{ "document_id": 14408, "page": 20, "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": 84, "counts_by_type": { "figure": 1, "formula": 15, "header": 4, "table": 1, "table_cell": 24, "text": 39 }, "build_ms": 10, "items": [ { "id": "p20.1", "order": 1, "type": "header", "bbox": { "l": 53.76, "t": 765.6, "r": 112.32, "b": 756 }, "text": "Invited Review", "attrs": { "block_label": "header" }, "level": 2 }, { "id": "p20.2", "order": 2, "type": "header", "bbox": { "l": 349.92, "t": 766.08, "r": 540.48, "b": 756 }, "text": "Journal of Natural Products, 1999, Vol. 62, No. 3", "attrs": { "block_label": "header" }, "level": 2 }, { "id": "p20.3", "order": 3, "type": "header", "bbox": { "l": 53.76, "t": 746.16, "r": 142.8, "b": 736.08 }, "text": "Table 4. (Continued)", "attrs": { "block_label": "header" }, "level": 2 }, { "id": "p20.4", "order": 4, "type": "header", "bbox": { "l": 542.88, "t": 765.6, "r": 559.2, "b": 756.96 }, "text": "523", "attrs": { "block_label": "number" }, "level": 2 }, { "id": "p20.5", "order": 5, "type": "text", "bbox": { "l": 237.36, "t": 733.92, "r": 374.4, "b": 724.32 }, "text": "Mono-THF Acetogenins (Continued)" }, { "id": "p20.6", "order": 6, "type": "text", "bbox": { "l": 64.08, "t": 725.04, "r": 239.76, "b": 714 }, "text": "55. cis-reticulatacin[p20.6.1] (C [p20.6.2]H [p20.6.3]O[p20.6.4], MW592)", "children": [ { "id": "p20.6.1", "order": 7, "type": "formula", "bbox": { "l": 64.08, "t": 725.04, "r": 239.76, "b": 714 }, "text": "^{*115}", "attrs": { "latex": "^{*115}", "inline": true, "text_offset": 21, "text_span": 9, "bbox_estimated": true, "notation": "latex", "alt": "to the power of *115", "mathml": "*115" } }, { "id": "p20.6.2", "order": 8, "type": "text", "bbox": { "l": 64.08, "t": 725.04, "r": 239.76, "b": 714 }, "text": "₃₇", "attrs": { "inline": true, "text_offset": 34, "text_span": 9, "bbox_estimated": true } }, { "id": "p20.6.3", "order": 9, "type": "formula", "bbox": { "l": 64.08, "t": 725.04, "r": 239.76, "b": 714 }, "text": "₆₉", "attrs": { "latex": "_{69}", "inline": true, "text_offset": 45, "text_span": 9, "bbox_estimated": true, "alt": "sub 69", "mathml": "69" } }, { "id": "p20.6.4", "order": 10, "type": "text", "bbox": { "l": 64.08, "t": 725.04, "r": 239.76, "b": 714 }, "text": "₅", "attrs": { "inline": true, "text_offset": 55, "text_span": 9, "bbox_estimated": true } } ] }, { "id": "p20.7", "order": 11, "type": "figure", "bbox": { "l": 66.96, "t": 716.64, "r": 538.8, "b": 57.36 }, "text": "", "attrs": { "block_label": "image" } }, { "id": "p20.8", "order": 12, "type": "text", "bbox": { "l": 155.28, "t": 657.84, "r": 314.88, "b": 648.24 }, "text": "Position 17 18 21 22" }, { "id": "p20.9", "order": 13, "type": "text", "bbox": { "l": 153.84, "t": 644.64, "r": 320.4, "b": 623.76 }, "text": "[p20.9.1]H (δ) 3.41 m 3.81 m 3.81 m 3.41 m\n [p20.9.2]C (δ) 74.3 82.7 82.7 74.3", "children": [ { "id": "p20.9.1", "order": 14, "type": "formula", "bbox": { "l": 153.84, "t": 644.64, "r": 320.4, "b": 623.76 }, "text": "¹", "attrs": { "latex": "^{1}", "inline": true, "text_offset": 0, "text_span": 9, "bbox_estimated": true, "alt": "to the power of 1", "mathml": "1" } }, { "id": "p20.9.2", "order": 15, "type": "formula", "bbox": { "l": 153.84, "t": 644.64, "r": 320.4, "b": 623.76 }, "text": "¹³", "attrs": { "latex": "^{13}", "inline": true, "text_offset": 