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"text": "Journal of Natural Products, 1999, Vol. 62, No. 3 517",
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"text": "\\text{White waxy solid. }[\\alpha]_D\\text{: }+19^\\circ\\text{ (}c\\text{ 1.08, CHCl}_3\\text{). UV (}\\lambda_{max}\\text{, MeOH, nm): 208.8 (log }\\epsilon\\text{ 4.6). NMR: }{}^1\\text{H NMR (400 MHz, CDCl}_3\\text{), }{}^{13}\\text{C NMR (50 MHz, CDCl}_3\\text{). Derivatives: peracetate (}{}^1\\text{H NMR), acetonide (}{}^1\\text{H NMR). Source: }\\textit{Annona coriacea}\\text{, roots.}\\\\ \\text{23. coriaheptocin B}^{*40}\\text{ (C}_{35}\\text{H}_{64}\\text{O}_{10}\\text{, MW 644})",
"attrs": {
"latex": "\\text{White waxy solid. }[\\alpha]_D\\text{: }+19^\\circ\\text{ (}c\\text{ 1.08, CHCl}_3\\text{). UV (}\\lambda_{max}\\text{, MeOH, nm): 208.8 (log }\\epsilon\\text{ 4.6). NMR: }{}^1\\text{H NMR (400 MHz, CDCl}_3\\text{), }{}^{13}\\text{C NMR (50 MHz, CDCl}_3\\text{). Derivatives: peracetate (}{}^1\\text{H NMR), acetonide (}{}^1\\text{H NMR). Source: }\\textit{Annona coriacea}\\text{, roots.}\\\\ \\text{23. coriaheptocin B}^{*40}\\text{ (C}_{35}\\text{H}_{64}\\text{O}_{10}\\text{, MW 644})",
"inline": true,
"text_offset": 58,
"text_span": 10,
"bbox_estimated": true,
"notation": "latex",
"alt": "White waxy solid. alpha sub D : plus 19 to the power of circ of c 1.08, CHCl sub 3 . UV of lambda sub max, MeOH, nm : 208.8 times log epsilon 4.6 . 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, acetonide of to the power of 1 H NMR . Source: textit Annona coriacea, roots. 23. coriaheptocin B to the power of *40 times C sub 35 H sub 64 O sub 10, MW 644",
"mathml": ""
}
},
{
"id": "p14.12.3",
"order": 48,
"type": "text",
"bbox": {
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"t": 480.72,
"r": 511.92,
"b": 456.96
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"text": "ε",
"attrs": {
"inline": true,
"text_offset": 91,
"text_span": 10,
"bbox_estimated": true
}
},
{
"id": "p14.12.4",
"order": 49,
"type": "text",
"bbox": {
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"t": 480.72,
"r": 511.92,
"b": 456.96
},
"text": "¹",
"attrs": {
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},
{
"id": "p14.12.5",
"order": 50,
"type": "text",
"bbox": {
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"r": 511.92,
"b": 456.96
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"text": "¹³",
"attrs": {
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"text_offset": 150,
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},
{
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"type": "text",
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"b": 456.96
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"text": "^{*40}",
"attrs": {
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},
{
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"type": "text",
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"b": 456.96
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"text": "C₂₅H₆₄O₁₀",
"attrs": {
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"text_offset": 303,
"text_span": 10,
"bbox_estimated": true
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}
]
},
{
"id": "p14.13",
"order": 53,
"type": "formula",
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"r": 448.32,
"b": 408.48
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"text": "",
"attrs": {
