漆斑菌中单端孢霉烯化合物及衍生物的细胞毒活性

doi:10.7503/cjcu20180007

摘要/Abstract

摘要：

从漆斑菌中分离得到了5个单端孢霉烯族化合物, 并确定了其平面结构; 选取其中获得量比较大的化合物进行结构改造, 得到4个新化合物; 分别对这9个化合物进行了抗菌和细胞毒活性测试. 结果表明, 化合物1结构中C12和C13位的环氧环打开后, 重新与C2位形成新的四元环氧环或对C2'位的羟基进行酰基保护后, 化合物的细胞毒活性下降.

关键词: 漆斑菌, 结构改造, 抗菌活性, 细胞毒活性

Abstract:

Five trichothecene compounds were obtained from Myrothecium sp. KX136897 and their structures were confirmed by means of ¹H NMR, ¹³C NMR and HRMS. Compound 1 was used for the further structural modifications and four new derivatives were synthesized. The structure of compound 6 was different from those of the other derivatives, which was identified via comparing its ¹³C NMR with the reported structure. Furthermore, compound 6 was confirmed by comparing the calculated data with the experimental data of ¹³C NMR. Compounds 1—9 were used for antibacterial and cytotoxic activity study, respectively. It was found that if the epoxy ring at positions C12 and C13 was opened and then reformed a new four-membered epoxy ring, the cytotoxic activity of compound 1 would decrease. Besides, the protection of hydroxyl at position C2' by acyl would also cause the decrease of cytotoxic activity.

Key words: Myrothecium sp., Structural modification, Antibacterial activity, Cytotoxic activity

中图分类号:

O626

TrendMD:

贾云静, 史文思, 胡飞柳, 朱华结, 刘莉, 马正月. 漆斑菌中单端孢霉烯化合物及衍生物的细胞毒活性. 高等学校化学学报, 2018, 39(8): 1668.

JIA Yunjing, SHI Wensi, HU Feiliu, ZHU Huajie, LIU Li, MA Zhengyue. Cytotoxic Activity of Trichothecene Compounds and Derivatives from Myrothecium sp.^†. Chem. J. Chinese Universities, 2018, 39(8): 1668.

图/表 7

Fig.1 Structures of compounds 1—5

Scheme 1 Synthetic routes of compounds 6—9

Table 1 Appearance, yields, [α]D20 and MS data of compounds 1—9

Compd.	Appearance	Yield(%)	[α $] D 20$ /(°)(c=2.0 mg/mL,CH₂Cl₂)	LC-MS, m/z [M+H]⁺
1	White amorphous solid	—	+261.80	503.40
2	White amorphous solid	—	+62.50	531.19
3	White amorphous solid	—	+139.13	485.16
4	White amorphous solid	—	+205.00	533.30
5	White amorphous solid	—	+58.82	501.15
6	White amorphous solid	55	+96.15	581.50
7	White amorphous solid	34	+89.75	539.50
8	White amorphous solid	52	+80.95	579.15
9	White amorphous solid	49	+117.00	573.21

Table 1 Appearance, yields, [α]D20 and MS data of compounds 1—9

Compd.	Appearance	Yield(%)	[α $] D 20$ /(°)(c=2.0 mg/mL,CH₂Cl₂)	LC-MS, m/z [M+H]⁺
1	White amorphous solid	—	+261.80	503.40
2	White amorphous solid	—	+62.50	531.19
3	White amorphous solid	—	+139.13	485.16
4	White amorphous solid	—	+205.00	533.30
5	White amorphous solid	—	+58.82	501.15
6	White amorphous solid	55	+96.15	581.50
7	White amorphous solid	34	+89.75	539.50
8	White amorphous solid	52	+80.95	579.15
9	White amorphous solid	49	+117.00	573.21

