{ "document_id": 14408, "page": 11, "width_pt": 612, "height_pt": 792, "rotation": 0, "pipeline_version": "paddleocr-vl-1.6+paul-48", "engine": "paddleocr_vl", "source_run_id": 14519, "item_count": 183, "counts_by_type": { "footnote": 2, "formula": 14, "header": 3, "heading": 1, "table": 4, "table_cell": 102, "text": 57 }, "build_ms": 29, "items": [ { "id": "p11.1", "order": 1, "type": "header", "bbox": { "l": 53.52, "t": 765.84, "r": 70.8, "b": 756.96 }, "text": "514", "attrs": { "block_label": "number" }, "level": 2 }, { "id": "p11.2", "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": "p11.3", "order": 3, "type": "header", "bbox": { "l": 501.12, "t": 766.08, "r": 559.92, "b": 756 }, "text": "Invited Review", "attrs": { "block_label": "header" }, "level": 2 }, { "id": "p11.4", "order": 4, "type": "heading", "bbox": { "l": 53.28, "t": 746.16, "r": 142.8, "b": 736.08 }, "text": "Table 4. (Continued)", "attrs": { "block_label": "paragraph_title" }, "level": 3 }, { "id": "p11.5", "order": 5, "type": "text", "bbox": { "l": 53.28, "t": 732.96, "r": 374.16, "b": 713.28 }, "text": "4. 4-deoxyannoreticuin[p11.5.1] ([p11.5.2], MW580) Mono-THF Acetogenins (Continued)", "children": [ { "id": "p11.5.1", "order": 6, "type": "formula", "bbox": { "l": 53.28, "t": 732.96, "r": 374.16, "b": 713.28 }, "text": "^{*109}", "attrs": { "latex": "^{*109}", "inline": true, "text_offset": 22, "text_span": 9, "bbox_estimated": true, "notation": "latex", "alt": "to the power of *109", "mathml": "*109" } }, { "id": "p11.5.2", "order": 7, "type": "formula", "bbox": { "l": 53.28, "t": 732.96, "r": 374.16, "b": 713.28 }, "text": "C₃₅H₆₄O₆", "attrs": { "latex": "C_{35}H_{64}O_{6}", "inline": true, "text_offset": 33, "text_span": 9, "bbox_estimated": true, "alt": "C sub 35 H sub 64 O sub 6", "mathml": "C35H64O6" } } ] }, { "id": "p11.6", "order": 8, "type": "formula", "bbox": { "l": 157.92, "t": 712.32, "r": 453.84, "b": 663.84 }, "text": "", "attrs": { "block_label": "image", "alt": "Skeletal structure of an annonaceous acetogenin: butenolide with a THF ring and hydroxyls at C-9, C-15 and C-20, C35 chain", "source": "vision" } }, { "id": "p11.7", "order": 9, "type": "table", "bbox": { "l": 157.2, "t": 654.24, "r": 359.76, "b": 618.72 }, "text": "", "attrs": { "block_label": "table", "n_rows": 3, "n_cols": 6, "integrity": { "skipped": "no_text_layer" } }, "children": [ { "id": "p11.7.1", "order": 10, "type": "table_cell", "bbox": { "l": 157.2, "t": 654.24, "r": 190.96, "b": 642.4 }, "text": "Position", "attrs": { "row": 0, "col": 0, "rowspan": 1, "colspan": 1, "column_header": true, "header_source": "heuristic" } }, { "id": "p11.7.2", "order": 11, "type": "table_cell", "bbox": { "l": 190.96, "t": 654.24, "r": 224.72, "b": 642.4 }, "text": "9", "attrs": { "row": 0, "col": 1, "rowspan": 1, "colspan": 1, "column_header": true, "header_source": "heuristic" } }, { "id": "p11.7.3", "order": 12, "type": "table_cell", "bbox": { "l": 224.72, "t": 654.24, "r": 258.48, "b": 642.4 }, "text": "15", "attrs": { "row": 0, "col": 2, "rowspan": 1, "colspan": 1, "column_header": true, "header_source": "heuristic" } }, { "id": "p11.7.4", "order": 13, "type": "table_cell", "bbox": { "l": 258.48, "t": 654.24, "r": 292.24, "b": 642.4 }, "text": "16", "attrs": { "row": 0, "col": 3, "rowspan": 1, "colspan": 1, "column_header": true, "header_source": "heuristic" } }, { "id": "p11.7.5", "order": 14, "type": "table_cell", "bbox": { "l": 292.24, "t": 654.24, "r": 326, "b": 642.4 }, "text": "19", "attrs": { "row": 0, "col": 4, "rowspan": 1, "colspan": 1, "column_header": true, "header_source": "heuristic" } }, { "id": "p11.7.6", "order": 15, "type": "table_cell", "bbox": { "l": 326, "t": 654.24, "r": 359.76, "b": 642.4 }, "text": "20", "attrs": { "row": 0, "col": 5, "rowspan": 1, "colspan": 1, "column_header": true, "header_source": "heuristic" } }, { "id": "p11.7.7", "order": 16, "type": "table_cell", "bbox": { "l": 157.2, "t": 642.4, "r": 190.96, "b": 630.56 }, "text": "¹H ( δ)", "attrs": { "row": 1, "col": 0, "rowspan": 1, "colspan": 1 } }, { "id": "p11.7.8", "order": 17, "type": "table_cell", "bbox": { "l": 190.96, "t": 642.4, "r": 224.72, "b": 630.56 }, "text": "3.58 m", "attrs": { "row": 1, "col": 1, "rowspan": 1, "colspan": 1 } }, { "id": "p11.7.9", "order": 18, "type": "table_cell", "bbox": { "l": 224.72, "t": 642.4, "r": 258.48, "b": 630.56 }, "text": "3.41 m", "attrs": { "row": 1, "col": 2, "rowspan": 1, "colspan": 1 } }, { "id": "p11.7.10", "order": 19, "type": "table_cell", "bbox": { "l": 258.48, "t": 642.4, "r": 292.24, "b": 630.56 }, "text": "3.80 m", "attrs": { "row": 1, "col": 3, "rowspan": 1, "colspan": 1 } }, { "id": "p11.7.11", "order": 20, "type": "table_cell", "bbox": { "l": 292.24, "t": 642.4, "r": 326, "b": 630.56 }, "text": "3.80 m", "attrs": { "row": 1, "col": 4, "rowspan": 1, "colspan": 1 } }, { "id": "p11.7.12", "order": 21, "type": "table_cell", "bbox": { "l": 326, "t": 642.4, "r": 359.76, "b": 630.56 }, "text": "3.41 m", "attrs": { "row": 1, "col": 5, "rowspan": 1, "colspan": 1 } }, { "id": "p11.7.13", "order": 22, "type": "table_cell", "bbox": { "l": 157.2, "t": 630.56, "r": 190.96, "b": 618.72 }, "text": "¹³C ( δ)", "attrs": { "row": 2, "col": 0, "rowspan": 1, "colspan": 1 } }, { "id": "p11.7.14", "order": 23, "type": "table_cell", "bbox": { "l": 190.96, "t": 630.56, "r": 224.72, "b": 618.72 }, "text": "71.90", "attrs": { "row": 2, "col": 1, "rowspan": 1, "colspan": 1 } }, { "id": "p11.7.15", "order": 24, "type": "table_cell", "bbox": { "l": 224.72, "t": 630.56, "r": 258.48, "b": 618.72 }, "text": "74.08", "attrs": { "row": 2, "col": 2, "rowspan": 1, "colspan": 1 } }, { "id": "p11.7.16", "order": 25, "type": "table_cell", "bbox": { "l": 258.48, "t": 630.56, "r": 292.24, "b": 618.72 }, "text": "82.53", "attrs": { "row": 2, "col": 3, "rowspan": 1, "colspan": 1 } }, { "id": "p11.7.17", "order": 26, "type": "table_cell", "bbox": { "l": 292.24, "t": 630.56, "r": 326, "b": 618.72 }, "text": "82.64", "attrs": { "row": 2, "col": 4, "rowspan": 1, "colspan": 1 } }, { "id": "p11.7.18", "order": 27, "type": "table_cell", "bbox": { "l": 326, "t": 630.56, "r": 359.76, "b": 618.72 }, "text": "74.06", "attrs": { "row": 2, "col": 5, "rowspan": 1, "colspan": 1 } } ] }, { "id": "p11.8", "order": 28, "type": "text", "bbox": { "l": 55.68, "t": 618, "r": 519.12, "b": 572.16 }, "text": "White amorphous powder.