{ "document_id": 13701, "page": 13, "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": 176, "counts_by_type": { "formula": 13, "header": 4, "table": 3, "table_cell": 78, "text": 78 }, "build_ms": 26, "items": [ { "id": "p13.1", "order": 1, "type": "header", "bbox": { "l": 53.52, "t": 765.6, "r": 70.8, "b": 756.96 }, "text": "516", "attrs": { "block_label": "number" }, "level": 2 }, { "id": "p13.2", "order": 2, "type": "header", "bbox": { "l": 75.6, "t": 766.08, "r": 264.24, "b": 756 }, "text": "Journal of Natural Products, 1999, Vol. 62, No. 3", "attrs": { "block_label": "header" }, "level": 2 }, { "id": "p13.3", "order": 3, "type": "header", "bbox": { "l": 501.12, "t": 766.08, "r": 559.68, "b": 756 }, "text": "Invited Review", "attrs": { "block_label": "header" }, "level": 2 }, { "id": "p13.4", "order": 4, "type": "header", "bbox": { "l": 53.28, "t": 746.16, "r": 142.8, "b": 736.08 }, "text": "Table 4. (Continued)", "attrs": { "block_label": "figure_title" }, "level": 2 }, { "id": "p13.5", "order": 5, "type": "text", "bbox": { "l": 236.16, "t": 732.48, "r": 374.16, "b": 710.88 }, "text": "Mono-THF Acetogenins (Continued)\nns mixture) ([p13.5.1], MW624)", "children": [ { "id": "p13.5.1", "order": 6, "type": "formula", "bbox": { "l": 236.16, "t": 732.48, "r": 374.16, "b": 710.88 }, "text": "C₃₇H₆₈O₇", "attrs": { "latex": "C_{37}H_{68}O_{7}", "inline": true, "text_offset": 46, "text_span": 9, "bbox_estimated": true, "alt": "C sub 37 H sub 68 O sub 7", "mathml": "C37H68O7" } } ] }, { "id": "p13.6", "order": 7, "type": "text", "bbox": { "l": 56.64, "t": 721.2, "r": 364.08, "b": 710.4 }, "text": "annomontacinone[p13.6.1] (reported as a cis and trans mixture) (C [p13.6.2]H [p13.6.3]O[p13.6.4], MW624)", "children": [ { "id": "p13.6.1", "order": 8, "type": "text", "bbox": { "l": 56.64, "t": 721.2, "r": 364.08, "b": 710.4 }, "text": "⁴⁷", "attrs": { "inline": true, "text_offset": 15, "text_span": 9, "bbox_estimated": true } }, { "id": "p13.6.2", "order": 9, "type": "text", "bbox": { "l": 56.64, "t": 721.2, "r": 364.08, "b": 710.4 }, "text": "₃₇", "attrs": { "inline": true, "text_offset": 66, "text_span": 9, "bbox_estimated": true } }, { "id": "p13.6.3", "order": 10, "type": "text", "bbox": { "l": 56.64, "t": 721.2, "r": 364.08, "b": 710.4 }, "text": "₆₈", "attrs": { "inline": true, "text_offset": 77, "text_span": 9, "bbox_estimated": true } }, { "id": "p13.6.4", "order": 11, "type": "text", "bbox": { "l": 56.64, "t": 721.2, "r": 364.08, "b": 710.4 }, "text": "₇", "attrs": { "inline": true, "text_offset": 87, "text_span": 9, "bbox_estimated": true } } ] }, { "id": "p13.7", "order": 12, "type": "formula", "bbox": { "l": 152.88, "t": 705.6, "r": 457.2, "b": 661.68 }, "text": "", "attrs": { "block_label": "image", "alt": "Skeletal structure of an annonaceous acetogenin-type molecule with a THF ring, hydroxyls at C-10, C-17 and C-22, and a buten…", "source": "vision" } }, { "id": "p13.8", "order": 13, "type": "text", "bbox": { "l": 57.6, "t": 659.52, "r": 184.32, "b": 649.92 }, "text": "16. (2,4-cis)-annomontacinone" }, { "id": "p13.9", "order": 14, "type": "table", "bbox": { "l": 203.52, "t": 650.16, "r": 408.48, "b": 560.64 }, "text": "", "attrs": { "block_label": "table", "n_rows": 6, "n_cols": 6, "integrity": { "skipped": "no_text_layer" } }, "children": [ { "id": "p13.9.1", "order": 15, "type": "table_cell", "bbox": { "l": 203.52, "t": 650.16, "r": 237.68, "b": 635.24 }, "text": "Position", "attrs": { "row": 0, "col": 0, "rowspan": 1, "colspan": 1, "column_header": true, "header_source": "heuristic" } }, { "id": "p13.9.2", "order": 16, "type": "table_cell", "bbox": { "l": 237.68, "t": 650.16, "r": 271.84, "b": 635.24 }, "text": "10", "attrs": { "row": 0, "col": 1, "rowspan": 1, "colspan": 1, "column_header": true, "header_source": "heuristic" } }, { "id": "p13.9.3", "order": 17, "type": "table_cell", "bbox": { "l": 271.84, "t": 650.16, "r": 306, "b": 635.24 }, "text": "17", "attrs": { "row": 0, "col": 2, "rowspan": 1, "colspan": 1, "column_header": true, 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"order": 27, "type": "table_cell", "bbox": { "l": 203.52, "t": 620.32, "r": 237.68, "b": 605.4 }, "text": "¹³C ( δ)", "attrs": { "row": 2, "col": 0, "rowspan": 1, "colspan": 1 } }, { "id": "p13.9.14", "order": 28, "type": "table_cell", "bbox": { "l": 237.68, "t": 620.32, "r": 271.84, "b": 605.4 }, "text": "71.86", "attrs": { "row": 2, "col": 1, "rowspan": 1, "colspan": 1 } }, { "id": "p13.9.15", "order": 29, "type": "table_cell", "bbox": { "l": 271.84, "t": 620.32, "r": 306, "b": 605.4 }, "text": "74.00", "attrs": { "row": 2, "col": 2, "rowspan": 1, "colspan": 1 } }, { "id": "p13.9.16", "order": 30, "type": "table_cell", "bbox": { "l": 306, "t": 620.32, "r": 340.16, "b": 605.4 }, "text": "82.64", "attrs": { "row": 2, "col": 3, "rowspan": 1, "colspan": 1 } }, { "id": "p13.9.17", "order": 31, "type": "table_cell", "bbox": { "l": 340.16, "t": 620.32, "r": 374.32, "b": 605.4 }, "text": "82.57", "attrs": { "row": 2, "col": 4, "rowspan": 1, "colspan": 1 } }, { "id": "p13.9.18", "order": 32, "type": "table_cell", "bbox": { "l": 374.32, "t": 620.32, "r": 408.48, "b": 605.4 }, "text": "74.06", "attrs": { "row": 2, "col": 5, "rowspan": 1, "colspan": 1 } }, { "id": "p13.9.19", "order": 33, "type": "table_cell", "bbox": { "l": 203.52, "t": 605.4, "r": 237.68, "b": 590.48 }, "text": "Position", "attrs": { "row": 3, "col": 0, "rowspan": 1, "colspan": 1 } }, { "id": "p13.9.20", "order": 34, "type": "table_cell", "bbox": { "l": 237.68, "t": 605.4, "r": 271.84, "b": 590.48 }, "text": "10", "attrs": { "row": 3, "col": 1, "rowspan": 1, "colspan": 1 } }, { "id": "p13.9.21", "order": 