{ "document_id": 14408, "page": 16, "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": 151, "counts_by_type": { "formula": 26, "header": 2, "heading": 2, "table": 2, "table_cell": 45, "text": 74 }, "build_ms": 20, "items": [ { "id": "p16.1", "order": 1, "type": "header", "bbox": { "l": 53.76, "t": 765.84, "r": 112.08, "b": 756.24 }, "text": "Invited Review", "attrs": { "block_label": "header" }, "level": 2 }, { "id": "p16.2", "order": 2, "type": "header", "bbox": { "l": 349.92, "t": 766.08, "r": 559.2, "b": 756.24 }, "text": "Journal of Natural Products, 1999, Vol. 62, No. 3 519", "attrs": { "block_label": "header" }, "level": 2 }, { "id": "p16.3", "order": 3, "type": "heading", "bbox": { "l": 53.52, "t": 746.16, "r": 142.8, "b": 736.08 }, "text": "Table 4. (Continued)", "attrs": { "block_label": "paragraph_title" }, "level": 3 }, { "id": "p16.4", "order": 4, "type": "text", "bbox": { "l": 71.52, "t": 721.92, "r": 171.84, "b": 712.56 }, "text": "33. 34-epi-donnaienin C" }, { "id": "p16.5", "order": 5, "type": "heading", "bbox": { "l": 237.6, "t": 732.48, "r": 373.92, "b": 723.12 }, "text": "Mono-THF Acetogenins (Continued)", "attrs": { "block_label": "paragraph_title" }, "level": 3 }, { "id": "p16.6", "order": 6, "type": "table", "bbox": { "l": 173.52, "t": 709.92, "r": 438.96, "b": 674.64 }, "text": "", "attrs": { "block_label": "table", "n_rows": 3, "n_cols": 8, "integrity": { "skipped": "no_text_layer" } }, "children": [ { "id": "p16.6.1", "order": 7, "type": "table_cell", "bbox": { "l": 173.52, "t": 709.92, "r": 206.7, "b": 698.16 }, "text": "Position", "attrs": { "row": 0, "col": 0, "rowspan": 1, "colspan": 1, "column_header": true, "header_source": "heuristic" } }, { "id": "p16.6.2", "order": 8, "type": "table_cell", "bbox": { "l": 206.7, "t": 709.92, "r": 239.88, "b": 698.16 }, "text": "4", "attrs": { "row": 0, "col": 1, "rowspan": 1, "colspan": 1, "column_header": true, "header_source": "heuristic" } }, { "id": "p16.6.3", "order": 9, "type": "table_cell", "bbox": { "l": 239.88, "t": 709.92, "r": 273.06, "b": 698.16 }, "text": "10", "attrs": { "row": 0, "col": 2, "rowspan": 1, "colspan": 1, "column_header": true, "header_source": "heuristic" } }, { "id": "p16.6.4", "order": 10, "type": "table_cell", "bbox": { "l": 273.06, "t": 709.92, "r": 306.24, "b": 698.16 }, "text": "15", "attrs": { "row": 0, "col": 3, "rowspan": 1, "colspan": 1, "column_header": true, "header_source": "heuristic" } }, { "id": "p16.6.5", "order": 11, "type": "table_cell", "bbox": { "l": 306.24, "t": 709.92, "r": 339.42, "b": 698.16 }, "text": "16", "attrs": { "row": 0, "col": 4, "rowspan": 1, "colspan": 1, "column_header": true, "header_source": "heuristic" } }, { "id": "p16.6.6", "order": 12, "type": "table_cell", "bbox": { "l": 339.42, "t": 709.92, "r": 372.6, "b": 698.16 }, "text": "19", "attrs": { "row": 0, "col": 5, "rowspan": 1, "colspan": 1, "column_header": true, "header_source": "heuristic" } }, { "id": "p16.6.7", "order": 13, "type": "table_cell", "bbox": { "l": 372.6, "t": 709.92, "r": 405.78, "b": 698.16 }, "text": "20", "attrs": { "row": 0, "col": 6, "rowspan": 1, "colspan": 1, "column_header": true, "header_source": "heuristic" } }, { "id": "p16.6.8", "order": 14, "type": "table_cell", "bbox": { "l": 405.78, "t": 709.92, "r": 438.96, "b": 698.16 }, "text": "34", "attrs": { "row": 0, "col": 7, "rowspan": 1, "colspan": 1, "column_header": true, "header_source": "heuristic" } }, { "id": "p16.6.9", "order": 15, "type": "table_cell", "bbox": { "l": 173.52, "t": 698.16, "r": 206.7, "b": 686.4 }, "text": "¹H ( δ)", "attrs": { "row": 1, "col": 0, "rowspan": 1, "colspan": 1 } }, { "id": "p16.6.10", "order": 16, "type": "table_cell", "bbox": { "l": 206.7, "t": 698.16, "r": 239.88, "b": 686.4 }, "text": "5.04 m", "attrs": { "row": 1, "col": 1, "rowspan": 1, "colspan": 1 } }, { "id": "p16.6.11", "order": 17, "type": "table_cell", "bbox": { "l": 239.88, "t": 698.16, "r": 273.06, "b": 686.4 }, "text": "3.61 m", "attrs": { "row": 1, "col": 2, "rowspan": 1, "colspan": 1 } }, { "id": "p16.6.12", "order": 18, "type": "table_cell", "bbox": { "l": 273.06, "t": 698.16, "r": 306.24, "b": 686.4 }, "text": "3.42 m", "attrs": { "row": 1, "col": 3, "rowspan": 1, "colspan": 1 } }, { "id": "p16.6.13", "order": 19, "type": "table_cell", "bbox": { "l": 306.24, "t": 698.16, "r": 339.42, "b": 686.4 }, "text": "3.80 m", "attrs": { "row": 1, "col": 4, "rowspan": 1, "colspan": 1 } }, { "id": "p16.6.14", "order": 20, "type": "table_cell", "bbox": { "l": 339.42, "t": 698.16, "r": 372.6, "b": 686.4 }, "text": "3.80 m", "attrs": { "row": 1, "col": 5, "rowspan": 1, "colspan": 1 } }, { "id": "p16.6.15", "order": 21, "type": "table_cell", "bbox": { "l": 372.6, "t": 698.16, "r": 405.78, "b": 686.4 }, "text": "3.42 m", "attrs": { "row": 1, "col": 6, "rowspan": 1, "colspan": 1 } }, { "id": "p16.6.16", "order": 22, "type": "table_cell", "bbox": { "l": 405.78, "t": 698.16, "r": 438.96, "b": 686.4 }, "text": "---", "attrs": { "row": 1, "col": 7, "rowspan": 1, "colspan": 1 } }, { "id": "p16.6.17", "order": 23, "type": "table_cell", "bbox": { "l": 173.52, "t": 686.4, "r": 206.7, "b": 674.64 }, "text": "¹³C ( δ)", "attrs": { "row": 2, "col": 0, "rowspan": 1, "colspan": 1 } }, { "id": "p16.6.18", "order": 24, "type": "table_cell", "bbox": { "l": 206.7, "t": 686.4, "r": 239.88, "b": 674.64 }, "text": "72.2", "attrs": { "row": 2, "col": 1, "rowspan": 1, "colspan": 1 } }, { "id": "p16.6.19", "order": 25, "type": "table_cell", "bbox": { "l": 239.88, "t": 686.4, "r": 273.06, "b": 674.64 }, "text": "71.5", "attrs": { "row": 2, "col": 2, "rowspan": 1, "colspan": 1 } }, { "id": "p16.6.20", "order": 26, "type": "table_cell", "bbox": { "l": 273.06, "t": 686.4, "r": 306.24, "b": 674.64 }, "text": "74.1", "attrs": { "row": 2, "col": 3, "rowspan": 1, "colspan": 1 } }, { "id": "p16.6.21", "order": 27, "type": "table_cell", "bbox": { "l": 306.24, "t": 686.4, "r": 339.42, "b": 674.64 }, "text": "82.5", "attrs": { "row": 2, "col": 4, "rowspan": 1, "colspan": 1 } }, { "id": "p16.6.22", "order": 28, "type": "table_cell", "bbox": { "l": 339.42, "t": 686.4, "r": 372.6, "b": 674.64 }, "text": "82.5", "attrs": { "row": 2, "col": 5, "rowspan": 1, "colspan": 1 } }, { "id": "p16.6.23", "order": 29, "type": "table_cell", "bbox": { "l": 372.6, "t": 686.4, "r": 405.78, "b": 674.64 }, "text": "74.0", "attrs": { "row": 2, "col": 6, "rowspan": 1, "colspan": 1 } }, { "id": "p16.6.24", "order": 30, "type": "table_cell", "bbox": { "l": 405.78, "t": 686.4, "r": 438.96, "b": 674.64 }, "text": "104.7", "attrs": { "row": 2, "col": 7, "rowspan": 