=lOHz, H-4a), 542 (lH, t, J=lOHz, H-3), 542 (lH, d, J
=10Hz,H-lOb),597(1H,t,J=10Hz,H-4),708,712(each2H,
s, galloyl H), 7 14 (lH, s, H-7) 13CNMR see Table 1 (Found
C, 52 17, H, 4 18 C,,H,,O,, 1/2H,O requires C, 5242, H,
3 90%)
4,11-D1-0-galloylbergenIn (2) Amorphous powder, [a];’
-125” (MeOH; c 0 5) Negative FABMS m/z 631 [M-H]-
‘H NMR (Me&O-d, + D,O) 6 3.90 (3H, s, OMe), 4 54 (lH, dd,
J=lO, 11 Hz,H-4a),501 (lH,brd,J=lOHz,H-11),5.37(1H,d,
J=llHz,H-lOb),566(1H,dd,J=9,10Hz,H-4),711(1H,s,H-
7), 7 20, 7 22 (each 2H, s, galloyl H) 13C NMR. see Table 1
(Found C, 5259, H, 4 16 CZ8HZ401, 1/2H,O requires C,
52 42, H, 3 90%)
3,4,1 I-Tn-0-galloylbergellln (3) Amorphous powder, [a];”
- 10 2” (MeOH. L 0 5) Negative FABMS m/z 783 [M-H] -
‘H NMR (Me,CO-d, + D,O) 6 3 92 (3H, s, OMe), 4 30 (lH, dd,
J=6, 12Hz, H-11), 475 (lH, t,J=lOHz, H-4a) 486(1H, dd, J
=2, 12 Hz, H-11), 5 53 (lH, d, I=lOHz, H-lob), 559 (lH, t, J
=10Hz,H-3),602(1H,t,J=10Hz,H-4),712(1H,s,H-7),710,
7 12,7 20 (each 2H, s, galloyl H) 13C NMR see Table 1. (Found
C, 52 50, H, 3 94 C 35H 280 21 H,O reqmres. C, 52 37, H, 3 74%)
4-0-Galloy[norbergenIn (4) Powder (H,O), mp 219-220”,
[~I;” -46 5” (MeOH, CO 8) Negative FABMS m/z 465 [M
-HI- ‘HNMR (Me&O-d,) 6441 (lH, dd, J=lO, 11 Hz, H-
4a),524(1H,d,J=l1Hz,H-lOb),560(1H,dd,J=9,10Hz,H-
4), 7 09 (lH, s, H-7), 7 19 (2H, s, galloyl H) 13C NMR see Table 1
(Found C, 47,16, H, 4 17 C20H,80,, 2H,O requires. C, 47 81,
H, 4 42%).
1-0-Galloyf-P-D-glucose (5). Powder (H,O), mp 205-206”,
[a];” - 18 6” (MeOH, c 10) ‘HNMR (Me&O-d,) 65 69 (lH,
d, J = 8 Hz, H-l), 7 22 (2H, s, galloyl H)
6-O-Galloyl-D-glucose (6) Amorphous powder, [alA + 28.3”
(MeOH, c IO) ‘H NMR (Me&O-d,) 64 61 (1/2H, d, .J=8 Hz,
H-l). 5 16 (1/2H, d, 5=3 Hz, H-l), 7 15 (2H, s, galloyl H)
l,6-Dt-O-yulloyl-P-D-glucose (7) Needles (H,O), mp 201-203”,
[?I: -219” (MeOH, c 10) ‘HNMR (Me,CO-d,) 6439 (lH,
dd,3=4,12Hz,H-6),457(1H,dd,5=2,12Hz,H-6),574(1H,d,
J =8 Hz, H-l), 7 13, 7 17 (each 2H, J, galloyl H)
1,2,3,6-Tetra-O-yalloyl_B-D-ylucoFe (8) Needles (H,O), mp
198-200”, [a];’ + 35 9” (Me,CO, c 0 7), ‘H NMR (Me&O-d,
+ D,O) 6550(1H,t,J=8Hz,H-2), 5.71 (lH,t,J=8Hz,H-3),
6 16 (lH, d, 5=8 Hz, H-l), 703, 707, 7 10, 7.15 (each 2H, s,
galloyl H)
1,2,4,6-Terra-O-qalloyl-a-D-g[ucose (9) Needles (H,O), mp
21 l-213”. [a];’ -4 8” (Me,CO, CO 7) ‘H NMR (Me,CO-d,
+D,O) 6541 (2H, t, J=9Hz, H-2 and H-4), 6.13 (lH, d, J
=8 Hz, H-l), 7 10, 7 11, 7 18, 7 21 (each 2H, s, galloyl H).