35, "type": "table_cell", "bbox": { "l": 271.84, "t": 605.4, "r": 306, "b": 590.48 }, "text": "17", "attrs": { "row": 3, "col": 2, "rowspan": 1, "colspan": 1 } }, { "id": "p13.9.22", "order": 36, "type": "table_cell", "bbox": { "l": 306, "t": 605.4, "r": 340.16, "b": 590.48 }, "text": "18", "attrs": { "row": 3, "col": 3, "rowspan": 1, "colspan": 1 } }, { "id": "p13.9.23", "order": 37, "type": "table_cell", "bbox": { "l": 340.16, "t": 605.4, "r": 374.32, "b": 590.48 }, "text": "21", "attrs": { "row": 3, "col": 4, "rowspan": 1, "colspan": 1 } }, { "id": "p13.9.24", "order": 38, "type": "table_cell", "bbox": { "l": 374.32, "t": 605.4, "r": 408.48, "b": 590.48 }, "text": "22", "attrs": { "row": 3, "col": 5, "rowspan": 1, "colspan": 1 } }, { "id": "p13.9.25", "order": 39, "type": "table_cell", "bbox": { "l": 203.52, "t": 590.48, "r": 237.68, "b": 575.56 }, "text": "¹H ( δ)", "attrs": { "row": 4, "col": 0, "rowspan": 1, "colspan": 1 } }, { "id": "p13.9.26", "order": 40, "type": "table_cell", "bbox": { "l": 237.68, "t": 590.48, "r": 271.84, "b": 575.56 }, "text": "3.58 m", "attrs": { "row": 4, "col": 1, "rowspan": 1, "colspan": 1 } }, { "id": "p13.9.27", "order": 41, "type": "table_cell", "bbox": { "l": 271.84, "t": 590.48, "r": 306, "b": 575.56 }, "text": "3.40 q", "attrs": { "row": 4, "col": 2, "rowspan": 1, "colspan": 1 } }, { "id": "p13.9.28", "order": 42, "type": "table_cell", "bbox": { "l": 306, "t": 590.48, "r": 340.16, "b": 575.56 }, "text": "3.80 q", "attrs": { "row": 4, "col": 3, "rowspan": 1, "colspan": 1 } }, { "id": "p13.9.29", "order": 43, "type": "table_cell", "bbox": { "l": 340.16, "t": 590.48, "r": 374.32, "b": 575.56 }, "text": "3.80 q", "attrs": { "row": 4, "col": 4, "rowspan": 1, "colspan": 1 } }, { "id": "p13.9.30", "order": 44, "type": "table_cell", "bbox": { "l": 374.32, "t": 590.48, "r": 408.48, "b": 575.56 }, "text": "3.40 q", "attrs": { "row": 4, "col": 5, "rowspan": 1, "colspan": 1 } }, { "id": "p13.9.31", "order": 45, "type": "table_cell", "bbox": { "l": 203.52, "t": 575.56, "r": 237.68, "b": 560.64 }, "text": "¹³C ( δ)", "attrs": { "row": 5, "col": 0, "rowspan": 1, "colspan": 1 } }, { "id": "p13.9.32", "order": 46, "type": "table_cell", "bbox": { "l": 237.68, "t": 575.56, "r": 271.84, "b": 560.64 }, "text": "71.86", "attrs": { "row": 5, "col": 1, "rowspan": 1, "colspan": 1 } }, { "id": "p13.9.33", "order": 47, "type": "table_cell", "bbox": { "l": 271.84, "t": 575.56, "r": 306, "b": 560.64 }, "text": "74.00", "attrs": { "row": 5, "col": 2, "rowspan": 1, "colspan": 1 } }, { "id": "p13.9.34", "order": 48, "type": "table_cell", "bbox": { "l": 306, "t": 575.56, "r": 340.16, "b": 560.64 }, "text": "82.64", "attrs": { "row": 5, "col": 3, "rowspan": 1, "colspan": 1 } }, { "id": "p13.9.35", "order": 49, "type": "table_cell", "bbox": { "l": 340.16, "t": 575.56, "r": 374.32, "b": 560.64 }, "text": "82.57", "attrs": { "row": 5, "col": 4, "rowspan": 1, "colspan": 1 } }, { "id": "p13.9.36", "order": 50, "type": "table_cell", "bbox": { "l": 374.32, "t": 575.56, "r": 408.48, "b": 560.64 }, "text": "74.06", "attrs": { "row": 5, "col": 5, "rowspan": 1, "colspan": 1 } } ] }, { "id": "p13.10", "order": 51, "type": "text", "bbox": { "l": 57.6, "t": 608.88, "r": 195.12, "b": 599.28 }, "text": "17. (2,4-trans)-annomontacinone" }, { "id": "p13.11", "order": 52, "type": "text", "bbox": { "l": 58.56, "t": 559.44, "r": 514.32, "b": 512.16 }, "text": "Whitish wax.[p13.11.1]: +13.6° (c 0.022, CHCl_{3}). IR ([p13.11.2], film, cm^{-1}): 3433, 2920, 2850, 1754, 1717, 1550, 1460, 1182, 1075, 727 NMR: [p13.11.3]H NMR (500 MHz, CDCl_{3}), [p13.11.4]C NMR (125 MHz, CDCl_{3}). Derivatives: peracetate (^{1}H NMR), per-MTPA esters (^{1}H NMR), formal acetal (^{1}H NMR), TMS (EIMS). Biological activities ( [p13.11.5]g/mL): BST LC[p13.11.6] 3.1[p13.11.7] 10^{-1}, A-549 ED[p13.11.8] 2.6, MCF-7 ED[p13.11.9] 3.2, HT-29 ED[p13.11.10] 2.6[p13.11.11] 10^{-1}, A-498 ED[p13.11.12] 1.4, PC-3 ED[p13.11.13] 1.0, PAC-2 ED[p13.11.14] 6.8[p13.11.15] 10^{-1}. Source: Goniothalamus giganteus, stem bark.", "children": [ { "id": "p13.11.1", "order": 53, "type": "formula", "bbox": { "l": 58.56, "t": 559.44, "r": 514.32, "b": 512.16 }, "text": "[\\alpha]_{D}", "attrs": { "latex": "[\\alpha]_{D}", "inline": true, "text_offset": 12, "text_span": 10, "bbox_estimated": true, "notation": "latex", "alt": "alpha sub D", "mathml": "[α]D" } }, { "id": "p13.11.2", "order": 54, "type": "text", "bbox": { "l": 58.56, "t": 559.44, "r": 514.32, "b": 512.16 }, "text": "\\nu_{max}", "attrs": { "inline": true, "text_offset": 56, "text_span": 10, "bbox_estimated": true } }, { "id": "p13.11.3", "order": 55, "type": "text", "bbox": { "l": 58.56, "t": 559.44, "r": 514.32, "b": 512.16 }, "text": "¹", "attrs": { "inline": true, "text_offset": 147, "text_span": 10, "bbox_estimated": true } }, { "id": "p13.11.4", "order": 56, "type": "text", "bbox": { "l": 58.56, "t": 559.44, "r": 514.32, "b": 512.16 }, "text": "¹³", "attrs": { "inline": true, "text_offset": 184, "text_span": 10, "bbox_estimated": true } }, { "id": "p13.11.5", "order": 57, "type": "text", "bbox": { "l": 58.56, "t": 559.44, "r": 514.32, "b": 512.16 }, "text": "μ", "attrs": { "inline": true, "text_offset": 350, "text_span": 10, "bbox_estimated": true } }, { "id": "p13.11.6", "order": 58, "type": "text", "bbox": { "l": 58.56, "t": 559.44, "r": 514.32, "b": 512.16 }, "text": "₅₀", "attrs": { "inline": true, "text_offset": 373, "text_span": 10, "bbox_estimated": true } }, { "id": "p13.11.7", "order": 59, "type": "text", "bbox": { "l": 58.56, "t": 559.44, "r": 514.32, "b": 512.16 }, "text": "×", "attrs": { "inline": true, "text_offset": 387, "text_span": 10, "bbox_estimated": true } }, { "id": "p13.11.8", "order": 