[p11.8.1]: +6.8° (c QO15, CH₂Cl₂). UV ([p11.8.2], MeOH, nm): 218 (log[p11.8.3] 3.61). IR ([p11.8.4], film, cm[p11.8.5]): 3423, 2926, 2854, 1755. MS: EIMS m/z 345, 311, 293, 275, 211, 193. NMR: [p11.8.6]H NMR (500MHz, CDCl₃), [p11.8.7]C NMR (125 MHz, CDCl₃). Derivatives: per-MTPA esters (¹H NMR). Biological activities ( [p11.8.8]g/mL): BST LC[p11.8.9] 8.9, A-549 ED[p11.8.10] 3.9, MCF-7 ED[p11.8.11] 2.2, HT-29 ED[p11.8.12] 1.7, A-498 ED[p11.8.13] 2.2, PC-3 ED[p11.8.14] 2.7, PAC-2 ED[p11.8.15] 2.9. Source: Annona squamosa, stem bark.\n5. cis-4-deoxyannoreticquin[p11.8.16] ([p11.8.17], MW580)", "children": [ { "id": "p11.8.1", "order": 29, "type": "formula", "bbox": { "l": 55.68, "t": 618, "r": 519.12, "b": 572.16 }, "text": "[\\alpha]_{D}", "attrs": { "latex": "[\\alpha]_{D}", "inline": true, "text_offset": 23, "text_span": 9, "bbox_estimated": true, "notation": "latex", "alt": "alpha sub D", "mathml": "[α]D" } }, { "id": "p11.8.2", "order": 30, "type": "formula", "bbox": { "l": 55.68, "t": 618, "r": 519.12, "b": 572.16 }, "text": "\\lambda_{max}", "attrs": { "latex": "\\lambda_{max}", "inline": true, "text_offset": 62, "text_span": 9, "bbox_estimated": true, "notation": "latex", "alt": "lambda sub max", "mathml": "λmax" } }, { "id": "p11.8.3", "order": 31, "type": "text", "bbox": { "l": 55.68, "t": 618, "r": 519.12, "b": 572.16 }, "text": "ε", "attrs": { "inline": true, "text_offset": 92, "text_span": 9, "bbox_estimated": true } }, { "id": "p11.8.4", "order": 32, "type": "text", "bbox": { "l": 55.68, "t": 618, "r": 519.12, "b": 572.16 }, "text": "\\nu_{max}", "attrs": { "inline": true, "text_offset": 113, "text_span": 9, "bbox_estimated": true } }, { "id": "p11.8.5", "order": 33, "type": "text", "bbox": { "l": 55.68, "t": 618, "r": 519.12, "b": 572.16 }, "text": "⁻¹", "attrs": { "inline": true, "text_offset": 132, "text_span": 9, "bbox_estimated": true } }, { "id": "p11.8.6", "order": 34, "type": "text", "bbox": { "l": 55.68, "t": 618, "r": 519.12, "b": 572.16 }, "text": "¹", "attrs": { "inline": true, "text_offset": 216, "text_span": 9, "bbox_estimated": true } }, { "id": "p11.8.7", "order": 35, "type": "text", "bbox": { "l": 55.68, "t": 618, "r": 519.12, "b": 572.16 }, "text": "¹³", "attrs": { "inline": true, "text_offset": 248, "text_span": 9, "bbox_estimated": true } }, { "id": "p11.8.8", "order": 36, "type": "text", "bbox": { "l": 55.68, "t": 618, "r": 519.12, "b": 572.16 }, "text": "μ", "attrs": { "inline": true, "text_offset": 344, "text_span": 9, "bbox_estimated": true } }, { "id": "p11.8.9", "order": 37, "type": "text", "bbox": { "l": 55.68, "t": 618, "r": 519.12, "b": 572.16 }, "text": "₅₀", "attrs": { "inline": true, "text_offset": 366, "text_span": 9, "bbox_estimated": true } }, { "id": "p11.8.10", "order": 38, "type": "text", "bbox": { "l": 55.68, "t": 618, "r": 519.12, "b": 572.16 }, "text": "₅₀", "attrs": { "inline": true, "text_offset": 389, "text_span": 10, "bbox_estimated": true } }, { "id": "p11.8.11", "order": 39, "type": "text", "bbox": { "l": 55.68, "t": 618, "r": 519.12, "b": 572.16 }, "text": "₅₀", "attrs": { "inline": true, "text_offset": 413, "text_span": 10, "bbox_estimated": true } }, { "id": "p11.8.12", "order": 40, "type": "text", "bbox": { "l": 55.68, "t": 618, "r": 519.12, "b": 572.16 }, "text": "₅₀", "attrs": { "inline": true, "text_offset": 437, "text_span": 10, "bbox_estimated": true } }, { "id": "p11.8.13", "order": 41, "type": "text", "bbox": { "l": 55.68, "t": 618, "r": 519.12, "b": 572.16 }, "text": "₅₀", "attrs": { "inline": true, "text_offset": 461, "text_span": 10, "bbox_estimated": true } }, { "id": "p11.8.14", "order": 42, "type": "text", "bbox": { "l": 55.68, "t": 618, "r": 519.12, "b": 572.16 }, "text": "₅₀", "attrs": { "inline": true, "text_offset": 484, "text_span": 10, "bbox_estimated": true } }, { "id": "p11.8.15", "order": 43, "type": "text", "bbox": { "l": 55.68, "t": 618, "r": 519.12, "b": 572.16 }, "text": "₅₀", "attrs": { "inline": true, "text_offset": 508, "text_span": 10, "bbox_estimated": true } }, { "id": "p11.8.16", "order": 44, "type": "text", "bbox": { "l": 55.68, "t": 618, "r": 519.12, "b": 572.16 }, "text": "^{*109}", "attrs": { "inline": true, "text_offset": 587, "text_span": 10, "bbox_estimated": true } }, { "id": "p11.8.17", "order": 45, "type": "formula", "bbox": { "l": 55.68, "t": 618, "r": 519.12, "b": 572.16 }, "text": "C₃₅H₆₄O₆", "attrs": { "latex": "C_{35}H_{64}O_{6}", "inline": true, "text_offset": 599, "text_span": 10, "bbox_estimated": true, "alt": "C sub 35 H sub 64 O sub 6", "mathml": "C35H64O6" } } ] }, { "id": "p11.9", "order": 46, "type": "formula", "bbox": { "l": 160.08, "t": 569.04, "r": 452.88, "b": 522.24 }, "text": "", "attrs": { "block_label": "image", "alt": "Skeletal structure of an annonaceous acetogenin: butenolide ring with a THF ring, hydroxyls at C9, C15 and C20, and a long a…", "source": "vision" } }, { "id": "p11.10", "order": 47, "type": "text", "bbox": { "l": 159.84, "t": 512.4, "r": 354.48, "b": 503.04 }, "text": "Position 9 15 16 19 20" }, { "id": "p11.11", "order": 48, "type": "table", "bbox": { "l": 158.88, "t": 499.44, "r": 359.04, "b": 476.4 }, "text": "", "attrs": { "block_label": "table", "n_rows": 