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"alt": "Skeletal structure of an annonaceous acetogenin: butenolide, THF ring, and multiple hydroxyls along a long C32 chain (C35H64…",
"source": "vision"
}
},
{
"id": "p14.14",
"order": 54,
"type": "text",
"bbox": {
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"r": 454.32,
"b": 389.04
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"text": "Position 7 8 11 12 14 16 19 20"
},
{
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"order": 55,
"type": "text",
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"r": 456.24,
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"text": "[p14.15.1] ([p14.15.2]) 74.3 82.9 82.5 74.3 67.8 67.4 71.3 70.9",
"children": [
{
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"type": "formula",
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"t": 384.24,
"r": 456.24,
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"text_offset": 0,
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"alt": "to the power of 13 C",
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}
},
{
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"type": "formula",
"bbox": {
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"r": 456.24,
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"text": "\\begin{aligned} &{}^{1}\\mathbf{H}\\ (\\delta) \\quad 3.45\\ \\text{m} \\quad 3.78\\ \\text{m} \\quad 3.81\\ \\text{m} \\quad 3.40\\ \\text{m} \\quad 3.90\\ \\text{m} \\quad 3.90\\ \\text{m} \\quad 3.74\\ \\text{m} \\quad 3.79\\ \\text{m} \\\\ &{}^{13}\\mathbf{C}\\ (\\delta) \\quad 74.3 \\quad 82.9 \\quad 82.5 \\quad 74.3 \\quad 67.8 \\quad 67.4 \\quad 71.3 \\quad 70.9 \\\\ &[\\alpha]_D \\ +25^\\circ\\ (c\\ 1.00,\\ \\text{CHCl}_3);\\ \\text{UV}\\ (\\lambda_{\\max},\\ \\text{MeOH},\\ \\text{nm}):\\ 207.2\\ (\\log \\varepsilon\\ 4.0);\\ \\text{NMR:}\\ {}^{1}\\text{H NMR}\\ (400\\ \\text{MHz}\\ldots \\end{aligned}",
"attrs": {
"latex": "\\begin{aligned} &{}^{1}\\mathbf{H}\\ (\\delta) \\quad 3.45\\ \\text{m} \\quad 3.78\\ \\text{m} \\quad 3.81\\ \\text{m} \\quad 3.40\\ \\text{m} \\quad 3.90\\ \\text{m} \\quad 3.90\\ \\text{m} \\quad 3.74\\ \\text{m} \\quad 3.79\\ \\text{m} \\\\ &{}^{13}\\mathbf{C}\\ (\\delta) \\quad 74.3 \\quad 82.9 \\quad 82.5 \\quad 74.3 \\quad 67.8 \\quad 67.4 \\quad 71.3 \\quad 70.9 \\\\ &[\\alpha]_D \\ +25^\\circ\\ (c\\ 1.00,\\ \\text{CHCl}_3);\\ \\text{UV}\\ (\\lambda_{\\max},\\ \\text{MeOH},\\ \\text{nm}):\\ 207.2\\ (\\log \\varepsilon\\ 4.0);\\ \\text{NMR:}\\ {}^{1}\\text{H NMR}\\ (400\\ \\text{MHz}\\ldots \\end{aligned}",
"inline": true,
"text_offset": 12,
"text_span": 10,
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"alt": "begin aligned & to the power of 1 mathbf H of delta 3.45 m 3.78 m 3.81 m 3.40 m 3.90 m 3.90 m 3.74 m 3.79 m & to the power of 13 mathbf C of delta 74.3 82.9 82.5 74.3 67.8 67.4 71.3 70.9 & alpha sub D plus 25 to the power of circ of c 1.00, CHCl sub 3 ; UV of lambda sub max, MeOH, nm : 207.2 times log varepsilon 4.0 ; NMR: to the power of 1 H NMR of 400 MHz ldots end aligned",
"notation": "latex",
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}
}
]
},
{
"id": "p14.16",
"order": 58,
"type": "text",
"bbox": {
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"t": 364.08,
"r": 548.16,
"b": 338.4
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"text": "White waxy solid.[p14.16.1]: +25° (c 1.00, CHCl_{3}). UV ([p14.16.2], MeOH, nm): 207.2 (log[p14.16.3] 4.0). NMR: [p14.16.4]H NMR (400MHz, CDCl_{3}), [p14.16.5]C NMR (50MHz, CDCl_{3}). Derivatives: peracetate (1H NMR), acetonide (1H NMR). Source: Annona coriacea, roots.\n24. coriacyclodienin[p14.16.6] ([p14.16.7], MW572)",
