "bbox_estimated": true } }, { "id": "p19.15.4", "order": 54, "type": "text", "bbox": { "l": 70.08, "t": 444.72, "r": 233.52, "b": 434.16 }, "text": "₅", "attrs": { "inline": true, "text_offset": 55, "text_span": 10, "bbox_estimated": true } } ] }, { "id": "p19.16", "order": 55, "type": "formula", "bbox": { "l": 157.44, "t": 431.28, "r": 453.12, "b": 385.44 }, "text": "", "attrs": { "block_label": "image", "alt": "Skeletal structure of an annonaceous acetogenin: butenolide ring with a THF ring and two hydroxyls at C13 and C18, long alky…", "source": "vision" } }, { "id": "p19.17", "order": 56, "type": "text", "bbox": { "l": 157.2, "t": 374.4, "r": 317.52, "b": 365.28 }, "text": "Position 13 14 17 18" }, { "id": "p19.18", "order": 57, "type": "text", "bbox": { "l": 156.72, "t": 362.16, "r": 323.04, "b": 341.04 }, "text": "[p19.18.1]H (δ) 3.41 m 3.81 m 3.81 m 3.41 m\n [p19.18.2]C (δ) 74.3 82.7 82.7 74.3", "children": [ { "id": "p19.18.1", "order": 58, "type": "formula", "bbox": { "l": 156.72, "t": 362.16, "r": 323.04, "b": 341.04 }, "text": "¹", "attrs": { "latex": "^{1}", "inline": true, "text_offset": 0, "text_span": 10, "bbox_estimated": true, "alt": "to the power of 1", "mathml": "1" } }, { "id": "p19.18.2", "order": 59, "type": "text", "bbox": { "l": 156.72, "t": 362.16, "r": 323.04, "b": 341.04 }, "text": "¹³", "attrs": { "inline": true, "text_offset": 45, "text_span": 10, "bbox_estimated": true } } ] }, { "id": "p19.19", "order": 60, "type": "text", "bbox": { "l": 69.36, "t": 337.2, "r": 503.28, "b": 300.96 }, "text": "White powder. Mp: 62–64 °C. [α]D: +20° (c 0.60, MeOH). UV (λmax, MeOH, nm): 219.6 (log ε 3.65). IR (νmax, film, cm⁻¹): 3420, 2917, 2841, 1760, 1471, 1324, 1120, 1078, 1033, 963, 753. MS: EIMS m/z 319, 297, 279, 267, 249, 227, 111, 97. NMR: ¹H NMR (400 MHz, CDCl₃), ¹³C NMR (50 MHz, CDCl₃). Source: Annona muricata, roots.\n53. cis-uvarimicin IV*115 (C₃₇H₆₉O₅, MW592)" }, { "id": "p19.20", "order": 61, "type": "formula", "bbox": { "l": 154.56, "t": 293.52, "r": 456, "b": 251.52 }, "text": "", "attrs": { "block_label": "image", "alt": "Skeletal structure of an annonaceous acetogenin: butenolide ring with a methyl group, a tetrahydrofuran ring, and two hydrox…", "source": "vision" } }, { "id": "p19.21", "order": 62, "type": "text", "bbox": { "l": 155.04, "t": 241.2, "r": 314.16, "b": 232.32 }, "text": "Position 13 14 17 18" }, { "id": "p19.22", "order": 63, "type": "text", "bbox": { "l": 154.08, "t": 228.48, "r": 318.96, "b": 206.16 }, "text": "[p19.22.1]H (δ) 3.41 m 3.82 m 3.82 m 3.41 m \n [p19.22.2]C (δ) 74.3 82.7 82.7 74.3", "children": [ { "id": "p19.22.1", "order": 64, "type": "formula", "bbox": { "l": 154.08, "t": 228.48, "r": 318.96, "b": 206.16 }, "text": "¹", "attrs": { "latex": "^{1}", "inline": true, "text_offset": 0, "text_span": 10, "bbox_estimated": true, "alt": "to the power of 1", "mathml": "1" } }, { "id": "p19.22.2", "order": 65, "type": "text", "bbox": { "l": 154.08, "t": 228.48, "r": 318.96, "b": 206.16 }, "text": "¹³", "attrs": { "inline": true, "text_offset": 46, "text_span": 10, "bbox_estimated": true } } ] }, { "id": "p19.23", "order": 66, "type": "text", "bbox": { "l": 71.52, "t": 204.96, "r": 494.64, "b": 189.36 }, "text": "White powder. Mp: 60–62°C. [α]D: +20° (c 0.15, MeOH). UV (λmax, MeOH, nm): 221.3 (log ε 3.58). IR (νmax, film, cm⁻¹): 3422 2916 2839 1762 1473 1325 1124 1077 1034 965 748 MS: FIMS (m/z) 337 325 319 267 255" }, { "id": "p19.24", "order": 67, "type": "text", "bbox": { "l": 72.96, "t": 198.24, "r": 512.4, "b": 169.2 }, "text": "cm[p19.24.1]): 3422, 2916, 2839, 1762, 1473, 1325, 1124, 1077, 1034, 965, 748. MS: EIMS (m/z) 337, 325, 319, 267, 255, 249, 111, 97. NMR: [p19.24.2]H NMR (400 MHz, CDCl[p19.24.3]), [p19.24.4]C NMR (50 MHz, CDCl[p19.24.5]). Source: Annona muricata, roots.