2, "n_cols": 6, "integrity": { "skipped": "no_text_layer" } }, "children": [ { "id": "p11.11.1", "order": 49, "type": "table_cell", "bbox": { "l": 158.88, "t": 499.44, "r": 192.24, "b": 487.92 }, "text": "¹H ( \\delta )", "attrs": { "row": 0, "col": 0, "rowspan": 1, "colspan": 1 } }, { "id": "p11.11.2", "order": 50, "type": "table_cell", "bbox": { "l": 192.24, "t": 499.44, "r": 225.6, "b": 487.92 }, "text": "3.59 m", "attrs": { "row": 0, "col": 1, "rowspan": 1, "colspan": 1 } }, { "id": "p11.11.3", "order": 51, "type": "table_cell", "bbox": { "l": 225.6, "t": 499.44, "r": 258.96, "b": 487.92 }, "text": "3.42 m", "attrs": { "row": 0, "col": 2, "rowspan": 1, "colspan": 1 } }, { "id": "p11.11.4", "order": 52, "type": "table_cell", "bbox": { "l": 258.96, "t": 499.44, "r": 292.32, "b": 487.92 }, "text": "3.82 m", "attrs": { "row": 0, "col": 3, "rowspan": 1, "colspan": 1 } }, { "id": "p11.11.5", "order": 53, "type": "table_cell", "bbox": { "l": 292.32, "t": 499.44, "r": 325.68, "b": 487.92 }, "text": "3.82 m", "attrs": { "row": 0, "col": 4, "rowspan": 1, "colspan": 1 } }, { "id": "p11.11.6", "order": 54, "type": "table_cell", "bbox": { "l": 325.68, "t": 499.44, "r": 359.04, "b": 487.92 }, "text": "3.42 m", "attrs": { "row": 0, "col": 5, "rowspan": 1, "colspan": 1 } }, { "id": "p11.11.7", "order": 55, "type": "table_cell", "bbox": { "l": 158.88, "t": 487.92, "r": 192.24, "b": 476.4 }, "text": "¹³C ( \\delta )", "attrs": { "row": 1, "col": 0, "rowspan": 1, "colspan": 1 } }, { "id": "p11.11.8", "order": 56, "type": "table_cell", "bbox": { "l": 192.24, "t": 487.92, "r": 225.6, "b": 476.4 }, "text": "71.86", "attrs": { "row": 1, "col": 1, "rowspan": 1, "colspan": 1 } }, { "id": "p11.11.9", "order": 57, "type": "table_cell", "bbox": { "l": 225.6, "t": 487.92, "r": 258.96, "b": 476.4 }, "text": "74.37", "attrs": { "row": 1, "col": 2, "rowspan": 1, "colspan": 1 } }, { "id": "p11.11.10", "order": 58, "type": "table_cell", "bbox": { "l": 258.96, "t": 487.92, "r": 292.32, "b": 476.4 }, "text": "82.67", "attrs": { "row": 1, "col": 3, "rowspan": 1, "colspan": 1 } }, { "id": "p11.11.11", "order": 59, "type": "table_cell", "bbox": { "l": 292.32, "t": 487.92, "r": 325.68, "b": 476.4 }, "text": "82.67", "attrs": { "row": 1, "col": 4, "rowspan": 1, "colspan": 1 } }, { "id": "p11.11.12", "order": 60, "type": "table_cell", "bbox": { "l": 325.68, "t": 487.92, "r": 359.04, "b": 476.4 }, "text": "74.37", "attrs": { "row": 1, "col": 5, "rowspan": 1, "colspan": 1 } } ] }, { "id": "p11.12", "order": 61, "type": "text", "bbox": { "l": 55.68, "t": 475.2, "r": 533.04, "b": 433.68 }, "text": "White amorphous powder.[p11.12.1]: +6.8° (c QO15, CHCl_{3}). UV ([p11.12.2], MeOH, nm): 218 ([p11.12.3] 3.61). IR ([p11.12.4], film, cm^{-1}): 3423, 1916, 2854, 1755. MS: EIMS m/z 345, 311, 293, 275, 211, 193. NMR: [p11.12.5]H NMR (500MHz, CDCl_{3}), [p11.12.6]C NMR (125MHz, CDCl_{3}). Derivatives: per-MTPA esters ( [p11.12.7]H NMR). Biological activities ( [p11.12.8]g/mL): BST LC_{50} 6.8, A-549ED_{50} 2.0, MCF-7 ED_{50} 1.7, HT-29 ED_{50} 1.4, A-498ED_{50} 1.8, PC-3 ED_{50} 2.1, PACA-2 ED_{50} 1.1. Source: Annona squamosa, stem bark. squamoxinone(9) (reported as a cis and trans mixture) (C_{6}-H_{2}-O). MW624", "children": [ { "id": "p11.12.1", "order": 62, "type": "formula", "bbox": { "l": 55.68, "t": 475.2, "r": 533.04, "b": 433.68 }, "text": "[\\alpha]_{D}", "attrs": { "latex": "[\\alpha]_{D}", "inline": true, "text_offset": 23, "text_span": 10, "bbox_estimated": true, "notation": "latex", "alt": "alpha sub D", "mathml": "[α]D" } }, { "id": "p11.12.2", "order": 63, "type": "text", "bbox": { "l": 55.68, "t": 475.2, "r": 533.04, "b": 433.68 }, "text": "\\lambda_{max}", "attrs": { "inline": true, "text_offset": 65, "text_span": 10, "bbox_estimated": true } }, { "id": "p11.12.3", "order": 64, "type": "text", "bbox": { "l": 55.68, "t": 475.2, "r": 533.04, "b": 433.68 }, "text": "\\log \\epsilon", "attrs": { "inline": true, "text_offset": 93, "text_span": 10, "bbox_estimated": true } }, { "id": "p11.12.4", "order": 65, "type": "text", "bbox": { "l": 55.68, "t": 475.2, "r": 533.04, "b": 433.68 }, "text": "\\nu_{max}", "attrs": { "inline": true, "text_offset": 115, "text_span": 10, "bbox_estimated": true } }, { "id": "p11.12.5", "order": 66, "type": "text", "bbox": { "l": 55.68, "t": 475.2, "r": 533.04, "b": 433.68 }, "text": "¹", "attrs": { "inline": true, "text_offset": 215, "text_span": 10, "bbox_estimated": true } }, { "id": "p11.12.6", "order": 67, "type": "text", "bbox": { "l": 55.68, "t": 475.2, "r": 533.04, "b": 433.68 }, "text": "¹³", "attrs": { "inline": true, "text_offset": 251, "text_span": 10, "bbox_estimated": true } }, { "id": "p11.12.7", "order": 68, "type": "text", "bbox": { "l": 55.68, "t": 475.2, "r": 533.04, "b": 433.68 }, "text": "¹", "attrs": { "inline": true, "text_offset": 318, "text_span": 10, "bbox_estimated": true } }, { "id": "p11.12.8", "order": 69, "type": "text", "bbox": { "l": 55.68, "t": 475.2, "r": 533.04, "b": 433.68 }, "text": "μ", "attrs": { "inline": true, "text_offset": 360, "text_span": 10, "bbox_estimated": true } } ] }, { "id": "p11.13", "order": 70, "type": "text", "bbox": { "l": 54.96, "t": 438.72, "r": 342.72, "b": 427.92 }, "text": "squamoxinone[p11.13.1] (reported as a cis and trans mixture) (C [p11.13.2]H [p11.13.3]O[p11.13.4], MW624)", "children": [ { "id": "p11.13.1", "order": 71, "type": "formula", "bbox": { "l": 54.96, "t": 438.72, "r": 342.72, "b": 427.92 }, "text": "¹⁰⁹", "attrs": { "latex": "^{109}", "inline": true, "text_offset": 12, "text_span": 10, "bbox_estimated": true, "alt": "to the power of 109", "mathml": "109" } }, { "id": "p11.13.2", "order": 72, "type": "text", "bbox": { "l": 54.96, "t": 438.72, "r": 342.72, "b": 427.92 }, "text": "₃₇", "attrs": { "inline": true, "text_offset": 