1, "colspan": 1 } } ] }, { "id": "p16.7", "order": 31, "type": "text", "bbox": { "l": 73.44, "t": 672, "r": 540.24, "b": 633.36 }, "text": "White amorphous powder. Mp: 92–94°C. [α]D: +17.4° (c O,O8, MeOH). IR (νmax, film, cm⁻¹): 3402, 2920, 2850, 1736. MS: EIMS m/z 455, 437, 419, 401, 385, 367, 349, 331, 299, 281, 269, 251, 199. NMR: ¹H NMR (500MHz, CDCl₃), ¹³C NMR (125MHz, CDCl₃). Derivatives: phenylhydrazone (¹H NMR), per-MTPA esters (¹H NMR). Biological activities (μg/mL): KB IC₅₀ >10, HCT-8IC₅₀ >10, Bel IC₅₀ 7.1. Source: Goniothalamus donnaiensis, roots." }, { "id": "p16.8", "order": 32, "type": "text", "bbox": { "l": 72, "t": 635.04, "r": 219.6, "b": 624.48 }, "text": "34. glauca filin[p16.8.1] (C [p16.8.2]H [p16.8.3]O[p16.8.4], MW596)", "children": [ { "id": "p16.8.1", "order": 33, "type": "formula", "bbox": { "l": 72, "t": 635.04, "r": 219.6, "b": 624.48 }, "text": "¹¹²", "attrs": { "latex": "^{112}", "inline": true, "text_offset": 16, "text_span": 9, "bbox_estimated": true, "alt": "to the power of 112", "mathml": "112" } }, { "id": "p16.8.2", "order": 34, "type": "text", "bbox": { "l": 72, "t": 635.04, "r": 219.6, "b": 624.48 }, "text": "₃₅", "attrs": { "inline": true, "text_offset": 29, "text_span": 9, "bbox_estimated": true } }, { "id": "p16.8.3", "order": 35, "type": "text", "bbox": { "l": 72, "t": 635.04, "r": 219.6, "b": 624.48 }, "text": "₆₅", "attrs": { "inline": true, "text_offset": 40, "text_span": 9, "bbox_estimated": true } }, { "id": "p16.8.4", "order": 36, "type": "text", "bbox": { "l": 72, "t": 635.04, "r": 219.6, "b": 624.48 }, "text": "₇", "attrs": { "inline": true, "text_offset": 50, "text_span": 9, "bbox_estimated": true } } ] }, { "id": "p16.9", "order": 37, "type": "formula", "bbox": { "l": 158.88, "t": 619.2, "r": 452.88, "b": 575.52 }, "text": "", "attrs": { "block_label": "image", "alt": "Skeletal structure of an annonaceous acetogenin-type molecule: butenolide ring, tetrahydrofuran ring, and hydroxyls at C4, C…", "source": "vision" } }, { "id": "p16.10", "order": 38, "type": "text", "bbox": { "l": 158.16, "t": 564.48, "r": 351.36, "b": 555.6 }, "text": "Position 12 15 16 19 20" }, { "id": "p16.11", "order": 39, "type": "text", "bbox": { "l": 157.2, "t": 551.76, "r": 356.16, "b": 530.4 }, "text": "[p16.11.1]H (δ) 3.89 m 3.82 m 3.45 m 3.60 m 3.60 m\n [p16.11.2]C (δ) 79.3 81.7 74.3 74.4 74.7", "children": [ { "id": "p16.11.1", "order": 40, "type": "formula", "bbox": { "l": 157.2, "t": 551.76, "r": 356.16, "b": 530.4 }, "text": "¹", "attrs": { "latex": "^{1}", "inline": true, "text_offset": 0, "text_span": 10, "bbox_estimated": true, "alt": "to the power of 1", "mathml": "1" } }, { "id": "p16.11.2", "order": 41, "type": "text", "bbox": { "l": 157.2, "t": 551.76, "r": 356.16, "b": 530.4 }, "text": "¹³", "attrs": { "inline": true, "text_offset": 52, "text_span": 10, "bbox_estimated": true } } ] }, { "id": "p16.12", "order": 42, "type": "text", "bbox": { "l": 73.2, "t": 527.76, "r": 521.04, "b": 499.92 }, "text": "Solid.[p16.12.1]: +30° (c O.2, CHCl_{3}). UV ([p16.12.2], EtOH, nm): 209 ([p16.12.3] 3.9). IR ([p16.12.4], film, cm^{-1}): 3367, 2920, 2851, 1743, 1439, 1376, 1061, 1032, 952, 756 MS: EIMS m/z 379, 361, 343, 309, 291, 286, 269, 251. NMR: [p16.12.5]H NMR (400 MHz, CDCl_{3}), [p16.12.6]C NMR (50 MHz, CDCl_{3}). Source: Annona glauca, seeds.", "children": [ { "id": "p16.12.1", "order": 43, "type": "formula", "bbox": { "l": 73.2, "t": 527.76, "r": 521.04, "b": 499.92 }, "text": "\\text{Solid. }[\\alpha]_{D}\\text{: }+30^\\circ\\,(c\\,0.2,\\ \\text{CHCl}_3)\\text{. UV }(\\lambda_{\\max},\\ \\text{EtOH, nm})\\text{: }209\\,(\\log \\epsilon\\ 3.9)\\text{. IR }(\\nu_{\\max},\\ \\text{film, cm}^{-1})\\text{: }3367,\\ 2920,\\ 2851,\\ 1743,\\ 1439,\\ 1376,\\ 1061,\\ 1032,\\ 952,\\ 756\\text{. MS: EIMS }m/z\\ 379,\\ 361,\\ 343,\\ 309,\\ 291,\\ 286,\\ 269,\\ 251\\text{. NMR: }{}^{1}\\text{H NMR (400 MHz, CDCl}_3),\\ {}^{13}\\text{C NMR (50 MHz, CDCl}_3)\\text{. Source: }\\textit{Annona glauca}\\text{, seeds.}", "attrs": { "latex": "\\text{Solid. }[\\alpha]_{D}\\text{: }+30^\\circ\\,(c\\,0.2,\\ \\text{CHCl}_3)\\text{. UV }(\\lambda_{\\max},\\ \\text{EtOH, nm})\\text{: }209\\,(\\log \\epsilon\\ 3.9)\\text{. IR }(\\nu_{\\max},\\ \\text{film, cm}^{-1})\\text{: }3367,\\ 2920,\\ 2851,\\ 1743,\\ 1439,\\ 1376,\\ 1061,\\ 1032,\\ 952,\\ 756\\text{. MS: EIMS }m/z\\ 379,\\ 361,\\ 343,\\ 309,\\ 291,\\ 286,\\ 269,\\ 251\\text{. NMR: }{}^{1}\\text{H NMR (400 MHz, CDCl}_3),\\ {}^{13}\\text{C NMR (50 MHz, CDCl}_3)\\text{. Source: }\\textit{Annona glauca}\\text{, seeds.}", "inline": true, "text_offset": 6, "text_span": 10, "bbox_estimated": true, "notation": "latex", "alt": "Solid. alpha sub D : plus 30 to the power of circ, c, 0.2, CHCl sub 3 . UV of lambda sub max, EtOH, nm : 209, log epsilon 3.9 . IR of nu sub max, film, cm to the power of minus 1 : 3367, 2920, 2851, 1743, 1439, 1376, 1061, 1032, 952, 756 . MS: EIMS m over z 379, 361, 343, 309, 291, 286, 269, 251 . NMR: to the power of 1 H NMR of 400 MHz, CDCl sub 3, to the power of 13 C NMR of 50 MHz, CDCl sub 3 . Source: textit Annona glauca, seeds.", "mathml": "Solid. [α]D: +30∘(c0.2, CHCl3). UV (λmax, EtOH, nm): 209(logϵ 3.9). IR (νmax, film, cm−1): 3367, 2920, 2851, 1743, 1439, 1376, 1061, 1032, 952, 756. MS: EIMS m/z 379, 361, 343, 309, 291, 286, 269, 251. NMR: 1H NMR (400 MHz, CDCl3), 13C NMR (50 MHz, CDCl3). Source: Annona glauca, seeds." } }, { "id": "p16.12.2", "order": 44, "type": "text", "bbox": { "l": 73.2, "t": 527.76, "r": 521.04, "b": 499.92 }, "text": "\\lambda_{max}", "attrs": { "inline": true, "text_offset": 46, "text_span": 10, "bbox_estimated": true } }, { "id": "p16.12.3", "order": 45, "type": "formula", "bbox": { "l": 73.2, "t": 527.76, "r": 521.04, "b": 499.92 }, "text": "\\text{Solid. }[\\alpha]_{D}\\text{: }+30^{\\circ}\\,(c\\ 0.2, \\text{CHCl}_3)\\text{. UV }(\\lambda_{\\max}\\text{, EtOH, nm)}\\text{: }209\\,(\\log \\epsilon\\ 3.9)\\text{. IR }(\\nu_{\\max}\\text{, film, cm}^{-1})\\text{: }3367, 2920, 2851, 1743, 1439, 1376, 1061, 1032, 952, 756\\text{. MS: EIMS }m/z\\ 379, 361, 343, 309, 291, 286, 269, 251\\text{. NMR: }{}^{1}\\text{H NMR (400 MHz, CDCl}_3\\text{), }{}^{13}\\text{C NMR (50 MHz, CDCl}_3\\text{). Source: }\\textit{Annona glauca}\\text{, seeds.}", "attrs": { "latex": "\\text{Solid. }[\\alpha]_{D}\\text{: }+30^{\\circ}\\,(c\\ 0.2, \\text{CHCl}_3)\\text{. UV }(\\lambda_{\\max}\\text{, EtOH, nm)}\\text{: }209\\,(\\log \\epsilon\\ 3.9)\\text{. IR }(\\nu_{\\max}\\text{, film, cm}^{-1})\\text{: }3367, 2920, 2851, 1743, 1439, 1376, 1061, 1032, 952, 756\\text{. MS: EIMS }m/z\\ 379, 361, 343, 309, 291, 286, 269, 251\\text{. NMR: }{}^{1}\\text{H NMR (400 MHz, CDCl}_3\\text{), }{}^{13}\\text{C NMR (50 MHz, CDCl}_3\\text{). Source: }\\textit{Annona glauca}\\text{, seeds.