{ "document_id": 14408, "page": 24, "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": 145, "counts_by_type": { "figure": 2, "form_field": 1, "formula": 29, "header": 4, "table": 2, "table_cell": 48, "text": 59 }, "build_ms": 17, "items": [ { "id": "p24.1", "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": "p24.2", "order": 2, "type": "header", "bbox": { "l": 350.16, "t": 766.08, "r": 540.72, "b": 756 }, "text": "Journal of Natural Products, 1999, Vol. 62, No. 3", "attrs": { "block_label": "header" }, "level": 2 }, { "id": "p24.3", "order": 3, "type": "header", "bbox": { "l": 53.76, "t": 746.16, "r": 142.56, "b": 736.08 }, "text": "Table 4. (Continued)", "attrs": { "block_label": "figure_title" }, "level": 2 }, { "id": "p24.4", "order": 4, "type": "header", "bbox": { "l": 543.12, "t": 765.84, "r": 558.72, "b": 756.96 }, "text": "527", "attrs": { "block_label": "number" }, "level": 2 }, { "id": "p24.5", "order": 5, "type": "text", "bbox": { "l": 223.92, "t": 733.2, "r": 386.64, "b": 723.12 }, "text": "Adjacent Bis-THF Acetogenins (Continued)" }, { "id": "p24.6", "order": 6, "type": "figure", "bbox": { "l": 149.28, "t": 726.24, "r": 459.12, "b": 601.2 }, "text": "", "attrs": { "block_label": "image", "embedded_text": "67 O 7 , MW 622)" }, "children": [ { "id": "p24.6.1", "order": 7, "type": "text", "bbox": { "l": 155.04, "t": 637.44, "r": 419.76, "b": 628.08 }, "text": "Position 89121314161" }, { "id": "p24.6.2", "order": 8, "type": "text", "bbox": { "l": 153.6, "t": 624.72, "r": 425.52, "b": 601.92 }, "text": "[p24.6.2.1]H (δ) 3.42 m 3.95 m 4.31 m 3.71 m 4.32 m 4.04 m 3.53 m\n [p24.6.2.2]C (δ) 73.6 83.4 78.9 83.5 72.8 79.9 73.7", "children": [ { "id": "p24.6.2.1", "order": 9, "type": "formula", "bbox": { "l": 153.6, "t": 624.72, "r": 425.52, "b": 601.92 }, "text": "¹", "attrs": { "latex": "^{1}", "inline": true, "text_offset": 0, "text_span": 11, "bbox_estimated": true, "alt": "to the power of 1", "mathml": "1" } }, { "id": "p24.6.2.2", "order": 10, "type": "text", "bbox": { "l": 153.6, "t": 624.72, "r": 425.52, "b": 601.92 }, "text": "¹³", "attrs": { "inline": true, "text_offset": 67, "text_span": 11, "bbox_estimated": true } } ] } ] }, { "id": "p24.7", "order": 11, "type": "text", "bbox": { "l": 69.84, "t": 722.64, "r": 205.92, "b": 712.56 }, "text": "75. mucoxin[p24.7.1] (C [p24.7.2]H [p24.7.3]O[p24.7.4], MW622)", "children": [ { "id": "p24.7.1", "order": 12, "type": "formula", "bbox": { "l": 69.84, "t": 722.64, "r": 205.92, "b": 712.56 }, "text": "^{*9}", "attrs": { "latex": "^{*9}", "inline": true, "text_offset": 11, "text_span": 9, "bbox_estimated": true, "notation": "latex", "alt": "to the power of *9", "mathml": "*9" } }, { "id": "p24.7.2", "order": 13, "type": "text", "bbox": { "l": 69.84, "t": 722.64, "r": 205.92, "b": 712.56 }, "text": "₃₇", "attrs": { "inline": true, "text_offset": 24, "text_span": 9, "bbox_estimated": true } }, { "id": "p24.7.3", "order": 14, "type": "text", "bbox": { "l": 69.84, "t": 722.64, "r": 205.92, "b": 712.56 }, "text": "₆₇", "attrs": { "inline": true, "text_offset": 35, "text_span": 9, "bbox_estimated": true } }, { "id": "p24.7.4", "order": 15, "type": "text", "bbox": { "l": 69.84, "t": 722.64, "r": 205.92, "b": 712.56 }, "text": "₇", "attrs": { "inline": true, "text_offset": 45, "text_span": 9, "bbox_estimated": true } } ] }, { "id": "p24.8", "order": 16, "type": "text", "bbox": { "l": 71.76, "t": 600.24, "r": 536.64, "b": 565.92 }, "text": "Colorless oil. MS: E1MS m/z 337, 319, 269, 267, 251, 249, 197. NMR: [p24.8.1]H NMR (500 MHz, CDCl[p24.8.2]), [p24.8.3]C NMR (125 MHz, CDCl[p24.8.4]). Derivatives: per-MTPA esters ( [p24.8.5]H NMR), TMS (EIMS). Biological activities ( [p24.8.6]g/mL): A-549 ED[p24.8.7] 3.6 × 10[p24.8.8], MCF-7 ED[p24.8.9] 3.7 × 10[p24.8.10], HT-29 ED[p24.8.11] 6.1 × 10[p24.8.12], A-498 ED[p24.8.13] 8.4 × 10[p24.8.14], PC-3 ED[p24.8.15] 3.1 × 10[p24.8.16], PAC-2 ED[p24.8.17] 3.3 × 10[p24.8.18]. Source: Rollinia mucosa leaves", "children": [ { "id": "p24.8.1", "order": 17, "type": "formula", "bbox": { "l": 71.76, "t": 600.24, "r": 536.64, "b": 565.92 }, "text": "¹", "attrs": { "latex": "^{1}", "inline": true, "text_offset": 68, "text_span": 9, "bbox_estimated": true, "alt": "to the power of 1", "mathml": "1" } }, { "id": "p24.8.2", "order": 18, "type": "text", "bbox": { "l": 71.76, "t": 600.24, "r": 536.64, "b": 565.92 }, "text": "₃", "attrs": { "inline": true, "text_offset": 97, "text_span": 9, "bbox_estimated": true } }, { "id": "p24.8.3", "order": 19, "type": "text", "bbox": { "l": 71.76, "t": 600.24, "r": 536.64, "b": 565.92 }, "text": "¹³", "attrs": { "inline": true, "text_offset": 109, "text_span": 9, "bbox_estimated": true } }, { "id": "p24.8.4", "order": 20, "type": "text", "bbox": { "l": 71.76, "t": 600.24, "r": 536.64, "b": 565.92 }, "text": "₃", "attrs": { "inline": true, "text_offset": 138, "text_span": 9, "bbox_estimated": true } }, { "id": "p24.8.5", "order": 21, "type": "formula", "bbox": { "l": 71.76, "t": 600.24, "r": 536.64, "b": 565.92 }, "text": "¹", "attrs": { "latex": "^{1}", "inline": true, "text_offset": 181, "text_span": 9, "bbox_estimated": true, "alt": "to the power of 1", "mathml": "1" } }, { "id": "p24.8.6", "order": 22, "type": "text", "bbox": { "l": 71.76, "t": 600.24, "r": 536.64, "b": 565.92 }, "text": "μ", "attrs": { "inline": true, "text_offset": 234, "text_span": 9, "bbox_estimated": true } }, { "id": "p24.8.7", "order": 23, "type": "text", "bbox": { "l": 71.76, "t": 600.24, "r": 536.64, "b": 565.92 }, "text": "₅₀", "attrs": { "inline": true, "text_offset": 258, "text_span": 9, "bbox_estimated": true } }, { "id": "p24.8.8", "order": 24, "type": "text", "bbox": { "l": 71.76, "t": 600.24, "r": 536.64, "b": 565.92 }, "text": "⁻²", "attrs": { "inline": true, "text_offset": 276, "text_span": 9, "bbox_estimated": true } }, { "id": "p24.8.9", "order": 25, "type": "text", "bbox": { "l": 71.76, "t": 600.24, "r": 536.64, "b": 565.92 }, "text": "₅₀", "attrs": { "inline": true, "text_offset": 295, "text_span": 9, "bbox_estimated": true } }, { "id": "p24.8.10", "order": 26, "type": "text", "bbox": { "l": 71.76, "t": 600.24, "r": 536.64, "b": 565.92 }, "text": "⁻³", "attrs": { "inline": true, "text_offset": 313, "text_span": 10, "bbox_estimated": true } }, { "id": "p24.8.11", "order": 27, "type": "text", "bbox": { "l": 71.76, "t": 600.24, "r": 536.64, "b": 565.92 }, "text": "₅₀", "attrs": { "inline": true, "text_offset": 333, "text_span": 10, "bbox_estimated": true } }, { "id": "p24.8.12", "order": 28, "type": "text", "bbox": { "l": 71.76, "t": 600.24, "r": 536.64, "b": 565.92 }, "text": "⁻¹", "attrs": { "inline": true, "text_offset": 