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Published April 30, 2021 | Version v1
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Heilaohuguosus A-S from the fruits of Kadsura coccinea and their hepatoprotective activity

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  • 1. ** & * & TCM and Ethnomedicine Innovation & Development International Laboratory, Innovative Materia Medica Research Institute, School of Pharmacy, Hunan University of

Description

Jia, Yan-Zhe, Yang, Yu-Pei, Cheng, Shao-Wu, Cao, Liang, Xie, Qing-Ling, Wang, Meng-Yun, Li, Bin, Jian, Yu-Qing, Liu, Bin, Peng, Cai-Yun, Wang, Wei (2021): Heilaohuguosus A-S from the fruits of Kadsura coccinea and their hepatoprotective activity. Phytochemistry (112678) 184: 1-10, DOI: 10.1016/j.phytochem.2021.112678, URL: http://dx.doi.org/10.1016/j.phytochem.2021.112678

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urn:lsid:plazi.org:pub:F23FFF81FF9CFF908549FFC5FFD8FFB8

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Figure: 10.5281/zenodo.8291994 (DOI)
Figure: 10.5281/zenodo.8291998 (DOI)

References

  • Heilaohuguosu A (1): white solid; [α]25 D +12 (c 0.07, CH3OH); CD (CH3OH) λ max nm (Δε) 223 (+4), 258 ( 2); UV (CH3OH) λ max 220 nm; IR (KBr) ν max 3447, 2929, 1714, 1598, 1436, 1407, 1233, 1107 cm 1; 1H and 13C NMR data, see Tables 1 and 2; positive HR-ESI-MS m/z 537.2111 [M+Na]+ (calcd. for C28H34O9Na, 537.2101).
  • Heilaohuguosu B (2): white solid; [α]25 D - 5 (c 0.33, CH3OH); CD (CH3OH) λ max nm (Δε) 228 (+7), 257 ( 6); UV (CH3OH) λ max 219 nm; IR (KBr) ν max 3483, 2950, 1699, 1652, 1634, 1417, 1105 cm 1 ; 1 H and 13C NMR data, see Tables 1 and 2; positive HR-ESI-MS m/z 553.2044 [M+Na]+ (calcd. for C28H34O10Na, 531.2050).
  • Heilaohuguosu C (3): white solid; [α]25 D +68 (c 0.47, CH3OH); CD (CH3OH) λ max nm (Δε) 237 (+2), 255 ( 2); UV (CH3OH) λ max 228, 287 nm; IR (KBr) ν max 3451, 2927, 1718, 1597, 1463, 1370, 1108 cm 1; 1H and 13C NMR data, see Tables 1 and 2; positive HR-ESI-MS m/z 543.2241 [M+H]+ (calcd. for C29H35O10, 543.2230).
  • Heilaohuguosu D (4): colorless oil; [α]25 D + 22 (c 0.27, CH3OH); CD (CH3OH) λ max nm (Δε) 233 (+10), 250 ( 13); UV (CH3OH) λ max 203 nm; IR (KBr) ν max 2932, 1734, 1716, 1653, 1457, 1233 cm 1; 1H and 13C NMR data, see Tables 1 and 2; positive HR-ESI-MS m/z 583.2526 [M+H]+ (calcd. for C32H39O10, 583.2543).
  • Heilaohuguosu E (5): white solid; [α]25 D +39 (c 0.27, CH3OH); CD (CH3OH) λ max nm (Δε) 233 (+11), 259 ( 6); UV (CH3OH) λ max 228 nm; IR (KBr) ν max 3494, 2937, 1700, 1683, 1506, 1456, 1233, 1104 cm 1; 1H and 13C NMR data, see Tables 1 and 2; negative HR-ESI-MS m/z 513.2123 [M - H]- (calcd. for C28H33O9, 513.2125).
  • Heilaohuguosu F (6): white solid; [α]25 D +29 (c 0.38, CH3OH); CD (CH3OH) λ max nm (Δε) 227 (+11), 258 ( 9); UV (CH3OH) λ max 239 nm; IR (KBr) ν max 2925, 1739, 1595, 1457, 1197, 1102 cm 1 ; 1 H and 13C NMR data, see Tables 1 and 2; positive HR-ESI-MS m/z 509.2158 [M+Na]+ (calcd. for C27H34O8Na, 509.2151).
  • Heilaohuguosu G (7): white solid; [α]25 D - 14 (c 0.50, CH3OH); CD (CH3OH) λ max nm (Δε) 226 (+4), 247 ( 5); UV (CH3OH) λ max 222 nm; IR (KBr) ν max 2931, 1718, 1597, 1463,1407, 1272, 1250,1108 cm 1; 1H and 13C NMR data, see Tables 1 and 2; positive HR-ESI-MS m/z 543.1998 [M+Na]+ (calcd. for C30H32O8Na, 543.1995).
  • Heilaohuguosu H (8): white solid; [α]25 D +56 (c 0.43, CH3OH); CD (CH3OH) λ max nm (Δε) 223 (+1), 243 ( 7); UV (CH3OH) λ max 211 nm; IR (KBr) ν max 3503, 2935, 1733, 1599, 1494, 1458, 1321, 1099 cm 1 ; 1 H and 13C NMR data, see Tables 3 and 4; negative HR-ESI-MS m/z 573.2695 [M-H]- (calcd. for C31H41O10, 573.2700).