}", "inline": true, "text_offset": 74, "text_span": 10, "bbox_estimated": true, "notation": "latex", "alt": "Solid. alpha sub D : plus 30 to the power of circ, c 0.2, CHCl sub 3 . UV of lambda sub max, EtOH, nm : 209, log epsilon 3.9 . IR of nu sub max, film, cm to the power of minus 1 : 3367, 2920, 2851, 1743, 1439, 1376, 1061, 1032, 952, 756 . MS: EIMS m over z 379, 361, 343, 309, 291, 286, 269, 251 . NMR: to the power of 1 H NMR of 400 MHz, CDCl sub 3, to the power of 13 C NMR of 50 MHz, CDCl sub 3 . Source: textit Annona glauca, seeds.", "mathml": "Solid. [α]D: +30∘(c 0.2,CHCl3). UV (λmax, EtOH, nm): 209(logϵ 3.9). IR (νmax, film, cm−1): 3367,2920,2851,1743,1439,1376,1061,1032,952,756. MS: EIMS m/z 379,361,343,309,291,286,269,251. NMR: 1H NMR (400 MHz, CDCl3), 13C NMR (50 MHz, CDCl3). Source: Annona glauca, seeds." } }, { "id": "p16.12.4", "order": 46, "type": "formula", "bbox": { "l": 73.2, "t": 527.76, "r": 521.04, "b": 499.92 }, "text": "\\text{Solid. }[\\alpha]_D\\text{: }+30^\\circ\\,(c\\,0.2,\\ \\text{CHCl}_3)\\text{. UV }(\\lambda_{max}\\text{, EtOH, nm)}\\text{: }209\\,(\\log\\epsilon\\,3.9)\\text{. IR }(\\nu_{max}\\text{, film, cm}^{-1})\\text{: }3367, 2920, 2851, 1743, 1439, 1376, 1061, 1032, 952, 756\\text{. MS: EIMS }m/z\\ 379, 361, 343, 309, 291, 286, 269, 251\\text{. NMR: }{}^{1}\\text{H NMR (400 MHz, CDCl}_3),\\ {}^{13}\\text{C NMR (50 MHz, CDCl}_3)\\text{. Source: }\\textit{Annona glauca}\\text{, seeds.}", "attrs": { "latex": "\\text{Solid. }[\\alpha]_D\\text{: }+30^\\circ\\,(c\\,0.2,\\ \\text{CHCl}_3)\\text{. UV }(\\lambda_{max}\\text{, EtOH, nm)}\\text{: }209\\,(\\log\\epsilon\\,3.9)\\text{. IR }(\\nu_{max}\\text{, film, cm}^{-1})\\text{: }3367, 2920, 2851, 1743, 1439, 1376, 1061, 1032, 952, 756\\text{. MS: EIMS }m/z\\ 379, 361, 343, 309, 291, 286, 269, 251\\text{. NMR: }{}^{1}\\text{H NMR (400 MHz, CDCl}_3),\\ {}^{13}\\text{C NMR (50 MHz, CDCl}_3)\\text{. Source: }\\textit{Annona glauca}\\text{, seeds.}", "inline": true, "text_offset": 95, "text_span": 10, "bbox_estimated": true, "notation": "latex", "alt": "Solid. alpha sub D : plus 30 to the power of circ, c, 0.2, CHCl sub 3 . UV of lambda sub max, EtOH, nm : 209, log epsilon, 3.9 . IR of nu sub max, film, cm to the power of minus 1 : 3367, 2920, 2851, 1743, 1439, 1376, 1061, 1032, 952, 756 . MS: EIMS m over z 379, 361, 343, 309, 291, 286, 269, 251 . NMR: to the power of 1 H NMR of 400 MHz, CDCl sub 3, to the power of 13 C NMR of 50 MHz, CDCl sub 3 . Source: textit Annona glauca, seeds.", "mathml": "Solid. [α]D: +30∘(c0.2, CHCl3). UV (λmax, EtOH, nm): 209(logϵ3.9). IR (νmax, film, cm−1): 3367,2920,2851,1743,1439,1376,1061,1032,952,756. MS: EIMS m/z 379,361,343,309,291,286,269,251. NMR: 1H NMR (400 MHz, CDCl3), 13C NMR (50 MHz, CDCl3). Source: Annona glauca, seeds." } }, { "id": "p16.12.5", "order": 47, "type": "text", "bbox": { "l": 73.2, "t": 527.76, "r": 521.04, "b": 499.92 }, "text": "¹", "attrs": { "inline": true, "text_offset": 238, "text_span": 10, "bbox_estimated": true } }, { "id": "p16.12.6", "order": 48, "type": "formula", "bbox": { "l": 73.2, "t": 527.76, "r": 521.04, "b": 499.92 }, "text": "¹³", "attrs": { "latex": "{}^{13}", "inline": true, "text_offset": 275, "text_span": 10, "bbox_estimated": true, "alt": "to the power of 13", "mathml": "13" } } ] }, { "id": "p16.13", "order": 49, "type": "text", "bbox": { "l": 72, "t": 498.72, "r": 242.16, "b": 488.88 }, "text": "35. annomuricin E[p16.13.1] (C [p16.13.2]H [p16.13.3]O[p16.13.4], MW612)", "children": [ { "id": "p16.13.1", "order": 50, "type": "formula", "bbox": { "l": 72, "t": 498.72, "r": 242.16, "b": 488.88 }, "text": "^{*113}", "attrs": { "latex": "^{*113}", "inline": true, "text_offset": 17, "text_span": 10, "bbox_estimated": true, "notation": "latex", "alt": "to the power of *113", "mathml": "*113" } }, { "id": "p16.13.2", "order": 51, "type": "formula", "bbox": { "l": 72, "t": 498.72, "r": 242.16, "b": 488.88 }, "text": "₃₅", "attrs": { "latex": "_{35}", "inline": true, "text_offset": 31, "text_span": 10, "bbox_estimated": true, "alt": "sub 35", "mathml": "35" } }, { "id": "p16.13.3", "order": 52, "type": "text", "bbox": { "l": 72, "t": 498.72, "r": 242.16, "b": 488.88 }, "text": "₆₄", "attrs": { "inline": true, "text_offset": 43, "text_span": 10, "bbox_estimated": true } }, { "id": "p16.13.4", "order": 53, "type": "formula", "bbox": { "l": 72, "t": 498.72, "r": 242.16, "b": 488.88 }, "text": "₈", "attrs": { "latex": "_{8}", "inline": true, "text_offset": 54, "text_span": 10, "bbox_estimated": true, "alt": "sub 8", "mathml": "8" } } ] }, { "id": "p16.14", "order": 54, "type": "formula", "bbox": { "l": 159.36, "t": 485.04, "r": 453.12, "b": 439.2 }, "text": "", "attrs": { "block_label": "image", "alt": "Skeletal structure of an annonaceous acetogenin: butenolide ring with hydroxyls at C4, C10, C11, C15, C20 and a bis-THF ring", "source": "vision" } }, { "id": "p16.15", "order": 55, "type": "text", "bbox": { "l": 159.12, "t": 429.6, "r": 387.6, "b": 420 }, "text": "Position 10 11 15 16 19 20" }, { "id": "p16.16", "order": 56, "type": "text", "bbox": { "l": 158.88, "t": 416.4, "r": 391.92, "b": 395.04 }, "text": "[p16.16.1] ([p16.16.2]) 3.60 m 3.60 m 3.45 m 3.79 m 3.79 m 3.43 m \n[p16.16.3] ([p16.16.4]) 74.2 74.3 74.5 82.8 82.6 73.9", "children": [ { "id": "p16.16.1", "order": 57, "type": "formula", "bbox": { "l": 158.88, "t": 416.4, "r": 391.92, "b": 395.04 }, "text": "¹H", "attrs": { "latex": "^{1}H", "inline": true, "text_offset": 0, "text_span": 10, "bbox_estimated": true, "alt": "to the power of 1 H", "mathml": "1H" } }, { "id": "p16.16.2", "order": 58, "type": "formula", "bbox": { "l": 158.88, "t": 416.4, "r": 391.92, "b": 395.04 }, "text": "δ", "attrs": { "latex": "\\delta", "inline": true, "text_offset": 12, "text_span": 10, "bbox_estimated": true, "alt": "delta", "mathml": "δ" } }, { "id": "p16.16.3", "order": 59, "type": "formula", "bbox": { "l": 158.88, "t": 416.4, "r": 391.92, "b": 395.04 }, "text": "\\begin{array}{l|cccccc} ^{1}\\mathrm{H}\\ (\\delta) & 3.60\\ \\mathrm{m} & 3.60\\ \\mathrm{m} & 3.45\\ \\mathrm{m} & 3.79\\ \\mathrm{m} & 3.79\\ \\mathrm{m} & 3.43\\ \\mathrm{m} \\\\ ^{13}\\mathrm{C}\\ (\\delta) & 74.2 & 74.3 & 74.5 & 82.8 & 82.6 & 73.9 \\end{array}", "attrs": { "latex": "\\begin{array}{l|cccccc} ^{1}\\mathrm{H}\\ (\\delta) & 3.60\\ \\mathrm{m} & 3.60\\ \\mathrm{m} & 3.45\\ \\mathrm{m} & 3.79\\ \\mathrm{m} & 3.79\\ \\mathrm{m} & 3.43\\ \\mathrm{m} \\\\ ^{13}\\mathrm{C}\\ (\\delta) & 74.2 & 74.3 & 74.5 & 82.8 & 82.6 & 73.9 \\end{array}", "inline": true, "text_offset": 67, "text_span": 10, "bbox_estimated": true, "alt": "begin array l cccccc to the power of 1 H of delta & 3.60 m & 3.60 m & 3.45 m & 3.79 m & 3.79 m & 3.43 m to the power of 13 C of delta & 74.2 & 74.3 & 74.5 & 82.8 & 82.6 & 73.9 end array", "notation": "latex", "mathml": "l|cccccc1H (δ)3.60 m3.60 m3.45 m3.79 m3.79 m3.43 m13C (δ)74.274.374.582.882.673.9" } }, { "id": "p16.16.4", "order": 60, "type": "formula", "bbox": { "l": 158.88, "t": 416.4, "r": 391.92, "b": 395.04 }, "text": "δ", "attrs": { "latex": "\\delta", "inline": true, "text_offset": 79, "text_span": 10, "bbox_estimated": true, "alt": "delta", "mathml": "δ" } } ] }, { "id": "p16.17", "order": 61, "type": "text", "bbox": { "l": 73.44, "t": 391.92, "r": 523.44, "b": 345.12 }, "text": "White solid.