44, "text_span": 9, "bbox_estimated": true, "alt": "to the power of 13", "mathml": "13" } } ] }, { "id": "p20.10", "order": 16, "type": "text", "bbox": { "l": 65.28, "t": 622.32, "r": 488.4, "b": 586.8 }, "text": "White powder. Mp: 60–62°C. [α]D: +1° (c O.4O, MeOH). UV (λmax, MeOH, nm): 220.8 (log ε =3.63). IR (νmax, film, cm⁻¹): 3423, 2916, 2840, 1760, 1474, 1325, 1120, 1073, 1032, 968, 742, 717. MS: EIMS m/z 393, 323, 269, 199, 111, 97. NMR: ¹H NMR (400MHz, CDCl₃), ¹³C NMR (50MHz, CDCl₃). Source: Annona muricata, roots.\n56. cis-reticulatacin-10-one[p20.10.1] (C [p20.10.2]H [p20.10.3]O[p20.10.4], MW606)", "children": [ { "id": "p20.10.1", "order": 17, "type": "text", "bbox": { "l": 65.28, "t": 622.32, "r": 488.4, "b": 586.8 }, "text": "^{*115}", "attrs": { "inline": true, "text_offset": 342, "text_span": 10, "bbox_estimated": true } }, { "id": "p20.10.2", "order": 18, "type": "text", "bbox": { "l": 65.28, "t": 622.32, "r": 488.4, "b": 586.8 }, "text": "₃₇", "attrs": { "inline": true, "text_offset": 356, "text_span": 10, "bbox_estimated": true } }, { "id": "p20.10.3", "order": 19, "type": "text", "bbox": { "l": 65.28, "t": 622.32, "r": 488.4, "b": 586.8 }, "text": "₆₇", "attrs": { "inline": true, "text_offset": 368, "text_span": 10, "bbox_estimated": true } }, { "id": "p20.10.4", "order": 20, "type": "text", "bbox": { "l": 65.28, "t": 622.32, "r": 488.4, "b": 586.8 }, "text": "₆", "attrs": { "inline": true, "text_offset": 379, "text_span": 10, "bbox_estimated": true } } ] }, { "id": "p20.11", "order": 21, "type": "text", "bbox": { "l": 153.84, "t": 526.8, "r": 355.2, "b": 492 }, "text": "Position 10 17 18 21 22\n [p20.11.1]H (δ) --- 3.41 m 3.81 m 3.81 m 3.41 m\n [p20.11.2]C (δ) 211.4 74.3 82.7 82.7 74.3", "children": [ { "id": "p20.11.1", "order": 22, "type": "formula", "bbox": { "l": 153.84, "t": 526.8, "r": 355.2, "b": 492 }, "text": "¹", "attrs": { "latex": "^{1}", "inline": true, "text_offset": 25, "text_span": 10, "bbox_estimated": true, "alt": "to the power of 1", "mathml": "1" } }, { "id": "p20.11.2", "order": 23, "type": "text", "bbox": { "l": 153.84, "t": 526.8, "r": 355.2, "b": 492 }, "text": "¹³", "attrs": { "inline": true, "text_offset": 74, "text_span": 10, "bbox_estimated": true } } ] }, { "id": "p20.12", "order": 24, "type": "text", "bbox": { "l": 65.76, "t": 490.56, "r": 510.24, "b": 452.4 }, "text": "White powder. Mp: 62–64 °C. [α]D: +23° (c O 18, MeOH). UV (λmax, MeOH, nm): 219.6 (log ε 3.59). IR (νmax, film, cm⁻¹): 3416, 2911, 2839, 1753, 1700, 1464, 1410, 1373, 1068, 1032, 958, 915. MS: EIMS m/z 407, 389, 371, 337, 319, 291, 251, 223, 199, 195, 181, 111, 97. NMR: ¹H NMR (400 MHz, CDCl₃), ¹³C NMR (50 MHz, CDCl₃). Source: Annona muricata, roots.\n57. dispalin³⁸ (C₃₉H₇₁O₈, M₅W₆₆)" }, { "id": "p20.13", "order": 25, "type": "text", "bbox": { "l": 65.28, "t": 454.32, "r": 198.72, "b": 444.96 }, "text": "57. dispalin [p20.13.1](C [p20.13.2]H [p20.13.3]O[p20.13.4], MW666)", "children": [ { "id": "p20.13.1", "order": 26, "type": "text", "bbox": { "l": 65.28, "t": 454.32, "r": 198.72, "b": 444.96 }, "text": "³⁸", "attrs": { "inline": true, "text_offset": 13, "text_span": 10, "bbox_estimated": true } }, { "id": "p20.13.2", "order": 27, "type": "text", "bbox": { "l": 65.28, "t": 454.32, "r": 198.72, "b": 444.96 }, "text": "₃₉", "attrs": { "inline": true, "text_offset": 26, "text_span": 10, "bbox_estimated": true } }, { "id": "p20.13.3", "order": 28, "type": "text", "bbox": { "l": 65.28, "t": 454.32, "r": 198.72, "b": 444.96 }, "text": "₇₁", "attrs": { "inline": true, "text_offset": 38, "text_span": 10, "bbox_estimated": true } }, { "id": "p20.13.4", "order": 29, "type": "text", "bbox": { "l": 65.28, "t": 454.32, "r": 198.72, "b": 444.96 }, "text": "₈", "attrs": { "inline": true, "text_offset": 49, "text_span": 10, "bbox_estimated": true } } ] }, { "id": "p20.14", "order": 30, "type": "text", "bbox": { "l": 153.84, "t": 387.6, "r": 353.52, "b": 352.08 }, "text": "Position 10 15 16 19 20\n[p20.14.1] ([p20.14.2]) 3.40 m 3.40 m 3.82 m 3.82 m 5.09 m\n[p20.14.3] ([p20.14.4]) 71.6 74.1 82.2 83.0 78.0\n¹H (δ) 3.40 m 3.40 m 3.82 m 3.82 m 5.09 m\n ¹³C (δ) 71.6 74.1 82.2 83.0 78.0", "children": [ { "id": "p20.14.1", "order": 31, "type": "formula", "bbox": { "l": 153.84, "t": 387.6, "r": 353.52, "b": 352.08 }, "text": "¹H", "attrs": { "latex": "^{1}H", "inline": true, "text_offset": 24, "text_span": 10, "bbox_estimated": true, "alt": "to the power of 1 H", "mathml": "1H" } }, { "id": "p20.14.2", "order": 32, "type": "text", "bbox": { "l": 153.84, "t": 387.6, "r": 353.52, "b": 352.08 }, "text": "δ", "attrs": { "inline": true, "text_offset": 36, "text_span": 10, "bbox_estimated": true } }, { "id": "p20.14.3", "order": 33, "type": "formula", "bbox": { "l": 153.84, "t": 387.6, "r": 353.52, "b": 352.08 }, "text": "¹³C", "attrs": { "latex": "^{13}C", "inline": true, "text_offset": 83, "text_span": 10, "bbox_estimated": true, "alt": "to the power of 13 C", "mathml": "13C" } }, { "id": "p20.14.4", "order": 34, "type": "text", "bbox": { "l": 153.84, "t": 387.6, "r": 353.52, "b": 352.08 }, "text": "δ", "attrs": { "inline": true, "text_offset": 95, "text_span": 10, "bbox_estimated": true } } ] }, { "id": "p20.15", "order": 35, "type": "text", "bbox": { "l": 65.04, "t": 350.88, "r": 544.32, "b": 320.16 }, "text": "Waxy solid.[p20.15.1]: +19.6° (c 1.0, CHCl_{3}). MS: EIMS (TMS) m/z 685, 613, 543, 509, 453, 419, 363, 339, 295, 279, 269, 209, 205, 213, 197, 123. NMR: [p20.15.2]H NMR (270 MHz, CDCl_{3}), [p20.15.3]C NMR (54 MHz, CDCl_{3}). Derivatives: peracetate (^{1}H NMR), TMS (EIMS).\nSource: Disepalum anomalum, stem bark.\n58. tonkinin A[p20.15.4] (C [p20.15.5]H [p20.15.6]O[p20.15.7], MW622)", "children": [ { "id": "p20.15.1", "order": 36, "type": "formula", "bbox": { "l": 65.04, "t": 350.88, "r": 544.32, "b": 320.16 }, "text": "[\\alpha]_{D}", "attrs": { "latex": "[\\alpha]_{D}", "inline": true, "text_offset": 11, "text_span": 10, "bbox_estimated": true, "notation": "latex", "alt": "alpha sub D", "mathml": "[α]D" } }, { "id": "p20.15.2", "order": 37, "type": "formula", "bbox": { "l": 65.04, "t": 350.88, "r": 544.32, "b": 320.16 }, "text": "¹", "attrs": { "latex": "^{1}", "inline": true, "text_offset": 153, "text_span": 10, "bbox_estimated": true, "alt": "to the power of 1", "mathml": "1" } }, { "id": "p20.15.3", "order": 38, "type": "text", "bbox": { "l": 65.04, "t": 350.88, "r": 544.32, "b": 320.16 }, "text": "¹³", "attrs": { "inline": true, "text_offset": 190, "text_span": 10, "bbox_estimated": true } }, { "id": "p20.15.4", "order": 39, "type": "text", "bbox": { "l": 65.04, "t": 350.88, "r": 544.32, "b": 320.16 }, "text": "^{*66}", "attrs": { "inline": true, "text_offset": 328, "text_span": 10, "bbox_estimated": true } }, { "id": "p20.15.5", "order": 40, "type": "text", "bbox": { "l": 65.04, "t": 350.88, "r": 544.32, "b": 320.16 }, "text": "₃₇", "attrs": { "inline": true, "text_offset": 342, "text_span": 10, "bbox_estimated": true } }, { "id": "p20.15.6", "order": 41, "type": "text", "bbox": { "l": 65.04, "t": 350.88, "r": 544.32, "b": 320.16 }, "text": "₆₆", "attrs": { "inline": true, "text_offset": 354, "text_span": 10, "bbox_estimated": true } }, { "id": "p20.15.7", "order": 42, "type": "text", "bbox": { "l": 65.04, "t": 350.88, "r": 544.32, "b": 320.16 }, "text": "₇", "attrs": { "inline": true, "text_offset": 365, "text_span": 10, "bbox_estimated": true } } ] }, { "id": "p20.16", "order": 43, "type": "table", "bbox": { "l": 152.64, "t": 256.8, "r": 422.4, "b": 221.52 }, "text": "", "attrs": { "block_label": "table", "n_rows": 3, "n_cols": 8, "integrity": { "skipped": "no_text_layer" } }, "children": [ { "id": "p20.16.1", "order": 44, "type": "table_cell", "bbox": { "l": 152.64, "t": 256.8, "r": 186.36, "b": 245.04 }, "text": "Position", "attrs": { "row": 0, "col": 0, "rowspan": 1, "colspan": 1, "column_header": true, "header_source": "heuristic" } }, { "id": "p20.16.2", "order": 45, "type": "table_cell", "bbox": { "l": 186.36, "t": 256.8, "r": 220.08, "b": 245.04 }, "text": "5", "attrs": { "row": 0, "col": 1, "rowspan": 1, "colspan": 1, "column_header": true, "header_source": "heuristic" } }, { "id": "p20.16.3", "order": 46, "type": "table_cell", "bbox": { "l": 220.08, "t": 256.8, "r": 253.8, "b": 245.04 }, "text": "15", "attrs": { "row": 0, "col": 2, "rowspan": 1, "colspan": 1, "column_header": true, "header_source": "heuristic" } }, { "id": "p20.16.4", "order": 47, "type": "table_cell", "bbox": { "l": 253.8, "t": 256.8, "r": 287.52, "b": 245.04 }, "text": "16", "attrs": { "row": 0, "col": 3, "rowspan": 1, "colspan": 1, "column_header": true, "header_source": "heuristic" } }, { "id": "p20.16.5", "order": 48, "type": "table_cell", "bbox": { "l": 287.52, "t": 256.8, "r": 321.24, "b": 245.04 }, "text": "17", "attrs": { "row": 0, "col": 4, "rowspan": 1, "colspan": 1, "column_header": true, "header_source": "heuristic" } }, { "id": "p20.16.6", "order": 49, "type": "table_cell", "bbox": { "l": 321.24, "t": 256.8, "r": 354.96, "b": 245.04 }, "text": "18", "attrs": { "row": 0, "col": 5, "rowspan": 1, "colspan": 1, "column_header": true, "header_source": "heuristic" } }, { "id": "p20.16.7", "order": 50, "type": "table_cell", "bbox": { "l": 354.96, "t": 256.8, "r": 388.68, "b": 245.04 }, "text": "21", "attrs": { "row": 0, "col": 6, "rowspan": 1, "colspan": 1, "column_header": true, "header_source": "heuristic" } }, { "id": "p20.16.8", "order": 51, "type": "table_cell", "bbox": { "l": 388.68, "t": 256.8, "r": 422.4, "b": 245.04 }, "text": "22", "attrs": { "row": 0, "col": 7, "rowspan": 1, "colspan": 1, "column_header": true, "header_source": "heuristic" } }, { "id": "p20.16.9", "order": 52, "type": "table_cell", "bbox": { "l": 152.64, "t": 245.04, "r": 186.36, "b": 233.28 }, "text": "¹H ( \\delta )", "attrs": { "row": 1, "col": 0, "rowspan": 1, "colspan": 1 } }, { "id": "p20.16.10", "order": 53, "type": "table_cell", "bbox": { "l": 186.36, "t": 245.04, "r": 220.08, "b": 233.28 }, "text": "---", "attrs": { "row": 1, "col": 1, "rowspan": 1, "colspan": 1 } }, { "id": "p20.16.11", "order": 54, "type": "table_cell", "bbox": { "l": 220.08, "t": 245.04, "r": 253.8, "b": 233.28 }, "text": "3.80 m", "attrs": { "row": 1, "col": 2, "rowspan": 1, "colspan": 1 } }, { "id": "p20.16.12", "order": 55, "type": "table_cell", "bbox": { "l": 253.8, "t": 245.04, "r": 287.52, "b": 233.28 }, "text": "1.54 m", "attrs": { "row": 1, "col": 3, "rowspan": 1, "colspan": 1 } }, { "id": "p20.16.13", "order": 56, "type": "table_cell", "bbox": { "l": 287.52, "t": 245.04, "r": 321.24, "b": 233.28 }, "text": "3.73 m", "attrs": { "row": 1, "col": 4, "rowspan": 1, "colspan": 1 } }, { "id": "p20.16.14", "order": 57, "type": "table_cell", "bbox": { "l": 321.24, "t": 245.04, "r": 354.96, "b": 233.28 }, "text": "3.89 m", "attrs": { "row": 1, "col": 5, "rowspan": 1, "colspan": 1 } }, { "id": "p20.16.15", "order": 58, "type": "table_cell", "bbox": { "l": 354.96, "t": 245.04, "r": 388.68, "b": 233.28 }, "text": "3.89 m", "attrs": { "row": 1, "col": 6, "rowspan": 1, "colspan": 1 } }, { "id": "p20.16.16", "order": 59, "type": "table_cell", "bbox": { "l": 388.68, "t": 245.04, "r": 422.4, "b": 233.28 }, "text": "3.89 m", "attrs": { "row": 1, "col": 7, "rowspan": 1, "colspan": 1 } }, { "id": "p20.16.17", "order": 60, "type": "table_cell", "bbox": { "l": 152.64, "t": 233.28, "r": 186.36, "b": 221.52 }, "text": "¹³C ( \\delta )", "attrs": { "row": 2, "col": 0, "rowspan": 1, "colspan": 1 } }, { "id": "p20.16.18", "order": 61, "type": "table_cell", "bbox": { "l": 186.36, "t": 233.28, "r": 220.08, "b": 221.52 }, "text": "209.45", "attrs": { "row": 2, "col": 1, "rowspan": 1, "colspan": 1 } }, { "id": "p20.16.19", "order": 62, "type": "table_cell", "bbox": { "l": 220.08, "t": 233.28, "r": 253.8, "b": 221.52 }, "text": "68.62", "attrs": { "row": 2, "col": 2, "rowspan": 1, "colspan": 1 } }, { "id": "p20.16.20", "order": 63, "type": "table_cell", "bbox": { "l": 253.8, "t": 233.28, "r": 287.52, "b": 221.52 }, "text": "37.58", "attrs": { "row": 2, "col": 3, "rowspan": 1, "colspan": 1 } }, { "id": "p20.16.21", "order": 64, "type": "table_cell", "bbox": { "l": 287.52, "t": 233.28, "r": 321.24, "b": 221.52 }, "text": "71.53", "attrs": { "row": 2, "col": 4, "rowspan": 1, "colspan": 1 } }, { "id": "p20.16.22", "order": 65, "type": "table_cell", "bbox": { "l": 321.24, "t": 233.28, "r": 354.96, "b": 221.52 }, "text": "83.12", "attrs": { "row": 2, "col": 5, "rowspan": 1, "colspan": 1 } }, { "id": "p20.16.23", "order": 66, "type": "table_cell", "bbox": { "l": 354.96, "t": 233.28, "r": 388.68, "b": 221.52 }, "text": "82.28", "attrs": { "row": 2, "col": 6, "rowspan": 1, "colspan": 1 } }, { "id": "p20.16.24", "order": 67, "type": "table_cell", "bbox": { "l": 388.68, "t": 233.28, "r": 422.4, "b": 221.52 }, "text": "71.83", "attrs": { "row": 2, "col": 7, "rowspan": 1, "colspan": 1 } } ] }, { "id": "p20.17", "order": 68, "type": "text", "bbox": { "l": 65.28, "t": 221.04, "r": 540.72, "b": 175.2 }, "text": "Crystal. Mp: 98–100°C.[p20.17.1]: +20.09° (cO.112, CHCl₃). IR ([p20.17.2], film, cm⁻¹): 3357, 2919, 2849, 1751, 1714, 1070 MS: EIMS m/z 569, 405, 387, 353, 335, 309, 291, 199, 181, 153, NMR: ¹H NMR (500MHz, CDCl₃), ¹³C NMR (125MHz, CDCl₃). Derivatives: peracetate (¹H NMR), TMS (EIMS). Biological activities ( [p20.17.3]g/mL): HCT-8IC₅₀ 5.9 × 10⁻¹, HL-60IC₅₀ 1.6 × 10⁻², KB IC₅₀ > 10, A278OIC₅₀ > 10. Source: Uvaria tonkinensis, roots.