64, "text_span": 10, "bbox_estimated": true } }, { "id": "p11.13.3", "order": 73, "type": "text", "bbox": { "l": 54.96, "t": 438.72, "r": 342.72, "b": 427.92 }, "text": "₆₈", "attrs": { "inline": true, "text_offset": 76, "text_span": 10, "bbox_estimated": true } }, { "id": "p11.13.4", "order": 74, "type": "text", "bbox": { "l": 54.96, "t": 438.72, "r": 342.72, "b": 427.92 }, "text": "₇", "attrs": { "inline": true, "text_offset": 87, "text_span": 10, "bbox_estimated": true } } ] }, { "id": "p11.14", "order": 75, "type": "formula", "bbox": { "l": 153.12, "t": 425.28, "r": 457.92, "b": 382.32 }, "text": "", "attrs": { "block_label": "image", "alt": "Skeletal structure of a polyketide with a tetrahydrofuran ring, a gamma-lactone, and hydroxyl groups at C11, C17 and C22, wi…", "source": "vision" } }, { "id": "p11.15", "order": 76, "type": "text", "bbox": { "l": 54.24, "t": 381.6, "r": 161.76, "b": 371.52 }, "text": "6. (2,4-cis)-squamoxinone" }, { "id": "p11.16", "order": 77, "type": "table", "bbox": { "l": 205.2, "t": 370.8, "r": 407.52, "b": 287.28 }, "text": "", "attrs": { "block_label": "table", "n_rows": 6, "n_cols": 6, "integrity": { "skipped": "no_text_layer" } }, "children": [ { "id": "p11.16.1", "order": 78, "type": "table_cell", "bbox": { "l": 205.2, "t": 370.8, "r": 238.92, "b": 356.88 }, "text": "Position", "attrs": { "row": 0, "col": 0, "rowspan": 1, "colspan": 1, "column_header": true, "header_source": "heuristic" } }, { "id": "p11.16.2", "order": 79, "type": "table_cell", "bbox": { "l": 238.92, "t": 370.8, "r": 272.64, "b": 356.88 }, "text": "11", "attrs": { "row": 0, "col": 1, "rowspan": 1, "colspan": 1, "column_header": true, "header_source": "heuristic" } }, { "id": "p11.16.3", "order": 80, "type": "table_cell", "bbox": { "l": 272.64, "t": 370.8, "r": 306.36, "b": 356.88 }, "text": "17", "attrs": { "row": 0, "col": 2, "rowspan": 1, "colspan": 1, "column_header": true, "header_source": "heuristic" } }, { "id": "p11.16.4", "order": 81, "type": "table_cell", "bbox": { "l": 306.36, "t": 370.8, "r": 340.08, "b": 356.88 }, "text": "18", "attrs": { "row": 0, "col": 3, "rowspan": 1, "colspan": 1, "column_header": true, "header_source": "heuristic" } }, { "id": "p11.16.5", "order": 82, "type": "table_cell", "bbox": { "l": 340.08, "t": 370.8, "r": 373.8, "b": 356.88 }, "text": "21", "attrs": { "row": 0, "col": 4, "rowspan": 1, "colspan": 1, "column_header": true, "header_source": "heuristic" } }, { "id": "p11.16.6", "order": 83, "type": "table_cell", "bbox": { "l": 373.8, "t": 370.8, "r": 407.52, "b": 356.88 }, "text": "22", "attrs": { "row": 0, "col": 5, "rowspan": 1, "colspan": 1, "column_header": true, "header_source": "heuristic" } }, { "id": "p11.16.7", "order": 84, "type": "table_cell", "bbox": { "l": 205.2, "t": 356.88, "r": 238.92, "b": 342.96 }, "text": "¹H ( δ)", "attrs": { "row": 1, "col": 0, "rowspan": 1, "colspan": 1 } }, { "id": "p11.16.8", "order": 85, "type": "table_cell", "bbox": { "l": 238.92, "t": 356.88, "r": 272.64, "b": 342.96 }, "text": "3.59 m", "attrs": { "row": 1, "col": 1, "rowspan": 1, "colspan": 1 } }, { "id": "p11.16.9", "order": 86, "type": "table_cell", "bbox": { "l": 272.64, "t": 356.88, "r": 306.36, "b": 342.96 }, "text": "3.41 m", "attrs": { "row": 1, "col": 2, "rowspan": 1, "colspan": 1 } }, { "id": "p11.16.10", "order": 87, "type": "table_cell", "bbox": { "l": 306.36, "t": 356.88, "r": 340.08, "b": 342.96 }, "text": "3.80 m", "attrs": { "row": 1, "col": 3, "rowspan": 1, "colspan": 1 } }, { "id": "p11.16.11", "order": 88, "type": "table_cell", "bbox": { "l": 340.08, "t": 356.88, "r": 373.8, "b": 342.96 }, "text": "3.80 m", "attrs": { "row": 1, "col": 4, "rowspan": 1, "colspan": 1 } }, { "id": "p11.16.12", "order": 89, "type": "table_cell", "bbox": { "l": 373.8, "t": 356.88, "r": 407.52, "b": 342.96 }, "text": "3.41 m", "attrs": { "row": 1, "col": 5, "rowspan": 1, "colspan": 1 } }, { "id": "p11.16.13", "order": 90, "type": "table_cell", "bbox": { "l": 205.2, "t": 342.96, "r": 238.92, "b": 329.04 }, "text": "¹³C ( δ)", "attrs": { "row": 2, "col": 0, "rowspan": 1, "colspan": 1 } }, { "id": "p11.16.14", "order": 91, "type": "table_cell", "bbox": { "l": 238.92, "t": 342.96, "r": 272.64, "b": 329.04 }, "text": "71.86", "attrs": { "row": 2, "col": 1, "rowspan": 1, "colspan": 1 } }, { "id": "p11.16.15", "order": 92, "type": "table_cell", "bbox": { "l": 272.64, "t": 342.96, "r": 306.36, "b": 329.04 }, "text": "74.02", "attrs": { "row": 2, "col": 2, "rowspan": 1, "colspan": 1 } }, { "id": "p11.16.16", "order": 93, "type": "table_cell", "bbox": { "l": 306.36, "t": 342.96, "r": 340.08, "b": 329.04 }, "text": "82.63", "attrs": { "row": 2, "col": 3, "rowspan": 1, "colspan": 1 } }, { "id": "p11.16.17", "order": 94, "type": "table_cell", "bbox": { "l": 340.08, "t": 342.96, "r": 373.8, "b": 329.04 }, "text": "82.58", "attrs": { "row": 2, "col": 4, "rowspan": 1, "colspan": 1 } }, { "id": "p11.16.18", "order": 95, "type": "table_cell", "bbox": { "l": 373.8, "t": 342.96, "r": 407.52, "b": 329.04 }, "text": "73.97", "attrs": { "row": 2, "col": 5, "rowspan": 1, "colspan": 1 } }, { "id": "p11.16.19", "order": 96, "type": "table_cell", "bbox": { "l": 205.2, "t": 329.04, "r": 238.92, "b": 315.12 }, "text": "Position", "attrs": { "row": 3, "col": 0, "rowspan": 1, "colspan": 1 } }, { "id": "p11.16.20", "order": 97, "type": "table_cell", "bbox": { "l": 238.92, "t": 329.04, "r": 272.64, "b": 315.12 }, "text": "11", "attrs": { "row": 3, "col": 1, "rowspan": 1, "colspan": 1 } }, { "id": "p11.16.21", "order": 98, "type": "table_cell", "bbox": { "l": 272.64, "t": 329.04, "r": 306.36, "b": 315.12 }, "text": "17", "attrs": { "row": 3, "col": 2, "rowspan": 1, "colspan": 1 } }, { "id": "p11.16.22", "order": 99, "type": "table_cell", "bbox": { "l": 306.36, "t": 329.04, "r": 