[p16.17.1]: +12.5° (c QO4, MeOH). UV ([p16.17.2], MeOH, nm): 218 (log[p16.17.3] 3.76). IR ([p16.17.4], film, cm[p16.17.5]): 3381, 2920, 2851, 1744, 1466. MS: EIMS m/z 377, 359, 353, 341, 335, 325, 317, 307, 289, 271, 269, 253, 251, 241, 223, 205, 199, 141, 123. NMR: [p16.17.6]H NMR (500 MHz, CDCl[p16.17.7]), [p16.17.8]C NMR (125 MHz, CDCl[p16.17.9]). Derivatives: acetonide (1H NMR). Biological activities ( [p16.17.10]g/mL): BST LC[p16.17.11] 18.4, A-549 ED[p16.17.12] 1.1[p16.17.13] 10[p16.17.14], MCF-7 ED[p16.17.15] 1.5[p16.17.16] 10[p16.17.17], HT-29 ED[p16.17.18] 6.7[p16.17.19] 10[p16.17.20], A-498 ED[p16.17.21] 1.4, PC-3 ED[p16.17.22] 1.5[p16.17.23] 10[p16.17.24], PAC-2 ED[p16.17.25] 2.4[p16.17.26] 10[p16.17.27]. Source: Annona muricata, leaves.", "children": [ { "id": "p16.17.1", "order": 62, "type": "formula", "bbox": { "l": 73.44, "t": 391.92, "r": 523.44, "b": 345.12 }, "text": "\\text{White solid. } [\\alpha]_{D}: +12.5^\\circ \\text{ (}c\\,0.04\\text{, MeOH). UV } (\\lambda_{\\max}\\text{, MeOH, nm): } 218 \\text{ (}\\log \\epsilon\\ 3.76\\text{). IR } (\\nu_{\\max}\\text{, film, cm}^{-1}\\text{): } 3381, 2920, 2851, 1744, 1466. \\text{ MS: EIMS } m/z\\ 377, 359, 353, 341, 335, 325, 317, 307, 289, 271, 269, 253, 251, 241, 223, 205, 199, 141, 123. \\text{ NMR: }{}^{1}\\text{H NMR (500 MHz, CDCl}_3\\text{), }{}^{13}\\text{C NMR (125 MHz, CDCl}_3\\text{). Derivatives: acetonide (}^{1}\\text{H NMR). Biological activities } (\\mu\\text{g/mL}): \\text{BST LC}_{50}\\ 18.4, \\text{A-549 ED}_{50}\\ 1.1\\times10^{-1}, \\text{MCF-7 ED}_{50}\\ 1.5\\times10^{-1}, \\text{HT-29 ED}_{50}\\ 6.7\\times10^{-1}, \\text{A-498 ED}_{50}\\ 1.4, \\text{PC-3 ED}_{50}\\ 1.5\\times10^{-1}, \\text{PACA-2 ED}_{50}\\ 2.4\\times10^{-1}. \\text{ Source: } \\textit{Annona muricata}\\text{, leaves.}", "attrs": { "latex": "\\text{White solid. } [\\alpha]_{D}: +12.5^\\circ \\text{ (}c\\,0.04\\text{, MeOH). UV } (\\lambda_{\\max}\\text{, MeOH, nm): } 218 \\text{ (}\\log \\epsilon\\ 3.76\\text{). IR } (\\nu_{\\max}\\text{, film, cm}^{-1}\\text{): } 3381, 2920, 2851, 1744, 1466. \\text{ MS: EIMS } m/z\\ 377, 359, 353, 341, 335, 325, 317, 307, 289, 271, 269, 253, 251, 241, 223, 205, 199, 141, 123. \\text{ NMR: }{}^{1}\\text{H NMR (500 MHz, CDCl}_3\\text{), }{}^{13}\\text{C NMR (125 MHz, CDCl}_3\\text{). Derivatives: acetonide (}^{1}\\text{H NMR). Biological activities } (\\mu\\text{g/mL}): \\text{BST LC}_{50}\\ 18.4, \\text{A-549 ED}_{50}\\ 1.1\\times10^{-1}, \\text{MCF-7 ED}_{50}\\ 1.5\\times10^{-1}, \\text{HT-29 ED}_{50}\\ 6.7\\times10^{-1}, \\text{A-498 ED}_{50}\\ 1.4, \\text{PC-3 ED}_{50}\\ 1.5\\times10^{-1}, \\text{PACA-2 ED}_{50}\\ 2.4\\times10^{-1}. \\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 12.5 to the power of circ of c, 0.04, MeOH . UV of lambda sub max, MeOH, nm : 218 times log epsilon 3.76 . IR of nu sub max, film, cm to the power of minus 1 : 3381, 2920, 2851, 1744, 1466. MS: EIMS m over z 377, 359, 353, 341, 335, 325, 317, 307, 289, 271, 269, 253, 251, 241, 223, 205, 199, 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 . Derivatives: acetonide of to the power of 1 H NMR . Biological activities of mu g over mL : BST LC sub 50 18.4, A minus 549 ED sub 50 1.1 times 10 to the power of minus 1, MCF minus 7 ED sub 50 1.5 times 10 to the power of minus 1, HT minus 29 ED sub 50 6.7 times 10 to the power of minus 1, A minus 498 ED sub 50 1.4, PC minus 3 ED sub 50 1.5 times 10 to the power of minus 1, PACA minus 2 ED sub 50 2.4 times 10 to the power of minus 1 . Source: textit Annona muricata, leaves.", "mathml": "White solid. [α]D:+12.5∘ (c0.04, MeOH). UV (λmax, MeOH, nm): 218 (logϵ 3.76). IR (νmax, film, cm−1): 3381,2920,2851,1744,1466. MS: EIMS m/z 377,359,353,341,335,325,317,307,289,271,269,253,251,241,223,205,199,141,123. NMR: 1H NMR (500 MHz, CDCl3), 13C NMR (125 MHz, CDCl3). Derivatives: acetonide (1H NMR). Biological activities (μg/mL):BST LC50 18.4,A-549 ED50 1.1×10−1,MCF-7 ED50 1.5×10−1,HT-29 ED50 6.7×10−1,A-498 ED50 1.4,PC-3 ED50 1.5×10−1,PACA-2 ED50 2.4×10−1. Source: Annona muricata, leaves." } }, { "id": "p16.17.2", "order": 63, "type": "text", "bbox": { "l": 73.44, "t": 391.92, "r": 523.44, "b": 345.12 }, "text": "\\lambda_{max}", "attrs": { "inline": true, "text_offset": 50, "text_span": 10, "bbox_estimated": true } }, { "id": "p16.17.3", "order": 64, "type": "text", "bbox": { "l": 73.44, "t": 391.92, "r": 523.44, "b": 345.12 }, "text": "ε", "attrs": { "inline": true, "text_offset": 81, "text_span": 10, "bbox_estimated": true } }, { "id": "p16.17.4", "order": 65, "type": "text", "bbox": { "l": 73.44, "t": 391.92, "r": 523.44, "b": 345.12 }, "text": "\\nu_{max}", "attrs": { "inline": true, "text_offset": 103, "text_span": 10, "bbox_estimated": true } }, { "id": "p16.17.5", "order": 66, "type": "text", "bbox": { "l": 73.44, "t": 391.92, "r": 523.44, "b": 345.12 }, "text": "⁻¹", "attrs": { "inline": true, "text_offset": 123, "text_span": 10, "bbox_estimated": true } }, { "id": "p16.17.6", "order": 67, "type": "text", "bbox": { "l": 73.44, "t": 391.92, "r": 523.44, "b": 345.12 }, "text": "¹", "attrs": { "inline": true, "text_offset": 279, "text_span": 10, "bbox_estimated": true } }, { "id": "p16.17.7", "order": 68, "type": "text", "bbox": { "l": 73.44, "t": 391.92, "r": 523.44, "b": 345.12 }, "text": "₃", "attrs": { "inline": true, "text_offset": 309, "text_span": 10, "bbox_estimated": true } }, { "id": "p16.17.8", "order": 69, "type": "text", "bbox": { "l": 73.44, "t": 391.92, "r": 523.44, "b": 345.12 }, "text": "¹³", "attrs": { "inline": true, "text_offset": 322, "text_span": 10, "bbox_estimated": true } }, { "id": "p16.17.9", "order": 70, "type": "text", "bbox": { "l": 73.44, "t": 391.92, "r": 523.44, "b": 345.12 }, "text": "₃", "attrs": { "inline": true, "text_offset": 352, "text_span": 10, "bbox_estimated": true } }, { "id": "p16.17.10", "order": 71, "type": "text", "bbox": { "l": 73.44, "t": 391.92, "r": 523.44, "b": 345.12 }, "text": "μ", "attrs": { "inline": true, "text_offset": 422, "text_span": 11, "bbox_estimated": true } }, { "id": "p16.17.11", "order": 72, "type": "text", "bbox": { "l": 73.44, "t": 391.92, "r": 523.44, "b": 345.12 }, "text": "₅₀", "attrs": { "inline": true, "text_offset": 446, "text_span": 11, "bbox_estimated": true } }, { "id": "p16.17.12", "order": 73, "type": "text", "bbox": { "l": 73.44, "t": 391.92, "r": 523.44, "b": 345.12 }, "text": "₅₀", "attrs": { "inline": true, "text_offset": 472, "text_span": 11, "bbox_estimated": true } }, { "id": "p16.17.13", "order": 74, "type": "text", "bbox": { "l": 73.44, "t": 391.92, "r": 523.44, "b": 345.12 }, "text": "×", "attrs": { "inline": true, "text_offset": 487, "text_span": 11, "bbox_estimated": true } }, { "id": "p16.17.14", "order": 75, "type": "text", "bbox": { "l": 73.44, "t": 391.92, "r": 523.44, "b": 345.12 }, "text": "⁻¹", "attrs": { "inline": true, "text_offset": 501, "text_span": 11, "bbox_estimated": true } }, { "id": "p16.17.15", "order": 76, "type": "text", "bbox": { "l": 73.44, "t": 391.92, "r": 523.44, "b": 345.12 }, "text": "₅₀", "attrs": { "inline": true, "text_offset": 522, "text_span": 11, "bbox_estimated": true } }, { "id": "p16.17.16", "order": 77, "type": "text", "bbox": { "l": 73.44, "t": 391.92, "r": 523.44, "b": 345.12 }, "text": "×", "attrs": { "inline": true, "text_offset": 537, "text_span": 11, "bbox_estimated": true } }, { "id": "p16.17.17", "order": 78, "type": "text", "bbox": { "l": 73.44, "t": 391.92, "r": 523.44, "b": 345.12 }, "text": "⁻¹", "attrs": { "inline": true, "text_offset": 551, "text_span": 11, "bbox_estimated": true } }, { "id": "p16.17.18", "order": 79, "type": "text", "bbox": { "l": 73.44, "t": 391.92, "r": 523.44, "b": 345.12 }, "text": "₅₀", "attrs": { "inline": true, "text_offset": 572, "text_span": 11, "bbox_estimated": true } }, { "id": "p16.17.19", "order": 80, "type": "text", "bbox": { "l": 73.44, "t": 391.92, "r": 523.44, "b": 345.12 }, "text": "×", "attrs": { "inline": true, "text_offset": 587, "text_span": 11, "bbox_estimated": true } }, { "id": "p16.17.20", "order": 81, "type": "text", "bbox": { "l": 73.44, "t": 391.92, "r": 523.44, "b": 345.12 }, "text": "⁻¹", "attrs": { "inline": true, "text_offset": 601, "text_span": 11, "bbox_estimated": true } }, { "id": "p16.17.21", "order": 82, "type": "text", "bbox": { "l": 73.44, "t": 391.92, "r": 523.44, "b": 345.12 }, "text": "₅₀", "attrs": { "inline": true, "text_offset": 622, "text_span": 11, "bbox_estimated": true } }, { "id": "p16.17.22", "order": 83, "type": "text", "bbox": { "l": 73.44, "t": 391.92, "r": 523.44, "b": 345.12 }, "text": "₅₀", "attrs": { "inline": true, "text_offset": 646, "text_span": 11, "bbox_estimated": true } }, { "id": "p16.17.23", "order": 84, "type": "text", "bbox": { "l": 73.44, "t": 391.92, "r": 523.44, "b": 345.12 }, "text": "×", "attrs": { "inline": true, "text_offset": 661, "text_span": 11, "bbox_estimated": true } }, { "id": "p16.17.24", "order": 85, "type": "text", "bbox": { "l": 73.44, "t": 391.92, "r": 523.44, "b": 345.12 }, "text": "⁻¹", "attrs": { "inline": true, "text_offset": 675, "text_span": 11, "bbox_estimated": true } }, { "id": "p16.17.25", "order": 86, "type": "text", "bbox": { "l": 73.44, "t": 391.92, "r": 523.44, "b": 345.12 }, "text": "₅₀", "attrs": { "inline": true, "text_offset": 696, "text_span": 11, "bbox_estimated": true } }, { "id": "p16.17.26", "order": 87, "type": "text", "bbox": { "l": 73.44, "t": 391.92, "r": 523.44, "b": 345.12 }, "text": "×", "attrs": { "inline": true, "text_offset": 711, "text_span": 11, "bbox_estimated": true } }, { "id": "p16.17.27", "order": 88, "type": "text", "bbox": { "l": 73.44, "t": 391.92, "r": 523.44, "b": 345.12 }, "text": "⁻¹", "attrs": { "inline": true, "text_offset": 725, "text_span": 11, "bbox_estimated": true } } ] }, { "id": "p16.18", "order": 89, "type": "text", "bbox": { "l": 72.24, "t": 345.36, "r": 245.76, "b": 334.8 }, "text": "36. muricapentocin[p16.18.1] (C [p16.18.2]H [p16.18.3]O[p16.18.4], MW612)", "children": [ { "id": "p16.18.1", "order": 90, "type": "formula", "bbox": { "l": 72.24, "t": 345.36, "r": 245.76, "b": 334.8 }, "text": "^{*113}", "attrs": { "latex": "^{*113}", "inline": true, "text_offset": 18, "text_span": 10, "bbox_estimated": true, "notation": "latex", "alt": "to the power of *113", "mathml": "*113" } }, { "id": "p16.18.2", "order": 91, "type": "text", "bbox": { "l": 72.24, "t": 345.36, "r": 245.76, "b": 334.8 }, "text": "₃₅", "attrs": { "inline": true, "text_offset": 32, "text_span": 10, "bbox_estimated": true } }, { "id": "p16.18.3", "order": 92, "type": "text", "bbox": { "l": 72.24, "t": 345.36, "r": 245.76, "b": 334.8 }, "text": "₆₄", "attrs": { "inline": true, "text_offset": 44, "text_span": 10, "bbox_estimated": true } }, { "id": "p16.18.4", "order": 93, "type": "text", "bbox": { "l": 72.24, "t": 345.36, "r": 245.76, "b": 334.8 }, "text": "₈", "attrs": { "inline": true, "text_offset": 55, "text_span": 10, "bbox_estimated": true } } ] }, { "id": "p16.19", "order": 94, "type": "formula", "bbox": { "l": 159.84, "t": 330.48, "r": 452.16, "b": 286.32 }, "text": "", "attrs": { "block_label": "image", "alt": "Skeletal structure of an annonaceous acetogenin: butenolide ring, tetrahydrofuran ring, and multiple hydroxyl groups on a lo…", "source": "vision" } }, { "id": "p16.20", "order": 95, "type": "text", "bbox": { "l": 159.12, "t": 276.72, "r": 387.36, "b": 267.36 }, "text": "Position 8 12 15 16 19 20" }, { "id": "p16.21", "order": 96, "type": "text", "bbox": { "l": 159.12, "t": 264, "r": 391.2, "b": 240.96 }, "text": "[p16.21.1]H (δ) 3.61 m 3.66 m 3.45 m 3.79 m 3.79 m 3.40 m\n [p16.21.2]C (δ) 71.3 71.3 74.3 82.8 82.3 74.2", "children": [ { "id": "p16.21.1", "order": 97, "type": "formula", "bbox": { "l": 159.12, "t": 264, "r": 391.2, "b": 240.96 }, "text": "¹", "attrs": { "latex": "^{1}", "inline": true, "text_offset": 0, "text_span": 10, "bbox_estimated": true, "alt": "to the power of 1", "mathml": "1" } }, { "id": "p16.21.2", "order": 98, "type": "formula", "bbox": { "l": 159.12, "t": 264, "r": 391.2, "b": 240.96 }, "text": "¹³", "attrs": { "latex": "^{13}", "inline": true, "text_offset": 59, "text_span": 10, "bbox_estimated": true, "alt": "to the power of 13", "mathml": "13" } } ] }, { "id": "p16.22", "order": 99, "type": "text", "bbox": { "l": 74.88, "t": 238.08, "r": 534.48, "b": 190.32 }, "text": "White solid.