1,2,3,4,6-Penta-0-gaI[oyI-B-D-glucose (10) Amorphous powder,
[a];’ + 18 3” (Me&O, c 0 4) ‘H NMR (Me,CO-d,) S5 61
(lH, t, J=8 Hz, H-2), 566 (lH, t, .J=8 Hz, H-4), 6.02 (lH, t, J
=8 Hz,H-3),6 34(1H,d,J=8Hz, H-1),697.702,7 06,7 11,7 18
(each 2H, s, galloyl H)
I-0-Galloylglycerol (11) Prisms (H,O), mp 188-190”, [alA
+2 5” (MeOH, c 1 1) ‘H NMR (Me&O-d, +D,O) 63 66 (2H,
d. .I=5 Hz, H-3), 396 (lH, m, H-2), 429 (2H, dd, 5=2, 5Hz,
H-l), 7 16 (2H, s, galloyl H)
3-0-Gafloylshkmtc actd (12) Powder (H,O), mp 254-255”,
[a];’ - 108 3” (MeOH, c 10) ‘H NMR (Me&O-d,) 6 2 39 (IH,
dd,J=5, 18Hz,H_2),285(1H,dd,J=5, 18Hz, H-2),404(1H,
dd,J=4,7Hz,H-4),450(1H,brt,J=4Hz,H-5),535(1H,m,H-
3), 6 89 (lH, br t, .I=4 Hz, H-6), 7 10 (2H, F, galloyl H)
Bergemn (13). Powder (H,O), mp 137-139”, [a]b* -39 3”
=lOHz, H-4a), 542 (lH, t, J=lOHz, H-3), 542 (lH, d, J=10Hz,H-lOb),597(1H,t,J=10Hz,H-4),708,712(each2H,s, galloyl H), 7 14 (lH, s, H-7) 13CNMR see Table 1 (FoundC, 52 17, H, 4 18 C,,H,,O,, 1/2H,O requires C, 5242, H,3 90%)4,11-D1-0-galloylbergenIn (2) Amorphous powder, [a];’-125” (MeOH; c 0 5) Negative FABMS m/z 631 [M-H]-‘H NMR (Me&O-d, + D,O) 6 3.90 (3H, s, OMe), 4 54 (lH, dd,J=lO, 11 Hz,H-4a),501 (lH,brd,J=lOHz,H-11),5.37(1H,d,J=llHz,H-lOb),566(1H,dd,J=9,10Hz,H-4),711(1H,s,H-7), 7 20, 7 22 (each 2H, s, galloyl H) 13C NMR. see Table 1(Found C, 5259, H, 4 16 CZ8HZ401, 1/2H,O requires C,52 42, H, 3 90%)3,4,1 I-Tn-0-galloylbergellln (3) Amorphous powder, [a];”- 10 2” (MeOH. L 0 5) Negative FABMS m/z 783 [M-H] -‘H NMR (Me,CO-d, + D,O) 6 3 92 (3H, s, OMe), 4 30 (lH, dd,J=6, 12Hz, H-11), 475 (lH, t,J=lOHz, H-4a) 486(1H, dd, J=2, 12 Hz, H-11), 5 53 (lH, d, I=lOHz, H-lob), 559 (lH, t, J=10Hz,H-3),602(1H,t,J=10Hz,H-4),712(1H,s,H-7),710,7 12,7 20 (each 2H, s, galloyl H) 13C NMR see Table 1. (FoundC, 52 50, H, 3 94 C 35H 280 21 H,O reqmres. C, 52 37, H, 3 74%)4-0-Galloy[norbergenIn (4) Powder (H,O), mp 219-220”,[~I;” -46 5” (MeOH, CO 8) Negative FABMS m/z 465 [M-HI- ‘HNMR (Me&O-d,) 6441 (lH, dd, J=lO, 11 