340.08, "b": 315.12 }, "text": "18", "attrs": { "row": 3, "col": 3, "rowspan": 1, "colspan": 1 } }, { "id": "p11.16.23", "order": 100, "type": "table_cell", "bbox": { "l": 340.08, "t": 329.04, "r": 373.8, "b": 315.12 }, "text": "21", "attrs": { "row": 3, "col": 4, "rowspan": 1, "colspan": 1 } }, { "id": "p11.16.24", "order": 101, "type": "table_cell", "bbox": { "l": 373.8, "t": 329.04, "r": 407.52, "b": 315.12 }, "text": "22", "attrs": { "row": 3, "col": 5, "rowspan": 1, "colspan": 1 } }, { "id": "p11.16.25", "order": 102, "type": "table_cell", "bbox": { "l": 205.2, "t": 315.12, "r": 238.92, "b": 301.2 }, "text": "¹H ( δ)", "attrs": { "row": 4, "col": 0, "rowspan": 1, "colspan": 1 } }, { "id": "p11.16.26", "order": 103, "type": "table_cell", "bbox": { "l": 238.92, "t": 315.12, "r": 272.64, "b": 301.2 }, "text": "3.59 m", "attrs": { "row": 4, "col": 1, "rowspan": 1, "colspan": 1 } }, { "id": "p11.16.27", "order": 104, "type": "table_cell", "bbox": { "l": 272.64, "t": 315.12, "r": 306.36, "b": 301.2 }, "text": "3.41 m", "attrs": { "row": 4, "col": 2, "rowspan": 1, "colspan": 1 } }, { "id": "p11.16.28", "order": 105, "type": "table_cell", "bbox": { "l": 306.36, "t": 315.12, "r": 340.08, "b": 301.2 }, "text": "3.80 m", "attrs": { "row": 4, "col": 3, "rowspan": 1, "colspan": 1 } }, { "id": "p11.16.29", "order": 106, "type": "table_cell", "bbox": { "l": 340.08, "t": 315.12, "r": 373.8, "b": 301.2 }, "text": "3.80 m", "attrs": { "row": 4, "col": 4, "rowspan": 1, "colspan": 1 } }, { "id": "p11.16.30", "order": 107, "type": "table_cell", "bbox": { "l": 373.8, "t": 315.12, "r": 407.52, "b": 301.2 }, "text": "3.41 m", "attrs": { "row": 4, "col": 5, "rowspan": 1, "colspan": 1 } }, { "id": "p11.16.31", "order": 108, "type": "table_cell", "bbox": { "l": 205.2, "t": 301.2, "r": 238.92, "b": 287.28 }, "text": "¹³C ( δ)", "attrs": { "row": 5, "col": 0, "rowspan": 1, "colspan": 1 } }, { "id": "p11.16.32", "order": 109, "type": "table_cell", "bbox": { "l": 238.92, "t": 301.2, "r": 272.64, "b": 287.28 }, "text": "71.86", "attrs": { "row": 5, "col": 1, "rowspan": 1, "colspan": 1 } }, { "id": "p11.16.33", "order": 110, "type": "table_cell", "bbox": { "l": 272.64, "t": 301.2, "r": 306.36, "b": 287.28 }, "text": "74.02", "attrs": { "row": 5, "col": 2, "rowspan": 1, "colspan": 1 } }, { "id": "p11.16.34", "order": 111, "type": "table_cell", "bbox": { "l": 306.36, "t": 301.2, "r": 340.08, "b": 287.28 }, "text": "82.63", "attrs": { "row": 5, "col": 3, "rowspan": 1, "colspan": 1 } }, { "id": "p11.16.35", "order": 112, "type": "table_cell", "bbox": { "l": 340.08, "t": 301.2, "r": 373.8, "b": 287.28 }, "text": "82.58", "attrs": { "row": 5, "col": 4, "rowspan": 1, "colspan": 1 } }, { "id": "p11.16.36", "order": 113, "type": "table_cell", "bbox": { "l": 373.8, "t": 301.2, "r": 407.52, "b": 287.28 }, "text": "73.97", "attrs": { "row": 5, "col": 5, "rowspan": 1, "colspan": 1 } } ] }, { "id": "p11.17", "order": 114, "type": "text", "bbox": { "l": 54.48, "t": 333.6, "r": 172.56, "b": 323.28 }, "text": "7. (2,4-trans)-squamoxinone" }, { "id": "p11.18", "order": 115, "type": "text", "bbox": { "l": 55.92, "t": 285.84, "r": 534.24, "b": 241.2 }, "text": "White amorphous powder.[p11.18.1]: +13.3° (c OO23, CH2Cl2). UV ([p11.18.2], MeOH, nm): 203 (log[p11.18.3] 3.20). IR ([p11.18.4], film, cm[p11.18.5]): 3445, 2919, 2850, 1755. MS: EIMS m/z 407, 389, 371, 337, 319, 255. NMR: [p11.18.6]H NMR (500MHz, CDCl[p11.18.7]), [p11.18.8]C NMR (125MHz, CDCl[p11.18.9]). Derivatives: per-MTPA esters ( [p11.18.10]H NMR). Biological activities ( [p11.18.11]g/mL): BST LC[p11.18.12] 2.7, A-549ED[p11.18.13] 1.9, MCF-7 ED[p11.18.14] 1.7, HT-29 ED[p11.18.15] 1.4, A-498ED[p11.18.16] 1.5, PC-3 ED[p11.18.17] 2.2, PAC-2 ED[p11.18.18] 4.5[p11.18.19] 10[p11.18.20]. Source: Annona squamosa, stem bark. xylomaticinone[p11.18.21] (reported as a cis and trans mixture) (C [p11.18.22]H [p11.18.23]O[p11.18.24], MW624)", "children": [ { "id": "p11.18.1", "order": 116, "type": "formula", "bbox": { "l": 55.92, "t": 285.84, "r": 534.24, "b": 241.2 }, "text": "\\text{White amorphous powder. } [\\alpha]_{D}: +13.3^{\\circ} (c\\,0.023, \\text{CH}_2\\text{Cl}_2). \\text{UV } (\\lambda_{\\max}, \\text{MeOH, nm}): 203 (\\log \\epsilon\\, 3.20). \\text{IR } (\\nu_{\\max}, \\text{film, cm}^{-1}): 3445, 2919, 2850, 1755. \\text{MS: EIMS } m/z\\ 407, 389, 371, 337, 319, 255. \\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}). \\text{Biological activities } (\\mu\\text{g/mL}): \\text{BST LC}_{50}\\ 2.7, \\text{A-549 ED}_{50}\\ 1.9, \\text{MCF-7 ED}_{50}\\ 1.7, \\text{HT-29 ED}_{50}\\ 1.4, \\text{A-498 ED}_{50}\\ 1.5, \\text{PC-3 ED}_{50}\\ 2.2, \\text{PACA-2 ED}_{50}\\ 4.5 \\times 10^{-3}. \\text{Source: } \\textit{Annona squamosa}\\text{, stem bark.} \\textbf{xylomaticinone}^{39} \\text{ (reported as a cis and trans mixture) (C}_{37}\\text{H}_{69}\\text{O}_{7}, \\text{MW 624)}", "attrs": { "latex": "\\text{White amorphous powder. } [\\alpha]_{D}: +13.3^{\\circ} (c\\,0.023, \\text{CH}_2\\text{Cl}_2). \\text{UV } (\\lambda_{\\max}, \\text{MeOH, nm}): 203 (\\log \\epsilon\\, 3.20). \\text{IR } (\\nu_{\\max}, \\text{film, cm}^{-1}): 3445, 2919, 2850, 1755. \\text{MS: EIMS } m/z\\ 407, 389, 371, 337, 319, 255. \\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}). \\text{Biological activities } (\\mu\\text{g/mL}): \\text{BST LC}_{50}\\ 2.7, \\text{A-549 ED}_{50}\\ 1.9, \\text{MCF-7 ED}_{50}\\ 1.7, \\text{HT-29 ED}_{50}\\ 1.4, \\text{A-498 ED}_{50}\\ 1.5, \\text{PC-3 ED}_{50}\\ 2.2, \\text{PACA-2 ED}_{50}\\ 4.5 \\times 10^{-3}. \\text{Source: } \\textit{Annona squamosa}\\text{, stem bark.