Table 2 1H NMR and 13C NMR data of compounds 1—9

Compd.	¹H NMR(CDCl₃, 600 MHz), δ	¹³C NMR(CDCl₃, 150MHz), δ
1	8.01(dd,J=15.6, 11.3 Hz, 1H, 8'-H), 6.65(t, J=11.3 Hz, 1H, 9'-H), 6.13(d, J=11.3 Hz, 1H, 10'-H), 6.02(d, J=15.6 Hz, 1H, 7'-H), 5.84—5.74(m, 1H, 4-H), 5.41(d, J=5.1 Hz, 1H, 10-H), 4.77(d, J=12.0 Hz, 1H, 15a-H), 4.54—4.43(m, 1H, 5'a-H), 4.19(d, J=12.0 Hz, 1H, 15b-H), 4.13(d, J=7.2 Hz, 1H, 2'-H), 3.96(t, J=11.4 Hz, 1H, 5'b-H), 3.84(d, J=4.6 Hz, 1H, 2-H), 3.55(d, J=5.1 Hz, 1H, 11-H), 3.15—3.05(m, 1H, 13a-H), 2.83—2.75(m, 1H, 13b-H), 2.48—2.44(m, 1H, 3a-H), 2.39—2.28(m, 1H, 3'-H), 2.22—2.19(m, 1H, 3b-H), 1.96—1.91(m, 2H, 8-H), 1.90—1.89(m, 1H, 7a-H), 1.89—1.86(m, 1H, 4'a-H), 1.78—1.75(m, 1H, 4'b-H), 1.73(s, 3H, 16-H), 1.68—1.67(m, 1H, 7b-H), 0.86(d, J=6.6 Hz, 3H, 12'-H), 0.83(s, 3H, 14-H)	174.80(C1'), 166.23(C6'), 165.55(C11'), 141.23(C9), 139.02(C8'), 138.91(C9'), 127.58(C7'), 125.88(C10'), 118.04(C10), 79.03(C2), 75.65(C4), 74.27(C2'), 67.00(C11), 65.32(C12), 63.58(C15), 61.23(C5'), 49.59(C5), 47.90(C13), 44.31(C6), 35.01(C3), 33.33(C3'), 32.32(C4'), 27.62(C8), 23.37(C16), 20.11(C7), 10.12(C12'), 7.43(C14)
2	7.52(dd,J=15.7, 11.6 Hz, 1H, 8'-H), 6.59(t, J=11.3 Hz, 1H, 9'-H), 5.96(dd, J=15.7, 3.2 Hz, 1H,7'-H), 5.84—5.82(m, 1H, 4-H), 5.81(d, J=11.3 Hz, 1H, 10'-H), 5.43(d, J=5.0 Hz, 1H, 10-H), 4.37(d, J=12.4 Hz, 1H, 15a-H), 4.26(d, J=12.4 Hz, 1H, 15b-H), 3.84(d, J=5.2 Hz, 1H, 2-H), 3.83—3.79(m, 1H, 11-H), 3.69—3.65(m, 1H, 6'-H), 3.65—3.61(m, 2H, 5'-H), 3.35—3.33(m, 1H, 13'-H), 3.30(s, 1H, 2'-H), 3.12(d, J=4.0 Hz, 1H, 13a-H), 2.81(d, J=4.0 Hz, 1H, 13b-H), 2.47—2.44(m, 1H, 3a-H), 2.17(dt, J=15.4, 4.6 Hz, 1H, 3b-H), 2.11—1.95(m, 2H, 8-H), 1.95—1.87(m, 2H, 7-H), 1.82—1.80(m, 1H, 4'a-H), 1.72(s, 3H, 16-H), 1.61(s, 3H, 12'-H), 1.47—1.44(m, 1H, 4'b-H), 1.20(d, J=6.2 Hz, 3H, 14'-H), 0.83(s, 3H, 14-H)	168.11(C1'), 166.36(C11'), 143.07(C9'), 140.64(C9), 138.21(C7'), 126.34(C8'), 118.46(C10), 118.15(C10'), 85.69(C6'), 79.05(C2), 74.46(C4), 70.86(C13'), 67.42(C5'), 67.07(C11), 65.34(C12), 64.56(C15), 63.21(C3'), 58.17(C2'), 49.17(C5), 47.79(C13), 43.22(C6), 39.59(C4'), 35.13(C3), 27.57(C8), 23.25(C16), 20.58(C7), 18.18(C14'), 17.40(C12'), 7.00(C14)