"children": [
{
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"text": "\\text{White waxy solid. } [\\alpha]_{D}: +25^\\circ\\ (c\\ 1.00, \\text{CHCl}_3). \\text{UV } (\\lambda_{\\max}, \\text{MeOH, nm}): 207.2\\ (\\log \\epsilon\\ 4.0). \\text{NMR: }{}^{1}\\text{H NMR (400 MHz, CDCl}_3), {}^{13}\\text{C NMR} (50\\text{ MHz, CDCl}_3). \\text{Derivatives: peracetate } ({}^{1}\\text{H NMR}), \\text{ acetonide } ({}^{1}\\text{H NMR}). \\text{Source: } \\textit{Annona coriacea}\\text{, roots.}\\\\ \\textbf{24. coriacyclodienin}^{111}\\ (\\text{C}_{37}\\text{H}_{64}\\text{O}_{7}, \\text{MW } 572)",
"attrs": {
"latex": "\\text{White waxy solid. } [\\alpha]_{D}: +25^\\circ\\ (c\\ 1.00, \\text{CHCl}_3). \\text{UV } (\\lambda_{\\max}, \\text{MeOH, nm}): 207.2\\ (\\log \\epsilon\\ 4.0). \\text{NMR: }{}^{1}\\text{H NMR (400 MHz, CDCl}_3), {}^{13}\\text{C NMR} (50\\text{ MHz, CDCl}_3). \\text{Derivatives: peracetate } ({}^{1}\\text{H NMR}), \\text{ acetonide } ({}^{1}\\text{H NMR}). \\text{Source: } \\textit{Annona coriacea}\\text{, roots.}\\\\ \\textbf{24. coriacyclodienin}^{111}\\ (\\text{C}_{37}\\text{H}_{64}\\text{O}_{7}, \\text{MW } 572)",
"inline": true,
"text_offset": 17,
"text_span": 10,
"bbox_estimated": true,
"notation": "latex",
"alt": "White waxy solid. alpha sub D : plus 25 to the power of circ of c 1.00, CHCl sub 3 . UV of lambda sub max, MeOH, nm : 207.2 times log epsilon 4.0 . 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, acetonide of to the power of 1 H NMR . Source: textit Annona coriacea, roots. textbf 24. coriacyclodienin to the power of 111 times C sub 37 H sub 64 O sub 7, MW 572",
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}
},
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"b": 338.4
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}
},
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"r": 548.16,
"b": 338.4
},
"text": "ε",
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},
{
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"r": 548.16,
"b": 338.4
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"text": "¹",
"attrs": {
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},
{
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"type": "text",
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"t": 364.08,
"r": 548.16,
"b": 338.4
},
"text": "¹³",
"attrs": {
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"text_offset": 149,
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"bbox_estimated": true
}
},
{
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"order": 64,
"type": "formula",
"bbox": {
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"t": 364.08,
"r": 548.16,
"b": 338.4
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"text": "¹¹¹",
"attrs": {
"latex": "^{111}",
"inline": true,
"text_offset": 290,
"text_span": 10,
"bbox_estimated": true,
"alt": "to the power of 111",
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}
},
{
"id": "p14.16.7",
"order": 65,
"type": "formula",
"bbox": {
"l": 62.64,
"t": 364.08,
"r": 548.16,
"b": 338.4
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"text": "\\text{White waxy solid. }[\\alpha]_D\\text{: }+25^\\circ\\text{ (}c\\text{ 1.00, CHCl}_3\\text{). UV }(\\lambda_{\\max}\\text{, MeOH, nm): 207.2 (log}\\,\\epsilon\\text{ 4.0). NMR: }{}^1\\text{H NMR (400 MHz, CDCl}_3\\text{), }{}^{13}\\text{C NMR (50 MHz, CDCl}_3\\text{). Derivatives: peracetate (}{}^1\\text{H NMR), acetonide (}{}^1\\text{H NMR). Source: }\\textit{Annona coriacea}\\text{, roots.} \\text{24. coriacyclodienin}^{111}\\text{ (C}_{37}\\text{H}_{64}\\text{O}_7\\text{, MW 572)}",