352, "text_span": 10, "bbox_estimated": true } }, { "id": "p24.8.13", "order": 29, "type": "text", "bbox": { "l": 71.76, "t": 600.24, "r": 536.64, "b": 565.92 }, "text": "₅₀", "attrs": { "inline": true, "text_offset": 372, "text_span": 10, "bbox_estimated": true } }, { "id": "p24.8.14", "order": 30, "type": "text", "bbox": { "l": 71.76, "t": 600.24, "r": 536.64, "b": 565.92 }, "text": "⁻¹", "attrs": { "inline": true, "text_offset": 391, "text_span": 10, "bbox_estimated": true } }, { "id": "p24.8.15", "order": 31, "type": "text", "bbox": { "l": 71.76, "t": 600.24, "r": 536.64, "b": 565.92 }, "text": "₅₀", "attrs": { "inline": true, "text_offset": 410, "text_span": 10, "bbox_estimated": true } }, { "id": "p24.8.16", "order": 32, "type": "text", "bbox": { "l": 71.76, "t": 600.24, "r": 536.64, "b": 565.92 }, "text": "⁻¹", "attrs": { "inline": true, "text_offset": 429, "text_span": 10, "bbox_estimated": true } }, { "id": "p24.8.17", "order": 33, "type": "text", "bbox": { "l": 71.76, "t": 600.24, "r": 536.64, "b": 565.92 }, "text": "₅₀", "attrs": { "inline": true, "text_offset": 449, "text_span": 10, "bbox_estimated": true } }, { "id": "p24.8.18", "order": 34, "type": "text", "bbox": { "l": 71.76, "t": 600.24, "r": 536.64, "b": 565.92 }, "text": "⁻¹", "attrs": { "inline": true, "text_offset": 468, "text_span": 10, "bbox_estimated": true } } ] }, { "id": "p24.9", "order": 35, "type": "text", "bbox": { "l": 80.16, "t": 571.92, "r": 172.08, "b": 563.52 }, "text": "Rollinia mucosa, leaves." }, { "id": "p24.10", "order": 36, "type": "text", "bbox": { "l": 70.8, "t": 563.28, "r": 212.16, "b": 552.72 }, "text": "76. carolin A[p24.10.1] (C [p24.10.2]H [p24.10.3]O[p24.10.4], MW622)", "children": [ { "id": "p24.10.1", "order": 37, "type": "text", "bbox": { "l": 70.8, "t": 563.28, "r": 212.16, "b": 552.72 }, "text": "^{*28}", "attrs": { "inline": true, "text_offset": 13, "text_span": 10, "bbox_estimated": true } }, { "id": "p24.10.2", "order": 38, "type": "text", "bbox": { "l": 70.8, "t": 563.28, "r": 212.16, "b": 552.72 }, "text": "₃₇", "attrs": { "inline": true, "text_offset": 27, "text_span": 10, "bbox_estimated": true } }, { "id": "p24.10.3", "order": 39, "type": "text", "bbox": { "l": 70.8, "t": 563.28, "r": 212.16, "b": 552.72 }, "text": "₆₆", "attrs": { "inline": true, "text_offset": 39, "text_span": 10, "bbox_estimated": true } }, { "id": "p24.10.4", "order": 40, "type": "formula", "bbox": { "l": 70.8, "t": 563.28, "r": 212.16, "b": 552.72 }, "text": "₇", "attrs": { "latex": "_{7}", "inline": true, "text_offset": 50, "text_span": 10, "bbox_estimated": true, "alt": "sub 7", "mathml": "7" } } ] }, { "id": "p24.11", "order": 41, "type": "figure", "bbox": { "l": 153.12, "t": 547.92, "r": 457.68, "b": 457.68 }, "text": "", "attrs": { "block_label": "image" }, "children": [ { "id": "p24.11.1", "order": 42, "type": "text", "bbox": { "l": 154.08, "t": 494.88, "r": 423.84, "b": 459.84 }, "text": "Position 15 16 19 20 23 24 28\n [p24.11.1.1]H (δ) 3.39 m 3.87 m 3.87 m 3.87 m 3.93 m 3.78 m 3.56 m\n [p24.11.1.2]C (δ) 73.9 83.0 82.6 82.4 81.9 71.6 71.3\n¹H (δ) 3.39 m 3.87 m 3.87 m 3.87 m 3.93 m 3.78 m 3.56 m\n ¹³C (δ) 73.9 83.0 82.6 82.4 81.9 71.6 71.3", "children": [ { "id": "p24.11.1.1", "order": 43, "type": "formula", "bbox": { "l": 154.08, "t": 494.88, "r": 423.84, "b": 459.84 }, "text": "¹", "attrs": { "latex": "^{1}", "inline": true, "text_offset": 31, "text_span": 12, "bbox_estimated": true, "alt": "to the power of 1", "mathml": "1" } }, { "id": "p24.11.1.2", "order": 44, "type": "text", "bbox": { "l": 154.08, "t": 494.88, "r": 423.84, "b": 459.84 }, "text": "¹³", "attrs": { "inline": true, "text_offset": 99, "text_span": 12, "bbox_estimated": true } } ] } ] }, { "id": "p24.12", "order": 45, "type": "text", "bbox": { "l": 71.04, "t": 457.92, "r": 532.32, "b": 420.96 }, "text": "Transparent oil. $ [\\alpha]_{D}: +22^{○} (c\\,1, CHCl_{3}) $. UV ( $ \\lambda_{max} $, MeOH, nm): 208 ([p24.12.2] 4.6). IR ( $ \\nu_{max} $, film, cm[p24.12.3]): 3675, 3474, 1749, 1652, 1458. NMR:[p24.12.4] NMR (400 MHz,[p24.12.5]),[p24.12.6] NMR (50 MHz,[p24.12.7]). Derivatives: per-acetate ([p24.12.8] NMR), formal acetal ([p24.12.9] NMR). Biological activities ( [p24.12.10]g/mL): KB ED[p24.12.11][p24.12.12], VERO KB ED[p24.12.13][p24.12.14]. Source: Annona spinescens, seeds.\n77. carolin B[p24.12.15] (C [p24.12.16]H [p24.12.17]O[p24.12.18], MW622)", "children": [ { "id": "p24.12.1", "order": 46, "type": "form_field", "bbox": { "l": 203.83, "t": 457.92, "r": 215.83, "b": 445.92 }, "text": "", "attrs": { "field_kind": "radio", "label": "} (c\\,1, CHCl_{3}) $. UV ( $ \\lambda_{max} $, MeOH, nm): 20…", "source": "glyph_estimate", "bbox_estimated": true, "label_source": "parent_text", "label_ref": "p24.12", "text_offset": 38, "text_span": 1 } }, { "id": "p24.12.2", "order": 47, "type": "formula", "bbox": { "l": 71.04, "t": 457.92, "r": 532.32, "b": 420.96 }, "text": "\\text{Transparent oil. } [\\alpha]_D: +22^\\circ\\ (c\\,1, \\text{CHCl}_3). \\text{UV } (\\lambda_{\\max}, \\text{MeOH, nm}): 208\\ (\\log \\epsilon\\ 4.6). \\text{IR } (\\nu_{\\max}, \\text{film, cm}^{-1}): 3675, 3474, 1749, 1652, 1458. \\text{NMR: }{}^{1}\\text{H NMR (400 MHz, CDCl}_3), {}^{13}\\text{C NMR (50 MHz, CDCl}_3). \\text{Derivatives: per-acetate (}{}^{1}\\text{H NMR), formal acetal (}{}^{1}\\text{H NMR). Biological activities } (\\mu\\text{g/mL}): \\text{KB ED}_{50}\\ 1\\times 10^{-7}, \\text{VERO KB ED}_{50}\\ 2\\times 10^{-3}. \\text{Source: } \\textit{Annona spinescens}\\text{, seeds.}\\\\ \\textbf{77. carolin B}^{*28}\\ (\\text{C}_{37}\\text{H}_{66}\\text{O}_7, \\text{MW}\\,622)", "attrs": { "latex": "\\text{Transparent oil. } [\\alpha]_D: +22^\\circ\\ (c\\,1, \\text{CHCl}_3). \\text{UV } (\\lambda_{\\max}, \\text{MeOH, nm}): 208\\ (\\log \\epsilon\\ 4.6). \\text{IR } (\\nu_{\\max}, \\text{film, cm}^{-1}): 3675, 3474, 1749, 1652, 1458. \\text{NMR: }{}^{1}\\text{H NMR (400 MHz, CDCl}_3), {}^{13}\\text{C NMR (50 MHz, CDCl}_3). \\text{Derivatives: per-acetate (}{}^{1}\\text{H NMR), formal acetal (}{}^{1}\\text{H NMR). Biological activities } (\\mu\\text{g/mL}): \\text{KB ED}_{50}\\ 1\\times 10^{-7}, \\text{VERO KB ED}_{50}\\ 2\\times 10^{-3}. \\text{Source: } \\textit{Annona spinescens}\\text{, seeds.}\\\\ \\textbf{77. carolin B}^{*28}\\ (\\text{C}_{37}\\text{H}_{66}\\text{O}_7, \\text{MW}\\,622)", "inline": true, "text_offset": 101, "text_span": 10, "bbox_estimated": true, "notation": "latex", "alt": "Transparent oil. alpha sub D : plus 22 to the power of circ of c, 1, CHCl sub 3 . UV of lambda sub max, MeOH, nm : 208 times log epsilon 4.6 . IR of nu sub max, film, cm to the power of minus 1 : 3675, 3474, 1749, 1652, 1458. 