60, "type": "text", "bbox": { "l": 58.56, "t": 559.44, "r": 514.32, "b": 512.16 }, "text": "₅₀", "attrs": { "inline": true, "text_offset": 415, "text_span": 10, "bbox_estimated": true } }, { "id": "p13.11.9", "order": 61, "type": "text", "bbox": { "l": 58.56, "t": 559.44, "r": 514.32, "b": 512.16 }, "text": "₅₀", "attrs": { "inline": true, "text_offset": 439, "text_span": 10, "bbox_estimated": true } }, { "id": "p13.11.10", "order": 62, "type": "text", "bbox": { "l": 58.56, "t": 559.44, "r": 514.32, "b": 512.16 }, "text": "₅₀", "attrs": { "inline": true, "text_offset": 463, "text_span": 11, "bbox_estimated": true } }, { "id": "p13.11.11", "order": 63, "type": "text", "bbox": { "l": 58.56, "t": 559.44, "r": 514.32, "b": 512.16 }, "text": "×", "attrs": { "inline": true, "text_offset": 478, "text_span": 11, "bbox_estimated": true } }, { "id": "p13.11.12", "order": 64, "type": "text", "bbox": { "l": 58.56, "t": 559.44, "r": 514.32, "b": 512.16 }, "text": "₅₀", "attrs": { "inline": true, "text_offset": 507, "text_span": 11, "bbox_estimated": true } }, { "id": "p13.11.13", "order": 65, "type": "text", "bbox": { "l": 58.56, "t": 559.44, "r": 514.32, "b": 512.16 }, "text": "₅₀", "attrs": { "inline": true, "text_offset": 531, "text_span": 11, "bbox_estimated": true } }, { "id": "p13.11.14", "order": 66, "type": "text", "bbox": { "l": 58.56, "t": 559.44, "r": 514.32, "b": 512.16 }, "text": "₅₀", "attrs": { "inline": true, "text_offset": 556, "text_span": 11, "bbox_estimated": true } }, { "id": "p13.11.15", "order": 67, "type": "text", "bbox": { "l": 58.56, "t": 559.44, "r": 514.32, "b": 512.16 }, "text": "×", "attrs": { "inline": true, "text_offset": 571, "text_span": 11, "bbox_estimated": true } } ] }, { "id": "p13.12", "order": 68, "type": "text", "bbox": { "l": 57.84, "t": 511.68, "r": 220.8, "b": 501.36 }, "text": "18. muricoreacin[p13.12.1] (C [p13.12.2]H [p13.12.3]O[p13.12.4], MW628)", "children": [ { "id": "p13.12.1", "order": 69, "type": "text", "bbox": { "l": 57.84, "t": 511.68, "r": 220.8, "b": 501.36 }, "text": "¹¹⁰", "attrs": { "inline": true, "text_offset": 16, "text_span": 10, "bbox_estimated": true } }, { "id": "p13.12.2", "order": 70, "type": "text", "bbox": { "l": 57.84, "t": 511.68, "r": 220.8, "b": 501.36 }, "text": "₃₅", "attrs": { "inline": true, "text_offset": 30, "text_span": 10, "bbox_estimated": true } }, { "id": "p13.12.3", "order": 71, "type": "text", "bbox": { "l": 57.84, "t": 511.68, "r": 220.8, "b": 501.36 }, "text": "₆₄", "attrs": { "inline": true, "text_offset": 42, "text_span": 10, "bbox_estimated": true } }, { "id": "p13.12.4", "order": 72, "type": "text", "bbox": { "l": 57.84, "t": 511.68, "r": 220.8, "b": 501.36 }, "text": "₉", "attrs": { "inline": true, "text_offset": 53, "text_span": 10, "bbox_estimated": true } } ] }, { "id": "p13.13", "order": 73, "type": "formula", "bbox": { "l": 156.96, "t": 499.44, "r": 452.64, "b": 404.4 }, "text": "", "attrs": { "block_label": "image", "alt": "Skeletal structure of a polyhydroxylated acetogenin-type butenolide with a THF ring, hydroxyls at C-4, 8, 10, 12, 15, 19, 20…", "source": "vision" } }, { "id": "p13.14", "order": 74, "type": "table", "bbox": { "l": 133.408487, "t": 441.36, "r": 430.08, "b": 391.432892 }, "text": "", "attrs": { "block_label": "table", "n_rows": 3, "n_cols": 8, "integrity": { "cells_checked": 24, "cells_flagged": 23, "flags": [ { "row": 0, "col": 0, "coverage": 0, "text": "Position" }, { "row": 0, "col": 1, "coverage": 0, "text": "8" }, { "row": 0, "col": 2, "coverage": 0, "text": "10" }, { "row": 0, "col": 3, "coverage": 0, "text": "12" }, { "row": 0, "col": 4, "coverage": 0, "text": "15" }, { "row": 0, "col": 6, "coverage": 0, "text": "19" }, { "row": 0, "col": 7, "coverage": 0, "text": "20" }, { "row": 1, "col": 0, "coverage": 0, "text": "¹H ( \\delta )" }, { "row": 1, "col": 1, "coverage": 0, "text": "3.86 m" }, { "row": 1, "col": 2, "coverage": 0, "text": "4.06 m" }, { "row": 1, "col": 3, "coverage": 0, "text": "4.15 m" }, { "row": 1, "col": 4, "coverage": 0, "text": "3.90 m" } ] } }, "children": [ { "id": "p13.14.1", "order": 75, "type": "table_cell", "bbox": { "l": 157.68, "t": 441.36, "r": 191.73, "b": 429.28 }, "text": "Position", "attrs": { "row": 0, "col": 0, "rowspan": 1, "colspan": 1, "column_header": true, "header_source": "heuristic" } }, { "id": "p13.14.2", "order": 76, "type": "table_cell", "bbox": { "l": 191.73, "t": 441.36, "r": 225.78, "b": 429.28 }, "text": "8", "attrs": { "row": 0, "col": 1, "rowspan": 1, "colspan": 1, "column_header": true, "header_source": "heuristic" } }, { "id": "p13.14.3", "order": 77, "type": "table_cell", "bbox": { "l": 225.78, "t": 441.36, "r": 259.83, "b": 429.28 }, "text": "10", "attrs": { "row": 0, "col": 2, "rowspan": 1, "colspan": 1, "column_header": true, "header_source": "heuristic" } }, { "id": "p13.14.4", "order": 78, "type": "table_cell", "bbox": { "l": 259.83, "t": 441.36, "r": 293.88, "b": 429.28 }, "text": "12", "attrs": { "row": 0, "col": 3, "rowspan": 1, "colspan": 1, "column_header": true, "header_source": "heuristic" } }, { "id": "p13.14.5", "order": 79, "type": "table_cell", "bbox": { "l": 293.88, "t": 441.36, "r": 327.93, "b": 429.28 }, "text": "15", "attrs": { "row": 0, "col": 4, "rowspan": 1, "colspan": 1, "column_header": true, "header_source": "heuristic" } }, { "id": "p13.14.6", "order": 80, "type": "table_cell", "bbox": { "l": 133.408487, "t": 406.79499, "r": 147.68459, "b": 391.432892 }, "text": "16", "attrs": { "row": 0, "col": 5, "rowspan": 1, "colspan": 1, "bbox_refit": true, "column_header": true, "header_source": "heuristic" } }, { "id": "p13.14.7", "order": 81, "type": "table_cell", "bbox": { "l": 