\n54. cis-uvarimicin I [p19.24.6]115 (C [p19.24.7]H [p19.24.8]O[p19.24.9], MW592)", "children": [ { "id": "p19.24.1", "order": 68, "type": "text", "bbox": { "l": 72.96, "t": 198.24, "r": 512.4, "b": 169.2 }, "text": "⁻¹", "attrs": { "inline": true, "text_offset": 2, "text_span": 10, "bbox_estimated": true } }, { "id": "p19.24.2", "order": 69, "type": "text", "bbox": { "l": 72.96, "t": 198.24, "r": 512.4, "b": 169.2 }, "text": "¹", "attrs": { "inline": true, "text_offset": 138, "text_span": 10, "bbox_estimated": true } }, { "id": "p19.24.3", "order": 70, "type": "text", "bbox": { "l": 72.96, "t": 198.24, "r": 512.4, "b": 169.2 }, "text": "₃", "attrs": { "inline": true, "text_offset": 168, "text_span": 10, "bbox_estimated": true } }, { "id": "p19.24.4", "order": 71, "type": "text", "bbox": { "l": 72.96, "t": 198.24, "r": 512.4, "b": 169.2 }, "text": "¹³", "attrs": { "inline": true, "text_offset": 181, "text_span": 10, "bbox_estimated": true } }, { "id": "p19.24.5", "order": 72, "type": "text", "bbox": { "l": 72.96, "t": 198.24, "r": 512.4, "b": 169.2 }, "text": "₃", "attrs": { "inline": true, "text_offset": 210, "text_span": 10, "bbox_estimated": true } }, { "id": "p19.24.6", "order": 73, "type": "formula", "bbox": { "l": 72.96, "t": 198.24, "r": 512.4, "b": 169.2 }, "text": "^{*}", "attrs": { "latex": "^{*}", "inline": true, "text_offset": 276, "text_span": 10, "bbox_estimated": true, "notation": "latex", "alt": "to the power of *", "mathml": "*" } }, { "id": "p19.24.7", "order": 74, "type": "text", "bbox": { "l": 72.96, "t": 198.24, "r": 512.4, "b": 169.2 }, "text": "₃₇", "attrs": { "inline": true, "text_offset": 293, "text_span": 10, "bbox_estimated": true } }, { "id": "p19.24.8", "order": 75, "type": "text", "bbox": { "l": 72.96, "t": 198.24, "r": 512.4, "b": 169.2 }, "text": "₆₉", "attrs": { "inline": true, "text_offset": 305, "text_span": 10, "bbox_estimated": true } }, { "id": "p19.24.9", "order": 76, "type": "text", "bbox": { "l": 72.96, "t": 198.24, "r": 512.4, "b": 169.2 }, "text": "₅", "attrs": { "inline": true, "text_offset": 316, "text_span": 10, "bbox_estimated": true } } ] }, { "id": "p19.25", "order": 77, "type": "figure", "bbox": { "l": 149.52, "t": 161.52, "r": 456.96, "b": 70.32 }, "text": "", "attrs": { "block_label": "image" }, "children": [ { "id": "p19.25.1", "order": 78, "type": "text", "bbox": { "l": 154.08, "t": 105.36, "r": 320.64, "b": 72.72 }, "text": "Position 15 16 19 20\n[p19.25.1.1] ([p19.25.1.2]) 3.41 m 3.81 m 3.81 m 3.41 m\n[p19.25.1.3] ([p19.25.1.4]) 74.3 82.7 82.7 74.3", "children": [ { "id": "p19.25.1.1", "order": 79, "type": "formula", "bbox": { "l": 154.08, "t": 105.36, "r": 320.64, "b": 72.72 }, "text": "¹H", "attrs": { "latex": "^{1}H", "inline": true, "text_offset": 21, "text_span": 12, "bbox_estimated": true, "alt": "to the power of 1 H", "mathml": "1H" } }, { "id": "p19.25.1.2", "order": 80, "type": "formula", "bbox": { "l": 154.08, "t": 105.36, "r": 320.64, "b": 72.72 }, "text": "δ", "attrs": { "latex": "\\delta", "inline": true, "text_offset": 35, "text_span": 12, "bbox_estimated": true, "alt": "delta", "mathml": "δ" } }, { "id": "p19.25.1.3", "order": 81, "type": "formula", "bbox": { "l": 154.08, "t": 105.36, "r": 320.64, "b": 72.72 }, "text": "¹³C", "attrs": { "latex": "^{13}C", "inline": true, "text_offset": 77, "text_span": 12, "bbox_estimated": true, "alt": "to the power of 13 C", "mathml": "13C" } }, { "id": "p19.25.1.4", "order": 82, "type": "formula", "bbox": { "l": 154.08, "t": 105.36, "r": 320.64, "b": 72.72 }, "text": "δ", "attrs": { "latex": "\\delta", "inline": true, "text_offset": 91, "text_span": 12, "bbox_estimated": true, "alt": "delta", "mathml": "δ" } } ] } ] }, { "id": "p19.26", "order": 83, "type": "text", "bbox": { "l": 70.08, "t": 71.52, "r": 489.12, "b": 43.92 }, "text": "White powder. Mp: 60–62°C. [α]D: +18° (c O.4O, MeOH). UV (λmax, MeOH, nm): 220.8 (log ε 3.63). IR (νmax, film, cm⁻¹): 3423, 2916, 2840, 1760, 1474, 1325, 1120, 1073, 1032, 968, 742, 717. MS: EIMS m/z 347, 297, 295, 227, 111, 97. NMR: ¹H NMR (400MHz, CDCl₃), ¹³C NMR (50MHz, CDCl₃). Source: Annona muricata, roots." } ], "excluded_furniture": { "first": [], "last": [] } }