"attrs": {
"latex": "\\text{White waxy solid. }[\\alpha]_D\\text{: }+25^\\circ\\text{ (}c\\text{ 1.00, CHCl}_3\\text{). UV }(\\lambda_{\\max}\\text{, MeOH, nm): 207.2 (log}\\,\\epsilon\\text{ 4.0). NMR: }{}^1\\text{H NMR (400 MHz, CDCl}_3\\text{), }{}^{13}\\text{C NMR (50 MHz, CDCl}_3\\text{). Derivatives: peracetate (}{}^1\\text{H NMR), acetonide (}{}^1\\text{H NMR). Source: }\\textit{Annona coriacea}\\text{, roots.} \\text{24. coriacyclodienin}^{111}\\text{ (C}_{37}\\text{H}_{64}\\text{O}_7\\text{, MW 572)}",
"inline": true,
"text_offset": 302,
"text_span": 10,
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"alt": "White waxy solid. alpha sub D : plus 25 to the power of circ of c 1.00, CHCl sub 3 . UV of lambda sub max, MeOH, nm : 207.2 times log, epsilon 4.0 . 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, acetonide of to the power of 1 H NMR . Source: textit Annona coriacea, roots. 24. coriacyclodienin to the power of 111 times C sub 37 H sub 64 O sub 7, MW 572",
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}
}
]
},
{
"id": "p14.17",
"order": 66,
"type": "formula",
"bbox": {
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"t": 335.28,
"r": 456.24,
"b": 293.28
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"text": "",
"attrs": {
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"alt": "Skeletal structure of an annonaceous acetogenin with a butenolide, a tetrahydrofuran ring, a hydroxyl at C-14, and two cis d…",
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}
},
{
"id": "p14.18",
"order": 67,
"type": "text",
"bbox": {
"l": 154.8,
"t": 282.24,
"r": 417.6,
"b": 274.08
},
"text": "Position 10 13 14 17 18 21 22"
},
{
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"order": 68,
"type": "text",
"bbox": {
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"t": 270.24,
"r": 422.4,
"b": 260.88
},
"text": "[p14.19.1] ([p14.19.2]) 3.86 m 3.78 td 3.38 m 5.40 m 5.40 m 5.40 m 5.40 m",
"children": [
{
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"type": "formula",
"bbox": {
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"t": 270.24,
"r": 422.4,
"b": 260.88
},
"text": "¹H",
"attrs": {
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"text_offset": 0,
"text_span": 10,
"bbox_estimated": true,
"alt": "to the power of 1 H",
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}
},
{
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"order": 70,
"type": "text",
"bbox": {
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"t": 270.24,
"r": 422.4,
"b": 260.88
},
"text": "δ",
"attrs": {
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"text_offset": 12,
"text_span": 10,
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}
}
]
},
{
"id": "p14.20",
"order": 71,
"type": "text",
"bbox": {
"l": 153.6,
"t": 257.52,
"r": 420.96,
"b": 248.4
},
"text": "79.2 81.8 73.5 130.4 129.5 129.8 129.0"
},
{
"id": "p14.21",
"order": 72,
"type": "text",
"bbox": {
"l": 63.36,
"t": 248.4,
"r": 510.24,
"b": 224.16
},
"text": "White oil. [α]D: +8.0° (c 1.2, CHCl₃). UV (λmax, MeOH, nm): 208 (log ε 3.87). IR (νmax, film, cm⁻¹): 3522, 2929, 2856, 17621076. MS: EIMS m/z 363, 295, 277, 265, 247, 223. NMR: ¹H NMR (400MHz, CDCl₃), ¹³C NMR (50MHz, CDCl₃). Derivatives: per-MTPA esters (¹H NMR). Source: Annona coriacea roots."