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 . Derivatives: per minus acetate of to the power of 1 H NMR, formal acetal of to the power of 1 H NMR . Biological activities of mu g over mL : KB ED sub 50 1 times 10 to the power of minus 7, VERO KB ED sub 50 2 times 10 to the power of minus 3 . Source: textit Annona spinescens, seeds. textbf 77. carolin B to the power of *28 times C sub 37 H sub 66 O sub 7, MW, 622", "mathml": "Transparent oil. [α]D:+22∘ (c1,CHCl3).UV (λmax,MeOH, nm):208 (logϵ 4.6).IR (νmax,film, cm−1):3675,3474,1749,1652,1458.NMR: 1H NMR (400 MHz, CDCl3),13C NMR (50 MHz, CDCl3).Derivatives: per-acetate (1H NMR), formal acetal (1H NMR). Biological activities (μg/mL):KB ED50 1×10−7,VERO KB ED50 2×10−3.Source: Annona spinescens, seeds.77. carolin B*28 (C37H66O7,MW622)" } }, { "id": "p24.12.3", "order": 48, "type": "formula", "bbox": { "l": 71.04, "t": 457.92, "r": 532.32, "b": 420.96 }, "text": "⁻¹", "attrs": { "latex": "^{-1}", "inline": true, "text_offset": 146, "text_span": 10, "bbox_estimated": true, "alt": "to the power of minus 1", "mathml": "−1" } }, { "id": "p24.12.4", "order": 49, "type": "formula", "bbox": { "l": 71.04, "t": 457.92, "r": 532.32, "b": 420.96 }, "text": "\\text{Transparent oil. }[\\alpha]_D\\text{: }+22^\\circ\\text{ (}c\\text{ 1, CHCl}_3\\text{). UV }(\\lambda_{\\max}\\text{, MeOH, nm): }208\\text{ (log }\\epsilon\\text{ 4.6). IR }(\\nu_{\\max}\\text{, film, cm}^{-1}\\text{): }3675,\\ 3474,\\ 1749,\\ 1652,\\ 1458.\\ \\text{NMR: }{}^{1}\\mathrm{H}\\text{ NMR (400 MHz, CDCl}_3\\text{), }{}^{13}\\mathrm{C}\\text{ NMR (50 MHz, CDCl}_3\\text{). Derivatives: per-acetate (}^{1}\\mathrm{H}\\text{ NMR), formal acetal (}^{1}\\mathrm{H}\\text{ NMR). Biological activities (}\\mu\\text{g/mL): KB ED}_{50}\\ 1\\times10^{-7},\\ \\text{VERO KB ED}_{50}\\ 2\\times10^{-3}.\\ \\text{Source: }\\textit{Annona spinescens}\\text{, seeds.}\\\\ \\textbf{77. carolin B}^{*28}\\text{ (C}_{37}\\text{H}_{66}\\text{O}_{7}\\text{, MW 622)}", "attrs": { "latex": "\\text{Transparent oil. }[\\alpha]_D\\text{: }+22^\\circ\\text{ (}c\\text{ 1, CHCl}_3\\text{). UV }(\\lambda_{\\max}\\text{, MeOH, nm): }208\\text{ (log }\\epsilon\\text{ 4.6). IR }(\\nu_{\\max}\\text{, film, cm}^{-1}\\text{): }3675,\\ 3474,\\ 1749,\\ 1652,\\ 1458.\\ \\text{NMR: }{}^{1}\\mathrm{H}\\text{ NMR (400 MHz, CDCl}_3\\text{), }{}^{13}\\mathrm{C}\\text{ NMR (50 MHz, CDCl}_3\\text{). Derivatives: per-acetate (}^{1}\\mathrm{H}\\text{ NMR), formal acetal (}^{1}\\mathrm{H}\\text{ NMR). Biological activities (}\\mu\\text{g/mL): KB ED}_{50}\\ 1\\times10^{-7},\\ \\text{VERO KB ED}_{50}\\ 2\\times10^{-3}.\\ \\text{Source: }\\textit{Annona spinescens}\\text{, seeds.}\\\\ \\textbf{77. carolin B}^{*28}\\text{ (C}_{37}\\text{H}_{66}\\text{O}_{7}\\text{, MW 622)}", "inline": true, "text_offset": 193, "text_span": 10, "bbox_estimated": true, "alt": "Transparent oil. alpha sub D : plus 22 to the power of circ of c 1, CHCl sub 3 . UV of lambda sub max, MeOH, nm : 208 times log epsilon 4.6 . IR of nu sub max, film, cm to the power of minus 1 : 3675, 3474, 1749, 1652, 1458. 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 . Derivatives: per minus acetate of to the power of 1 H NMR, formal acetal of to the power of 1 H NMR . Biological activities of mu g over mL : KB ED sub 50 1 times 10 to the power of minus 7, VERO KB ED sub 50 2 times 10 to the power of minus 3 . Source: textit Annona spinescens, seeds. textbf 77. carolin B to the power of *28 times C sub 37 H sub 66 O sub 7, MW 622", "notation": "latex", "mathml": "Transparent oil. [α]D: +22∘ (c 1, CHCl3). UV (λmax, MeOH, nm): 208 (log ϵ 4.6). IR (νmax, film, cm−1): 3675, 3474, 1749, 1652, 1458. NMR: 1H NMR (400 MHz, CDCl3), 13C NMR (50 MHz, CDCl3). Derivatives: per-acetate (1H NMR), formal acetal (1H NMR). Biological activities (μg/mL): KB ED50 1×10−7, VERO KB ED50 2×10−3. Source: Annona spinescens, seeds.77. carolin B*28 (C37H66O7, MW 622)" } }, { "id": "p24.12.5", "order": 50, "type": "formula", "bbox": { "l": 71.04, "t": 457.92, "r": 532.32, "b": 420.96 }, "text": "\\text{Transparent oil. }[\\alpha]_{D}\\text{: }+22^{\\circ}\\text{ (}c\\text{ 1, CHCl}_3\\text{). UV }(\\lambda_{\\max}\\text{, MeOH, nm): 208 (log }\\epsilon\\text{ 4.6). IR }(\\nu_{\\max}\\text{, film, cm}^{-1}\\text{): 3675, 3474, 1749, 1652, 1458. NMR: }^{1}\\text{H NMR (400 MHz, CDCl}_3\\text{), }^{13}\\text{C NMR (50 MHz, CDCl}_3\\text{). Derivatives: per-acetate (}^{1}\\text{H NMR), formal acetal (}^{1}\\text{H NMR). Biological activities (}\\mu\\text{g/mL): KB ED}_{50}\\text{ 1 }\\times 10^{-7}\\text{, VERO KB ED}_{50}\\text{ 2}\\times 10^{-3}\\text{. Source: }\\textit{Annona spinescens}\\text{, seeds.}\\\\ \\textbf{77. carolin B}^{*28}\\text{ (C}_{37}\\text{H}_{66}\\text{O}_{7}\\text{, MW 622)}", "attrs": { "latex": "\\text{Transparent oil. }[\\alpha]_{D}\\text{: }+22^{\\circ}\\text{ (}c\\text{ 1, CHCl}_3\\text{). UV }(\\lambda_{\\max}\\text{, MeOH, nm): 208 (log }\\epsilon\\text{ 4.6). IR }(\\nu_{\\max}\\text{, film, cm}^{-1}\\text{): 3675, 3474, 1749, 1652, 1458. NMR: }^{1}\\text{H NMR (400 MHz, CDCl}_3\\text{), }^{13}\\text{C NMR (50 MHz, CDCl}_3\\text{). Derivatives: per-acetate (}^{1}\\text{H NMR), formal acetal (}^{1}\\text{H NMR). Biological activities (}\\mu\\text{g/mL): KB ED}_{50}\\text{ 1 }\\times 10^{-7}\\text{, VERO KB ED}_{50}\\text{ 2}\\times 10^{-3}\\text{. Source: }\\textit{Annona spinescens}\\text{, seeds.}\\\\ \\textbf{77. carolin B}^{*28}\\text{ (C}_{37}\\text{H}_{66}\\text{O}_{7}\\text{, MW 622)}", "inline": true, "text_offset": 217, "text_span": 10, "bbox_estimated": true, "alt": "Transparent oil. alpha sub D : plus 22 to the power of circ of c 1, CHCl sub 3 . UV of lambda sub max, MeOH, nm : 208 times log epsilon 4.6 . IR of nu sub max, film, cm to the power of minus 1 : 3675, 3474, 1749, 1652, 1458. 