361.98, "t": 441.36, "r": 396.03, "b": 429.28 }, "text": "19", "attrs": { "row": 0, "col": 6, "rowspan": 1, "colspan": 1, "column_header": true, "header_source": "heuristic" } }, { "id": "p13.14.8", "order": 82, "type": "table_cell", "bbox": { "l": 396.03, "t": 441.36, "r": 430.08, "b": 429.28 }, "text": "20", "attrs": { "row": 0, "col": 7, "rowspan": 1, "colspan": 1, "column_header": true, "header_source": "heuristic" } }, { "id": "p13.14.9", "order": 83, "type": "table_cell", "bbox": { "l": 157.68, "t": 429.28, "r": 191.73, "b": 417.2 }, "text": "¹H ( \\delta )", "attrs": { "row": 1, "col": 0, "rowspan": 1, "colspan": 1 } }, { "id": "p13.14.10", "order": 84, "type": "table_cell", "bbox": { "l": 191.73, "t": 429.28, "r": 225.78, "b": 417.2 }, "text": "3.86 m", "attrs": { "row": 1, "col": 1, "rowspan": 1, "colspan": 1 } }, { "id": "p13.14.11", "order": 85, "type": "table_cell", "bbox": { "l": 225.78, "t": 429.28, "r": 259.83, "b": 417.2 }, "text": "4.06 m", "attrs": { "row": 1, "col": 2, "rowspan": 1, "colspan": 1 } }, { "id": "p13.14.12", "order": 86, "type": "table_cell", "bbox": { "l": 259.83, "t": 429.28, "r": 293.88, "b": 417.2 }, "text": "4.15 m", "attrs": { "row": 1, "col": 3, "rowspan": 1, "colspan": 1 } }, { "id": "p13.14.13", "order": 87, "type": "table_cell", "bbox": { "l": 293.88, "t": 429.28, "r": 327.93, "b": 417.2 }, "text": "3.90 m", "attrs": { "row": 1, "col": 4, "rowspan": 1, "colspan": 1 } }, { "id": "p13.14.14", "order": 88, "type": "table_cell", "bbox": { "l": 327.93, "t": 429.28, "r": 361.98, "b": 417.2 }, "text": "3.49 m", "attrs": { "row": 1, "col": 5, "rowspan": 1, "colspan": 1 } }, { "id": "p13.14.15", "order": 89, "type": "table_cell", "bbox": { "l": 361.98, "t": 429.28, "r": 396.03, "b": 417.2 }, "text": "3.59 m", "attrs": { "row": 1, "col": 6, "rowspan": 1, "colspan": 1 } }, { "id": "p13.14.16", "order": 90, "type": "table_cell", "bbox": { "l": 396.03, "t": 429.28, "r": 430.08, "b": 417.2 }, "text": "3.59 m", "attrs": { "row": 1, "col": 7, "rowspan": 1, "colspan": 1 } }, { "id": "p13.14.17", "order": 91, "type": "table_cell", "bbox": { "l": 157.68, "t": 417.2, "r": 191.73, "b": 405.12 }, "text": "¹³C ( \\delta )", "attrs": { "row": 2, "col": 0, "rowspan": 1, "colspan": 1 } }, { "id": "p13.14.18", "order": 92, "type": "table_cell", "bbox": { "l": 191.73, "t": 417.2, "r": 225.78, "b": 405.12 }, "text": "71.6", "attrs": { "row": 2, "col": 1, "rowspan": 1, "colspan": 1 } }, { "id": "p13.14.19", "order": 93, "type": "table_cell", "bbox": { "l": 225.78, "t": 417.2, "r": 259.83, "b": 405.12 }, "text": "72.2", "attrs": { "row": 2, "col": 2, "rowspan": 1, "colspan": 1 } }, { "id": "p13.14.20", "order": 94, "type": "table_cell", "bbox": { "l": 259.83, "t": 417.2, "r": 293.88, "b": 405.12 }, "text": "79.1", "attrs": { "row": 2, "col": 3, "rowspan": 1, "colspan": 1 } }, { "id": "p13.14.21", "order": 95, "type": "table_cell", "bbox": { "l": 293.88, "t": 417.2, "r": 327.93, "b": 405.12 }, "text": "82.3", "attrs": { "row": 2, "col": 4, "rowspan": 1, "colspan": 1 } }, { "id": "p13.14.22", "order": 96, "type": "table_cell", "bbox": { "l": 327.93, "t": 417.2, "r": 361.98, "b": 405.12 }, "text": "73.8", "attrs": { "row": 2, "col": 5, "rowspan": 1, "colspan": 1 } }, { "id": "p13.14.23", "order": 97, "type": "table_cell", "bbox": { "l": 361.98, "t": 417.2, "r": 396.03, "b": 405.12 }, "text": "74.8", "attrs": { "row": 2, "col": 6, "rowspan": 1, "colspan": 1 } }, { "id": "p13.14.24", "order": 98, "type": "table_cell", "bbox": { "l": 396.03, "t": 417.2, "r": 430.08, "b": 405.12 }, "text": "74.6", "attrs": { "row": 2, "col": 7, "rowspan": 1, "colspan": 1 } } ] }, { "id": "p13.15", "order": 99, "type": "text", "bbox": { "l": 58.56, "t": 402.72, "r": 552.96, "b": 357.84 }, "text": "White solid.[p13.15.1]: +1.6° (c 0.06, CHCl_{3}). UV ([p13.15.2], MeOH, nm): 220 (log[p13.15.3] 3.65). IR ([p13.15.4], film, cm^{-1}): 3347, 2916, 2849, 1743, 1470. MS: EIMS m/z 429, 411, 393, 375, 357, 341, 339, 323, 305, 287, 269, 257, 251, 239, 221, 213, 203, 199, 195, 181, 177, 141, 123. NMR: ^1H NMR (500 MHz, CDCl_{3}), ^13C NMR (125 MHz, CDCl_{3}). Biological activities ( [p13.15.5]g/mL): BST LC[p13.15.6] 19, A-549 ED[p13.15.7] 2.3[p13.15.8] 10[p13.15.9], MCF-7 ED[p13.15.10] 1.3, HT-29 ED[p13.15.11] 5.7[p13.15.12] 10[p13.15.13], A-498 ED[p13.15.14] 7.1[p13.15.15] 10[p13.15.16], PC-3 ED[p13.15.17] 2.5[p13.15.18] 10[p13.15.19], PAC-2 ED[p13.15.20] 2.3 Source: Annona muricata, leaves.", "children": [ { "id": "p13.15.1", "order": 100, "type": "formula", "bbox": { "l": 58.56, "t": 402.72, "r": 552.96, "b": 357.84 }, "text": "\\text{White solid. } [\\alpha]_{D}: +1.6^\\circ \\; (c\\,0.06, \\text{CHCl}_3). \\text{UV } (\\lambda_{\\max}, \\text{MeOH, nm}): 220 (\\log \\epsilon\\, 3.65). \\text{IR } (\\nu_{\\max}, \\text{film, cm}^{-1}): 3347, 2916, 2849, 1743, 1470.\\\\ \\text{MS: EIMS } m/z\\; 429, 411, 393, 375, 357, 341, 339, 323, 305, 287, 269, 257, 251, 239, 221, 213, 203, 199, 195, 181, 177, 141, 123.\\\\ \\text{NMR: }{}^{1}\\text{H NMR (500 MHz, CDCl}_3), {}^{13}\\text{C NMR (125 MHz, CDCl}_3). \\text{Biological activities } (\\mu\\text{g/mL}): \\text{BST LC}_{50}\\,19, \\text{A-549 ED}_{50}\\,2.3\\times 10^{-1}, \\text{MCF-7 ED}_{50}\\,1.3, \\text{HT-29 ED}_{50}\\,5.7\\times 10^{-1}, \\text{A-498 ED}_{50}\\,7.1\\times 10^{-1}, \\text{PC-3 ED}_{50}\\,2.5\\times 10^{-2}, \\text{PACA-2 ED}_{50}\\,2.3. \\text{Source: } \\textit{Annona muricata}\\text{, leaves.}", "attrs": { "latex": "\\text{White solid. } [\\alpha]_{D}: +1.6^\\circ \\; (c\\,0.06, \\text{CHCl}_3). \\text{UV } (\\lambda_{\\max}, \\text{MeOH, nm}): 220 (\\log \\epsilon\\, 3.65). \\text{IR } (\\nu_{\\max}, \\text{film, cm}^{-1}): 3347, 2916, 2849, 1743, 1470.