  • Heilaohuguosu I (9): white solid; [α]25 D + 1 (c 0.09, CH3OH); CD (CH3OH) λ max nm (Δε) 221 (+10), 241 ( 9); UV (CH3OH) λ max 216 nm; IR (KBr) ν max 3458, 2912, 1612, 1409 cm 1; 1H and 13C NMR data, see Tables 3 and 4; positive HR-ESI-MS m/z 581.2358 [M+Na]+ (calcd. for C30H38O10Na, 581.2363).
  • Heilaohuguosu J (10): white solid; [α]25 D + 30 (c 0.33, CH3OH); CD (CH3OH) λ max nm (Δε) 219 (+7), 241 ( 3); UV (CH3OH) λ max 211 nm; IR (KBr) ν max 3502, 2983, 1700, 1596, 1462, 1405, 1105 cm 1; 1H and 13C NMR data, see Tables 3 and 4; positive HR-ESI-MS m/z 513.2103 [M+Na]+ (calcd. for C26H34O9Na, 513.2101).
  • Heilaohuguosu K (11): white solid; [α]25 D + 28 (c 0.47, CH3OH); CD (CH3OH) λ max nm (Δε) 222 (+6), 252 ( 4); UV (CH3OH) λ max 214 nm; IR (KBr) ν max 3433, 2937, 1596, 1490, 1327, 1105 cm 1; 1H and 13C NMR data, see Tables 3 and 4; positive HR-ESI-MS m/z 485.2149 [M+Na]+ (calcd. for C25H34O8Na, 485.2152).
  • Heilaohuguosu L (12): white solid; [α]25 D + 22 (c 0.43, CH3OH); CD (CH3OH) λ max nm (Δε) 219 (+6), 250 ( 2); UV (CH3OH) λ max 215 nm; IR (KBr) ν max 3487, 2951, 1729, 1596, 1461, 1238, 1105 cm 1; 1H and 13C NMR data, see Tables 3 and 4; positive HR-ESI-MS m/z 513.2106 [M+Na]+ (calcd. for C26H34O9Na, 513.2101).
  • Heilaohuguosu M (13): white solid; [α]25 D +7 (c 0.43, CH3OH); CD (CH3OH) λ max nm (Δε) 254 (+3), 212 ( 5); UV (CH3OH) λ max 209 nm; IR (KBr) ν max 3483, 2997, 1614, 1459, 1425, 1456, 1204, 1108 cm 1; 1H and 13C NMR data, see Tables 3 and 4; negative HR-ESI-MS m/z 401.1593 [M-H]- (calcd. for C22H25O7, 401.1600).
  • Heilaohuguosu N (14): white solid; [α]25 D + 21 (c 0.17,CH3OH); UV (CH3OH) λ max 228, 270, 302 nm; IR (KBr) ν max 3483, 2934, 1615, 1475, 1425, 1204, 1108, 1076 cm 1; 1H and 13C NMR data, see Tables 3 and 4; positive HRESIMS m/z 443.1683 [M+Na]+ (calcd. for C22H28O8Na, 443.1682).
  • Heilaohuguosu O (15): white solid; [α]25 D - 8 (c 0.13, CH3OH); CD (CH3OH) λ max nm (Δε) 206 ( 9), 219 (+5), 279 ( 0.5), 287 (+0.3); UV (CH3OH) λ max 206 nm; IR (KBr) ν max 3426, 2959, 1597, 1501, 1457, 1346, 1200, 1106 cm 1; 1H and 13C NMR data, see Table 5; positive HR-ESI-MS m/z 389.1963 [M+H]+ (calcd. for C22H29O6, 389.1964).
  • Heilaohuguosu P (16): white solid; [α]25 D - 19 (c 0.43, CH3OH); CD (CH3OH) λ max nm (Δε) 206 ( 20), 223 (+4), 283 (+1.3); UV (CH3OH) λ max 207 nm; IR (KBr) ν max 3450, 2956, 1591, 1507, 1456, 1427, 1433, 1196, 1110 cm 1; 1H and 13C NMR data, see Table 5; negative HR-ESI-MS m/z 387.1808 [M-H]- (calcd. for C22H27O6, 387.1808).
  • Heilaohuguosu Q (17): white solid; [α]25 D - 5 (c 0.47, CH3OH); CD (CH3OH) λ max nm (Δε) 203 ( 5), 216 (+5), 239 ( 1.8), 285 (+0.7); UV (CH3OH) λ max 205 nm; IR (KBr) ν max 3433, 2963, 1591, 1508, 1456, 1430, 1353, 1247, 1110 cm 1; 1H and 13C NMR data, see Table 5; positive HR-ESI-MS m/z 373.1999 [M+H]+ (calcd. for C22H29O5, 373.2015).
  • Heilaohuguosu R (18): white solid; [α]25 D - 1 (c 0.08, CH3OH); CD (CH3OH) λ max nm (Δε) 216 (+5), 235 ( 2.5), 272 (+0.4); UV (CH3OH) λ max 207 nm; IR (KBr) ν max 3452, 2950, 1607, 1499, 1405, 1229, 1120 cm 1; 1H and 13C NMR data, see Table 5; positive HR-ESI-MS m/z 411.1773 [M+Na]+ (calcd. for C22H28O6Na, 411.1765).
  • Heilaohuguosu S (19): white solid; [α]25 D +9 (c 0.33, CH3OH); CD (CH3OH) λ max nm (Δε) 216 (+5), 235 ( 2.5), 272 (+0.4); UV (CH3OH) λ max 207 nm; IR (KBr) ν max 3462, 2950, 1607, 1500, 1456, 1217, 1119 cm 1; 1H and 13C NMR data, see Table 5; positive HR-ESI-MS m/z 405.1907 [M+H]+ (calcd. for C22H29O7, 405.1913).