3	8.07(dd,J=15.7, 11.3 Hz, 1H, 8'-H), 6.61(t, J=11.3 Hz, 1H, 9'-H), 6.09(d, J=11.3 Hz, 1H, 10'-H), 6.02—5.99(m, 1H, 7'-H), 6.00—5.98(m, 1H, 4-H), 5.82(s, 1H, 2'-H), 5.46(d, J=5.0 Hz, 1H, 10-H), 4.47—4.44(m, 1H, 5'a-H), 4.42(d, J=12.6 Hz, 1H, 15a-H), 4.17—4.13(m, 1H, 5'b-H), 3.97(d, J=12.6 Hz, 1H, 15b-H), 3.85(d, J=5.1 Hz, 1H, 2-H), 3.75(d, J=5.0 Hz, 1H, 11-H), 3.14(d, J=4.0 Hz, 1H, 13a-H), 2.83(d, J=4.0 Hz, 1H, 13b-H), 2.53—2.52(m, 1H, 3a-H), 2.52—2.50(m, 2H, 4'-H), 2.28(s, 3H, 12'-H), 2.18—2.14(m, 1H, 3b-H), 2.05—1.97(m, 2H, 8-H), 1.99—1.94(m, 1H, 7a-H), 1.84—1.80(m, 1H, 7b-H), 1.71(s, 3H, 16-H), 0.83(s, 3H, 14-H)	166.08(C1'), 165.80(C11'), 165.51(C6'), 156.54(C3'), 140.40(C9), 139.44(C9'), 139.13(C8'), 127.38(C7'), 125.52(C10'), 118.68(C10), 118.16(C2'), 79.06(C2), 75.36(C4), 67.30(C11), 65.47(C12), 63.34(C15), 60.42(C5'), 48.86(C5), 48.05(C13), 43.07(C6), 40.22(C4'), 35.14(C3), 27.68(C8), 23.24(C16), 20.79(C7), 17.20(C12'), 6.97(C14)
4	7.65(dd,J=15.4, 11.7 Hz, 1H, 8'-H), 6.64(t, J=11.4 Hz, 1H, 9'-H), 5.98(dd, J=15.4, 3.0 Hz, 1H, 7'-H), 5.78(d, J=11.4 Hz, 1H, 10'-H),	174.79(C1'), 166.46(C11'), 143.84(C9'), 140.85(C9), 139.14(C7'), 126.04
Compd.	¹H NMR(CDCl₃, 600 MHz), δ	¹³C NMR(CDCl₃, 150MHz), δ
4	5.78—5.76(m, 1H, 4-H), 5.41(d, J=4.6 Hz, 1H, 10-H), 4.40(s, 2H, 15-H), 4.09—4.07(m, 1H, 2'-H), 3.84(d, J=5.1 Hz, 1H, 2-H), 3.65—3.63(m, 1H, 6'-H), 3.61—3.58(m, 1H, 11-H), 3.58—3.57(m, 1H, 13'-H), 3.53—3.51(m, 2H, 5'-H), 3.10(d, J=4.0 Hz, 1H, 13a-H), 2.78(d, J=4.0 Hz, 1H, 13b-H), 2.78—2.75(m, 1H, 3'-H), 2.43(dd, J=15.4, 8.3 Hz, 1H, 3a-H), 2.19(dt, J=15.4, 4.7 Hz, 1H, 3b-H), 2.03—1.96(m, 2H, 8-H), 1.91—1.84(m, 2H, 7-H), 1.79—1.75(m, 2H, 4'-H), 1.72(s, 3H, 16-H), 1.18(d, J=6.2 Hz, 3H, 14'-H), 1.07(d, J=6.9 Hz, 3H, 12'-H), 0.79(s, 3H, 14-H)	(C8'), 118.20(C10), 117.47(C10'), 83.96(C6'), 79.00(C2), 75.53(C2'), 74.26(C4), 70.74(C13'), 69.79(C5'), 67.11(C11), 65.17(C12), 64.49(C15), 49.30(C5), 47.71(C13), 43.71(C6), 37.07(C3'), 34.78(C3), 33.00(C4'), 27.64(C8), 23.23(C16), 20.20(C7), 18.19(C14'), 14.70(C12'), 7.43(C14)
5	7.89(dd,J=15.7, 11.3 Hz, 1H, 8'-H), 6.62(t, J=11.3 Hz, 1H, 9'-H), 6.16(d, J=11.3 Hz, 1H, 10'-H), 6.06(d, J=15.7 Hz, 1H, 7'-H), 5.84(dd, J=8.2, 4.4 Hz, 1H, 4-H), 5.43(d, J=5.2 Hz, 1H, 10-H), 4.49(d, J=12.4 Hz, 1H, 15a-H), 4.39—4.35(m, 2H, 5'-H), 4.33—4.29(m, 1H, 15b-H), 3.86(d, J=5.2 Hz, 1H, 11-H), 3.59(d, J=5.2 Hz, 1H, 2-H), 3.39(s, 1H, 2'-H), 3.14(d, J=4.0 Hz, 1H, 13a-H), 2.82(d, 1H, J=4.0 Hz, 13b-H), 2.54—2.50(m, 1H, 3a-H), 2.32—2.29(m, 1H, 4'a-H), 2.22—2.18(m, 1H, 3b-H), 2.05—2.01(m, 2H, 8-H), 