\n\n59. tonkinin[p20.17.4] ([p20.17.5], MW622)\n59. tonkinin B *66 ( C₃₇H₆₆O₇, MW622)", "children": [ { "id": "p20.17.1", "order": 69, "type": "formula", "bbox": { "l": 65.28, "t": 221.04, "r": 540.72, "b": 175.2 }, "text": "\\text{Crystal. Mp: } 98\\text{--}100\\,^{\\circ}\\text{C. } [\\alpha]_{D}\\text{: } +20.09^{\\circ}\\ (c\\,0.112,\\ \\text{CHCl}_3)\\text{. IR } (\\nu_{\\max}\\text{, film, cm}^{-1})\\text{: } 3357, 2919, 2849, 1751, 1714, 1070\\text{. MS: EIMS } m/z\\ 569, 405, 387, 353, 335, 309, 291, 199, 181, 153\\text{. NMR: }{}^{1}\\text{H NMR (500 MHz, CDCl}_3), {}^{13}\\text{C NMR (125 MHz, CDCl}_3)\\text{.}\\\\ \\text{Derivatives: peracetate (}^{1}\\text{H NMR), TMS (EIMS). Biological activities } (\\mu\\text{g/mL})\\text{: HCT-8 IC}_{50}\\ 5.9\\times10^{-1}\\text{, HL-60 IC}_{50}\\ 1.6\\times10^{-2}\\text{, KB IC}_{50} > 10\\text{, A2780 IC}_{50} > 10\\text{. Source: } \\textit{Uvaria tonkinensis}\\text{, roots.}\\\\ \\textbf{59. tonkinin B}^{*66}\\ (\\text{C}_{37}\\text{H}_{66}\\text{O}_{7}\\text{, MW 622})", "attrs": { "latex": "\\text{Crystal. Mp: } 98\\text{--}100\\,^{\\circ}\\text{C. } [\\alpha]_{D}\\text{: } +20.09^{\\circ}\\ (c\\,0.112,\\ \\text{CHCl}_3)\\text{. IR } (\\nu_{\\max}\\text{, film, cm}^{-1})\\text{: } 3357, 2919, 2849, 1751, 1714, 1070\\text{. MS: EIMS } m/z\\ 569, 405, 387, 353, 335, 309, 291, 199, 181, 153\\text{. NMR: }{}^{1}\\text{H NMR (500 MHz, CDCl}_3), {}^{13}\\text{C NMR (125 MHz, CDCl}_3)\\text{.}\\\\ \\text{Derivatives: peracetate (}^{1}\\text{H NMR), TMS (EIMS). Biological activities } (\\mu\\text{g/mL})\\text{: HCT-8 IC}_{50}\\ 5.9\\times10^{-1}\\text{, HL-60 IC}_{50}\\ 1.6\\times10^{-2}\\text{, KB IC}_{50} > 10\\text{, A2780 IC}_{50} > 10\\text{. Source: } \\textit{Uvaria tonkinensis}\\text{, roots.}\\\\ \\textbf{59. tonkinin B}^{*66}\\ (\\text{C}_{37}\\text{H}_{66}\\text{O}_{7}\\text{, MW 622})", "inline": true, "text_offset": 22, "text_span": 10, "bbox_estimated": true, "notation": "latex", "alt": "Crystal. Mp: 98 minus minus 100, to the power of circ C. alpha sub D : plus 20.09 to the power of circ of c, 0.112, CHCl sub 3 . IR of nu sub max, film, cm to the power of minus 1 : 3357, 2919, 2849, 1751, 1714, 1070 . MS: EIMS m over z 569, 405, 387, 353, 335, 309, 291, 199, 181, 153 . 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: peracetate of to the power of 1 H NMR, TMS of EIMS . Biological activities of mu g over mL : HCT minus 8 IC sub 50 5.9 times 10 to the power of minus 1, HL minus 60 IC sub 50 1.6 times 10 to the power of minus 2, KB IC sub 50 is greater than 10, A2780 IC sub 50 is greater than 10 . Source: textit Uvaria tonkinensis, roots. textbf 59. tonkinin B to the power of *66 times C sub 37 H sub 66 O sub 7, MW 622", "mathml": "Crystal. Mp: 98--100∘C. [α]D: +20.09∘ (c0.112, CHCl3). IR (νmax, film, cm−1): 3357,2919,2849,1751,1714,1070. MS: EIMS m/z 569,405,387,353,335,309,291,199,181,153. NMR: 1H NMR (500 MHz, CDCl3),13C NMR (125 MHz, CDCl3).Derivatives: peracetate (1H NMR), TMS (EIMS). Biological activities (μg/mL): HCT-8 IC50 5.9×10−1, HL-60 IC50 1.6×10−2, KB IC50>10, A2780 IC50>10. Source: Uvaria tonkinensis, roots.59. tonkinin B*66 (C37H66O7, MW 622)" } }, { "id": "p20.17.2", "order": 