\\\\ \\text{MS: EIMS } m/z\\; 429, 411, 393, 375, 357, 341, 339, 323, 305, 287, 269, 257, 251, 239, 221, 213, 203, 199, 195, 181, 177, 141, 123.\\\\ \\text{NMR: }{}^{1}\\text{H NMR (500 MHz, CDCl}_3), {}^{13}\\text{C NMR (125 MHz, CDCl}_3). \\text{Biological activities } (\\mu\\text{g/mL}): \\text{BST LC}_{50}\\,19, \\text{A-549 ED}_{50}\\,2.3\\times 10^{-1}, \\text{MCF-7 ED}_{50}\\,1.3, \\text{HT-29 ED}_{50}\\,5.7\\times 10^{-1}, \\text{A-498 ED}_{50}\\,7.1\\times 10^{-1}, \\text{PC-3 ED}_{50}\\,2.5\\times 10^{-2}, \\text{PACA-2 ED}_{50}\\,2.3. \\text{Source: } \\textit{Annona muricata}\\text{, leaves.}", "inline": true, "text_offset": 12, "text_span": 10, "bbox_estimated": true, "notation": "latex", "alt": "White solid. alpha sub D : plus 1.6 to the power of circ ; c, 0.06, CHCl sub 3 . UV of lambda sub max, MeOH, nm : 220 times log epsilon, 3.65 . IR of nu sub max, film, cm to the power of minus 1 : 3347, 2916, 2849, 1743, 1470. MS: EIMS m over z ; 429, 411, 393, 375, 357, 341, 339, 323, 305, 287, 269, 257, 251, 239, 221, 213, 203, 199, 195, 181, 177, 141, 123. 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 . Biological activities of mu g over mL : BST LC sub 50, 19, A minus 549 ED sub 50, 2.3 times 10 to the power of minus 1, MCF minus 7 ED sub 50, 1.3, HT minus 29 ED sub 50, 5.7 times 10 to the power of minus 1, A minus 498 ED sub 50, 7.1 times 10 to the power of minus 1, PC minus 3 ED sub 50, 2.5 times 10 to the power of minus 2, PACA minus 2 ED sub 50, 2.3. Source: textit Annona muricata, leaves.", "mathml": "White solid. [α]D:+1.6∘(c0.06,CHCl3).UV (λmax,MeOH, nm):220(logϵ3.65).IR (νmax,film, cm−1):3347,2916,2849,1743,1470.MS: EIMS m/z429,411,393,375,357,341,339,323,305,287,269,257,251,239,221,213,203,199,195,181,177,141,123.NMR: 1H NMR (500 MHz, CDCl3),13C NMR (125 MHz, CDCl3).Biological activities (μg/mL):BST LC5019,A-549 ED502.3×10−1,MCF-7 ED501.3,HT-29 ED505.7×10−1,A-498 ED507.1×10−1,PC-3 ED502.5×10−2,PACA-2 ED502.3.Source: Annona muricata, leaves." } }, { "id": "p13.15.2", "order": 101, "type": "formula", "bbox": { "l": 58.56, "t": 402.72, "r": 552.96, "b": 357.84 }, "text": "\\lambda_{max}", "attrs": { "latex": "\\lambda_{max}", "inline": true, "text_offset": 54, "text_span": 10, "bbox_estimated": true, "notation": "latex", "alt": "lambda sub max", "mathml": "λmax" } }, { "id": "p13.15.3", "order": 102, "type": "text", "bbox": { "l": 58.56, "t": 402.72, "r": 552.96, "b": 357.84 }, "text": "ε", "attrs": { "inline": true, "text_offset": 85, "text_span": 10, "bbox_estimated": true } }, { "id": "p13.15.4", "order": 103, "type": "formula", "bbox": { "l": 58.56, "t": 402.72, "r": 552.96, "b": 357.84 }, "text": "\\text{White solid. }[\\alpha]_D: +1.6^\\circ (c\\,0.06, \\text{CHCl}_3). \\text{UV} (\\lambda_{max}, \\text{MeOH, nm}): 220 (\\log \\epsilon\\, 3.65). \\text{IR} (\\nu_{max}, \\text{film, cm}^{-1}): 3347, 2916, 2849, 1743, 1470. \\text{MS: EIMS } m/z\\ 429, 411, 393, 375, 357, 341, 339, 323, 305, 287, 269, 257, 251, 239, 221, 213, 203, 199, 195, 181, 177, 141, 123. \\text{NMR: }{}^1\\text{H NMR (500 MHz, CDCl}_3), {}^{13}\\text{C NMR (125 MHz, CDCl}_3). \\text{Biological activities } (\\mu\\text{g/mL}): \\text{BST LC}_{50}\\, 19, \\text{A-549 ED}_{50}\\, 2.3\\times 10^{-1}, \\text{MCF-7 ED}_{50}\\, 1.3, \\text{HT-29 ED}_{50}\\, 5.7\\times 10^{-1}, \\text{A-498 ED}_{50}\\, 7.1\\times 10^{-1}, \\text{PC-3 ED}_{50}\\, 2.5\\times 10^{-2}, \\text{PACA-2 ED}_{50}\\, 2.3. \\text{Source: } \\textit{Annona muricata}, \\text{leaves}.", "attrs": { "latex": "\\text{White solid. }[\\alpha]_D: +1.6^\\circ (c\\,0.06, \\text{CHCl}_3). \\text{UV} (\\lambda_{max}, \\text{MeOH, nm}): 220 (\\log \\epsilon\\, 3.65). \\text{IR} (\\nu_{max}, \\text{film, cm}^{-1}): 3347, 2916, 2849, 1743, 1470. \\text{MS: EIMS } m/z\\ 429, 411, 393, 375, 357, 341, 339, 323, 305, 287, 269, 257, 251, 239, 221, 213, 203, 199, 195, 181, 177, 141, 123. \\text{NMR: }{}^1\\text{H NMR (500 MHz, CDCl}_3), {}^{13}\\text{C NMR (125 MHz, CDCl}_3). \\text{Biological activities } (\\mu\\text{g/mL}): \\text{BST LC}_{50}\\, 19, \\text{A-549 ED}_{50}\\, 2.3\\times 10^{-1}, \\text{MCF-7 ED}_{50}\\, 1.3, \\text{HT-29 ED}_{50}\\, 5.7\\times 10^{-1}, \\text{A-498 ED}_{50}\\, 7.1\\times 10^{-1}, \\text{PC-3 ED}_{50}\\, 2.5\\times 10^{-2}, \\text{PACA-2 ED}_{50}\\, 2.3. \\text{Source: } \\textit{Annona muricata}, \\text{leaves}.", "inline": true, "text_offset": 107, "text_span": 10, "bbox_estimated": true, "notation": "latex", "alt": "White solid. alpha sub D : plus 1.6 to the power of circ of c, 0.06, CHCl sub 3 . UV of lambda sub max, MeOH, nm : 220 times log epsilon, 3.65 . IR of nu sub max, film, cm to the power of minus 1 : 3347, 2916, 2849, 1743, 1470. MS: EIMS m over z 429, 411, 393, 375, 357, 341, 339, 323, 305, 287, 269, 257, 251, 239, 221, 213, 203, 199, 195, 181, 177, 141, 123. 