1.95—1.90(m, 1H, 7a-H), 1.82—1.80(m, 1H, 4'b-H), 1.73(s, 3H, 16-H), 1.71—1.67(m, 1H, 7b-H), 1.56(s, 3H, 12'-H), 0.88(s, 3H, 14-H)	167.75(C1'), 166.27(C6'), 165.35(C11'), 141.12(C9), 138.58(C9'), 138.31(C8'), 127.60(C7'), 125.97(C10'), 118.02(C10), 79.00(C2), 75.60(C4), 67.24(C11), 65.25(C12), 63.88(C15), 61.66(C3'), 60.73(C5'), 58.44(C2'), 49.30(C5), 47.98(C13), 43.88(C6), 37.07(C4'), 35.06(C3), 27.60(C8), 23.26(C16), 20.09(C7), 16.01(C12'), 7.73(C14)
6	8.43(dd, 1H,J=15.6, 11.4 Hz, 8'-H), 6.76(t, 1H, J=11.4 Hz, 9'-H), 6.09(d, 1H, J=10.8 Hz, 10'-H), 6.06(d, 1H, J=15.6 Hz, 7'-H), 5.84(d, 1H, J=6.6 Hz, 4-H), 5.55—5.50(m, 1H, 10-H), 4.61—4.58(m, 2H, 13-H), 4.61—4.58(m, 1H, 2'-H), 4.50—4.46(m, 1H, 2-H), 4.50—4.47(m, 1H, 5'a-H), 4.30(d, 1H, J=12.6 Hz, 15a-H), 4.25(d, 1H, J=11.4 Hz, 15b-H), 4.04—4.00(m, 1H, 5'b-H), 3.69(d, 1H, J=4.8 Hz, 11-H), 2.54(d, 1H, J=6.0 Hz, 3a-H), 2.52—2.47(m, 1H, 3'-H), 2.35(d, 1H, J=15.6 Hz, 3b-H), 2.11(s, 3H, 14'-H), 1.98—1.95(m, 2H, 8-H), 1.95—1.91(m, 1H, 7a-H), 1.85—1.82(m, 1H, 4'a-H), 1.73(s, 3H, 16-H), 1.75—1.71(m, 1H, 7b-H), 1.65—1.63(m, 1H, 4'b-H), 1.13(s, 3H, 14-H), 0.88(d, 3H, J=7.2 Hz, 12'-H)	174.70(C1'), 171.00(C13'), 165.36(C6'), 165.01(C11'), 140.56(C8'), 140.56(C9), 139.19(C9'), 127.60(C7'), 124.81(C10'), 117.57(C10), 95.24(C2), 78.73(C4), 76.36(C2'), 73.64(C13), 67.34(C12), 64.50(C15), 63.25(C5'), 62.03(C11), 61.54(C5), 48.26(C6), 41.29(C3), 33.42(C3'), 32.18(C4'), 27.39(C8), 23.29(C16), 22.76(C7), 20.99(C14'), 13.37(C12'), 11.92(C14)
7	8.38(dd, 1H,J=15.6, 11.4 Hz, 8'-H), 6.69(t, 1H, J=11.4 Hz, 9'-H), 6.03(d, 1H, J=10.8 Hz, 7'-H), 5.99(d, 1H, J=16.2 Hz, 10'-H), 5.81(d, 1H, J=6.0 Hz, 4-H), 5.45—5.42(m, 1H, 10-H), 4.54—4.48(m, 2H, 13-H), 4.40—4.37(m, 1H, 2-H), 4.40—4.37(m, 1H, 2'-H), 4.2(d, 1H, J=12.6 Hz, 15a-H), 3.99—3.94(m, 2H, 5'-H), 3.79(d, 1H, J=12.0 Hz, 15b-H), 3.64(d, 1H, J=5.4 Hz, 11-H), 2.49(d, 1H, J=5.4 Hz, 3a-H), 2.44—2.41(m, 1H, 3'-H), 2.27(d, 1H, J=15.6 Hz, 3b-H), 1.90—1.87(m, 2H, 8-H), 1.87—1.84(m, 1H, 7a-H), 1.72—1.70(m, 2H, 4'-H), 1.67(s, 3H, 16-H), 1.65—1.61(m, 1H, 7b-H), 1.02(s, 3H, 14-H), 0.82(d, 3H, J=6.6 Hz, 12'-H)	173.72(C1'), 164.38(C6'), 164.03(C11'), 139.40(C9), 139.32(C8'), 138.23(C9'), 126.36(C7'), 124.02(C10'), 116.69(C10), 95.95(C2), 78.00(C4), 75.06(C2'), 72.57(C13), 64.02(C12), 63.52(C15), 62.37(C5'), 60.99(C11), 59.49(C5), 47.34(C6), 40.16(C3), 32.39(C3'), 31.18(C4'), 28.68(C8), 26.32(C16), 22.27(C7), 12.06(C12'), 11.01(C14)