70, "type": "text", "bbox": { "l": 65.28, "t": 221.04, "r": 540.72, "b": 175.2 }, "text": "\\nu_{max}", "attrs": { "inline": true, "text_offset": 63, "text_span": 10, "bbox_estimated": true } }, { "id": "p20.17.3", "order": 71, "type": "text", "bbox": { "l": 65.28, "t": 221.04, "r": 540.72, "b": 175.2 }, "text": "μ", "attrs": { "inline": true, "text_offset": 310, "text_span": 10, "bbox_estimated": true } }, { "id": "p20.17.4", "order": 72, "type": "formula", "bbox": { "l": 65.28, "t": 221.04, "r": 540.72, "b": 175.2 }, "text": "\\tilde{\\mathbf{B}}^{*66}", "attrs": { "latex": "\\tilde{\\mathbf{B}}^{*66}", "inline": true, "text_offset": 449, "text_span": 10, "bbox_estimated": true, "notation": "latex", "alt": "tilde mathbf B to the power of *66", "mathml": "𝐁~*66" } }, { "id": "p20.17.5", "order": 73, "type": "text", "bbox": { "l": 65.28, "t": 221.04, "r": 540.72, "b": 175.2 }, "text": "C₃₇H₆₆O₇", "attrs": { "inline": true, "text_offset": 461, "text_span": 10, "bbox_estimated": true } } ] }, { "id": "p20.18", "order": 74, "type": "text", "bbox": { "l": 153.84, "t": 118.56, "r": 417.84, "b": 108.48 }, "text": "Position 5 15 16 17 18 21 22\n[p20.18.1] ([p20.18.2]) --- 3.81 m 1.60 m 3.76 m 3.88 m 3.88 m 3.41 m\n[p20.18.3] ([p20.18.4]) 209.44 68.46 37.56 71.49 82.80 82.47 71.44", "children": [ { "id": "p20.18.1", "order": 75, "type": "text", "bbox": { "l": 153.84, "t": 118.56, "r": 417.84, "b": 108.48 }, "text": "¹H", "attrs": { "inline": true, "text_offset": 29, "text_span": 10, "bbox_estimated": true } }, { "id": "p20.18.2", "order": 76, "type": "text", "bbox": { "l": 153.84, "t": 118.56, "r": 417.84, "b": 108.48 }, "text": "δ", "attrs": { "inline": true, "text_offset": 41, "text_span": 10, "bbox_estimated": true } }, { "id": "p20.18.3", "order": 77, "type": "text", "bbox": { "l": 153.84, "t": 118.56, "r": 417.84, "b": 108.48 }, "text": "¹³C", "attrs": { "inline": true, "text_offset": 99, "text_span": 10, "bbox_estimated": true } }, { "id": "p20.18.4", "order": 78, "type": "text", "bbox": { "l": 153.84, "t": 118.56, "r": 417.84, "b": 108.48 }, "text": "δ", "attrs": { "inline": true, "text_offset": 111, "text_span": 10, "bbox_estimated": true } } ] }, { "id": "p20.19", "order": 79, "type": "text", "bbox": { "l": 65.28, "t": 81.6, "r": 543.12, "b": 44.16 }, "text": "Waxy solid. Mp: 95–96°C.[p20.19.1]: +28.20° (c Q098, CHCl_{3}). IR ([p20.19.2], film, cm^{-1}): 3410, 2920, 2849, 1738, 1711, 1068, 1029. MS: EIMS m/z 423, 405, 387, 353, 335, 309, 291, 269, 181, 168, 153. NMR: [p20.19.3]H NMR (500MHz, CDCl_{3}), [p20.19.4]C NMR (125MHz, CDCl_{3}). Derivatives: peracetate (^{1}H NMR), TMS (EIMS). Biological activities ( [p20.19.5]g/mL): HCT-81C50 24, HL-60IC50 6.0 × 10^{-2}, KB IC_{50} > 10, A2780IC_{50} > 10. Source: Uvaria tonkinensis, roots.", "children": [ { "id": "p20.19.1", "order": 80, "type": "formula", "bbox": { "l": 65.28, "t": 81.6, "r": 543.12, "b": 44.16 }, "text": "\\text{Waxy solid. Mp: } 95\\text{--}96\\,^\\circ\\text{C. } [\\alpha]_{D}: +28.20^\\circ (c\\,0.098, \\text{CHCl}_3). \\text{IR } (\\nu_{\\max}, \\text{film, cm}^{-1}): 3410, 2920, 2849, 1738, 1711, 1068, 1029. \\text{MS: EIMS } m/z\\ 423, 405, 387, 353, 335, 309, 291, 269, 181, 168, 153. \\text{NMR: } {}^{1}\\text{H NMR (500 MHz, CDCl}_3), {}^{13}\\text{C NMR (125 MHz, CDCl}_3). \\text{Derivatives: peracetate } ({}^{1}\\text{H NMR}), \\text{TMS (EIMS)}. \\text{Biological activities } (\\mu\\text{g/mL}): \\text{HCT-8 IC}_{50}\\ 2.4, \\text{HL-60 IC}_{50}\\ 6.0 \\times 10^{-2}, \\text{KB IC}_{50} > 10, \\text{A2780 IC}_{50} > 10. \\text{Source: } \\textit{Uvaria tonkinensis}\\text{, roots.