} \\textbf{xylomaticinone}^{39} \\text{ (reported as a cis and trans mixture) (C}_{37}\\text{H}_{69}\\text{O}_{7}, \\text{MW 624)}", "inline": true, "text_offset": 23, "text_span": 10, "bbox_estimated": true, "notation": "latex", "alt": "White amorphous powder. alpha sub D : plus 13.3 to the power of circ of c, 0.023, CH sub 2 Cl sub 2 . UV of lambda sub max, MeOH, nm : 203 times log epsilon, 3.20 . IR of nu sub max, film, cm to the power of minus 1 : 3445, 2919, 2850, 1755. MS: EIMS m over z 407, 389, 371, 337, 319, 255. 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 2.7, A minus 549 ED sub 50 1.9, MCF minus 7 ED sub 50 1.7, HT minus 29 ED sub 50 1.4, A minus 498 ED sub 50 1.5, PC minus 3 ED sub 50 2.2, PACA minus 2 ED sub 50 4.5 times 10 to the power of minus 3 . Source: textit Annona squamosa, stem bark. textbf xylomaticinone to the power of 39 times reported as a cis and trans mixture times C sub 37 H sub 69 O sub 7, MW 624", "mathml": "White amorphous powder. [α]D:+13.3∘(c0.023,CH2Cl2).UV (λmax,MeOH, nm):203(logϵ3.20).IR (νmax,film, cm−1):3445,2919,2850,1755.MS: EIMS m/z 407,389,371,337,319,255.NMR: 1H NMR (500 MHz, CDCl3),13C NMR (125 MHz, CDCl3).Derivatives: per-MTPA esters (1H NMR).Biological activities (μg/mL):BST LC50 2.7,A-549 ED50 1.9,MCF-7 ED50 1.7,HT-29 ED50 1.4,A-498 ED50 1.5,PC-3 ED50 2.2,PACA-2 ED50 4.5×10−3.Source: Annona squamosa, stem bark.xylomaticinone39 (reported as a cis and trans mixture) (C37H69O7,MW 624)" } }, { "id": "p11.18.2", "order": 117, "type": "formula", "bbox": { "l": 55.92, "t": 285.84, "r": 534.24, "b": 241.2 }, "text": "\\text{White amorphous powder. }[\\alpha]_D\\text{: }+13.3^\\circ\\text{ (}c\\text{ 0.023, CH}_2\\text{Cl}_2\\text{). UV (}\\lambda_{max}\\text{, MeOH, nm): 203 (log }\\epsilon\\text{ 3.20). IR (}\\nu_{max}\\text{, film, cm}^{-1}\\text{): 3445, 2919, 2850, 1755. MS: EIMS }m/z\\text{ 407, 389, 371, 337, 319, 255. NMR: }^1\\text{H NMR (500 MHz, CDCl}_3\\text{), }^{13}\\text{C NMR (125 MHz, CDCl}_3\\text{). Derivatives: per-MTPA esters (}^1\\text{H NMR). Biological activities (}\\mu\\text{g/mL): BST LC}_{50}\\text{ 2.7, A-549 ED}_{50}\\text{ 1.9, MCF-7 ED}_{50}\\text{ 1.7, HT-29 ED}_{50}\\text{ 1.4, A-498 ED}_{50}\\text{ 1.5, PC-3 ED}_{50}\\text{ 2.2, PACA-2 ED}_{50}\\text{ 4.5}\\times10^{-3}\\text{. Source: }\\textit{Annona squamosa}\\text{, stem bark.}\\\\\\textbf{xylomaticinone}^{39}\\text{ (reported as a cis and trans mixture) (C}_{37}\\text{H}_{69}\\text{O}_7\\text{, MW 624)}", "attrs": { "latex": "\\text{White amorphous powder. }[\\alpha]_D\\text{: }+13.3^\\circ\\text{ (}c\\text{ 0.023, CH}_2\\text{Cl}_2\\text{). UV (}\\lambda_{max}\\text{, MeOH, nm): 203 (log }\\epsilon\\text{ 3.20). IR (}\\nu_{max}\\text{, film, cm}^{-1}\\text{): 3445, 2919, 2850, 1755. MS: EIMS }m/z\\text{ 407, 389, 371, 337, 319, 255. NMR: }^1\\text{H NMR (500 MHz, CDCl}_3\\text{), }^{13}\\text{C NMR (125 MHz, CDCl}_3\\text{). Derivatives: per-MTPA esters (}^1\\text{H NMR). Biological activities (}\\mu\\text{g/mL): BST LC}_{50}\\text{ 2.7, A-549 ED}_{50}\\text{ 1.9, MCF-7 ED}_{50}\\text{ 1.7, HT-29 ED}_{50}\\text{ 1.4, A-498 ED}_{50}\\text{ 1.5, PC-3 ED}_{50}\\text{ 2.2, PACA-2 ED}_{50}\\text{ 4.5}\\times10^{-3}\\text{. Source: }\\textit{Annona squamosa}\\text{, stem bark.}\\\\\\textbf{xylomaticinone}^{39}\\text{ (reported as a cis and trans mixture) (C}_{37}\\text{H}_{69}\\text{O}_7\\text{, MW 624)}", "inline": true, "text_offset": 64, "text_span": 10, "bbox_estimated": true, "notation": "latex", "alt": "White amorphous powder. alpha sub D : plus 13.3 to the power of circ of c 0.023, CH sub 2 Cl sub 2 . UV of lambda sub max, MeOH, nm : 203 times log epsilon 3.20 . IR of nu sub max, film, cm to the power of minus 1 : 3445, 2919, 2850, 1755. MS: EIMS m over z 407, 389, 371, 337, 319, 255. 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 2.7, A minus 549 ED sub 50 1.9, MCF minus 7 ED sub 50 1.7, HT minus 29 ED sub 50 1.4, A minus 498 ED sub 50 1.5, PC minus 3 ED sub 50 2.2, PACA minus 2 ED sub 50 4.5 times 10 to the power of minus 3 . Source: textit Annona squamosa, stem bark. textbf xylomaticinone to the power of 39 times reported as a cis and trans mixture times C sub 37 H sub 69 O sub 7, MW 624", "mathml": "White amorphous powder. [α]D: +13.3∘ (c 0.023, CH2Cl2). UV (λmax, MeOH, nm): 203 (log ϵ 3.20). IR (νmax, film, cm−1): 3445, 2919, 2850, 1755. MS: EIMS m/z 407, 389, 371, 337, 319, 255. NMR: 1H NMR (500 MHz, CDCl3), 13C NMR (125 MHz, CDCl3). Derivatives: per-MTPA esters (1H NMR). Biological activities (μg/mL): BST LC50 2.7, A-549 ED50 1.9, MCF-7 ED50 1.7, HT-29 ED50 1.4, A-498 ED50 1.5, PC-3 ED50 2.2, PACA-2 ED50 4.5×10−3. Source: Annona squamosa, stem bark.xylomaticinone39 (reported as a cis and trans mixture) (C37H69O7, MW 624)" } }, { "id": "p11.18.3", "order": 118, "type": "text", "bbox": { "l": 55.92, "t": 285.84, "r": 534.24, "b": 241.2 }, "text": "ε", "attrs": { "inline": true, "text_offset": 95, "text_span": 10, "bbox_estimated": true } }, { "id": "p11.18.4", "order": 119, "type": "text", "bbox": { "l": 55.92, "t": 285.84, "r": 534.24, "b": 241.2 }, "text": "\\nu_{max}", "attrs": { "inline": true, "text_offset": 117, "text_span": 10, "bbox_estimated": true } }, { "id": "p11.18.5", "order": 120, "type": "text", "bbox": { "l": 55.92, "t": 285.84, "r": 534.24, "b": 241.2 }, "text": "⁻¹", "attrs": { "inline": true, "text_offset": 137, "text_span": 10, "bbox_estimated": true } }, { "id": "p11.18.6", "order": 121, "type": "text", "bbox": { "l": 55.92, "t": 285.84, "r": 534.24, "b": 241.2 }, "text": "¹", "attrs": { "inline": true, "text_offset": 222, "text_span": 10, "bbox_estimated": true } }, { "id": "p11.18.7", "order": 122, "type": "text", "bbox": { "l": 55.92, "t": 285.84, "r": 534.24, "b": 241.2 }, "text": "₃", "attrs": { "inline": true, "text_offset": 251, "text_span": 10, "bbox_estimated": true } }, { "id": "p11.18.8", "order": 123, "type": "text", "bbox": { "l": 55.92, "t": 285.84, "r": 534.24, "b": 241.2 }, "text": "¹³", "attrs": { "inline": true, "text_offset": 264, "text_span": 10, "bbox_estimated": true } }, { "id": "p11.18.9", "order": 124, "type": "text", "bbox": { "l": 55.92, "t": 285.84, "r": 534.24, "b": 241.2 }, "text": "₃", "attrs": { "inline": true, "text_offset": 293, "text_span": 10, "bbox_estimated": true } }, { "id": "p11.18.10", "order": 125, "type": "text", "bbox": { "l": 55.92, "t": 285.84, "r": 534.24, "b": 241.2 }, "text": "¹", "attrs": { "inline": true, "text_offset": 337, "text_span": 11, "bbox_estimated": true } }, { "id": "p11.18.11", "order": 126, "type": "text", "bbox": { "l": 55.92, "t": 285.84, "r": 534.24, "b": 241.2 }, "text": "μ", "attrs": { "inline": true, "text_offset": 380, "text_span": 11, "bbox_estimated": true } }, { "id": "p11.18.12", "order": 127, "type": "text", "bbox": { "l": 55.92, "t": 285.84, "r": 534.24, "b": 241.2 }, "text": "₅₀", "attrs": { "inline": true, "text_offset": 404, "text_span": 11, "bbox_estimated": true } }, { "id": "p11.18.13", "order": 128, "type": "text", "bbox": { "l": 55.92, "t": 285.84, "r": 534.24, "b": 241.2 }, "text": "₅₀", "attrs": { "inline": true, "text_offset": 428, "text_span": 11, "bbox_estimated": true } }, { "id": "p11.18.14", "order": 129, "type": "text", "bbox": { "l": 55.92, "t": 285.84, "r": 534.24, "b": 241.2 }, "text": "₅₀", "attrs": { "inline": true, "text_offset": 453, "text_span": 11, "bbox_estimated": true } }, { "id": "p11.18.15", "order": 130, "type": "text", "bbox": { "l": 55.92, "t": 285.84, "r": 534.24, "b": 241.2 }, "text": "₅₀", "attrs": { "inline": true, "text_offset": 478, "text_span": 11, "bbox_estimated": true } }, { "id": "p11.18.16", "order": 131, "type": "text", "bbox": { "l": 55.92, "t": 285.84, "r": 534.24, "b": 241.2 }, "text": "₅₀", "attrs": { "inline": true, "text_offset": 502, "text_span": 11, "bbox_estimated": true } }, { "id": "p11.18.17", "order": 132, "type": "text", "bbox": { "l": 55.92, "t": 285.84, "r": 534.24, "b": 241.2 }, "text": "₅₀", "attrs": { "inline": true, "text_offset": 526, "text_span": 11, "bbox_estimated": true } }, { "id": "p11.18.18", "order": 133, "type": "text", "bbox": { "l": 55.92, "t": 285.84, "r": 534.24, "b": 241.2 }, "text": "₅₀", "attrs": { "inline": true, "text_offset": 551, "text_span": 11, "bbox_estimated": true } }, { "id": "p11.18.19", "order": 134, "type": "text", "bbox": { "l": 55.92, "t": 285.84, "r": 534.24, "b": 241.2 }, "text": "×", "attrs": { "inline": true, "text_offset": 566, "text_span": 11, "bbox_estimated": true } }, { "id": "p11.18.20", "order": 135, "type": "text", "bbox": { "l": 55.92, "t": 285.84, "r": 534.24, "b": 241.2 }, "text": "⁻³", "attrs": { "inline": true, "text_offset": 580, "text_span": 11, "bbox_estimated": true } }, { "id": "p11.18.21", "order": 136, "type": "formula", "bbox": { "l": 55.92, "t": 285.84, "r": 534.24, "b": 241.2 }, "text": "³⁹", "attrs": { "latex": "^{39}", "inline": true, "text_offset": 643, "text_span": 11, "bbox_estimated": true, "alt": "to the power of 39", "mathml": "39" } }, { "id": "p11.18.22", "order": 137, "type": "text", "bbox": { "l": 55.92, "t": 285.84, "r": 534.24, "b": 241.2 }, "text": "₃₇", "attrs": { "inline": true, "text_offset": 696, "text_span": 11, "bbox_estimated": true } }, { "id": "p11.18.23", "order": 138, "type": "text", "bbox": { "l": 55.92, "t": 285.84, "r": 534.24, "b": 241.2 }, "text": "₆₉", "attrs": { "inline": true, "text_offset": 709, "text_span": 11, "bbox_estimated": true } }, { "id": "p11.18.24", "order": 139, "type": "text", "bbox": { "l": 55.92, "t": 285.84, "r": 534.24, "b": 241.2 }, "text": "₇", "attrs": { "inline": true, "text_offset": 721, "text_span": 11, "bbox_estimated": true } } ] }, { "id": "p11.19", "order": 140, "type": "formula", "bbox": { "l": 153.12, "t": 235.68, "r": 457.68, "b": 191.28 }, "text": "", "attrs": { "block_label": "image", "alt": "Skeletal structure of an acetogenin-type lactone with a tetrahydrofuran ring, hydroxyl groups at C10, C15 and C20, and a met…", "source": "vision" } }, { "id": "p11.20", "order": 141, "type": "text", "bbox": { "l": 54.24, "t": 190.8, "r": 165.84, "b": 180.48 }, "text": "8. (2,4-cis)-xylomaticinone" }, { "id": "p11.21", "order": 142, "type": "table", "bbox": { "l": 204.24, "t": 180, "r": 407.04, "b": 98.16 }, "text": "", "attrs": { "block_label": "table", "n_rows": 6, "n_cols": 6, "integrity": { "skipped": "no_text_layer" } }, "children": [ { "id": "p11.21.1", "order": 143, "type": "table_cell", "bbox": { "l": 204.24, "t": 180, "r": 238.04, "b": 166.36 }, "text": "Position", "attrs": { "row": 0, "col": 0, "rowspan": 1, "colspan": 1, "column_header": true, "header_source": "heuristic" } }, { "id": "p11.21.2", "order": 144, "type": "table_cell", "bbox": { "l": 238.04, "t": 180, "r": 271.84, "b": 166.36 }, "text": "10", "attrs": { "row": 0, "col": 1, "rowspan": 1, "colspan": 1, "column_header": true, "header_source": "heuristic" } }, { "id": "p11.21.3", "order": 145, "type": "table_cell", "bbox": { "l": 271.84, "t": 180, "r": 305.64, "b": 166.36 }, "text": "15", "attrs": { "row": 0, "col": 2, "rowspan": 1, "colspan": 1, "column_header": true, "header_source": "heuristic" } }, { "id": "p11.21.4", "order": 146, "type": "table_cell", "bbox": { "l": 305.64, "t": 180, "r": 339.44, "b": 166.36 }, "text": "16", "attrs": { "row": 0, "col": 3, "rowspan": 1, "colspan": 1, "column_header": true, "header_source": "heuristic" } }, { "id": "p11.21.5", "order": 147, "type": "table_cell", "bbox": { "l": 339.44, "t": 180, "r": 373.24, "b": 166.36 }, "text": "19", "attrs": { "row": 0, "col": 4, "rowspan": 1, "colspan": 1, "column_header": true, "header_source": "heuristic" } }, { "id": "p11.21.6", "order": 148, "type": "table_cell", "bbox": { "l": 373.24, "t": 180, "r": 407.04, "b": 166.36 }, "text": "20", "attrs": { "row": 0, "col": 