8	7.95(dd, 1H,J=16.2, 12.0 Hz, 8'-H), 6.61(t, 1H, J=11.4 Hz, 9'-H), 6.10(d, 1H, J=10.8 Hz, 10'-H), 5.98(d, 1H, J=15.6 Hz, 7'-H), 5.74—5.72(m, 1H, 4-H), 5.37—5.32(m, 1H, 10-H), 4.84—4.80(m, 1H, 2'-H), 4.63(d, 1H, J=12.0 Hz, 15a-H), 4.42—4.40(m, 1H, 5'a-H), 4.15(d, 1H, J=12.0 Hz, 15b-H), 4.12(s, 2H, 14'-H), 3.96—3.91(m, 1H, 5'b-H), 3.79(d, 1H, J=4.8 Hz, 2-H), 3.49(d, 1H, J=5.4 Hz, 11-H), 3.06(d, 1H, J=4.2 Hz, 13a-H), 2.75(d, 1H, J=4.2 Hz, 13b-H), 2.48—2.44(m, 1H, 3'-H), 2.43—2.39(m, 1H, 3a-H), 2.18—2.15(m, 1H, 3b-H), 1.96—1.92(m, 1H, 7a-H), 1.88—1.83(m, 2H, 8-H), 1.83—	167.22(C1'), 166.27(C13'), 165.20(C6'), 164.24(C11'), 140.61(C9), 137.86(C8'), 137.86(C9'), 126.28(C7'), 124.96(C10'), 116.64(C10), 77.90(C2), 76.47(C4), 74.71(C2'), 65.94(C11), 64.23(C12), 62.20(C15), 59.62(C5'), 48.47(C5), 46.84(C13), 43.22(C6), 39.46(C14'), 33.87(C3), 31.68(C3'), 29.94(C4'), 28.68(C8),
Compd.	¹H NMR(CDCl₃, 600 MHz), δ	¹³C NMR(CDCl₃, 150MHz), δ
8	1.80(m, 1H, 4'a-H), 1.77—1.73(m, 1H, 4'b-H), 1.67(s, 3H, 16-H), 1.66—1.61(m, 1H,7b-H), 0.98(d, 3H, J=7.2 Hz, 12'-H), 0.80(s, 3H, 14-H)	26.24(C16), 22.32(C7), 10.29(C12'), 6.35(C14)
9	7.93(dd, 1H,J=15.6, 11.4 Hz, 8'-H), 6.60(t, 1H, J=11.4 Hz, 9'-H), 6.10(d, 1H, J=10.8 Hz, 10'-H), 5.97(d, 1H, J=15.6 Hz, 7'-H), 5.74—5.72(m, 1H, 4-H), 5.36—5.31(m, 1H, 10-H), 4.75—4.73(m, 1H, 15a-H), 4.63—4.60(m, 1H, 2'-H), 4.41—4.38(m, 1H, 5'a-H), 4.14—4.11(m, 1H, 15b-H), 3.96—3.92(m, 1H, 5'b-H), 3.79(d, 1H, J=4.8 Hz, 2-H), 3.49(d, 1H, J=4.8 Hz, 11-H), 3.05(d, 1H, J=3.6 Hz, 13a-H), 2.75(d, 1H, J=3.6 Hz, 13b-H), 2.43—2.39(m, 1H, 3a-H), 2.37—2.31(m, 1H, 3'-H), 2.18—2.14(m, 1H, 3b-H), 1.98—1.93(m, 1H, 14'a-H), 1.90—1.85(m, 1H, 14'b-H), 1.85—1.80(m, 2H, 8-H), 1.80—1.75(m, 1H, 7a-H), 1.80—1.75(m, 1H, 4'a-H), 1.67(s, 3H,16-H), 1.65—1.62(m, 1H, 4'b-H), 1.62—1.60(m, 1H, 7b-H), 0.97(d, 3H, J=6.6 Hz, 12'-H), 0.94—0.91(m, 2H, 15'-H), 0.90—0.83(m, 3H, 16'-H), 0.81—0.77(m, 3H, 14-H)	172.49(C1'), 168.01(C6'), 165.18(C13'), 164.32(C11'), 140.65(C9), 137.86(C8'), 137.86(C9'), 126.31(C7'), 124.99(C10'), 116.64(C10), 77.91(C2), 74.88(C4), 74.76(C2'), 66.01(C11), 64.27(C12), 61.78(C15), 59.78(C5'), 48.49(C5), 46.85(C13), 43.24(C6), 34.83(C14'), 33.91(C3), 31.91(C3'), 29.80(C4'), 28.68(C8), 26.22(C16), 22.33(C7), 17.39(C15'), 12.54(C16'), 10.46(C12'), 6.34(C14)

