{ "document_id": 13696, "page": 3, "width_pt": 589, "height_pt": 783, "rotation": 0, "pipeline_version": "paddleocr-vl-1.6+paul-48", "engine": "paddleocr_vl", "source_run_id": 13808, "item_count": 32, "counts_by_type": { "caption": 2, "formula": 2, "header": 3, "heading": 2, "text": 23 }, "build_ms": 5, "items": [ { "id": "p3.1", "order": 1, "type": "header", "bbox": { "l": 41.7458, "t": 761.1633, "r": 74.3747, "b": 751.3249 }, "text": "Reviews", "attrs": { "block_label": "header" }, "level": 2 }, { "id": "p3.2", "order": 2, "type": "header", "bbox": { "l": 334.2065, "t": 761.8832, "r": 523.7422, "b": 751.0849 }, "text": "Journal of Natural Products, 2008, Vol. 71, No. 7", "attrs": { "block_label": "header" }, "level": 2 }, { "id": "p3.3", "order": 3, "type": "header", "bbox": { "l": 528.3006, "t": 761.8832, "r": 548.4538, "b": 752.2847 }, "text": "1313", "attrs": { "block_label": "number" }, "level": 2 }, { "id": "p3.4", "order": 4, "type": "text", "bbox": { "l": 132.435, "t": 741.0064, "r": 148.7495, "b": 733.0876 }, "text": "threo" }, { "id": "p3.5", "order": 5, "type": "formula", "bbox": { "l": 47.9837, "t": 737.647, "r": 279.0253, "b": 447.2914 }, "text": "", "attrs": { "block_label": "image", "alt": "Skeletal structures of asimicin (1), goniothalamicin (2) and annonacin (3), bis-THF acetogenins with butenolide and hydroxyl…", "source": "vision" } }, { "id": "p3.6", "order": 6, "type": "caption", "bbox": { "l": 41.266, "t": 436.4931, "r": 285.5031, "b": 413.2167 }, "text": "representing numerous uninvestigated genera and hundreds of uninvestigated species. [p3.6.1]", "attrs": { "block_label": "figure_title" }, "children": [ { "id": "p3.6.1", "order": 7, "type": "text", "bbox": { "l": 41.266, "t": 436.4931, "r": 285.5031, "b": 413.2167 }, "text": "²⁴", "attrs": { "inline": true, "text_offset": 84, "text_span": 8, "bbox_estimated": true } } ] }, { "id": "p3.7", "order": 8, "type": "heading", "bbox": { "l": 41.0261, "t": 400.0187, "r": 114.2012, "b": 389.7003 }, "text": "The Annonaceae", "attrs": { "block_label": "paragraph_title" }, "level": 3 }, { "id": "p3.8", "order": 9, "type": "text", "bbox": { "l": 40.3063, "t": 386.5808, "r": 285.9829, "b": 227.7251 }, "text": "The Annonaceae is comprised of some 120 genera and includes over 2100 species. Asimina triloba (paw paw) is the only temperate species; the rest of the family is tropical or subtropical. The fruits of paw paw have nourished wild animals and mankind in eastern North America for thousands of years, and paw paw festivals are to be found in September throughout the Midwestern United States. Many of the tropical species also bear edible fruits and have been naturalized from central and South America to other warm climates in Asia and Africa. The late Julia Morton has summarized the economic potential of the annonaceous fruits and noted that certain parts of several species are poisonous and/or pesticidal.[p3.8.1] Sour sop (guanabana) and cherimolia are two of the best known annonaceous fruits and are sold either fresh or in processed forms; thousands of pounds of the seeds of these commercial species, with their rich concentrations of acetogenins, are discarded during the processing.", "children": [ { "id": "p3.8.1", "order": 10, "type": "text", "bbox": { "l": 40.3063, "t": 386.5808, "r": 285.9829, "b": 227.7251 }, "text": "²⁵", "attrs": { "inline": true, "text_offset": 709, "text_span": 8, "bbox_estimated": true } } ] }, { "id": "p3.9", "order": 11, "type": "text", "bbox": { "l": 40.3063, "t": 228.205, "r": 285.743, "b": 27.1158 }, "text": "The research group of Andre Cavé in France is well known for their phytochemical studies of the Annonaeae,[p3.9.1] but the annonaceous acetogenins were overlooked until the discovery in 1982 of uvaricin (4) by the group of Jack Cole at the University of Arizona; 4 was isolated from Uvaria accuminata following 3PS activity and was significantly active.[p3.9.2] Desacetyluvaricin was found subsequently.