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 . Biological activities of mu g over mL : BST LC sub 50, 19, A minus 549 ED sub 50, 2.3 times 10 to the power of minus 1, MCF minus 7 ED sub 50, 1.3, HT minus 29 ED sub 50, 5.7 times 10 to the power of minus 1, A minus 498 ED sub 50, 7.1 times 10 to the power of minus 1, PC minus 3 ED sub 50, 2.5 times 10 to the power of minus 2, PACA minus 2 ED sub 50, 2.3. Source: textit Annona muricata, leaves .", "mathml": "White solid. [α]D:+1.6∘(c0.06,CHCl3).UV(λmax,MeOH, nm):220(logϵ3.65).IR(νmax,film, cm−1):3347,2916,2849,1743,1470.MS: EIMS m/z 429,411,393,375,357,341,339,323,305,287,269,257,251,239,221,213,203,199,195,181,177,141,123.NMR: 1H NMR (500 MHz, CDCl3),13C NMR (125 MHz, CDCl3).Biological activities (μg/mL):BST LC5019,A-549 ED502.3×10−1,MCF-7 ED501.3,HT-29 ED505.7×10−1,A-498 ED507.1×10−1,PC-3 ED502.5×10−2,PACA-2 ED502.3.Source: Annona muricata,leaves." } }, { "id": "p13.15.5", "order": 104, "type": "text", "bbox": { "l": 58.56, "t": 402.72, "r": 552.96, "b": 357.84 }, "text": "μ", "attrs": { "inline": true, "text_offset": 381, "text_span": 10, "bbox_estimated": true } }, { "id": "p13.15.6", "order": 105, "type": "text", "bbox": { "l": 58.56, "t": 402.72, "r": 552.96, "b": 357.84 }, "text": "₅₀", "attrs": { "inline": true, "text_offset": 404, "text_span": 10, "bbox_estimated": true } }, { "id": "p13.15.7", "order": 106, "type": "text", "bbox": { "l": 58.56, "t": 402.72, "r": 552.96, "b": 357.84 }, "text": "₅₀", "attrs": { "inline": true, "text_offset": 427, "text_span": 10, "bbox_estimated": true } }, { "id": "p13.15.8", "order": 107, "type": "text", "bbox": { "l": 58.56, "t": 402.72, "r": 552.96, "b": 357.84 }, "text": "×", "attrs": { "inline": true, "text_offset": 441, "text_span": 10, "bbox_estimated": true } }, { "id": "p13.15.9", "order": 108, "type": "text", "bbox": { "l": 58.56, "t": 402.72, "r": 552.96, "b": 357.84 }, "text": "⁻¹", "attrs": { "inline": true, "text_offset": 454, "text_span": 10, "bbox_estimated": true } }, { "id": "p13.15.10", "order": 109, "type": "text", "bbox": { "l": 58.56, "t": 402.72, "r": 552.96, "b": 357.84 }, "text": "₅₀", "attrs": { "inline": true, "text_offset": 474, "text_span": 11, "bbox_estimated": true } }, { "id": "p13.15.11", "order": 110, "type": "text", "bbox": { "l": 58.56, "t": 402.72, "r": 552.96, "b": 357.84 }, "text": "₅₀", "attrs": { "inline": true, "text_offset": 499, "text_span": 11, "bbox_estimated": true } }, { "id": "p13.15.12", "order": 111, "type": "text", "bbox": { "l": 58.56, "t": 402.72, "r": 552.96, "b": 357.84 }, "text": "×", "attrs": { "inline": true, "text_offset": 514, "text_span": 11, "bbox_estimated": true } }, { "id": "p13.15.13", "order": 112, "type": "text", "bbox": { "l": 58.56, "t": 402.72, "r": 552.96, "b": 357.84 }, "text": "⁻¹", "attrs": { "inline": true, "text_offset": 528, "text_span": 11, "bbox_estimated": true } }, { "id": "p13.15.14", "order": 113, "type": "text", "bbox": { "l": 58.56, "t": 402.72, "r": 552.96, "b": 357.84 }, "text": "₅₀", "attrs": { "inline": true, "text_offset": 549, "text_span": 11, "bbox_estimated": true } }, { "id": "p13.15.15", "order": 114, "type": "text", "bbox": { "l": 58.56, "t": 402.72, "r": 552.96, "b": 357.84 }, "text": "×", "attrs": { "inline": true, "text_offset": 564, "text_span": 11, "bbox_estimated": true } }, { "id": "p13.15.16", "order": 115, "type": "text", "bbox": { "l": 58.56, "t": 402.72, "r": 552.96, "b": 357.84 }, "text": "⁻¹", "attrs": { "inline": true, "text_offset": 578, "text_span": 11, "bbox_estimated": true } }, { "id": "p13.15.17", "order": 116, "type": "text", "bbox": { "l": 58.56, "t": 402.72, "r": 552.96, "b": 357.84 }, "text": "₅₀", "attrs": { "inline": true, "text_offset": 598, "text_span": 11, "bbox_estimated": true } }, { "id": "p13.15.18", "order": 117, "type": "text", "bbox": { "l": 58.56, "t": 402.72, "r": 552.96, "b": 357.84 }, "text": "×", "attrs": { "inline": true, "text_offset": 613, "text_span": 11, "bbox_estimated": true } }, { "id": "p13.15.19", "order": 118, "type": "text", "bbox": { "l": 58.56, "t": 402.72, "r": 552.96, "b": 357.84 }, "text": "⁻²", "attrs": { "inline": true, "text_offset": 627, "text_span": 11, "bbox_estimated": true } }, { "id": "p13.15.20", "order": 119, "type": "text", "bbox": { "l": 58.56, "t": 402.72, "r": 552.96, "b": 357.84 }, "text": "₅₀", "attrs": { "inline": true, "text_offset": 648, "text_span": 11, "bbox_estimated": true } } ] }, { "id": "p13.16", "order": 120, "type": "text", "bbox": { "l": 58.56, "t": 355.92, "r": 217.44, "b": 346.32 }, "text": "19. murihexocin [p13.16.1](C [p13.16.2]H [p13.16.3]O[p13.16.4], MW628)", "children": [ { "id": "p13.16.1", "order": 121, "type": "text", "bbox": { "l": 58.56, "t": 355.92, "r": 217.44, "b": 346.32 }, "text": "^{*110}", "attrs": { "inline": true, "text_offset": 16, "text_span": 10, "bbox_estimated": true } }, { "id": "p13.16.2", "order": 122, "type": "text", "bbox": { "l": 58.56, "t": 355.92, "r": 217.44, "b": 346.32 }, "text": "₃₇", "attrs": { "inline": true, "text_offset": 29, "text_span": 10, "bbox_estimated": true } }, { "id": "p13.16.3", "order": 123, "type": "text", "bbox": { "l": 58.56, "t": 355.92, "r": 217.44, "b": 346.32 }, "text": "₆₈", "attrs": { "inline": true, "text_offset": 41, "text_span": 10, "bbox_estimated": true } }, { "id": "p13.16.4", "order": 124, "type": "text", "bbox": { "l": 58.56, "t": 355.92, "r": 217.44, "b": 346.32 }, "text": "₇", "attrs": { "inline": true, "text_offset": 52, "text_span": 10, "bbox_estimated": true } } ] }, { "id": "p13.17", "order": 125, "type": "formula", "bbox": { "l": 156.48, "t": 343.2, "r": 453.36, "b": 248.16 }, "text": "", "attrs": { "block_label": "image", "alt": "Bond-line structure of an annonaceous acetogenin-type butenolide with a THF ring, four hydroxyls, and a long alkyl chain, wi…", "source": "vision" } }, { "id": "p13.18", "order": 126, "type": "text", "bbox": { "l": 57.36, "t": 245.76, "r": 520.08, "b": 189.6 }, "text": "White solid.[p13.18.1]: +37.5° (c QO4, CHCl_{3}). UV ([p13.18.2], MeOH, nm): 220 ([p13.18.3] 3.69). IR ([p13.18.4], film, cm^{-1}): 3367, 2915, 2849, 1743, 1474. MS: EIMS m/z 429, 411, 393, 375, 357, 341, 339, 323, 305, 299, 287, 281, 269, 263, 251, 245, 211, 199, 193, 181, 163, 141, 123. NMR: [p13.18.5]H NMR (500MHz, CDCl_{3}), [p13.18.6]C NMR (125 MHz, CDCl_{3}). Biological activities ( [p13.18.7]g/mL): BST LC_{50} 10, A-549 ED_{50} 1.1, MCF-7 ED_{50} 3.8, HT-29 ED_{50} 1.3, A-498 ED_{50} 2.5, PC-3 ED_{50} 8.6 × 10^{-1}, PAC-2 ED_{50} 4.9 × 10^{-1}.