[p16.22.1]: +8.0° (c 0.05, MeOH). UV ([p16.22.2], MeOH, nm): 220 (log[p16.22.3] 3.54). IR ([p16.22.4], film, cm[p16.22.5]): 3398, 2920, 2851, 1743, 1458. MS: EIMS m/z 377, 359, 343, 341, 325, 307, 289, 271, 269, 231, 213, 199, 195, 177, 141, 123. NMR: [p16.22.6]H NMR (500 MHz, CDCl[p16.22.7]), [p16.22.8]C NMR (125 MHz, CDCl[p16.22.9]). Derivatives: acetonide (1H NMR). Biological activities ( [p16.22.10]g/mL): BST LC[p16.22.11] 1.8, A-549 ED[p16.22.12] 1.9[p16.22.13] 10[p16.22.14], MCF-7 ED[p16.22.15] 1.9, HT-29 ED[p16.22.16] 7.1[p16.22.17] 10[p16.22.18], A-498 ED[p16.22.19] 1.7, PC-3 ED[p16.22.20] 4.5[p16.22.21] 10[p16.22.22], PAC-2 ED[p16.22.23] 5.0[p16.22.24] 10[p16.22.25]. Source: Annona muricata, leaves.", "children": [ { "id": "p16.22.1", "order": 100, "type": "formula", "bbox": { "l": 74.88, "t": 238.08, "r": 534.48, "b": 190.32 }, "text": "\\text{White solid. }[\\alpha]_{D}\\text{: }+8.0^{\\circ}\\text{ (}c\\,0.05\\text{, MeOH). UV (}\\lambda_{\\max}\\text{, MeOH, nm): 220 (}\\log \\epsilon\\ 3.54\\text{). IR (}\\nu_{\\max}\\text{, film, cm}^{-1}\\text{): 3398, 2920, 2851, 1743, 1458. MS: EIMS } m/z\\ 377, 359, 343, 341, 325, 307, 289, 271, 269, 231, 213, 199, 195, 177, 141, 123. \\text{NMR: }{}^{1}\\text{H NMR (500 MHz, CDCl}_3\\text{), }{}^{13}\\text{C NMR (125 MHz, CDCl}_3\\text{). Derivatives: acetonide (}{}^{1}\\text{H NMR). Biological activities (}\\mu\\text{g/mL): BST LC}_{50}\\ 1.8,\\ \\text{A-549 ED}_{50}\\ 1.9\\times10^{-1},\\ \\text{MCF-7 ED}_{50}\\ 1.9,\\ \\text{HT-29 ED}_{50}\\ 7.1\\times10^{-2},\\ \\text{A-498 ED}_{50}\\ 1.7,\\ \\text{PC-3 ED}_{50}\\ 4.5\\times10^{-1},\\ \\text{PACA-2 ED}_{50}\\ 5.0\\times10^{-2}\\text{. Source: }\\textit{Annona muricata}\\text{, leaves.}\\\\ \\textbf{37. donnaienin}^{33}\\text{ (C}_{35}\\text{H}_{64}\\text{O}_{8}\\text{, MW 612)}", "attrs": { "latex": "\\text{White solid. }[\\alpha]_{D}\\text{: }+8.0^{\\circ}\\text{ (}c\\,0.05\\text{, MeOH). UV (}\\lambda_{\\max}\\text{, MeOH, nm): 220 (}\\log \\epsilon\\ 3.54\\text{). IR (}\\nu_{\\max}\\text{, film, cm}^{-1}\\text{): 3398, 2920, 2851, 1743, 1458. MS: EIMS } m/z\\ 377, 359, 343, 341, 325, 307, 289, 271, 269, 231, 213, 199, 195, 177, 141, 123. \\text{NMR: }{}^{1}\\text{H NMR (500 MHz, CDCl}_3\\text{), }{}^{13}\\text{C NMR (125 MHz, CDCl}_3\\text{). Derivatives: acetonide (}{}^{1}\\text{H NMR). Biological activities (}\\mu\\text{g/mL): BST LC}_{50}\\ 1.8,\\ \\text{A-549 ED}_{50}\\ 1.9\\times10^{-1},\\ \\text{MCF-7 ED}_{50}\\ 1.9,\\ \\text{HT-29 ED}_{50}\\ 7.1\\times10^{-2},\\ \\text{A-498 ED}_{50}\\ 1.7,\\ \\text{PC-3 ED}_{50}\\ 4.5\\times10^{-1},\\ \\text{PACA-2 ED}_{50}\\ 5.0\\times10^{-2}\\text{. Source: }\\textit{Annona muricata}\\text{, leaves.}\\\\ \\textbf{37. donnaienin}^{33}\\text{ (C}_{35}\\text{H}_{64}\\text{O}_{8}\\text{, MW 612)}", "inline": true, "text_offset": 12, "text_span": 10, "bbox_estimated": true, "notation": "latex", "alt": "White solid. alpha sub D : plus 8.0 to the power of circ of c, 0.05, MeOH . UV of lambda sub max, MeOH, nm : 220 times log epsilon 3.54 . IR of nu sub max, film, cm to the power of minus 1 : 3398, 2920, 2851, 1743, 1458. MS: EIMS m over z 377, 359, 343, 341, 325, 307, 289, 271, 269, 231, 213, 199, 195, 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 . Derivatives: acetonide of to the power of 1 H NMR . Biological activities of mu g over mL : BST LC sub 50 1.8, A minus 549 ED sub 50 1.9 times 10 to the power of minus 1, MCF minus 7 ED sub 50 1.9, HT minus 29 ED sub 50 7.1 times 10 to the power of minus 2, A minus 498 ED sub 50 1.7, PC minus 3 ED sub 50 4.5 times 10 to the power of minus 1, PACA minus 2 ED sub 50 5.0 times 10 to the power of minus 2 . Source: textit Annona muricata, leaves. textbf 37. donnaienin to the power of 33 times C sub 35 H sub 64 O sub 8, MW 612", "mathml": "White solid. [α]D: +8.0∘ (c0.05, MeOH). UV (λmax, MeOH, nm): 220 (logϵ 3.54). IR (νmax, film, cm−1): 3398, 2920, 2851, 1743, 1458. MS: EIMS m/z 377,359,343,341,325,307,289,271,269,231,213,199,195,177,141,123.NMR: 1H NMR (500 MHz, CDCl3), 13C NMR (125 MHz, CDCl3). Derivatives: acetonide (1H NMR). Biological activities (μg/mL): BST LC50 1.8, A-549 ED50 1.9×10−1, MCF-7 ED50 1.9, HT-29 ED50 7.1×10−2, A-498 ED50 1.7, PC-3 ED50 4.5×10−1, PACA-2 ED50 5.0×10−2. Source: Annona muricata, leaves.37.donnaienin33 (C35H64O8, MW 612)" } }, { "id": "p16.22.2", "order": 101, "type": "formula", "bbox": { "l": 74.88, "t": 238.08, "r": 534.48, "b": 190.32 }, "text": "\\text{White solid. }[\\alpha]_D\\text{: }+8.0^\\circ\\,(c\\,0.05,\\text{MeOH}).\\ \\text{UV}\\,(\\lambda_{max}\\text{, MeOH, nm: }220\\,(\\log\\epsilon\\,3.54)).\\ \\text{IR}\\,(\\nu_{max}\\text{, film, cm}^{-1}\\text{: }3398, 2920, 2851, 1743, 1458).\\ \\text{MS: EIMS } m/z\\ 377, 359, 343, 341, 325, 307, 289, 271, 269, 231, 213, 199, 195, 177, 141, 123.\\ \\text{NMR: }{}^1\\text{H NMR (500 MHz, CDCl}_3\\text{), }{}^{13}\\text{C NMR (125 MHz, CDCl}_3\\text{). Derivatives: acetonide (}{}^1\\text{H NMR}\\text{). Biological activities (}\\mu\\text{g/mL}\\text{): BST LC}_{50}\\ 1.8,\\ \\text{A-549 ED}_{50}\\ 1.9\\times10^{-1},\\ \\text{MCF-7 ED}_{50}\\ 1.9,\\ \\text{HT-29 ED}_{50}\\ 7.1\\times10^{-2},\\ \\text{A-498 ED}_{50}\\ 1.7,\\ \\text{PC-3 ED}_{50}\\ 4.5\\times10^{-1},\\ \\text{PACA-2 ED}_{50}\\ 5.0\\times10^{-2}.\\ \\text{Source: }\\textit{Annona muricata}\\text{, leaves.}\\\\ \\text{37. donnaienin}^{33}\\ (\\text{C}_{35}\\text{H}_{64}\\text{O}_{8}\\text{, MW 612})", "attrs": { "latex": "\\text{White solid. }[\\alpha]_D\\text{: }+8.0^\\circ\\,(c\\,0.05,\\text{MeOH}).\\ \\text{UV}\\,(\\lambda_{max}\\text{, MeOH, nm: }220\\,(\\log\\epsilon\\,3.54)).\\ \\text{IR}\\,(\\nu_{max}\\text{, film, cm}^{-1}\\text{: }3398, 2920, 2851, 1743, 1458).\\ \\text{MS: EIMS } m/z\\ 377, 359, 343, 341, 325, 307, 289, 271, 269, 231, 213, 199, 195, 177, 141, 123.\\ \\text{NMR: }{}^1\\text{H NMR (500 MHz, CDCl}_3\\text{), }{}^{13}\\text{C NMR (125 MHz, CDCl}_3\\text{). Derivatives: acetonide (}{}^1\\text{H NMR}\\text{). Biological activities (}\\mu\\text{g/mL}\\text{): BST LC}_{50}\\ 1.8,\\ \\text{A-549 ED}_{50}\\ 1.9\\times10^{-1},\\ \\text{MCF-7 ED}_{50}\\ 1.9,\\ \\text{HT-29 ED}_{50}\\ 7.1\\times10^{-2},\\ \\text{A-498 ED}_{50}\\ 1.7,\\ \\text{PC-3 ED}_{50}\\ 4.5\\times10^{-1},\\ \\text{PACA-2 ED}_{50}\\ 5.0\\times10^{-2}.\\ \\text{Source: }\\textit{Annona muricata}\\text{, leaves.