[p3.9.3] Our work eventually focused on 14 annonaceous species that yielded acetogenins; these were Asimina triloba (paw paw), Goniothalamus giganteus, Annona squamosa L. (sugar apple), A. muricata L. (sour sop, graviola, guanabana), A. bullata Rich., Asimina parviflora (Michx.) Dunal (dwarf paw paw), A. longifolia Kral. (long-leafed dwarf paw paw), Annona reticulata L. (custard apple), A. glabra L. (pond apple), A. jahnii Saff., A. cherimolia Mill. (cherimolia), Xylopia aromatica (Mart.) Lam., Rollinia mucosa (Jacq.) Baill. (biriba), and R. emarginata Schlecht. From the paw paw and these additional species, my research group isolated and characterized over 200 new annonaceous acetogenins, which represents approximately one-half of these compounds that have been reported to date. We published, in sequence, five comprehensive reviews that consolidated the chemical and biological findings published in this field of work up to 1999.[p3.9.4] Cavé's group has also reviewed the acetogenins,[p3.9.5] and Cortes has published a more recent review. [p3.9.6]", "children": [ { "id": "p3.9.1", "order": 12, "type": "text", "bbox": { "l": 40.3063, "t": 228.205, "r": 285.743, "b": 27.1158 }, "text": "²⁶", "attrs": { "inline": true, "text_offset": 106, "text_span": 8, "bbox_estimated": true } }, { "id": "p3.9.2", "order": 13, "type": "text", "bbox": { "l": 40.3063, "t": 228.205, "r": 285.743, "b": 27.1158 }, "text": "²⁷", "attrs": { "inline": true, "text_offset": 353, "text_span": 8, "bbox_estimated": true } }, { "id": "p3.9.3", "order": 14, "type": "text", "bbox": { "l": 40.3063, "t": 228.205, "r": 285.743, "b": 27.1158 }, "text": "²⁸", "attrs": { "inline": true, "text_offset": 403, "text_span": 8, "bbox_estimated": true } }, { "id": "p3.9.4", "order": 15, "type": "text", "bbox": { "l": 40.3063, "t": 228.205, "r": 285.743, "b": 27.1158 }, "text": "²⁹⁻³³", "attrs": { "inline": true, "text_offset": 1346, "text_span": 8, "bbox_estimated": true } }, { "id": "p3.9.5", "order": 16, "type": "text", "bbox": { "l": 40.3063, "t": 228.205, "r": 285.743, "b": 27.1158 }, "text": "³⁴⁻³⁶", "attrs": { "inline": true, "text_offset": 1402, "text_span": 8, "bbox_estimated": true } }, { "id": "p3.9.6", "order": 17, "type": "text", "bbox": { "l": 40.3063, "t": 228.205, "r": 285.743, "b": 27.1158 }, "text": "³⁷", "attrs": { "inline": true, "text_offset": 1458, "text_span": 8, "bbox_estimated": true } } ] }, { "id": "p3.10", "order": 18, "type": "text", "bbox": { "l": 304.6965, "t": 742.2063, "r": 549.4134, "b": 699.2528 }, "text": "hensive reviews that consolidated the chemical and biological findings published in this field of work up to 1999.[p3.10.1] Cavé's group has also reviewed the acetogenins,[p3.10.2] and Cortes has published a more recent review. [p3.10.3]", "children": [ { "id": "p3.10.1", "order": 19, "type": "text", "bbox": { "l": 304.6965, "t": 742.2063, "r": 549.4134, "b": 699.2528 }, "text": "^{[29-33]}", "attrs": { "inline": true, "text_offset": 114, "text_span": 9, "bbox_estimated": true } }, { "id": "p3.10.2", "order": 20, "type": "text", "bbox": { "l": 304.6965, "t": 742.2063, "r": 549.4134, "b": 699.2528 }, "text": "^{[34-36]}", "attrs": { "inline": true, "text_offset": 171, "text_span": 9, "bbox_estimated": true } }, { "id": "p3.10.3", "order": 21, "type": "text", "bbox": { "l": 304.6965, "t": 742.2063, "r": 549.4134, "b": 699.2528 }, "text": "^{[37]}", "attrs": { "inline": true, "text_offset": 228, "text_span": 9, "bbox_estimated": true } } ] }, { "id": "p3.11", "order": 22, "type": "formula", "bbox": { "l": 319.0916, "t": 688.9344, "r": 535.0183, "b": 391.38 }, "text": "", "attrs": { "block_label": "image", "alt": "Skeletal structure of bullatacin (6), a bis-tetrahydrofuran annonaceous acetogenin with hydroxyl groups and a butenolide ring", "source": "vision" } }, { "id": "p3.12", "order": 23, "type": "caption", "bbox": { "l": 406.422, "t": 399.7787, "r": 449.8473, "b": 389.2203 }, "text": "bullatacin (6)", "attrs": { "block_label": "figure_title" } }, { "id": "p3.13", "order": 