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 . Derivatives: per minus acetate of to the power of 1 H NMR, formal acetal of to the power of 1 H NMR . Biological activities of mu g over mL : KB ED sub 50 1 times 10 to the power of minus 7, VERO KB ED sub 50 2 times 10 to the power of minus 3 . Source: textit Annona spinescens, seeds. textbf 77. carolin B to the power of *28 times C sub 37 H sub 66 O sub 7, MW 622", "notation": "latex", "mathml": "Transparent oil. [α]D: +22∘ (c 1, CHCl3). UV (λmax, MeOH, nm): 208 (log ϵ 4.6). IR (νmax, film, cm−1): 3675, 3474, 1749, 1652, 1458. NMR: 1H NMR (400 MHz, CDCl3), 13C NMR (50 MHz, CDCl3). Derivatives: per-acetate (1H NMR), formal acetal (1H NMR). Biological activities (μg/mL): KB ED50 1 ×10−7, VERO KB ED50 2×10−3. Source: Annona spinescens, seeds.77. carolin B*28 (C37H66O7, MW 622)" } }, { "id": "p24.12.6", "order": 51, "type": "text", "bbox": { "l": 71.04, "t": 457.92, "r": 532.32, "b": 420.96 }, "text": "¹³C", "attrs": { "inline": true, "text_offset": 229, "text_span": 10, "bbox_estimated": true } }, { "id": "p24.12.7", "order": 52, "type": "formula", "bbox": { "l": 71.04, "t": 457.92, "r": 532.32, "b": 420.96 }, "text": "\\text{Transparent oil. }[\\alpha]_{D}\\text{: }+22^{\\circ}\\text{ (}c\\text{ 1, CHCl}_3\\text{). UV }(\\lambda_{\\max}\\text{, MeOH, nm): 208 (log }\\epsilon\\text{ 4.6). IR }(\\nu_{\\max}\\text{, film, cm}^{-1}\\text{): 3675, 3474, 1749, 1652, 1458. NMR: }^{1}\\text{H NMR (400 MHz, CDCl}_3\\text{), }^{13}\\text{C NMR (50 MHz, CDCl}_3\\text{). Derivatives: per-acetate (}^{1}\\text{H NMR), formal acetal (}^{1}\\text{H NMR). Biological activities (}\\mu\\text{g/mL): KB ED}_{50}\\text{ 1 }\\times 10^{-7}\\text{, VERO KB ED}_{50}\\text{ 2}\\times 10^{-3}\\text{. Source: }\\textit{Annona spinescens}\\text{, seeds.}\\\\ \\textbf{77. carolin B}^{*28}\\text{ (C}_{37}\\text{H}_{66}\\text{O}_{7}\\text{, MW 622)}", "attrs": { "latex": "\\text{Transparent oil. }[\\alpha]_{D}\\text{: }+22^{\\circ}\\text{ (}c\\text{ 1, CHCl}_3\\text{). UV }(\\lambda_{\\max}\\text{, MeOH, nm): 208 (log }\\epsilon\\text{ 4.6). IR }(\\nu_{\\max}\\text{, film, cm}^{-1}\\text{): 3675, 3474, 1749, 1652, 1458. NMR: }^{1}\\text{H NMR (400 MHz, CDCl}_3\\text{), }^{13}\\text{C NMR (50 MHz, CDCl}_3\\text{). Derivatives: per-acetate (}^{1}\\text{H NMR), formal acetal (}^{1}\\text{H NMR). Biological activities (}\\mu\\text{g/mL): KB ED}_{50}\\text{ 1 }\\times 10^{-7}\\text{, VERO KB ED}_{50}\\text{ 2}\\times 10^{-3}\\text{. Source: }\\textit{Annona spinescens}\\text{, seeds.}\\\\ \\textbf{77. carolin B}^{*28}\\text{ (C}_{37}\\text{H}_{66}\\text{O}_{7}\\text{, MW 622)}", "inline": true, "text_offset": 252, "text_span": 10, "bbox_estimated": true, "alt": "Transparent oil. alpha sub D : plus 22 to the power of circ of c 1, CHCl sub 3 . UV of lambda sub max, MeOH, nm : 208 times log epsilon 4.6 . IR of nu sub max, film, cm to the power of minus 1 : 3675, 3474, 1749, 1652, 1458. 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 . Derivatives: per minus acetate of to the power of 1 H NMR, formal acetal of to the power of 1 H NMR . Biological activities of mu g over mL : KB ED sub 50 1 times 10 to the power of minus 7, VERO KB ED sub 50 2 times 10 to the power of minus 3 . Source: textit Annona spinescens, seeds. textbf 77. carolin B to the power of *28 times C sub 37 H sub 66 O sub 7, MW 622", "notation": "latex", "mathml": "Transparent oil. [α]D: +22∘ (c 1, CHCl3). UV (λmax, MeOH, nm): 208 (log ϵ 4.6). IR (νmax, film, cm−1): 3675, 3474, 1749, 1652, 1458. NMR: 1H NMR (400 MHz, CDCl3), 13C NMR (50 MHz, CDCl3). Derivatives: per-acetate (1H NMR), formal acetal (1H NMR). Biological activities (μg/mL): KB ED50 1 ×10−7, VERO KB ED50 2×10−3. Source: Annona spinescens, seeds.77. carolin B*28 (C37H66O7, MW 622)" } }, { "id": "p24.12.8", "order": 53, "type": "formula", "bbox": { "l": 71.04, "t": 457.92, "r": 532.32, "b": 420.96 }, "text": "\\text{Transparent oil. }[\\alpha]_D\\text{: }+22^\\circ\\text{ (}c\\text{ 1, CHCl}_3\\text{). UV }(\\lambda_{\\max}\\text{, MeOH, nm): }208\\text{ (log }\\epsilon\\text{ 4.6). IR }(\\nu_{\\max}\\text{, film, cm}^{-1}\\text{): }3675,\\ 3474,\\ 1749,\\ 1652,\\ 1458.\\ \\text{NMR: }{}^{1}\\mathrm{H}\\text{ NMR (400 MHz, CDCl}_3\\text{), }{}^{13}\\mathrm{C}\\text{ NMR (50 MHz, CDCl}_3\\text{). Derivatives: per-acetate (}^{1}\\mathrm{H}\\text{ NMR), formal acetal (}^{1}\\mathrm{H}\\text{ NMR). Biological activities (}\\mu\\text{g/mL): KB ED}_{50}\\ 1\\times10^{-7},\\ \\text{VERO KB ED}_{50}\\ 2\\times10^{-3}.\\ \\text{Source: }\\textit{Annona spinescens}\\text{, seeds.}\\\\ \\textbf{77. carolin B}^{*28}\\text{ (C}_{37}\\text{H}_{66}\\text{O}_{7}\\text{, MW 622)}", "attrs": { "latex": "\\text{Transparent oil. }[\\alpha]_D\\text{: }+22^\\circ\\text{ (}c\\text{ 1, CHCl}_3\\text{). UV }(\\lambda_{\\max}\\text{, MeOH, nm): }208\\text{ (log }\\epsilon\\text{ 4.6). IR }(\\nu_{\\max}\\text{, film, cm}^{-1}\\text{): }3675,\\ 3474,\\ 1749,\\ 1652,\\ 1458.\\ \\text{NMR: }{}^{1}\\mathrm{H}\\text{ NMR (400 MHz, CDCl}_3\\text{), }{}^{13}\\mathrm{C}\\text{ NMR (50 MHz, CDCl}_3\\text{). Derivatives: per-acetate (}^{1}\\mathrm{H}\\text{ NMR), formal acetal (}^{1}\\mathrm{H}\\text{ NMR). Biological activities (}\\mu\\text{g/mL): KB ED}_{50}\\ 1\\times10^{-7},\\ \\text{VERO KB ED}_{50}\\ 2\\times10^{-3}.\\ \\text{Source: }\\textit{Annona spinescens}\\text{, seeds.}\\\\ \\textbf{77. carolin B}^{*28}\\text{ (C}_{37}\\text{H}_{66}\\text{O}_{7}\\text{, MW 622)}", "inline": true, "text_offset": 291, "text_span": 10, "bbox_estimated": true, "alt": "Transparent oil. alpha sub D : plus 22 to the power of circ of c 1, CHCl sub 3 . UV of lambda sub max, MeOH, nm : 208 times log epsilon 4.6 . IR of nu sub max, film, cm to the power of minus 1 : 3675, 3474, 1749, 1652, 1458. 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 . Derivatives: per minus acetate of to the power of 1 H NMR, formal acetal of to the power of 1 H NMR . Biological activities of mu g over mL : KB ED sub 50 1 times 10 to the power of minus 7, VERO KB ED sub 50 2 times 10 to the power of minus 3 . Source: textit Annona spinescens, seeds. textbf 77. carolin B to the power of *28 times C sub 37 H sub 66 O sub 7, MW 622", "notation": "latex", "mathml": "Transparent oil. [α]D: +22∘ (c 1, CHCl3). UV (λmax, MeOH, nm): 208 (log ϵ 4.6). IR (νmax, film, cm−1): 3675, 3474, 1749, 1652, 1458. NMR: 1H NMR (400 MHz, CDCl3), 13C NMR (50 MHz, CDCl3). Derivatives: per-acetate (1H NMR), formal acetal (1H NMR). Biological activities (μg/mL): KB ED50 1×10−7, VERO KB ED50 2×10−3. Source: Annona spinescens, seeds.77. carolin B*28 (C37H66O7, MW 622)" } }, { "id": "p24.12.9", "order": 54, "type": "formula", "bbox": { "l": 71.04, "t": 457.92, "r": 532.32, "b": 420.96 }, "text": "\\text{Transparent oil. }[\\alpha]_D\\text{: }+22^\\circ\\text{ (}c\\text{ 1, CHCl}_3\\text{). UV }(\\lambda_{\\max}\\text{, MeOH, nm): }208\\text{ (log }\\epsilon\\text{ 4.6). IR }(\\nu_{\\max}\\text{, film, cm}^{-1}\\text{): }3675,\\ 3474,\\ 1749,\\ 1652,\\ 1458.\\ \\text{NMR: }{}^{1}\\mathrm{H}\\text{ NMR (400 MHz, CDCl}_3\\text{), }{}^{13}\\mathrm{C}\\text{ NMR (50 MHz, CDCl}_3\\text{). Derivatives: per-acetate (}^{1}\\mathrm{H}\\text{ NMR), formal acetal (}^{1}\\mathrm{H}\\text{ NMR). Biological activities (}\\mu\\text{g/mL): KB ED}_{50}\\ 1\\times10^{-7},\\ \\text{VERO KB ED}_{50}\\ 2\\times10^{-3}.