}\\\\ \\text{37. donnaienin}^{33}\\ (\\text{C}_{35}\\text{H}_{64}\\text{O}_{8}\\text{, MW 612})", "inline": true, "text_offset": 50, "text_span": 10, "bbox_estimated": true, "notation": "latex", "alt": "White solid. alpha sub D : plus 8.0 to the power of circ, c, 0.05, MeOH . UV, lambda sub max, MeOH, nm: 220, log epsilon, 3.54 . IR, nu sub max, film, cm to the power of minus 1 : 3398, 2920, 2851, 1743, 1458 . MS: EIMS m over z 377, 359, 343, 341, 325, 307, 289, 271, 269, 231, 213, 199, 195, 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 . Derivatives: acetonide of to the power of 1 H NMR . Biological activities of mu g over mL : BST LC sub 50 1.8, A minus 549 ED sub 50 1.9 times 10 to the power of minus 1, MCF minus 7 ED sub 50 1.9, HT minus 29 ED sub 50 7.1 times 10 to the power of minus 2, A minus 498 ED sub 50 1.7, PC minus 3 ED sub 50 4.5 times 10 to the power of minus 1, PACA minus 2 ED sub 50 5.0 times 10 to the power of minus 2 . Source: textit Annona muricata, leaves. 37. donnaienin to the power of 33 times C sub 35 H sub 64 O sub 8, MW 612", "mathml": "White solid. [α]D: +8.0∘(c0.05,MeOH). UV(λmax, MeOH, nm: 220(logϵ3.54)). IR(νmax, film, cm−1: 3398,2920,2851,1743,1458). MS: EIMS m/z 377,359,343,341,325,307,289,271,269,231,213,199,195,177,141,123. NMR: 1H NMR (500 MHz, CDCl3), 13C NMR (125 MHz, CDCl3). Derivatives: acetonide (1H NMR). Biological activities (μg/mL): BST LC50 1.8, A-549 ED50 1.9×10−1, MCF-7 ED50 1.9, HT-29 ED50 7.1×10−2, A-498 ED50 1.7, PC-3 ED50 4.5×10−1, PACA-2 ED50 5.0×10−2. Source: Annona muricata, leaves.37.donnaienin33 (C35H64O8, MW 612)" } }, { "id": "p16.22.3", "order": 102, "type": "text", "bbox": { "l": 74.88, "t": 238.08, "r": 534.48, "b": 190.32 }, "text": "ε", "attrs": { "inline": true, "text_offset": 81, "text_span": 10, "bbox_estimated": true } }, { "id": "p16.22.4", "order": 103, "type": "text", "bbox": { "l": 74.88, "t": 238.08, "r": 534.48, "b": 190.32 }, "text": "\\nu_{max}", "attrs": { "inline": true, "text_offset": 103, "text_span": 10, "bbox_estimated": true } }, { "id": "p16.22.5", "order": 104, "type": "text", "bbox": { "l": 74.88, "t": 238.08, "r": 534.48, "b": 190.32 }, "text": "⁻¹", "attrs": { "inline": true, "text_offset": 123, "text_span": 10, "bbox_estimated": true } }, { "id": "p16.22.6", "order": 105, "type": "text", "bbox": { "l": 74.88, "t": 238.08, "r": 534.48, "b": 190.32 }, "text": "¹", "attrs": { "inline": true, "text_offset": 264, "text_span": 10, "bbox_estimated": true } }, { "id": "p16.22.7", "order": 106, "type": "text", "bbox": { "l": 74.88, "t": 238.08, "r": 534.48, "b": 190.32 }, "text": "₃", "attrs": { "inline": true, "text_offset": 294, "text_span": 10, "bbox_estimated": true } }, { "id": "p16.22.8", "order": 107, "type": "formula", "bbox": { "l": 74.88, "t": 238.08, "r": 534.48, "b": 190.32 }, "text": "¹³", "attrs": { "latex": "{}^{13}", "inline": true, "text_offset": 307, "text_span": 10, "bbox_estimated": true, "alt": "to the power of 13", "mathml": "13" } }, { "id": "p16.22.9", "order": 108, "type": "text", "bbox": { "l": 74.88, "t": 238.08, "r": 534.48, "b": 190.32 }, "text": "₃", "attrs": { "inline": true, "text_offset": 337, "text_span": 10, "bbox_estimated": true } }, { "id": "p16.22.10", "order": 109, "type": "text", "bbox": { "l": 74.88, "t": 238.08, "r": 534.48, "b": 190.32 }, "text": "μ", "attrs": { "inline": true, "text_offset": 407, "text_span": 11, "bbox_estimated": true } }, { "id": "p16.22.11", "order": 110, "type": "text", "bbox": { "l": 74.88, "t": 238.08, "r": 534.48, "b": 190.32 }, "text": "₅₀", "attrs": { "inline": true, "text_offset": 431, "text_span": 11, "bbox_estimated": true } }, { "id": "p16.22.12", "order": 111, "type": "text", "bbox": { "l": 74.88, "t": 238.08, "r": 534.48, "b": 190.32 }, "text": "₅₀", "attrs": { "inline": true, "text_offset": 456, "text_span": 11, "bbox_estimated": true } }, { "id": "p16.22.13", "order": 112, "type": "text", "bbox": { "l": 74.88, "t": 238.08, "r": 534.48, "b": 190.32 }, "text": "×", "attrs": { "inline": true, "text_offset": 471, "text_span": 11, "bbox_estimated": true } }, { "id": "p16.22.14", "order": 113, "type": "text", "bbox": { "l": 74.88, "t": 238.08, "r": 534.48, "b": 190.32 }, "text": "⁻¹", "attrs": { "inline": true, "text_offset": 485, "text_span": 11, "bbox_estimated": true } }, { "id": "p16.22.15", "order": 114, "type": "text", "bbox": { "l": 74.88, "t": 238.08, "r": 534.48, "b": 190.32 }, "text": "₅₀", "attrs": { "inline": true, "text_offset": 506, "text_span": 11, "bbox_estimated": true } }, { "id": "p16.22.16", "order": 115, "type": "text", "bbox": { "l": 74.88, "t": 238.08, "r": 534.48, "b": 190.32 }, "text": "₅₀", "attrs": { "inline": true, "text_offset": 531, "text_span": 11, "bbox_estimated": true } }, { "id": "p16.22.17", "order": 116, "type": "text", "bbox": { "l": 74.88, "t": 238.08, "r": 534.48, "b": 190.32 }, "text": "×", "attrs": { "inline": true, "text_offset": 546, "text_span": 11, "bbox_estimated": true } }, { "id": "p16.22.18", "order": 117, "type": "text", "bbox": { "l": 74.88, "t": 238.08, "r": 534.48, "b": 190.32 }, "text": "⁻²", "attrs": { "inline": true, "text_offset": 560, "text_span": 11, "bbox_estimated": true } }, { "id": "p16.22.19", "order": 118, "type": "text", "bbox": { "l": 74.88, "t": 238.08, "r": 534.48, "b": 190.32 }, "text": "₅₀", "attrs": { "inline": true, "text_offset": 581, "text_span": 11, "bbox_estimated": true } }, { "id": "p16.22.20", "order": 119, "type": "text", "bbox": { "l": 74.88, "t": 238.08, "r": 534.48, "b": 190.32 }, "text": "₅₀", "attrs": { "inline": true, "text_offset": 605, "text_span": 11, "bbox_estimated": true } }, { "id": "p16.22.21", "order": 120, "type": "text", "bbox": { "l": 74.88, "t": 238.08, "r": 534.48, "b": 190.32 }, "text": "×", "attrs": { "inline": true, "text_offset": 620, "text_span": 11, "bbox_estimated": true } }, { "id": "p16.22.22", "order": 121, "type": "text", "bbox": { "l": 74.88, "t": 238.08, "r": 534.48, "b": 190.32 }, "text": "⁻¹", "attrs": { "inline": true, "text_offset": 634, "text_span": 11, "bbox_estimated": true } }, { "id": "p16.22.23", "order": 122, "type": "text", "bbox": { "l": 74.88, "t": 238.08, "r": 534.48, "b": 190.32 }, "text": "₅₀", "attrs": { "inline": true, "text_offset": 655, "text_span": 11, "bbox_estimated": true } }, { "id": "p16.22.24", "order": 123, "type": "text", "bbox": { "l": 74.88, "t": 238.08, "r": 534.48, "b": 190.32 }, "text": "×", "attrs": { "inline": true, "text_offset": 670, "text_span": 11, "bbox_estimated": true } }, { "id": "p16.22.25", "order": 124, "type": "text", "bbox": { "l": 74.88, "t": 238.08, "r": 534.48, "b": 190.32 }, "text": "⁻²", "attrs": { "inline": true, "text_offset": 