},
{
"id": "p14.22",
"order": 73,
"type": "formula",
"bbox": {
"l": 157.68,
"t": 214.08,
"r": 453.36,
"b": 167.04
},
"text": "",
"attrs": {
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"alt": "Skeletal structure of an annonaceous acetogenin-type butenolide with a THF ring, a hydroxyl at C-14, and a Z-alkene at C-17",
"source": "vision"
}
},
{
"id": "p14.23",
"order": 74,
"type": "text",
"bbox": {
"l": 157.44,
"t": 155.28,
"r": 350.16,
"b": 146.64
},
"text": "Position 10 13 14 17 18"
},
{
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"order": 75,
"type": "text",
"bbox": {
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"t": 142.8,
"r": 355.68,
"b": 133.68
},
"text": "[p14.24.1] ([p14.24.2]) 3.87 m 3.78 td 3.38 m 5.35 m 5.38 m",
"children": [
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"type": "formula",
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"t": 142.8,
"r": 355.68,
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"text": "\\begin{aligned} & ^{1}\\mathrm{H}\\ (\\delta) \\quad 3.87\\ \\mathrm{m} \\quad 3.78\\ \\mathrm{td} \\quad 3.38\\ \\mathrm{m} \\quad 5.35\\ \\mathrm{m} \\quad 5.38\\ \\mathrm{m} \\end{aligned}",
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}
},
{
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"type": "formula",
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"t": 142.8,
"r": 355.68,
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"text": "\\begin{aligned} & {}^{1}\\mathbf{H}\\ (\\delta) \\quad 3.87\\ \\text{m} \\quad 3.78\\ \\text{td} \\quad 3.38\\ \\text{m} \\quad 5.35\\ \\text{m} \\quad 5.38\\ \\text{m} \\end{aligned}",
"attrs": {
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"inline": true,
"text_offset": 12,
"text_span": 10,
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"alt": "begin aligned & to the power of 1 mathbf H of delta 3.87 m 3.78 td 3.38 m 5.35 m 5.38 m end aligned",
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}
}
]
},
{
"id": "p14.25",
"order": 78,
"type": "text",
"bbox": {
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"t": 132,
"r": 353.28,
"b": 121.68
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"text": "[p14.25.1]C ([p14.25.2]) 79.2 81.8 73.6 130.6 129.0",
"children": [
{
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"order": 79,
"type": "text",
"bbox": {
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"t": 132,
"r": 353.28,
"b": 121.68
},
"text": "¹³",
"attrs": {
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"text_span": 10,
"bbox_estimated": true
}
},
{
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"type": "formula",
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"t": 132,
"r": 353.28,
"b": 121.68
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"text": "δ",
"attrs": {
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"text_offset": 13,
"text_span": 10,
"bbox_estimated": true,
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}
]
},
{
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"order": 81,
"type": "text",
"bbox": {
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"t": 121.92,
"r": 543.84,
"b": 104.16
},
"text": "White waxy solid.[p14.26.1]: +6.0° (c O.5, CHCl_{3}). UV ([p14.26.2], MeOH, nm): 207 (log[p14.26.3] 3.40). IR ([p14.26.4], film, cm^{-1}): 3488, 2929, 2856, 1761, 1465, 1075. MS: EIMS m/z 295, 277, 265, 247, 223. NMR: ^1H NMR (400MHz, CDCl_{3}), ^13C NMR (50MHz, CDCl_{3}).",
"children": [
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"order": 82,
"type": "text",
"bbox": {
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"t": 121.92,
"r": 543.84,
"b": 104.16
},
"text": "[\\alpha]_{D}",
"attrs": {
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"text_offset": 17,
"text_span": 10,
"bbox_estimated": true
}
},
{
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"order": 83,
"type": "text",
"bbox": {
"l": 65.52,
"t": 121.92,
"r": 543.84,
"b": 104.16
},
"text": "\\lambda_{max}",
"attrs": {
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"text_offset": 58,
"text_span": 10,
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}
},
{
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"order": 84,
"type": "text",
"bbox": {
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"t": 121.92,
"r": 543.84,
"b": 104.16
},
"text": "ε",
"attrs": {
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