Table 2 1H NMR and 13C NMR data of compounds 1—9

Compd.	¹H NMR(CDCl₃, 600 MHz), δ	¹³C NMR(CDCl₃, 150MHz), δ
1	8.01(dd,J=15.6, 11.3 Hz, 1H, 8'-H), 6.65(t, J=11.3 Hz, 1H, 9'-H), 6.13(d, J=11.3 Hz, 1H, 10'-H), 6.02(d, J=15.6 Hz, 1H, 7'-H), 5.84—5.74(m, 1H, 4-H), 5.41(d, J=5.1 Hz, 1H, 10-H), 4.77(d, J=12.0 Hz, 1H, 15a-H), 4.54—4.43(m, 1H, 5'a-H), 4.19(d, J=12.0 Hz, 1H, 15b-H), 4.13(d, J=7.2 Hz, 1H, 2'-H), 3.96(t, J=11.4 Hz, 1H, 5'b-H), 3.84(d, J=4.6 Hz, 1H, 2-H), 3.55(d, J=5.1 Hz, 1H, 11-H), 3.15—3.05(m, 1H, 13a-H), 2.83—2.75(m, 1H, 13b-H), 2.48—2.44(m, 1H, 3a-H), 2.39—2.28(m, 1H, 3'-H), 2.22—2.19(m, 1H, 3b-H), 1.96—1.91(m, 2H, 8-H), 1.90—1.89(m, 1H, 7a-H), 1.89—1.86(m, 1H, 4'a-H), 1.78—1.75(m, 1H, 4'b-H), 1.73(s, 3H, 16-H), 1.68—1.67(m, 1H, 7b-H), 0.86(d, J=6.6 Hz, 3H, 12'-H), 0.83(s, 3H, 14-H)	174.80(C1'), 166.23(C6'), 165.55(C11'), 141.23(C9), 139.02(C8'), 138.91(C9'), 127.58(C7'), 125.88(C10'), 118.04(C10), 79.03(C2), 75.65(C4), 74.27(C2'), 67.00(C11), 65.32(C12), 63.58(C15), 61.23(C5'), 49.59(C5), 47.90(C13), 44.31(C6), 35.01(C3), 33.33(C3'), 32.32(C4'), 27.62(C8), 23.37(C16), 20.11(C7), 10.12(C12'), 7.43(C14)
2	7.52(dd,J=15.7, 11.6 Hz, 1H, 8'-H), 6.59(t, J=11.3 Hz, 1H, 9'-H), 5.96(dd, J=15.7, 3.2 Hz, 1H,7'-H), 5.84—5.82(m, 1H, 4-H), 5.81(d, J=11.3 Hz, 1H, 10'-H), 5.43(d, J=5.0 Hz, 1H, 10-H), 4.37(d, J=12.4 Hz, 1H, 15a-H), 4.26(d, J=12.4 Hz, 1H, 15b-H), 3.84(d, J=5.2 Hz, 1H, 2-H), 3.83—3.79(m, 1H, 11-H), 3.69—3.65(m, 1H, 6'-H), 3.65—3.61(m, 2H, 5'-H), 3.35—3.33(m, 1H, 13'-H), 3.30(s, 1H, 2'-H), 3.12(d, J=4.0 Hz, 1H, 13a-H), 2.81(d, J=4.0 Hz, 1H, 13b-H), 2.47—2.44(m, 1H, 3a-H), 2.17(dt, J=15.4, 4.6 Hz, 1H, 3b-H), 2.11—1.95(m, 2H, 8-H), 1.95—1.87(m, 2H, 7-H), 1.82—1.80(m, 1H, 4'a-H), 1.72(s, 3H, 16-H), 1.61(s, 3H, 12'-H), 1.47—1.44(m, 1H, 4'b-H), 1.20(d, J=6.2 Hz, 3H, 14'-H), 0.83(s, 3H, 14-H)	168.11(C1'), 166.36(C11'), 143.07(C9'), 140.64(C9), 138.21(C7'), 126.34(C8'), 118.46(C10), 118.15(C10'), 85.69(C6'), 79.05(C2), 74.46(C4), 70.86(C13'), 67.42(C5'), 67.07(C11), 65.34(C12), 64.56(C15), 63.21(C3'), 58.17(C2'), 49.17(C5), 47.79(C13), 43.22(C6), 39.59(C4'), 35.13(C3), 27.57(C8), 23.25(C16), 20.58(C7), 18.18(C14'), 17.40(C12'), 7.00(C14)
3	8.07(dd,J=15.7, 11.3 Hz, 1H, 8'-H), 6.61(t, J=11.3 Hz, 1H, 9'-H), 6.09(d, J=11.3 Hz, 1H, 10'-H), 6.02—5.99(m, 1H, 7'-H), 6.00—5.98(m, 1H, 4-H), 5.82(s, 1H, 2'-H), 5.46(d, J=5.0 Hz, 1H, 10-H), 4.47—4.44(m, 1H, 5'a-H), 4.42(d, J=12.6 Hz, 1H, 15a-H), 4.17—4.13(m, 1H, 5'b-H), 3.97(d, J=12.6 Hz, 1H, 15b-H), 3.85(d, J=5.1 Hz, 1H, 2-H), 3.75(d, J=5.0 Hz, 1H, 11-H), 3.14(d, J=4.0 Hz, 1H, 13a-H), 2.83(d, J=4.0 Hz, 1H, 13b-H), 2.53—2.52(m, 1H, 3a-H), 2.52—2.50(m, 2H, 4'-H), 2.28(s, 3H, 12'-H), 2.18—2.14(m, 1H, 3b-H), 2.05—1.97(m, 2H, 8-H), 1.99—1.94(m, 1H, 7a-H), 1.84—1.80(m, 1H, 7b-H), 1.71(s, 3H, 16-H), 0.83(s, 3H, 14-H)	166.08(C1'), 165.80(C11'), 165.51(C6'), 156.54(C3'), 140.40(C9), 139.44(C9'), 139.13(C8'), 127.38(C7'), 125.52(C10'), 118.68(C10), 118.16(C2'), 79.06(C2), 75.36(C4), 67.30(C11), 65.47(C12), 63.34(C15), 60.42(C5'), 48.86(C5), 48.05(C13), 43.07(C6), 40.22(C4'), 35.14(C3), 27.68(C8), 23.24(C16), 20.79(C7), 17.20(C12'), 6.97(C14)
