Multibiphenyl A (1)
Pale yellow gum; [α]D –11.0 (c 0.07, MeOH); UV (MeOH) lmax / nm (log ε) 570 (2.16), 205 (4.71); IR (KBr) n / cm-1 3422, 2939, 1721, 1611, 1589, 1498, 1443, 1357, 1266, 1172, 1102, 1045, 1023, 838; 1H and 13C NMR data (400 and 100 MHz, CD3OD), see Table 1; ESI-MS (positive mode) m/z 381 [M + Na]+; EI-HRMS (M+) calcd.: 358.1416; found: 358.1408 (C20H22O6).
No. | 1 | 2 | 3 | |||
---|---|---|---|---|---|---|
δC (m) / ppm | δH (m, J , Hz) / ppm | δC (m) / ppm | δH (m, J , Hz) / ppm | δC (m) / ppm | δH (m, J , Hz) / ppm | |
1 | 129.6 s | 132.4 s | 132.3 s | |||
2 | 119.7 s | 114.2 s | 112.4 s | |||
3 | 144.9 s | 142.0 s | 141.5 s | |||
4 | 135.0 s | 131.9 s | 132.7 s | |||
5 | 147.2 s | 149.6 s | 144.8 s | |||
6 | 105.9 d | 6.26 (s, 1H ) | 106.6 d | 6.44 (s, 1H) | 105.5 d | 6.43 (s, 1H) |
7 | 133.8 s | 134.6 s | 132.7 s | |||
8 | 131.7 d | 7.00 (dd, 1H, J 8.8 Hz, 2.4) | 131.8 d | 7.11 (dd, 1H, J 8.4 Hz, 1.9) | 130.3 d | 7.16 (d, 1H, J 8.6 Hz) |
9 | 115.7 d | 6.74 (dd, 1H, J 8.8 Hz, 2.4) | 116.0 d | 6.82 (dd, 1H, J 8.4 Hz, 1.9) | 114.8 d | 6.86 (d, 1H, J 8.6 Hz) |
10 | 157.1 s | 157.7 s | 155.5 s | |||
11 | 115.7 d | 6.74 (dd, 1H, J 8.8 Hz, 2.4) | 116.0 d | 6.82 (dd, 1H, J 8.4 Hz, 1.9) | 114.8 d | 6.86 (d, 1H, J 8.6 Hz) |
12 | 131.7 d | 7.00 (dd, 1H, J 8.8 Hz, 2.4) | 131.8 d | 7.11 (dd, 1H, J 8.4 Hz, 1.9) | 130.3 d | 7.16 (d, 1H, J 8.6 Hz) |
1′ | 26.8 t | 3.21 (d, 2H, J 6.7 Hz, CH2) | 124.7 d | 6.41 (d, 1H, J 10.1 Hz) | 21.1 t | 2.59 (t, 2H, J 6.6 Hz, CH2) |
2′ | 130.7 d | 5.44 (t, 1H, J 6.7 Hz) | 124.4 d | 5.48 (d, 1H, J 10.1 Hz) | 33.0 t | 1.72 (t, 2H, J 6.6 Hz, CH2) |
3′ | 134.6 s | 77.6 s | 74.7 s | |||
4′ | 71.5 t | 4.33 (s, 3H, CH3) | 69.0 t | 4.27 (d, 1H, J 11.5 Hz, CH2) | 26.7 q | 1.39 (s, 3H, CH3) |
4.14 (d, 1H, J 11.5 Hz, CH2) | ||||||
5′ | 14.0 q | 1.39 (s, 3H, CH3) | 23.4 q | 1.47 (s, 3H, CH3) | 26.7 q | 1.39 (s, 3H, CH3) |
3-OMe | 56.5 q | 3.76 (s, 3H, OCH3) | 56.5 q | 3.85 (s, 3H, OCH3) | 56.1 q | 3.86 (s, 3H, OCH3) |
5′- OAc | 172.9 s | 172.6 s | ||||
20.8 q | 1.99 (s, 3H, COCH3) | 20.7 q | 2.00 (s, 3H, COCH3) |
Journal of the Brazilian Chemical Society
On-line version ISSN 1678-4790
J. Braz. Chem. Soc. vol.27 no.1 São Paulo Jan. 2016
http://dx.doi.org/10.5935/0103-5053.20150235
ARTICLES
New Biphenyls from Garcinia multiflora
aKey Laboratory of Chemistry in Ethnic Medicinal Resources, State Ethnic Affairs Commission & Ministry of Education, Kunming, P. R. China
bJoint Research Centre for International Cross-Border Ethnic Regions Biomass Clean Utilization in Yunnan, Yunnan Minzu University, 650031 Kunming, P. R. China
cCollege of Resource and Environment, Yuxi Normal University, 653100 Yuxi, P. R. China
Three new biphenyls were isolated from Garcinia multiflora. The structures of these biphenyls were elucidated by spectroscopic methods, and their rotavirus activity was evaluated.
Key words: Garcinia multiflora, biphenyls, anti-rotavirus activity
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