24, "type": "heading", "bbox": { "l": 304.4566, "t": 378.9019, "r": 489.4338, "b": 367.8636 }, "text": "Structures of the Annonaceous Acetogenins", "attrs": { "block_label": "paragraph_title" }, "level": 3 }, { "id": "p3.14", "order": 25, "type": "text", "bbox": { "l": 303.9768, "t": 364.0242, "r": 549.4134, "b": 80.3877 }, "text": "Chemically, the annonaceous acetogenins are white, waxy, derivatives of long-chain ([p3.14.1] or[p3.14.2]) fatty acids that have been combined with a 2-propanol unit at C-2 to form a methyl-substituted [p3.14.3]-unsaturated [p3.14.4]-lactone; sometimes the lactone is rearranged with a hydroxyl at C-4 to create a mixture of 2,4-cis- and 2,4-trans-ketolactones such as the bullatacinones (5). Biogenetically, epoxidation of strategically placed double bonds, followed by cyclizations, gives rise to one to three tetrahydrofuran (THF) or tetrahydropyran (THP) rings. The ring systems can be single, adjacent, or nonadjacent types, and these systems, with their flanking hydroxyls, create a number of chiral centers. A complex mixture of diastereomers is the usual result. The stereochemistry of the ring systems leads to subclasses of acetogenins, and these subclasses are subsequently named after the first compound within that subclass to have its relative configuration determined. For example, extracts of paw paw contain single THF, nonadjacent bis-THF, and adjacent bis-THF classes (or types) of acetogenins. Most of the acetogenins in paw paw are of the adjacent bis-THF class. However, when observing the relative stereochemistry from C-15 to C-24, three major subclasses are revealed; these are named for asimicin (1), which is threo, trans, threo, trans, threo; bullatacin (6), which is threo, trans, threo, trans, erythro; and trilobacin (7), which is threo, trans, erythro, cis, threo. The chain length of the fatty acid ([p3.14.5] or[p3.14.6]) adds an additional variable in naming and classifying these compounds. Most of the acetogenins isolated from the paw paw are of the asimicin subclass and contain a total of 37 carbon atoms, which includes the three carbons of the 2-propanol subunit.", "children": [ { "id": "p3.14.1", "order": 26, "type": "text", "bbox": { "l": 303.9768, "t": 364.0242, "r": 549.4134, "b": 80.3877 }, "text": "C₃₂", "attrs": { "inline": true, "text_offset": 84, "text_span": 9, "bbox_estimated": true } }, { "id": "p3.14.2", "order": 27, "type": "text", "bbox": { "l": 303.9768, "t": 364.0242, "r": 549.4134, "b": 80.3877 }, "text": "C₃₄", "attrs": { "inline": true, "text_offset": 96, "text_span": 9, "bbox_estimated": true } }, { "id": "p3.14.3", "order": 28, "type": "text", "bbox": { "l": 303.9768, "t": 364.0242, "r": 549.4134, "b": 80.3877 }, "text": "α,β", "attrs": { "inline": true, "text_offset": 202, "text_span": 9, "bbox_estimated": true } }, { "id": "p3.14.4", "order": 29, "type": "text", "bbox": { "l": 303.9768, "t": 364.0242, "r": 549.4134, "b": 80.3877 }, "text": "γ", "attrs": { "inline": true, "text_offset": 224, "text_span": 9, "bbox_estimated": true } }, { "id": "p3.14.5", "order": 30, "type": "text", "bbox": { "l": 303.9768, "t": 364.0242, "r": 549.4134, "b": 80.3877 }, "text": "C₃₂", "attrs": { "inline": true, "text_offset": 1533, "text_span": 9, "bbox_estimated": true } }, { "id": "p3.14.6", "order": 31, "type": "text", "bbox": { "l": 303.9768, "t": 364.0242, "r": 549.4134, "b": 80.3877 }, "text": "C₃₄", "attrs": { "inline": true, "text_offset": 1545, "text_span": 9, "bbox_estimated": true } } ] }, { "id": "p3.15", "order": 32, "type": "text", "bbox": { "l": 303.9768, "t": 80.6276, "r": 549.8933, "b": 28.0757 }, "text": "Separation of these complex mixtures of acetogenins in annonaceous plant extracts, for their isolation, characterization, and biological evaluation, has been facilitated by various high-performance liquid chromatographic methods (HPLC). In addition, countercurrent chromatography has been useful in the isolation of" } ], "excluded_furniture": { "first": [], "last": [] } }