5, "rowspan": 1, "colspan": 1, "column_header": true, "header_source": "heuristic" } }, { "id": "p11.21.7", "order": 149, "type": "table_cell", "bbox": { "l": 204.24, "t": 166.36, "r": 238.04, "b": 152.72 }, "text": "¹H ( δ)", "attrs": { "row": 1, "col": 0, "rowspan": 1, "colspan": 1 } }, { "id": "p11.21.8", "order": 150, "type": "table_cell", "bbox": { "l": 238.04, "t": 166.36, "r": 271.84, "b": 152.72 }, "text": "3.59 m", "attrs": { "row": 1, "col": 1, "rowspan": 1, "colspan": 1 } }, { "id": "p11.21.9", "order": 151, "type": "table_cell", "bbox": { "l": 271.84, "t": 166.36, "r": 305.64, "b": 152.72 }, "text": "3.41 m", "attrs": { "row": 1, "col": 2, "rowspan": 1, "colspan": 1 } }, { "id": "p11.21.10", "order": 152, "type": "table_cell", "bbox": { "l": 305.64, "t": 166.36, "r": 339.44, "b": 152.72 }, "text": "3.80 m", "attrs": { "row": 1, "col": 3, "rowspan": 1, "colspan": 1 } }, { "id": "p11.21.11", "order": 153, "type": "table_cell", "bbox": { "l": 339.44, "t": 166.36, "r": 373.24, "b": 152.72 }, "text": "3.80 m", "attrs": { "row": 1, "col": 4, "rowspan": 1, "colspan": 1 } }, { "id": "p11.21.12", "order": 154, "type": "table_cell", "bbox": { "l": 373.24, "t": 166.36, "r": 407.04, "b": 152.72 }, "text": "3.41 m", "attrs": { "row": 1, "col": 5, "rowspan": 1, "colspan": 1 } }, { "id": 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"id": "p11.21.23", "order": 165, "type": "table_cell", "bbox": { "l": 339.44, "t": 139.08, "r": 373.24, "b": 125.44 }, "text": "19", "attrs": { "row": 3, "col": 4, "rowspan": 1, "colspan": 1 } }, { "id": "p11.21.24", "order": 166, "type": "table_cell", "bbox": { "l": 373.24, "t": 139.08, "r": 407.04, "b": 125.44 }, "text": "20", "attrs": { "row": 3, "col": 5, "rowspan": 1, "colspan": 1 } }, { "id": "p11.21.25", "order": 167, "type": "table_cell", "bbox": { "l": 204.24, "t": 125.44, "r": 238.04, "b": 111.8 }, "text": "¹H ( δ)", "attrs": { "row": 4, "col": 0, "rowspan": 1, "colspan": 1 } }, { "id": "p11.21.26", "order": 168, "type": "table_cell", "bbox": { "l": 238.04, "t": 125.44, "r": 271.84, "b": 111.8 }, "text": "3.59 m", "attrs": { "row": 4, "col": 1, "rowspan": 1, "colspan": 1 } }, { "id": "p11.21.27", "order": 169, "type": "table_cell", "bbox": { "l": 271.84, "t": 125.44, "r": 305.64, "b": 111.8 }, "text": "3.41 m", "attrs": { "row": 4, "col": 2, "rowspan": 1, "colspan": 1 } }, { "id": "p11.21.28", "order": 170, "type": "table_cell", "bbox": { "l": 305.64, "t": 125.44, "r": 339.44, "b": 111.8 }, "text": "3.80 m", "attrs": { "row": 4, "col": 3, "rowspan": 1, "colspan": 1 } }, { "id": "p11.21.29", "order": 171, "type": "table_cell", "bbox": { "l": 339.44, "t": 125.44, "r": 373.24, "b": 111.8 }, "text": "3.80 m", "attrs": { "row": 4, "col": 4, "rowspan": 1, "colspan": 1 } }, { "id": "p11.21.30", "order": 172, "type": "table_cell", "bbox": { "l": 373.24, "t": 125.44, "r": 407.04, "b": 111.8 }, "text": "3.41 m", "attrs": { "row": 4, "col": 5, "rowspan": 1, "colspan": 1 } }, { "id": "p11.21.31", "order": 173, "type": "table_cell", "bbox": { "l": 204.24, "t": 111.8, "r": 238.04, "b": 98.16 }, "text": "¹³C ( δ)", "attrs": { "row": 5, "col": 0, "rowspan": 1, "colspan": 1 } }, { "id": "p11.21.32", "order": 174, "type": "table_cell", "bbox": { "l": 238.04, "t": 111.8, "r": 271.84, "b": 98.16 }, "text": "71.7", "attrs": { "row": 5, "col": 1, "rowspan": 1, "colspan": 1 } }, { "id": "p11.21.33", "order": 175, "type": "table_cell", "bbox": { "l": 271.84, "t": 111.8, "r": 305.64, "b": 98.16 }, "text": "73.97", "attrs": { "row": 5, "col": 2, "rowspan": 1, "colspan": 1 } }, { "id": "p11.21.34", "order": 176, "type": "table_cell", "bbox": { "l": 305.64, "t": 111.8, "r": 339.44, "b": 98.16 }, "text": "82.60", "attrs": { "row": 5, "col": 3, "rowspan": 1, "colspan": 1 } }, { "id": "p11.21.35", "order": 177, "type": "table_cell", "bbox": { "l": 339.44, "t": 111.8, "r": 373.24, "b": 98.16 }, "text": "82.66", "attrs": { "row": 5, "col": 4, "rowspan": 1, "colspan": 1 } }, { "id": "p11.21.36", "order": 178, "type": "table_cell", "bbox": { "l": 373.24, "t": 111.8, "r": 407.04, "b": 98.16 }, "text": "74.04", "attrs": { "row": 5, "col": 5, "rowspan": 1, "colspan": 1 } } ] }, { "id": "p11.22", "order": 179, "type": "text", "bbox": { "l": 54.24, "t": 143.52, "r": 176.16, "b": 133.2 }, "text": "9. (2,4-trans)-xylomaticinone" }, { "id": "p11.23", "order": 180, "type": "footnote", "bbox": { "l": 54.72, "t": 96.24, "r": 445.2, "b": 86.88 }, "text": "White wax. $ [\\alpha]_{D} $: +26.2° (c 0.08,[p11.23.1]). IR ( $ \\nu_{max} $, film, cm[p11.23.2]): 3454, 2916, 2848, 1756, 1716, 1470, 1070.", "attrs": { "block_label": "vision_footnote" }, "children": [ { "id": "p11.23.1", "order": 181, "type": "text", "bbox": { "l": 54.72, "t": 96.24, "r": 445.2, "b": 86.88 }, "text": "CHCl₃", "attrs": { "inline": true, "text_offset": 44, "text_span": 10, "bbox_estimated": true } }, { "id": "p11.23.2", "order": 182, "type": "text", "bbox": { "l": 54.72, "t": 96.24, "r": 445.2, "b": 86.88 }, "text": "⁻¹", "attrs": { "inline": true, "text_offset": 85, "text_span": 10, "bbox_estimated": true } } ] }, { "id": "p11.24", "order": 183, "type": "footnote", "bbox": { "l": 56.4, "t": 93.36, "r": 555.36, "b": 50.64 }, "text": "White wax. [α]D: +26.2 (c 0.08, CHCl₃). IR (νmax, film, cm⁻¹): 3454, 2916, 2848, 1756, 1716, 1470, 1070. MS: EIMS m/z 379, 361, 343, 309, 297, 291, 279, 273, 241, 227, 141. NMR: ¹H NMR (500MHz, CDCl₃), ¹³C NMR (125MHz, CDCl₃). Derivatives: per-MTPA esters (¹H NMR). Biological activities (μg/mL): BST LC₅₀, 0.4 × 10⁻¹, A-549ED₅₀, 1.4 × 10⁻², MCF-7 ED₅₀, 7.6 × 10⁻⁴, HT-29ED₅₀, 7.4 × 10⁻⁴, A-498ED₅₀, 1.2 × 10⁻¹, PC-3ED₅₀, 5.7 × 10⁻², PACA-2ED₅₀, 7.4 × 10⁻². Source: Annona squamosa, stem bark.", "attrs": { "block_label": "vision_footnote" } } ], "excluded_furniture": { "first": [], "last": [] } }