\\ \\text{Source: }\\textit{Annona spinescens}\\text{, seeds.}\\\\ \\textbf{77. carolin B}^{*28}\\text{ (C}_{37}\\text{H}_{66}\\text{O}_{7}\\text{, MW 622)}", "attrs": { "latex": "\\text{Transparent oil. }[\\alpha]_D\\text{: }+22^\\circ\\text{ (}c\\text{ 1, CHCl}_3\\text{). UV }(\\lambda_{\\max}\\text{, MeOH, nm): }208\\text{ (log }\\epsilon\\text{ 4.6). IR }(\\nu_{\\max}\\text{, film, cm}^{-1}\\text{): }3675,\\ 3474,\\ 1749,\\ 1652,\\ 1458.\\ \\text{NMR: }{}^{1}\\mathrm{H}\\text{ NMR (400 MHz, CDCl}_3\\text{), }{}^{13}\\mathrm{C}\\text{ NMR (50 MHz, CDCl}_3\\text{). Derivatives: per-acetate (}^{1}\\mathrm{H}\\text{ NMR), formal acetal (}^{1}\\mathrm{H}\\text{ NMR). Biological activities (}\\mu\\text{g/mL): KB ED}_{50}\\ 1\\times10^{-7},\\ \\text{VERO KB ED}_{50}\\ 2\\times10^{-3}.\\ \\text{Source: }\\textit{Annona spinescens}\\text{, seeds.}\\\\ \\textbf{77. carolin B}^{*28}\\text{ (C}_{37}\\text{H}_{66}\\text{O}_{7}\\text{, MW 622)}", "inline": true, "text_offset": 323, "text_span": 10, "bbox_estimated": true, "alt": "Transparent oil. alpha sub D : plus 22 to the power of circ of c 1, CHCl sub 3 . UV of lambda sub max, MeOH, nm : 208 times log epsilon 4.6 . IR of nu sub max, film, cm to the power of minus 1 : 3675, 3474, 1749, 1652, 1458. 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 . Derivatives: per minus acetate of to the power of 1 H NMR, formal acetal of to the power of 1 H NMR . Biological activities of mu g over mL : KB ED sub 50 1 times 10 to the power of minus 7, VERO KB ED sub 50 2 times 10 to the power of minus 3 . Source: textit Annona spinescens, seeds. textbf 77. carolin B to the power of *28 times C sub 37 H sub 66 O sub 7, MW 622", "notation": "latex", "mathml": "Transparent oil. [α]D: +22∘ (c 1, CHCl3). UV (λmax, MeOH, nm): 208 (log ϵ 4.6). IR (νmax, film, cm−1): 3675, 3474, 1749, 1652, 1458. NMR: 1H NMR (400 MHz, CDCl3), 13C NMR (50 MHz, CDCl3). Derivatives: per-acetate (1H NMR), formal acetal (1H NMR). Biological activities (μg/mL): KB ED50 1×10−7, VERO KB ED50 2×10−3. Source: Annona spinescens, seeds.77. carolin B*28 (C37H66O7, MW 622)" } }, { "id": "p24.12.10", "order": 55, "type": "text", "bbox": { "l": 71.04, "t": 457.92, "r": 532.32, "b": 420.96 }, "text": "μ", "attrs": { "inline": true, "text_offset": 364, "text_span": 11, "bbox_estimated": true } }, { "id": "p24.12.11", "order": 56, "type": "text", "bbox": { "l": 71.04, "t": 457.92, "r": 532.32, "b": 420.96 }, "text": "₅₀", "attrs": { "inline": true, "text_offset": 387, "text_span": 11, "bbox_estimated": true } }, { "id": "p24.12.12", "order": 57, "type": "formula", "bbox": { "l": 71.04, "t": 457.92, "r": 532.32, "b": 420.96 }, "text": "1 × 10⁻⁷", "attrs": { "latex": "1 \\times 10^{-7}", "inline": true, "text_offset": 398, "text_span": 11, "bbox_estimated": true, "alt": "1 times 10 to the power of minus 7", "mathml": "1×10−7" } }, { "id": "p24.12.13", "order": 58, "type": "text", "bbox": { "l": 71.04, "t": 457.92, "r": 532.32, "b": 420.96 }, "text": "₅₀", "attrs": { "inline": true, "text_offset": 421, "text_span": 11, "bbox_estimated": true } }, { "id": "p24.12.14", "order": 59, "type": "text", "bbox": { "l": 71.04, "t": 457.92, "r": 532.32, "b": 420.96 }, "text": "2 × 10⁻³", "attrs": { "inline": true, "text_offset": 432, "text_span": 11, "bbox_estimated": true } }, { "id": "p24.12.15", "order": 60, "type": "text", "bbox": { "l": 71.04, "t": 457.92, "r": 532.32, "b": 420.96 }, "text": "^{*28}", "attrs": { "inline": true, "text_offset": 492, "text_span": 11, "bbox_estimated": true } }, { "id": "p24.12.16", "order": 61, "type": "text", "bbox": { "l": 71.04, "t": 457.92, "r": 532.32, "b": 420.96 }, "text": "₃₇", "attrs": { "inline": true, "text_offset": 507, "text_span": 11, "bbox_estimated": true } }, { "id": "p24.12.17", "order": 62, "type": "formula", "bbox": { "l": 71.04, "t": 457.92, "r": 532.32, "b": 420.96 }, "text": "₆₆", "attrs": { "latex": "_{66}", "inline": true, "text_offset": 520, "text_span": 11, "bbox_estimated": true, "alt": "sub 66", "mathml": "66" } }, { "id": "p24.12.18", "order": 63, "type": "formula", "bbox": { "l": 71.04, "t": 457.92, "r": 532.32, "b": 420.96 }, "text": "₇", "attrs": { "latex": "_{7}", "inline": true, "text_offset": 532, "text_span": 11, "bbox_estimated": true, "alt": "sub 7", "mathml": "7" } } ] }, { "id": "p24.13", "order": 64, "type": "formula", "bbox": { "l": 153.84, "t": 411.6, "r": 457.92, "b": 368.4 }, "text": "", "attrs": { "block_label": "image", "alt": "Skeletal structure of an annonaceous acetogenin: bis-tetrahydrofuran core with hydroxyls at C-15, C-24 and C-29, ending in a…", "source": "vision" } }, { "id": "p24.14", "order": 65, "type": "table", "bbox": { "l": 152.64, "t": 360.24, "r": 423.36, "b": 324.72 }, "text": "", "attrs": { "block_label": "table", "n_rows": 3, "n_cols": 8, "integrity": { "skipped": "no_text_layer" } }, "children": [ { "id": "p24.14.1", "order": 66, "type": "table_cell", "bbox": { "l": 152.64, "t": 360.24, "r": 186.48, "b": 348.4 }, "text": "Position", "attrs": { "row": 0, "col": 0, "rowspan": 1, "colspan": 1, "column_header": true, "header_source": "heuristic" } }, { "id": "p24.14.2", "order": 67, "type": "table_cell", "bbox": { "l": 186.48, "t": 360.24, "r": 220.32, "b": 348.4 }, "text": "15", "attrs": { "row": 0, "col": 1, "rowspan": 1, "colspan": 1, "column_header": true, "header_source": "heuristic" } }, { "id": "p24.14.3", "order": 68, "type": "table_cell", "bbox": { "l": 220.32, "t": 360.24, "r": 254.16, "b": 348.4 }, "text": "16", "attrs": { "row": 0, "col": 2, "rowspan": 1, "colspan": 1, "column_header": true, "header_source": "heuristic" } }, { "id": "p24.14.4", "order": 69, "type": "table_cell", "bbox": { "l": 254.16, "t": 360.24, "r": 288, "b": 348.4 }, "text": "19", "attrs": { "row": 0, "col": 3, "rowspan": 1, "colspan": 1, "column_header": true, "header_source": "heuristic" } }, { "id": "p24.14.5", "order": 70, "type": "table_cell", "bbox": { "l": 288, "t": 360.24, "r": 321.84, "b": 348.4 }, "text": "20", "attrs": { "row": 0, "col": 4, "rowspan": 1, "colspan": 1, "column_header": true, "header_source": "heuristic" } }, { "id": "p24.14.6", "order": 71, "type": "table_cell", "bbox": { "l": 321.84, "t": 360.24, "r": 355.68, "b": 348.4 }, "text": "23", "attrs": { "row": 0, "col": 5, "rowspan": 1, "colspan": 1, "column_header": true, "header_source": "heuristic" } }, { "id": "p24.14.7", "order": 72, "type": "table_cell", "bbox": { "l": 355.68, "t": 360.24, "r": 389.52, "b": 348.4 }, "text": "24", "attrs": { "row": 0, "col": 6, "rowspan": 1, "colspan": 1, "column_header": true, "header_source": "heuristic" } }, { "id": "p24.14.8", "order": 