684, "text_span": 11, "bbox_estimated": true } } ] }, { "id": "p16.23", "order": 125, "type": "text", "bbox": { "l": 72.24, "t": 192, "r": 220.08, "b": 181.68 }, "text": "37. donnaienin[p16.23.1] ([p16.23.2], MW612)", "children": [ { "id": "p16.23.1", "order": 126, "type": "formula", "bbox": { "l": 72.24, "t": 192, "r": 220.08, "b": 181.68 }, "text": "³³", "attrs": { "latex": "^{33}", "inline": true, "text_offset": 14, "text_span": 10, "bbox_estimated": true, "alt": "to the power of 33", "mathml": "33" } }, { "id": "p16.23.2", "order": 127, "type": "formula", "bbox": { "l": 72.24, "t": 192, "r": 220.08, "b": 181.68 }, "text": "C₃₅H₆₄O₈", "attrs": { "latex": "C_{35}H_{64}O_{8}", "inline": true, "text_offset": 26, "text_span": 10, "bbox_estimated": true, "alt": "C sub 35 H sub 64 O sub 8", "mathml": "C35H64O8" } } ] }, { "id": "p16.24", "order": 128, "type": "formula", "bbox": { "l": 159.6, "t": 178.08, "r": 452.88, "b": 133.68 }, "text": "", "attrs": { "block_label": "image", "alt": "Skeletal structure of an annonaceous acetogenin-type polyketide: butenolide ring, THF ring, and hydroxyls at C4, C10, C13, C…", "source": "vision" } }, { "id": "p16.25", "order": 129, "type": "table", "bbox": { "l": 158.16, "t": 119.76, "r": 391.68, "b": 86.4 }, "text": "", "attrs": { "block_label": "table", "n_rows": 3, "n_cols": 7, "integrity": { "skipped": "no_text_layer" } }, "children": [ { "id": "p16.25.1", "order": 130, "type": "table_cell", "bbox": { "l": 158.16, "t": 119.76, "r": 191.52, "b": 108.64 }, "text": "Position", "attrs": { "row": 0, "col": 0, "rowspan": 1, "colspan": 1, "column_header": true, "header_source": "heuristic" } }, { "id": "p16.25.2", "order": 131, "type": "table_cell", "bbox": { "l": 191.52, "t": 119.76, "r": 224.88, "b": 108.64 }, "text": "10", "attrs": { "row": 0, "col": 1, "rowspan": 1, "colspan": 1, "column_header": true, "header_source": "heuristic" } }, { "id": "p16.25.3", "order": 132, "type": "table_cell", "bbox": { "l": 224.88, "t": 119.76, "r": 258.24, "b": 108.64 }, "text": "13", "attrs": { "row": 0, "col": 2, "rowspan": 1, "colspan": 1, "column_header": true, "header_source": "heuristic" } }, { "id": "p16.25.4", "order": 133, "type": "table_cell", "bbox": { "l": 258.24, "t": 119.76, "r": 291.6, "b": 108.64 }, "text": "14", "attrs": { "row": 0, "col": 3, "rowspan": 1, "colspan": 1, "column_header": true, "header_source": "heuristic" } }, { "id": "p16.25.5", "order": 134, "type": "table_cell", "bbox": { "l": 291.6, "t": 119.76, "r": 324.96, "b": 108.64 }, "text": "15", "attrs": { "row": 0, "col": 4, "rowspan": 1, "colspan": 1, "column_header": true, "header_source": "heuristic" } }, { "id": "p16.25.6", "order": 135, "type": "table_cell", "bbox": { "l": 324.96, "t": 119.76, "r": 358.32, "b": 108.64 }, "text": "17", "attrs": { "row": 0, "col": 5, "rowspan": 1, "colspan": 1, "column_header": true, "header_source": "heuristic" } }, { "id": "p16.25.7", "order": 136, "type": "table_cell", "bbox": { "l": 358.32, "t": 119.76, "r": 391.68, "b": 108.64 }, "text": "18", "attrs": { "row": 0, "col": 6, "rowspan": 1, "colspan": 1, "column_header": true, "header_source": "heuristic" } }, { "id": "p16.25.8", "order": 137, "type": "table_cell", "bbox": { "l": 158.16, "t": 108.64, "r": 191.52, "b": 97.52 }, "text": "¹H ( \\delta )", "attrs": { "row": 1, "col": 0, "rowspan": 1, "colspan": 1 } }, { "id": "p16.25.9", "order": 138, "type": "table_cell", "bbox": { "l": 191.52, "t": 108.64, "r": 224.88, "b": 97.52 }, "text": "3.70 m", "attrs": { "row": 1, "col": 1, "rowspan": 1, "colspan": 1 } }, { "id": "p16.25.10", "order": 139, "type": "table_cell", "bbox": { "l": 224.88, "t": 108.64, "r": 258.24, "b": 97.52 }, "text": "3.62 m", "attrs": { "row": 1, "col": 2, "rowspan": 1, "colspan": 1 } }, { "id": "p16.25.11", "order": 140, "type": "table_cell", "bbox": { "l": 258.24, "t": 108.64, "r": 291.6, "b": 97.52 }, "text": "3.75 m", "attrs": { "row": 1, "col": 3, "rowspan": 1, "colspan": 1 } }, { "id": "p16.25.12", "order": 141, "type": "table_cell", "bbox": { "l": 291.6, "t": 108.64, "r": 324.96, "b": 97.52 }, "text": "4.38 m", "attrs": { "row": 1, "col": 4, "rowspan": 1, "colspan": 1 } }, { "id": "p16.25.13", "order": 142, "type": "table_cell", "bbox": { "l": 324.96, "t": 108.64, "r": 358.32, "b": 97.52 }, "text": "4.14 m", "attrs": { "row": 1, "col": 5, "rowspan": 1, "colspan": 1 } }, { "id": "p16.25.14", "order": 143, "type": "table_cell", "bbox": { "l": 358.32, "t": 108.64, "r": 391.68, "b": 97.52 }, "text": "3.47 m", "attrs": { "row": 1, "col": 6, "rowspan": 1, "colspan": 1 } }, { "id": "p16.25.15", "order": 144, "type": "table_cell", "bbox": { "l": 158.16, "t": 97.52, "r": 191.52, "b": 86.4 }, "text": "¹³C ( \\delta )", "attrs": { "row": 2, "col": 0, "rowspan": 1, "colspan": 1 } }, { "id": "p16.25.16", "order": 145, "type": "table_cell", "bbox": { "l": 191.52, "t": 97.52, "r": 224.88, "b": 86.4 }, "text": "72.0", "attrs": { "row": 2, "col": 1, "rowspan": 1, "colspan": 1 } }, { "id": "p16.25.17", "order": 146, "type": "table_cell", "bbox": { "l": 224.88, "t": 97.52, "r": 258.24, "b": 86.4 }, "text": "71.5", "attrs": { "row": 2, "col": 2, "rowspan": 1, "colspan": 1 } }, { "id": "p16.25.18", "order": 147, "type": "table_cell", "bbox": { "l": 258.24, "t": 97.52, "r": 291.6, "b": 86.4 }, "text": "89.0", "attrs": { "row": 2, "col": 3, "rowspan": 1, "colspan": 1 } }, { "id": "p16.25.19", "order": 148, "type": "table_cell", "bbox": { "l": 291.6, "t": 97.52, "r": 324.96, "b": 86.4 }, "text": "73.6", "attrs": { "row": 2, "col": 4, "rowspan": 1, "colspan": 1 } }, { "id": "p16.25.20", "order": 149, "type": "table_cell", "bbox": { "l": 324.96, "t": 97.52, "r": 358.32, "b": 86.4 }, "text": "81.2", "attrs": { "row": 2, "col": 5, "rowspan": 1, "colspan": 1 } }, { "id": "p16.25.21", "order": 150, "type": "table_cell", "bbox": { "l": 358.32, "t": 97.52, "r": 391.68, "b": 86.4 }, "text": "73.8", "attrs": { "row": 2, "col": 6, "rowspan": 1, "colspan": 1 } } ] }, { "id": "p16.26", "order": 151, "type": "text", "bbox": { "l": 73.92, "t": 84, "r": 521.28, "b": 46.56 }, "text": "White amorphous powder. Mp: 90–92°C. [α]D: +O (c O.25, MeOH). IR (νmax, film, cm⁻¹): 3429, 2920, 2850, 1746, 1469. MS: EIMS m/z 385, 367, 349, 331, 313, 299, 281, 263, 245, 241, 227, 141. NMR: ¹H NMR (500MHz, CDCl₃), ¹³C NMR (125MHz, CDCl₃). Derivatives: peracetate (¹H NMR), formal acetal (¹H NMR), TMS (EIMS). Biological activities (μg/mL): KB IC₅₀ >10, HCT-8IC₅₀ >10, Bel IC₅₀ 6.7. Source: Goniothalamus donnaiensis, roots." } ], "excluded_furniture": { "first": [], "last": [] } }