4	7.65(dd,J=15.4, 11.7 Hz, 1H, 8'-H), 6.64(t, J=11.4 Hz, 1H, 9'-H), 5.98(dd, J=15.4, 3.0 Hz, 1H, 7'-H), 5.78(d, J=11.4 Hz, 1H, 10'-H),	174.79(C1'), 166.46(C11'), 143.84(C9'), 140.85(C9), 139.14(C7'), 126.04
Compd.	¹H NMR(CDCl₃, 600 MHz), δ	¹³C NMR(CDCl₃, 150MHz), δ
4	5.78—5.76(m, 1H, 4-H), 5.41(d, J=4.6 Hz, 1H, 10-H), 4.40(s, 2H, 15-H), 4.09—4.07(m, 1H, 2'-H), 3.84(d, J=5.1 Hz, 1H, 2-H), 3.65—3.63(m, 1H, 6'-H), 3.61—3.58(m, 1H, 11-H), 3.58—3.57(m, 1H, 13'-H), 3.53—3.51(m, 2H, 5'-H), 3.10(d, J=4.0 Hz, 1H, 13a-H), 2.78(d, J=4.0 Hz, 1H, 13b-H), 2.78—2.75(m, 1H, 3'-H), 2.43(dd, J=15.4, 8.3 Hz, 1H, 3a-H), 2.19(dt, J=15.4, 4.7 Hz, 1H, 3b-H), 2.03—1.96(m, 2H, 8-H), 1.91—1.84(m, 2H, 7-H), 1.79—1.75(m, 2H, 4'-H), 1.72(s, 3H, 16-H), 1.18(d, J=6.2 Hz, 3H, 14'-H), 1.07(d, J=6.9 Hz, 3H, 12'-H), 0.79(s, 3H, 14-H)	(C8'), 118.20(C10), 117.47(C10'), 83.96(C6'), 79.00(C2), 75.53(C2'), 74.26(C4), 70.74(C13'), 69.79(C5'), 67.11(C11), 65.17(C12), 64.49(C15), 49.30(C5), 47.71(C13), 43.71(C6), 37.07(C3'), 34.78(C3), 33.00(C4'), 27.64(C8), 23.23(C16), 20.20(C7), 18.19(C14'), 14.70(C12'), 7.43(C14)
5	7.89(dd,J=15.7, 11.3 Hz, 1H, 8'-H), 6.62(t, J=11.3 Hz, 1H, 9'-H), 6.16(d, J=11.3 Hz, 1H, 10'-H), 6.06(d, J=15.7 Hz, 1H, 7'-H), 5.84(dd, J=8.2, 4.4 Hz, 1H, 4-H), 5.43(d, J=5.2 Hz, 1H, 10-H), 4.49(d, J=12.4 Hz, 1H, 15a-H), 4.39—4.35(m, 2H, 5'-H), 4.33—4.29(m, 1H, 15b-H), 3.86(d, J=5.2 Hz, 1H, 11-H), 3.59(d, J=5.2 Hz, 1H, 2-H), 3.39(s, 1H, 2'-H), 3.14(d, J=4.0 Hz, 1H, 13a-H), 2.82(d, 1H, J=4.0 Hz, 13b-H), 2.54—2.50(m, 1H, 3a-H), 2.32—2.29(m, 1H, 4'a-H), 2.22—2.18(m, 1H, 3b-H), 2.05—2.01(m, 2H, 8-H), 1.95—1.90(m, 1H, 7a-H), 1.82—1.80(m, 1H, 4'b-H), 1.73(s, 3H, 16-H), 1.71—1.67(m, 1H, 7b-H), 1.56(s, 3H, 12'-H), 0.88(s, 3H, 14-H)	167.75(C1'), 166.27(C6'), 165.35(C11'), 141.12(C9), 138.58(C9'), 138.31(C8'), 127.60(C7'), 125.97(C10'), 118.02(C10), 79.00(C2), 75.60(C4), 67.24(C11), 65.25(C12), 63.88(C15), 61.66(C3'), 60.73(C5'), 58.44(C2'), 49.30(C5), 47.98(C13), 43.88(C6), 37.07(C4'), 35.06(C3), 27.60(C8), 23.26(C16), 20.09(C7), 16.01(C12'), 7.73(C14)