Hz, H-4a),524(1H,d,J=l1Hz,H-lOb),560(1H,dd,J=9,10Hz,H-4), 7 09 (lH, s, H-7), 7 19 (2H, s, galloyl H) 13C NMR see Table 1(Found C, 47,16, H, 4 17 C20H,80,, 2H,O requires. C, 47 81,H, 4 42%).1-0-Galloyf-P-D-glucose (5). Powder (H,O), mp 205-206”,[a];” - 18 6” (MeOH, c 10) ‘HNMR (Me&O-d,) 65 69 (lH,d, J = 8 Hz, H-l), 7 22 (2H, s, galloyl H)6-O-Galloyl-D-glucose (6) Amorphous powder, [alA + 28.3”(MeOH, c IO) ‘H NMR (Me&O-d,) 64 61 (1/2H, d, .J=8 Hz,H-l). 5 16 (1/2H, d, 5=3 Hz, H-l), 7 15 (2H, s, galloyl H)l,6-Dt-O-yulloyl-P-D-glucose (7) Needles (H,O), mp 201-203”,[?I: -219” (MeOH, c 10) ‘HNMR (Me,CO-d,) 6439 (lH,dd,3=4,12Hz,H-6),457(1H,dd,5=2,12Hz,H-6),574(1H,d,J =8 Hz, H-l), 7 13, 7 17 (each 2H, J, galloyl H)1,2,3,6-Tetra-O-yalloyl_B-D-ylucoFe (8) Needles (H,O), mp198-200”, [a];’ + 35 9” (Me,CO, c 0 7), ‘H NMR (Me&O-d,+ D,O) 6550(1H,t,J=8Hz,H-2), 5.71 (lH,t,J=8Hz,H-3),6 16 (lH, d, 5=8 Hz, H-l), 703, 707, 7 10, 7.15 (each 2H, s,galloyl H)1,2,4,6-Terra-O-qalloyl-a-D-g[ucose (9) Needles (H,O), mp21 l-213”. [a];’ -4 8” (Me,CO, CO 7) ‘H NMR (Me,CO-d,+D,O) 6541 (2H, t, J=9Hz, H-2 and H-4), 6.13 (lH, d, J=8 Hz, H-l), 7 10, 7 11, 7 18, 7 21 (each 2H, s, galloyl H).1,2,3,4,6-Penta-0-gaI[oyI-B-D-glucose (10) Amorphous powder,[a];’ + 18 3” (Me&O, c 0 4) ‘H NMR (Me,CO-d,) S5 61(lH, t, J=8 Hz, H-2), 566 (lH, t, .J=8 Hz, H-4), 6.02 (lH, t, J=8 Hz,H-3),6 34(1H,d,J=8Hz, H-1),697.702,7 06,7 11,7 18(each 2H, s, galloyl H)I-0-Galloylglycerol (11) Prisms (H,O), mp 188-190”, [alA+2 5” (MeOH, c 1 1) ‘H NMR (Me&O-d, +D,O) 63 66 (2H,d ฉัน = 5 Hz, H-3), 396 (lH เมตร H-2), 429 (2 H, dd, 5 = 2, 5 HzH-l), 16 7 (2 H, s, galloyl H)3-0-Gafloylshkmtc actd (12) ผง (H, O), mp 254-255"[a];’ -108 3" (MeOH, c 10) ' H NMR (Me & O-d,) 6 2 39 (IHdd, J = 5, 18 Hz, H_2), 285 (1 H, dd, J = 5, 18 Hz, H-2), 404 (1 Hdd, J = 4, 7 Hz, H-4), 450 (1 H ไปทางด่วน brt, J = 4 Hz, H-5), 535 (1 H, m, H -3), 6 89 (lH, br t, ฉัน = 4 Hz, H-6), 7 10 (galloyl 2 H, F, H)Bergemn (13) ผง (H, O), mp 137-139" [a] b * -39 3 "
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