73, "type": "table_cell", "bbox": { "l": 389.52, "t": 360.24, "r": 423.36, "b": 348.4 }, "text": "29", "attrs": { "row": 0, "col": 7, "rowspan": 1, "colspan": 1, "column_header": true, "header_source": "heuristic" } }, { "id": "p24.14.9", "order": 74, "type": "table_cell", "bbox": { "l": 152.64, "t": 348.4, "r": 186.48, "b": 336.56 }, "text": "¹H ( \\delta )", "attrs": { "row": 1, "col": 0, "rowspan": 1, "colspan": 1 } }, { "id": "p24.14.10", "order": 75, "type": "table_cell", "bbox": { "l": 186.48, "t": 348.4, "r": 220.32, "b": 336.56 }, "text": "3.35 m", "attrs": { "row": 1, "col": 1, "rowspan": 1, "colspan": 1 } }, { "id": "p24.14.11", "order": 76, "type": "table_cell", "bbox": { "l": 220.32, "t": 348.4, "r": 254.16, "b": 336.56 }, "text": "3.89 m", "attrs": { "row": 1, "col": 2, "rowspan": 1, "colspan": 1 } }, { "id": "p24.14.12", "order": 77, "type": "table_cell", "bbox": { "l": 254.16, "t": 348.4, "r": 288, "b": 336.56 }, "text": "3.89 m", "attrs": { "row": 1, "col": 3, "rowspan": 1, "colspan": 1 } }, { "id": "p24.14.13", "order": 78, "type": "table_cell", "bbox": { "l": 288, "t": 348.4, "r": 321.84, "b": 336.56 }, "text": "3.89 m", "attrs": { "row": 1, "col": 4, "rowspan": 1, "colspan": 1 } }, { "id": "p24.14.14", "order": 79, "type": "table_cell", "bbox": { "l": 321.84, "t": 348.4, "r": 355.68, "b": 336.56 }, "text": "3.90 m", "attrs": { "row": 1, "col": 5, "rowspan": 1, "colspan": 1 } }, { "id": "p24.14.15", "order": 80, "type": "table_cell", "bbox": { "l": 355.68, "t": 348.4, "r": 389.52, "b": 336.56 }, "text": "3.78 m", "attrs": { "row": 1, "col": 6, "rowspan": 1, "colspan": 1 } }, { "id": "p24.14.16", "order": 81, "type": "table_cell", "bbox": { "l": 389.52, "t": 348.4, "r": 423.36, "b": 336.56 }, "text": "3.55 m", "attrs": { "row": 1, "col": 7, "rowspan": 1, "colspan": 1 } }, { "id": "p24.14.17", "order": 82, "type": "table_cell", "bbox": { "l": 152.64, "t": 336.56, "r": 186.48, "b": 324.72 }, "text": "¹³C ( \\delta )", "attrs": { "row": 2, "col": 0, "rowspan": 1, "colspan": 1 } }, { "id": "p24.14.18", "order": 83, "type": "table_cell", "bbox": { "l": 186.48, "t": 336.56, "r": 220.32, "b": 324.72 }, "text": "73.9", "attrs": { "row": 2, "col": 1, "rowspan": 1, "colspan": 1 } }, { "id": "p24.14.19", "order": 84, "type": "table_cell", "bbox": { "l": 220.32, "t": 336.56, "r": 254.16, "b": 324.72 }, "text": "83.0", "attrs": { "row": 2, "col": 2, "rowspan": 1, "colspan": 1 } }, { "id": "p24.14.20", "order": 85, "type": "table_cell", "bbox": { "l": 254.16, "t": 336.56, "r": 288, "b": 324.72 }, "text": "82.6", "attrs": { "row": 2, "col": 3, "rowspan": 1, "colspan": 1 } }, { "id": "p24.14.21", "order": 86, "type": "table_cell", "bbox": { "l": 288, "t": 336.56, "r": 321.84, "b": 324.72 }, "text": "82.4", "attrs": { "row": 2, "col": 4, "rowspan": 1, "colspan": 1 } }, { "id": "p24.14.22", "order": 87, "type": "table_cell", "bbox": { "l": 321.84, "t": 336.56, "r": 355.68, "b": 324.72 }, "text": "81.9", "attrs": { "row": 2, "col": 5, "rowspan": 1, "colspan": 1 } }, { "id": "p24.14.23", "order": 88, "type": "table_cell", "bbox": { "l": 355.68, "t": 336.56, "r": 389.52, "b": 324.72 }, "text": "71.5", "attrs": { "row": 2, "col": 6, "rowspan": 1, "colspan": 1 } }, { "id": "p24.14.24", "order": 89, "type": "table_cell", "bbox": { "l": 389.52, "t": 336.56, "r": 423.36, "b": 324.72 }, "text": "71.3", "attrs": { "row": 2, "col": 7, "rowspan": 1, "colspan": 1 } } ] }, { "id": "p24.15", "order": 90, "type": "text", "bbox": { "l": 72.24, "t": 322.56, "r": 534.48, "b": 292.8 }, "text": "Transparent oil.[p24.15.1]: +5° (c O.5, CHCl_{3}). UV ([p24.15.2], MeOH, nm): 208 ([p24.15.3] 3.6). IR ([p24.15.4], film, cm^{-1}): 3677. 3575, 1753, 1619. NMR: [p24.15.5]H NMR (400 MHz, CDCl_{3}), [p24.15.6]C NMR (50 MHz, CDCl_{3}). Derivatives: peracetate (^{1}H NMR). Biological activities ( [p24.15.7]g/mL): KB ED_{50} 5[p24.15.8] 10^{-6}, VERO ED_{50} 37[p24.15.9] 10^{-3}. Source: Annona spinescens, seeds.", "children": [ { "id": "p24.15.1", "order": 91, "type": "formula", "bbox": { "l": 72.24, "t": 322.56, "r": 534.48, "b": 292.8 }, "text": "[\\alpha]_{D}", "attrs": { "latex": "[\\alpha]_{D}", "inline": true, "text_offset": 16, "text_span": 10, "bbox_estimated": true, "notation": "latex", "alt": "alpha sub D", "mathml": "[α]D" } }, { "id": "p24.15.2", "order": 92, "type": "formula", "bbox": { "l": 72.24, "t": 322.56, "r": 534.48, "b": 292.8 }, "text": "\\lambda_{max}", "attrs": { "latex": "\\lambda_{max}", "inline": true, "text_offset": 55, "text_span": 10, "bbox_estimated": true, "notation": "latex", "alt": "lambda sub max", "mathml": "λmax" } }, { "id": "p24.15.3", "order": 93, "type": "formula", "bbox": { "l": 72.24, "t": 322.56, "r": 534.48, "b": 292.8 }, "text": "\\log \\epsilon", "attrs": { "latex": "\\log \\epsilon", "inline": true, "text_offset": 83, "text_span": 10, "bbox_estimated": true, "notation": "latex", "alt": "log epsilon", "mathml": "logϵ" } }, { "id": "p24.15.4", "order": 94, "type": "text", "bbox": { "l": 72.24, "t": 322.56, "r": 534.48, "b": 292.8 }, "text": "\\nu_{max}", "attrs": { "inline": true, "text_offset": 104, "text_span": 10, "bbox_estimated": true } }, { "id": "p24.15.5", "order": 95, "type": "text", "bbox": { "l": 72.24, "t": 322.56, "r": 534.48, "b": 292.8 }, "text": "¹", "attrs": { "inline": true, "text_offset": 161, "text_span": 10, "bbox_estimated": true } }, { "id": "p24.15.6", "order": 96, "type": "formula", "bbox": { "l": 72.24, "t": 322.56, "r": 534.48, "b": 292.8 }, "text": "¹³", "attrs": { "latex": "{}^{13}", "inline": true, "text_offset": 198, "text_span": 10, "bbox_estimated": true, "alt": "to the power of 13", "mathml": "13" } }, { "id": "p24.15.7", "order": 97, "type": "text", "bbox": { "l": 72.24, "t": 322.56, "r": 534.48, "b": 292.8 }, "text": "μ", "attrs": { "inline": true, "text_offset": 295, "text_span": 10, "bbox_estimated": true } }, { "id": "p24.15.8", "order": 98, "type": "formula", "bbox": { "l": 72.24, "t": 322.56, "r": 534.48, "b": 292.8 }, "text": "×", "attrs": { "latex": "\\times", "inline": true, "text_offset": 324, "text_span": 10, "bbox_estimated": true, "alt": "times", "mathml": "×" } }, { "id": "p24.15.9", "order": 99, "type": "formula", "bbox": { "l": 72.24, "t": 322.56, "r": 534.48, "b": 292.8 }, "text": "×", "attrs": { "latex": "\\times", "inline": true, "text_offset": 359, "text_span": 10, "bbox_estimated": true, "alt": "times", "mathml": "×" } } ] }, { "id": "p24.16", "order": 100, "type": "text", "bbox": { "l": 70.08, "t": 294.24, "r": 211.68, "b": 284.4 }, "text": "78. carolin C[p24.16.1] (C [p24.16.2]H [p24.16.3]O[p24.16.4], MW594)", "children": [ { "id": "p24.16.1", "order": 101, "type": "formula", "bbox": { "l": 70.08, "t": 294.24, "r": 211.68, "b": 284.4 }, "text": "²⁸", "attrs": { "latex": "^{28}", "inline": true, "text_offset": 13, "text_span": 10, "bbox_estimated": true, "alt": "to the power of 28", "mathml": "28" } }, { "id": "p24.16.2", "order": 102, "type": "text", "bbox": { "l": 70.08, "t": 294.24, "r": 211.68, "b": 284.4 }, "text": "₃₅", "attrs": { "inline": true, "text_offset": 27, "text_span": 10, "bbox_estimated": true } }, { "id": "p24.16.3", "order": 103, "type": "text", "bbox": { "l": 70.08, "t": 294.24, "r": 211.68, "b": 284.4 }, "text": "₆₂", "attrs": { "inline": true, "text_offset": 39, "text_span": 10, "bbox_estimated": true } }, { "id": "p24.16.4", "order": 104, "type": "formula", "bbox": { "l": 70.08, "t": 294.24, "r": 211.68, "b": 284.4 }, "text": "₇", "attrs": { "latex": "_{7}", "inline": true, "text_offset": 50, "text_span": 10, "bbox_estimated": true, "alt": "sub 7", "mathml": "7" } } ] }, { "id": "p24.17", "order": 105, "type": "formula", "bbox": { "l": 157.92, "t": 281.76, "r": 450.24, "b": 187.44 }, "text": "", "attrs": { "block_label": "image", "alt": "Skeletal structure of an annonaceous acetogenin-type bis-THF compound with two hydroxyls, a butenolide terminus, and NMR shi…", "source": "vision" } }, { "id": "p24.18", "order": 106, "type": "text", "bbox": { "l": 72.72, "t": 187.2, "r": 534.24, "b": 156.96 }, "text": "Transparent oil.[p24.18.1]: +8° (c O.5, CHCl_{3}). UV ([p24.18.2], MeOH, nm): 205 ([p24.18.3] 4.0). IR ([p24.18.4], film, cm^{-1}): 3657, 2479, 1751, 1625. NMR: [p24.18.5]H NMR (400 MHz, CDCl_{3}), [p24.18.6]C NMR (50 MHz, CDCl_{3}). Derivatives: peracetate (^{1}H NMR). Biological activities ( [p24.18.7]g/mL): KB ED_{50} 2[p24.18.8] 10^{-4}, VERO ED_{50} 5[p24.18.9] 10^{-2}. Source: Annona spinescens, seeds.", "children": [ { "id": "p24.18.1", "order": 107, "type": "formula", "bbox": { "l": 72.72, "t": 187.2, "r": 534.24, "b": 156.96 }, "text": "\\begin{aligned}&\\text{Transparent oil. }[\\alpha]_{D}:\\ +8^{\\circ}\\ (c\\ 0.5,\\ \\text{CHCl}_3).\\ \\text{UV}\\ (\\lambda_{\\max},\\ \\text{MeOH, nm}):\\ 205\\ (\\log \\epsilon\\ 4.0).\\ \\text{IR}\\ (\\nu_{\\max},\\ \\text{film, cm}^{-1}):\\ 3657,\\ 2479,\\ 1751,\\ 1625.\\\\&\\text{NMR: }{}^{1}\\text{H NMR (400 MHz, CDCl}_3),\\ {}^{13}\\text{C NMR (50 MHz, CDCl}_3).\\ \\text{Derivatives: peracetate (}{}^{1}\\text{H NMR}).\\ \\text{Biological activities}\\\\&(\\mu\\text{g/mL}):\\ \\text{KB ED}_{50}\\ 2\\times10^{-4},\\ \\text{VERO ED}_{50}\\ 5\\times10^{-2}.\\ \\text{Source: }\\textit{Annona spinescens}\\text{, seeds.}\\\\&\\textbf{9-hydroxyvasicinone}^{42}\\ \\text{(reported as a cis and trans mixture) (C}_{37}\\text{H}_{66}\\text{O}_{8}\\text{, MW 638)}\\end{aligned}", "attrs": { "latex": "\\begin{aligned}&\\text{Transparent oil. }[\\alpha]_{D}:\\ +8^{\\circ}\\ (c\\ 0.5,\\ \\text{CHCl}_3).\\ \\text{UV}\\ (\\lambda_{\\max},\\ \\text{MeOH, nm}):\\ 205\\ (\\log \\epsilon\\ 4.0).\\ \\text{IR}\\ (\\nu_{\\max},\\ \\text{film, cm}^{-1}):\\ 3657,\\ 2479,\\ 1751,\\ 1625.\\\\&\\text{NMR: }{}^{1}\\text{H NMR (400 MHz, CDCl}_3),\\ {}^{13}\\text{C NMR (50 MHz, CDCl}_3).\\ \\text{Derivatives: peracetate (}{}^{1}\\text{H NMR}).\\ \\text{Biological activities}\\\\&(\\mu\\text{g/mL}):\\ \\text{KB ED}_{50}\\ 2\\times10^{-4},\\ \\text{VERO ED}_{50}\\ 5\\times10^{-2}.\\ \\text{Source: }\\textit{Annona spinescens}\\text{, seeds.}\\\\&\\textbf{9-hydroxyvasicinone}^{42}\\ \\text{(reported as a cis and trans mixture) (C}_{37}\\text{H}_{66}\\text{O}_{8}\\text{, MW 638)}\\end{aligned}", "inline": true, "text_offset": 16, "text_span": 10, "bbox_estimated": true, "notation": "latex", "alt": "begin aligned & Transparent oil. alpha sub D : plus 8 to the power of circ of c 0.5, CHCl sub 3 . UV of lambda sub max, MeOH, nm : 205 times log epsilon 4.0 . IR of nu sub max, film, cm to the power of minus 1 : 3657, 2479, 1751, 1625. & 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 . Derivatives: peracetate of to the power of 1 H NMR . Biological activities & mu g over mL : KB ED sub 50 2 times 10 to the power of minus 4, VERO ED sub 50 5 times 10 to the power of minus 2 . Source: textit Annona spinescens, seeds. & textbf 9 minus hydroxyvasicinone to the power of 42 times reported as a cis and trans mixture times C sub 37 H sub 66 O sub 8, MW 638 end aligned", "mathml": "&Transparent oil. [α]D: +8∘ (c 0.5, CHCl3). UV (λmax, MeOH, nm): 205 (logϵ 4.0). IR (νmax, film, cm−1): 3657, 2479, 1751, 1625.&NMR: 1H NMR (400 MHz, CDCl3), 13C NMR (50 MHz, CDCl3). Derivatives: peracetate (1H NMR). Biological activities&(μg/mL): KB ED50 2×10−4, VERO ED50 5×10−2. Source: Annona spinescens, seeds.&9-hydroxyvasicinone42 (reported as a cis and trans mixture) (C37H66O8, MW 638)" } }, { "id": "p24.18.2", "order": 108, "type": "text", "bbox": { "l": 72.72, "t": 187.2, "r": 534.24, "b": 156.96 }, "text": "\\lambda_{max}", "attrs": { "inline": true, "text_offset": 55, "text_span": 10, "bbox_estimated": true } }, { "id": "p24.18.3", "order": 109, "type": "text", "bbox": { "l": 72.72, "t": 187.2, "r": 534.24, "b": 156.96 }, "text": "\\log \\epsilon", "attrs": { "inline": true, "text_offset": 83, "text_span": 10, "bbox_estimated": true } }, { "id": "p24.18.4", "order": 110, "type": "text", "bbox": { "l": 72.72, "t": 187.2, "r": 534.24, "b": 156.96 }, "text": "\\nu_{max}", "attrs": { "inline": true, "text_offset": 104, "text_span": 10, "bbox_estimated": true } }, { "id": "p24.18.5", "order": 111, "type": "text", "bbox": { "l": 72.72, "t": 187.2, "r": 534.24, "b": 156.96 }, "text": "¹", "attrs": { "inline": true, "text_offset": 161, "text_span": 10, "bbox_estimated": true } }, { "id": "p24.18.6", "order": 112, "type": "text", "bbox": { "l": 72.72, "t": 187.2, "r": 534.24, "b": 156.96 }, "text": "¹³", "attrs": { "inline": true, "text_offset": 198, "text_span": 10, "bbox_estimated": true } }, { "id": "p24.18.7", "order": 113, "type": "text", "bbox": { "l": 72.72, "t": 187.2, "r": 534.24, "b": 156.96 }, "text": "μ", "attrs": { "inline": true, "text_offset": 295, "text_span": 10, "bbox_estimated": true } }, { "id": "p24.18.8", "order": 114, "type": "text", "bbox": { "l": 72.72, "t": 187.2, "r": 534.24, "b": 156.96 }, "text": "×", "attrs": { "inline": true, "text_offset": 324, "text_span": 10, "bbox_estimated": true } }, { "id": "p24.18.9", "order": 115, "type": "text", "bbox": { "l": 72.72, "t": 187.2, "r": 534.24, "b": 156.96 }, "text": "×", "attrs": { "inline": true, "text_offset": 358, "text_span": 10, "bbox_estimated": true } } ] }, { "id": "p24.19", "order": 116, "type": "text", "bbox": { "l": 69.84, "t": 158.88, "r": 