}", "attrs": { "latex": "\\text{Waxy solid. Mp: } 95\\text{--}96\\,^\\circ\\text{C. } [\\alpha]_{D}: +28.20^\\circ (c\\,0.098, \\text{CHCl}_3). \\text{IR } (\\nu_{\\max}, \\text{film, cm}^{-1}): 3410, 2920, 2849, 1738, 1711, 1068, 1029. \\text{MS: EIMS } m/z\\ 423, 405, 387, 353, 335, 309, 291, 269, 181, 168, 153. \\text{NMR: } {}^{1}\\text{H NMR (500 MHz, CDCl}_3), {}^{13}\\text{C NMR (125 MHz, CDCl}_3). \\text{Derivatives: peracetate } ({}^{1}\\text{H NMR}), \\text{TMS (EIMS)}. \\text{Biological activities } (\\mu\\text{g/mL}): \\text{HCT-8 IC}_{50}\\ 2.4, \\text{HL-60 IC}_{50}\\ 6.0 \\times 10^{-2}, \\text{KB IC}_{50} > 10, \\text{A2780 IC}_{50} > 10. \\text{Source: } \\textit{Uvaria tonkinensis}\\text{, roots.}", "inline": true, "text_offset": 24, "text_span": 10, "bbox_estimated": true, "notation": "latex", "alt": "Waxy solid. Mp: 95 minus minus 96, to the power of circ C. alpha sub D : plus 28.20 to the power of circ of c, 0.098, CHCl sub 3 . IR of nu sub max, film, cm to the power of minus 1 : 3410, 2920, 2849, 1738, 1711, 1068, 1029. MS: EIMS m over z 423, 405, 387, 353, 335, 309, 291, 269, 181, 168, 153. 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: peracetate of to the power of 1 H NMR, TMS of EIMS . Biological activities of mu g over mL : HCT minus 8 IC sub 50 2.4, HL minus 60 IC sub 50 6.0 times 10 to the power of minus 2, KB IC sub 50 is greater than 10, A2780 IC sub 50 is greater than 10. Source: textit Uvaria tonkinensis, roots.", "mathml": "Waxy solid. Mp: 95--96∘C. [α]D:+28.20∘(c0.098,CHCl3).IR (νmax,film, cm−1):3410,2920,2849,1738,1711,1068,1029.MS: EIMS m/z 423,405,387,353,335,309,291,269,181,168,153.NMR: 1H NMR (500 MHz, CDCl3),13C NMR (125 MHz, CDCl3).Derivatives: peracetate (1H NMR),TMS (EIMS).Biological activities (μg/mL):HCT-8 IC50 2.4,HL-60 IC50 6.0×10−2,KB IC50>10,A2780 IC50>10.Source: Uvaria tonkinensis, roots." } }, { "id": "p20.19.2", "order": 81, "type": "formula", "bbox": { "l": 65.28, "t": 81.6, "r": 543.12, "b": 44.16 }, "text": "\\nu_{max}", "attrs": { "latex": "\\nu_{max}", "inline": true, "text_offset": 68, "text_span": 10, "bbox_estimated": true, "notation": "latex", "alt": "nu sub max", "mathml": "νmax" } }, { "id": "p20.19.3", "order": 82, "type": "formula", "bbox": { "l": 65.28, "t": 81.6, "r": 543.12, "b": 44.16 }, "text": "¹", "attrs": { "latex": "{}^{1}", "inline": true, "text_offset": 211, "text_span": 10, "bbox_estimated": true, "alt": "to the power of 1", "mathml": "1" } }, { "id": "p20.19.4", "order": 83, "type": "formula", "bbox": { "l": 65.28, "t": 81.6, "r": 543.12, "b": 44.16 }, "text": "¹³", "attrs": { "latex": "{}^{13}", "inline": true, "text_offset": 247, "text_span": 10, "bbox_estimated": true, "alt": "to the power of 13", "mathml": "13" } }, { "id": "p20.19.5", "order": 84, "type": "text", "bbox": { "l": 65.28, "t": 81.6, "r": 543.12, "b": 44.16 }, "text": "μ", "attrs": { "inline": true, "text_offset": 356, "text_span": 10, "bbox_estimated": true } } ] } ], "excluded_furniture": { "first": [], "last": [] } }