\nSource: Annona muricata, leaves.\n20. glacin A^{25} (C_{35}H_{64}O_{7}, MW596)", "children": [ { "id": "p13.18.1", "order": 127, "type": "formula", "bbox": { "l": 57.36, "t": 245.76, "r": 520.08, "b": 189.6 }, "text": "[\\alpha]_{D}", "attrs": { "latex": "[\\alpha]_{D}", "inline": true, "text_offset": 12, "text_span": 10, "bbox_estimated": true, "notation": "latex", "alt": "alpha sub D", "mathml": "[α]D" } }, { "id": "p13.18.2", "order": 128, "type": "formula", "bbox": { "l": 57.36, "t": 245.76, "r": 520.08, "b": 189.6 }, "text": "\\text{White solid. }[\\alpha]_{D}: +37.5^\\circ\\ (c\\,0.04, \\text{CHCl}_3).\\ \\text{UV } (\\lambda_{max}, \\text{MeOH, nm}): 220\\ (\\log \\epsilon\\ 3.69).\\ \\text{IR } (\\nu_{max}, \\text{film, cm}^{-1}): 3367, 2915, 2849, 1743, 1474.\\ \\text{MS: EIMS } m/z\\ 429, 411, 393, 375, 357, 341, 339, 323, 305, 299, 287, 281, 269, 263, 251, 245, 211, 199, 193, 181, 163, 141, 123.\\ \\text{NMR: }{}^{1}\\text{H NMR (500 MHz, CDCl}_3), {}^{13}\\text{C NMR (125 MHz, CDCl}_3).\\ \\text{Biological activities } (\\mu\\text{g/mL}): \\text{BST LC}_{50}\\ 10,\\ \\text{A-549 ED}_{50}\\ 1.1,\\ \\text{MCF-7 ED}_{50}\\ 3.8,\\ \\text{HT-29 ED}_{50}\\ 1.3,\\ \\text{A-498 ED}_{50}\\ 2.5,\\ \\text{PC-3 ED}_{50}\\ 8.6\\times 10^{-1},\\ \\text{PACA-2 ED}_{50}\\ 4.9\\times 10^{-1}.\\ \\text{Source: }\\textit{Annona muricata}\\text{, leaves.}\\ \\textbf{20. glacin A}^{25}\\ (\\text{C}_{35}\\text{H}_{64}\\text{O}_{7}, \\text{MW }596)", "attrs": { "latex": "\\text{White solid. }[\\alpha]_{D}: +37.5^\\circ\\ (c\\,0.04, \\text{CHCl}_3).\\ \\text{UV } (\\lambda_{max}, \\text{MeOH, nm}): 220\\ (\\log \\epsilon\\ 3.69).\\ \\text{IR } (\\nu_{max}, \\text{film, cm}^{-1}): 3367, 2915, 2849, 1743, 1474.\\ \\text{MS: EIMS } m/z\\ 429, 411, 393, 375, 357, 341, 339, 323, 305, 299, 287, 281, 269, 263, 251, 245, 211, 199, 193, 181, 163, 141, 123.\\ \\text{NMR: }{}^{1}\\text{H NMR (500 MHz, CDCl}_3), {}^{13}\\text{C NMR (125 MHz, CDCl}_3).\\ \\text{Biological activities } (\\mu\\text{g/mL}): \\text{BST LC}_{50}\\ 10,\\ \\text{A-549 ED}_{50}\\ 1.1,\\ \\text{MCF-7 ED}_{50}\\ 3.8,\\ \\text{HT-29 ED}_{50}\\ 1.3,\\ \\text{A-498 ED}_{50}\\ 2.5,\\ \\text{PC-3 ED}_{50}\\ 8.6\\times 10^{-1},\\ \\text{PACA-2 ED}_{50}\\ 4.9\\times 10^{-1}.\\ \\text{Source: }\\textit{Annona muricata}\\text{, leaves.}\\ \\textbf{20. glacin A}^{25}\\ (\\text{C}_{35}\\text{H}_{64}\\text{O}_{7}, \\text{MW }596)", "inline": true, "text_offset": 54, "text_span": 10, "bbox_estimated": true, "notation": "latex", "alt": "White solid. alpha sub D : plus 37.5 to the power of circ of c, 0.04, CHCl sub 3 . UV of lambda sub max, MeOH, nm : 220 times log epsilon 3.69 . IR of nu sub max, film, cm to the power of minus 1 : 3367, 2915, 2849, 1743, 1474. MS: EIMS m over z 429, 411, 393, 375, 357, 341, 339, 323, 305, 299, 287, 281, 269, 263, 251, 245, 211, 199, 193, 181, 163, 141, 123. 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 . Biological activities of mu g over mL : BST LC sub 50 10, A minus 549 ED sub 50 1.1, MCF minus 7 ED sub 50 3.8, HT minus 29 ED sub 50 1.3, A minus 498 ED sub 50 2.5, PC minus 3 ED sub 50 8.6 times 10 to the power of minus 1, PACA minus 2 ED sub 50 4.9 times 10 to the power of minus 1 . Source: textit Annona muricata, leaves. textbf 20. glacin A to the power of 25 times C sub 35 H sub 64 O sub 7, MW 596", "mathml": "White solid. [α]D:+37.5∘ (c0.04,CHCl3). UV (λmax,MeOH, nm):220 (logϵ 3.69). IR (νmax,film, cm−1):3367,2915,2849,1743,1474. MS: EIMS m/z 429,411,393,375,357,341,339,323,305,299,287,281,269,263,251,245,211,199,193,181,163,141,123. NMR: 1H NMR (500 MHz, CDCl3),13C NMR (125 MHz, CDCl3). Biological activities (μg/mL):BST LC50 10, A-549 ED50 1.1, MCF-7 ED50 3.8, HT-29 ED50 1.3, A-498 ED50 2.5, PC-3 ED50 8.6×10−1, PACA-2 ED50 4.9×10−1. Source: Annona muricata, leaves. 20. glacin A25 (C35H64O7,MW 596)" } }, { "id": "p13.18.3", "order": 129, "type": "text", "bbox": { "l": 57.36, "t": 245.76, "r": 520.08, "b": 189.6 }, "text": "\\log \\epsilon", "attrs": { "inline": true, "text_offset": 82, "text_span": 10, "bbox_estimated": true } }, { "id": "p13.18.4", "order": 130, "type": "formula", "bbox": { "l": 57.36, "t": 245.76, "r": 520.08, "b": 189.6 }, "text": "\\nu_{max}", "attrs": { "latex": "\\nu_{max}", "inline": true, "text_offset": 104, "text_span": 10, "bbox_estimated": true, "notation": "latex", "alt": "nu sub max", "mathml": "νmax" } }, { "id": "p13.18.5", "order": 131, "type": "text", "bbox": { "l": 57.36, "t": 245.76, "r": 520.08, "b": 189.6 }, "text": "¹", "attrs": { "inline": true, "text_offset": 295, "text_span": 10, "bbox_estimated": true } }, { "id": "p13.18.6", "order": 132, "type": "text", "bbox": { "l": 57.36, "t": 245.76, "r": 520.08, "b": 189.6 }, "text": "¹³", "attrs": { "inline": true, "text_offset": 331, "text_span": 10, "bbox_estimated": true } }, { "id": "p13.18.7", "order": 133, "type": "text", "bbox": { "l": 57.36, "t": 245.76, "r": 520.08, "b": 189.6 }, "text": "μ", "attrs": { "inline": true, "text_offset": 392, "text_span": 10, "bbox_estimated": true } } ] }, { "id": "p13.19", "order": 134, "type": "formula", "bbox": { "l": 159.12, "t": 182.4, "r": 451.92, "b": 140.4 }, "text": "", "attrs": { "block_label": "image", "alt": "Skeletal structure of an annonaceous acetogenin: butenolide ring linked to a chain with hydroxyls at C-4, C-12, C-17, C-22 a…", "source": "vision" } }, { "id": "p13.20", "order": 135, "type": "table", "bbox": { "l": 158.16, "t": 130.32, "r": 357.84, "b": 94.56 }, "text": "", "attrs": { "block_label": "table", "n_rows": 3, "n_cols": 6, "integrity": { "skipped": "no_text_layer" } }, "children": [ { "id": "p13.20.1", "order": 136, "type": "table_cell", "bbox": { "l": 