386.16, "b": 148.8 }, "text": "9-hydroxyasimicinone[p24.19.1] (reported as a cis and trans mixture) ([p24.19.2], MW638)", "children": [ { "id": "p24.19.1", "order": 117, "type": "text", "bbox": { "l": 69.84, "t": 158.88, "r": 386.16, "b": 148.8 }, "text": "⁴²", "attrs": { "inline": true, "text_offset": 20, "text_span": 10, "bbox_estimated": true } }, { "id": "p24.19.2", "order": 118, "type": "formula", "bbox": { "l": 69.84, "t": 158.88, "r": 386.16, "b": 148.8 }, "text": "C₃₇H₆₆O₈", "attrs": { "latex": "C_{37}H_{66}O_{8}", "inline": true, "text_offset": 70, "text_span": 10, "bbox_estimated": true, "alt": "C sub 37 H sub 66 O sub 8", "mathml": "C37H66O8" } } ] }, { "id": "p24.20", "order": 119, "type": "formula", "bbox": { "l": 155.52, "t": 145.68, "r": 456.24, "b": 100.08 }, "text": "", "attrs": { "block_label": "image", "alt": "Skeletal structure of a polyketide with two tetrahydrofuran rings, hydroxyls at C9, C15 and C24, and a lactone with a cis/tr…", "source": "vision" } }, { "id": "p24.21", "order": 120, "type": "text", "bbox": { "l": 70.32, "t": 98.16, "r": 213.12, "b": 88.32 }, "text": "79. (2,4-cis)-9-hydroxyasimicinone" }, { "id": "p24.22", "order": 121, "type": "table", "bbox": { "l": 170.64, "t": 87.12, "r": 440.4, "b": 49.92 }, "text": "", "attrs": { "block_label": "table", "n_rows": 3, "n_cols": 8, "integrity": { "skipped": "no_text_layer" } }, "children": [ { "id": "p24.22.1", "order": 122, "type": "table_cell", "bbox": { "l": 170.64, "t": 87.12, "r": 204.36, "b": 74.72 }, "text": "Position", "attrs": { "row": 0, "col": 0, "rowspan": 1, "colspan": 1, "column_header": true, "header_source": "heuristic" } }, { "id": "p24.22.2", "order": 123, "type": "table_cell", "bbox": { "l": 204.36, "t": 87.12, "r": 238.08, "b": 74.72 }, "text": "9", "attrs": { "row": 0, "col": 1, "rowspan": 1, "colspan": 1, "column_header": true, "header_source": "heuristic" } }, { "id": "p24.22.3", "order": 124, "type": "table_cell", "bbox": { "l": 238.08, "t": 87.12, "r": 271.8, "b": 74.72 }, "text": "15", "attrs": { "row": 0, "col": 2, "rowspan": 1, "colspan": 1, "column_header": true, "header_source": "heuristic" } }, { "id": "p24.22.4", "order": 125, "type": "table_cell", "bbox": { "l": 271.8, "t": 87.12, "r": 305.52, "b": 74.72 }, "text": "16", "attrs": { "row": 0, "col": 3, "rowspan": 1, "colspan": 1, "column_header": true, "header_source": "heuristic" } }, { "id": "p24.22.5", "order": 126, "type": "table_cell", "bbox": { "l": 305.52, "t": 87.12, "r": 339.24, "b": 74.72 }, "text": "19", "attrs": { "row": 0, "col": 4, "rowspan": 1, "colspan": 1, "column_header": true, "header_source": "heuristic" } }, { "id": "p24.22.6", "order": 127, "type": "table_cell", "bbox": { "l": 339.24, "t": 87.12, "r": 372.96, "b": 74.72 }, "text": "20", "attrs": { "row": 0, "col": 5, "rowspan": 1, "colspan": 1, "column_header": true, "header_source": "heuristic" } }, { "id": "p24.22.7", "order": 128, "type": "table_cell", "bbox": { "l": 372.96, "t": 87.12, "r": 406.68, "b": 74.72 }, "text": "23", "attrs": { "row": 0, "col": 6, "rowspan": 1, "colspan": 1, "column_header": true, "header_source": "heuristic" } }, { "id": "p24.22.8", "order": 129, "type": "table_cell", "bbox": { "l": 406.68, "t": 87.12, "r": 440.4, "b": 74.72 }, "text": "24", "attrs": { "row": 0, "col": 7, "rowspan": 1, "colspan": 1, "column_header": true, "header_source": "heuristic" } }, { "id": "p24.22.9", "order": 130, "type": "table_cell", "bbox": { "l": 170.64, "t": 74.72, "r": 204.36, "b": 62.32 }, "text": "¹H ( δ)", "attrs": { "row": 1, "col": 0, "rowspan": 1, "colspan": 1 } }, { "id": "p24.22.10", "order": 131, "type": "table_cell", "bbox": { "l": 204.36, "t": 74.72, "r": 238.08, "b": 62.32 }, "text": "3.58 m", "attrs": { "row": 1, "col": 1, "rowspan": 1, "colspan": 1 } }, { "id": "p24.22.11", "order": 132, "type": "table_cell", "bbox": { "l": 238.08, "t": 74.72, "r": 271.8, "b": 62.32 }, "text": "3.39 m", "attrs": { "row": 1, "col": 2, "rowspan": 1, "colspan": 1 } }, { "id": "p24.22.12", "order": 133, "type": "table_cell", "bbox": { "l": 271.8, "t": 74.72, "r": 305.52, "b": 62.32 }, "text": "3.85 m", "attrs": { "row": 1, "col": 3, "rowspan": 1, "colspan": 1 } }, { "id": "p24.22.13", "order": 134, "type": "table_cell", "bbox": { "l": 305.52, "t": 74.72, "r": 339.24, "b": 62.32 }, "text": "3.85 m", "attrs": { "row": 1, "col": 4, "rowspan": 1, "colspan": 1 } }, { "id": "p24.22.14", "order": 135, "type": "table_cell", "bbox": { "l": 339.24, "t": 74.72, "r": 372.96, "b": 62.32 }, "text": "3.85 m", "attrs": { "row": 1, "col": 5, "rowspan": 1, "colspan": 1 } }, { "id": "p24.22.15", "order": 136, "type": "table_cell", "bbox": { "l": 372.96, "t": 74.72, "r": 406.68, "b": 62.32 }, "text": "3.85 m", "attrs": { "row": 1, "col": 6, "rowspan": 1, "colspan": 1 } }, { "id": "p24.22.16", "order": 137, "type": "table_cell", "bbox": { "l": 406.68, "t": 74.72, "r": 440.4, "b": 62.32 }, "text": "3.39 m", "attrs": { "row": 1, "col": 7, "rowspan": 1, "colspan": 1 } }, { "id": "p24.22.17", "order": 138, "type": "table_cell", "bbox": { "l": 170.64, "t": 62.32, "r": 204.36, "b": 49.92 }, "text": "¹³C ( δ)", "attrs": { "row": 2, "col": 0, "rowspan": 1, "colspan": 1 } }, { "id": "p24.22.18", "order": 139, "type": "table_cell", "bbox": { "l": 204.36, "t": 62.32, "r": 238.08, "b": 49.92 }, "text": "71.64", "attrs": { "row": 2, "col": 1, "rowspan": 1, "colspan": 1 } }, { "id": "p24.22.19", "order": 140, "type": "table_cell", "bbox": { "l": 238.08, "t": 62.32, "r": 271.8, "b": 49.92 }, "text": "74.05", "attrs": { "row": 2, "col": 2, "rowspan": 1, "colspan": 1 } }, { "id": "p24.22.20", "order": 141, "type": "table_cell", "bbox": { "l": 271.8, "t": 62.32, "r": 305.52, "b": 49.92 }, "text": "83.06", "attrs": { "row": 2, "col": 3, "rowspan": 1, "colspan": 1 } }, { "id": "p24.22.21", "order": 142, "type": "table_cell", "bbox": { "l": 305.52, "t": 62.32, "r": 339.24, "b": 49.92 }, "text": "81.79", "attrs": { "row": 2, "col": 4, "rowspan": 1, "colspan": 1 } }, { "id": "p24.22.22", "order": 143, "type": "table_cell", "bbox": { "l": 339.24, "t": 62.32, "r": 372.96, "b": 49.92 }, "text": "81.76", "attrs": { "row": 2, "col": 5, "rowspan": 1, "colspan": 1 } }, { "id": "p24.22.23", "order": 144, "type": "table_cell", "bbox": { "l": 372.96, "t": 62.32, "r": 406.68, "b": 49.92 }, "text": "83.16", "attrs": { "row": 2, "col": 6, "rowspan": 1, "colspan": 1 } }, { "id": "p24.22.24", "order": 145, "type": "table_cell", "bbox": { "l": 406.68, "t": 62.32, "r": 440.4, "b": 49.92 }, "text": "73.96", "attrs": { "row": 2, "col": 7, "rowspan": 1, "colspan": 1 } } ] } ], "excluded_furniture": { "first": [], "last": [] } }