158.16, "t": 130.32, "r": 191.44, "b": 118.4 }, "text": "Position", "attrs": { "row": 0, "col": 0, "rowspan": 1, "colspan": 1, "column_header": true, "header_source": "heuristic" } }, { "id": "p13.20.2", "order": 137, "type": "table_cell", "bbox": { "l": 191.44, "t": 130.32, "r": 224.72, "b": 118.4 }, "text": "12", "attrs": { "row": 0, "col": 1, "rowspan": 1, "colspan": 1, "column_header": true, "header_source": "heuristic" } }, { "id": "p13.20.3", "order": 138, "type": "table_cell", "bbox": { "l": 224.72, "t": 130.32, "r": 258, "b": 118.4 }, "text": "17", "attrs": { "row": 0, "col": 2, "rowspan": 1, "colspan": 1, "column_header": true, "header_source": "heuristic" } }, { "id": "p13.20.4", "order": 139, "type": "table_cell", "bbox": { "l": 258, "t": 130.32, "r": 291.28, "b": 118.4 }, "text": "18", "attrs": { "row": 0, "col": 3, "rowspan": 1, "colspan": 1, "column_header": true, "header_source": "heuristic" } }, { "id": "p13.20.5", "order": 140, "type": "table_cell", "bbox": { "l": 291.28, "t": 130.32, "r": 324.56, "b": 118.4 }, "text": "21", "attrs": { "row": 0, "col": 4, "rowspan": 1, "colspan": 1, "column_header": true, "header_source": "heuristic" } }, { "id": "p13.20.6", "order": 141, "type": "table_cell", "bbox": { "l": 324.56, "t": 130.32, "r": 357.84, "b": 118.4 }, "text": "22", "attrs": { "row": 0, "col": 5, "rowspan": 1, "colspan": 1, "column_header": true, "header_source": "heuristic" } }, { "id": "p13.20.7", "order": 142, "type": "table_cell", "bbox": { "l": 158.16, "t": 118.4, "r": 191.44, "b": 106.48 }, "text": "¹H ( δ)", "attrs": { "row": 1, "col": 0, "rowspan": 1, "colspan": 1 } }, { "id": "p13.20.8", "order": 143, "type": "table_cell", "bbox": { "l": 191.44, "t": 118.4, "r": 224.72, "b": 106.48 }, "text": "3.60 m", "attrs": { "row": 1, "col": 1, "rowspan": 1, "colspan": 1 } }, { "id": "p13.20.9", "order": 144, "type": "table_cell", "bbox": { "l": 224.72, "t": 118.4, "r": 258, "b": 106.48 }, "text": "3.41 m", "attrs": { "row": 1, "col": 2, "rowspan": 1, "colspan": 1 } }, { "id": "p13.20.10", "order": 145, "type": "table_cell", "bbox": { "l": 258, "t": 118.4, "r": 291.28, "b": 106.48 }, "text": "3.80 m", "attrs": { "row": 1, "col": 3, "rowspan": 1, "colspan": 1 } }, { "id": "p13.20.11", "order": 146, "type": "table_cell", "bbox": { "l": 291.28, "t": 118.4, "r": 324.56, "b": 106.48 }, "text": "3.80 m", "attrs": { "row": 1, "col": 4, "rowspan": 1, "colspan": 1 } }, { "id": "p13.20.12", "order": 147, "type": "table_cell", "bbox": { "l": 324.56, "t": 118.4, "r": 357.84, "b": 106.48 }, "text": "3.41 m", "attrs": { "row": 1, "col": 5, "rowspan": 1, "colspan": 1 } }, { "id": "p13.20.13", "order": 148, "type": "table_cell", "bbox": { "l": 158.16, "t": 106.48, "r": 191.44, "b": 94.56 }, "text": "¹³C ( δ)", "attrs": { "row": 2, "col": 0, "rowspan": 1, "colspan": 1 } }, { "id": "p13.20.14", "order": 149, "type": "table_cell", "bbox": { "l": 191.44, "t": 106.48, "r": 224.72, "b": 94.56 }, "text": "71.82", "attrs": { "row": 2, "col": 1, "rowspan": 1, "colspan": 1 } }, { "id": "p13.20.15", "order": 150, "type": "table_cell", "bbox": { "l": 224.72, "t": 106.48, "r": 258, "b": 94.56 }, "text": "74.07", "attrs": { "row": 2, "col": 2, "rowspan": 1, "colspan": 1 } }, { "id": "p13.20.16", "order": 151, "type": "table_cell", "bbox": { "l": 258, "t": 106.48, "r": 291.28, "b": 94.56 }, "text": "82.65", "attrs": { "row": 2, "col": 3, "rowspan": 1, "colspan": 1 } }, { "id": "p13.20.17", "order": 152, "type": "table_cell", "bbox": { "l": 291.28, "t": 106.48, "r": 324.56, "b": 94.56 }, "text": "82.59", "attrs": { "row": 2, "col": 4, "rowspan": 1, "colspan": 1 } }, { "id": "p13.20.18", "order": 153, "type": "table_cell", "bbox": { "l": 324.56, "t": 106.48, "r": 357.84, "b": 94.56 }, "text": "73.98", "attrs": { "row": 2, "col": 5, "rowspan": 1, "colspan": 1 } } ] }, { "id": "p13.21", "order": 154, "type": "text", "bbox": { "l": 58.32, "t": 91.68, "r": 535.68, "b": 45.84 }, "text": "Whitish waxy solid.[p13.21.1]: +6.0° (CHCl₃). UV ([p13.21.2], MeOH, nm): 218 (log[p13.21.3] 3.83). IR ([p13.21.4], film, cm[p13.21.5]): 3461, 2919, 2851, 1734, 1717, 1464, 1318, 1203, 1075. MS: EIMS m/z 425, 407, 355, 337, 319, 301, 269, 251, 241, 233, 223, 171, 141. NMR: [p13.21.6]H NMR (500 MHz, CDCl₃), {}^{13}C NMR (125 MHz, CDCl₃). Derivatives: per-MTPA esters (¹H NMR). Biological activities [p13.21.7]g/mL): BST LC[p13.21.8] 1.1[p13.21.9] 10[p13.21.10], A-549 ED[p13.21.11] 1.5, MCF-7 ED[p13.21.12] 4.4[p13.21.13] 10[p13.21.14], HT-29 ED[p13.21.15] 2.3, A-498 ED[p13.21.16] 1.3, PC-3 ED[p13.21.17] 9.8[p13.21.18] 10[p13.21.19], PAC-2 ED[p13.21.20] 8.6[p13.21.21] 10[p13.21.22]. Source: Annona glabra, leaves.", "children": [ { "id": "p13.21.1", "order": 155, "type": "formula", "bbox": { "l": 58.32, "t": 91.68, "r": 535.68, "b": 45.84 }, "text": "[\\alpha]_{D}", "attrs": { "latex": "[\\alpha]_{D}", "inline": true, "text_offset": 19, "text_span": 10, "bbox_estimated": true, "notation": "latex", "alt": "alpha sub D", "mathml": "[α]D" } }, { "id": "p13.21.2", "order": 156, "type": "text", "bbox": { "l": 58.32, "t": 91.68, "r": 535.68, "b": 45.84 }, "text": "\\lambda_{max}", "attrs": { "inline": true, "text_offset": 50, "text_span": 10, "bbox_estimated": true } }, { "id": "p13.21.3", "order": 157, "type": "text", "bbox": { "l": 58.32, "t": 91.68, "r": 535.68, "b": 45.84 }, "text": "ε", "attrs": { "inline": true, "text_offset": 81, "text_span": 10, "bbox_estimated": true } }, { "id": "p13.21.4", "order": 158, "type": "text", "bbox": { "l": 58.32, "t": 91.68, "r": 535.68, "b": 45.84 }, "text": "\\nu_{max}", "attrs": { "inline": true, "text_offset": 103, "text_span": 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