6	8.43(dd, 1H,J=15.6, 11.4 Hz, 8'-H), 6.76(t, 1H, J=11.4 Hz, 9'-H), 6.09(d, 1H, J=10.8 Hz, 10'-H), 6.06(d, 1H, J=15.6 Hz, 7'-H), 5.84(d, 1H, J=6.6 Hz, 4-H), 5.55—5.50(m, 1H, 10-H), 4.61—4.58(m, 2H, 13-H), 4.61—4.58(m, 1H, 2'-H), 4.50—4.46(m, 1H, 2-H), 4.50—4.47(m, 1H, 5'a-H), 4.30(d, 1H, J=12.6 Hz, 15a-H), 4.25(d, 1H, J=11.4 Hz, 15b-H), 4.04—4.00(m, 1H, 5'b-H), 3.69(d, 1H, J=4.8 Hz, 11-H), 2.54(d, 1H, J=6.0 Hz, 3a-H), 2.52—2.47(m, 1H, 3'-H), 2.35(d, 1H, J=15.6 Hz, 3b-H), 2.11(s, 3H, 14'-H), 1.98—1.95(m, 2H, 8-H), 1.95—1.91(m, 1H, 7a-H), 1.85—1.82(m, 1H, 4'a-H), 1.73(s, 3H, 16-H), 1.75—1.71(m, 1H, 7b-H), 1.65—1.63(m, 1H, 4'b-H), 1.13(s, 3H, 14-H), 0.88(d, 3H, J=7.2 Hz, 12'-H)	174.70(C1'), 171.00(C13'), 165.36(C6'), 165.01(C11'), 140.56(C8'), 140.56(C9), 139.19(C9'), 127.60(C7'), 124.81(C10'), 117.57(C10), 95.24(C2), 78.73(C4), 76.36(C2'), 73.64(C13), 67.34(C12), 64.50(C15), 63.25(C5'), 62.03(C11), 61.54(C5), 48.26(C6), 41.29(C3), 33.42(C3'), 32.18(C4'), 27.39(C8), 23.29(C16), 22.76(C7), 20.99(C14'), 13.37(C12'), 11.92(C14)
7	8.38(dd, 1H,J=15.6, 11.4 Hz, 8'-H), 6.69(t, 1H, J=11.4 Hz, 9'-H), 6.03(d, 1H, J=10.8 Hz, 7'-H), 5.99(d, 1H, J=16.2 Hz, 10'-H), 5.81(d, 1H, J=6.0 Hz, 4-H), 5.45—5.42(m, 1H, 10-H), 4.54—4.48(m, 2H, 13-H), 4.40—4.37(m, 1H, 2-H), 4.40—4.37(m, 1H, 2'-H), 4.2(d, 1H, J=12.6 Hz, 15a-H), 3.99—3.94(m, 2H, 5'-H), 3.79(d, 1H, J=12.0 Hz, 15b-H), 3.64(d, 1H, J=5.4 Hz, 11-H), 2.49(d, 1H, J=5.4 Hz, 3a-H), 2.44—2.41(m, 1H, 3'-H), 2.27(d, 1H, J=15.6 Hz, 3b-H), 1.90—1.87(m, 2H, 8-H), 1.87—1.84(m, 1H, 7a-H), 1.72—1.70(m, 2H, 4'-H), 1.67(s, 3H, 16-H), 1.65—1.61(m, 1H, 7b-H), 1.02(s, 3H, 14-H), 0.82(d, 3H, J=6.6 Hz, 12'-H)	173.72(C1'), 164.38(C6'), 164.03(C11'), 139.40(C9), 139.32(C8'), 138.23(C9'), 126.36(C7'), 124.02(C10'), 116.69(C10), 95.95(C2), 78.00(C4), 75.06(C2'), 72.57(C13), 64.02(C12), 63.52(C15), 62.37(C5'), 60.99(C11), 59.49(C5), 47.34(C6), 40.16(C3), 32.39(C3'), 31.18(C4'), 28.68(C8), 26.32(C16), 22.27(C7), 12.06(C12'), 11.01(C14)
8	7.95(dd, 1H,J=16.2, 12.0 Hz, 8'-H), 6.61(t, 1H, J=11.4 Hz, 9'-H), 6.10(d, 1H, J=10.8 Hz, 10'-H), 5.98(d, 1H, J=15.6 Hz, 7'-H), 5.74—5.72(m, 1H, 4-H), 5.37—5.32(m, 1H, 10-H), 4.84—4.80(m, 1H, 2'-H), 4.63(d, 1H, J=12.0 Hz, 15a-H), 4.42—4.40(m, 1H, 5'a-H), 4.15(d, 1H, J=12.0 Hz, 15b-H), 4.12(s, 2H, 14'-H), 3.96—3.91(m, 1H, 5'b-H), 3.79(d, 1H, J=4.8 Hz, 2-H), 3.49(d, 1H, J=5.4 Hz, 11-H), 3.06(d, 1H, J=4.2 Hz, 13a-H), 2.75(d, 1H, J=4.2 Hz, 13b-H), 2.48—2.44(m, 1H, 3'-H), 2.43—2.39(m, 1H, 3a-H), 2.18—2.15(m, 1H, 3b-H), 1.96—1.92(m, 1H, 7a-H), 1.88—1.83(m, 2H, 8-H), 1.83—	167.22(C1'), 166.27(C13'), 165.20(C6'), 164.24(C11'), 140.61(C9), 137.86(C8'), 137.86(C9'), 126.28(C7'), 124.96(C10'), 116.64(C10), 77.90(C2), 76.47(C4), 74.71(C2'), 65.94(C11), 64.23(C12), 62.20(C15), 59.62(C5'), 48.47(C5), 46.84(C13), 43.22(C6), 39.46(C14'), 33.87(C3), 31.68(C3'), 29.94(C4'), 28.68(C8),
Compd.	¹H NMR(CDCl₃, 600 MHz), δ	¹³C NMR(CDCl₃, 150MHz), δ
8	1.80(m, 1H, 4'a-H), 1.77—1.73(m, 1H, 4'b-H), 1.67(s, 3H, 16-H), 1.66—1.61(m, 1H,7b-H), 0.98(d, 3H, J=7.2 Hz, 12'-H), 0.80(s, 3H, 14-H)	26.24(C16), 22.32(C7), 10.29(C12'), 6.35(C14)
9	7.93(dd, 1H,J=15.6, 11.4 Hz, 8'-H), 6.60(t, 1H, J=11.4 Hz, 9'-H), 6.10(d, 1H, J=10.8 Hz, 10'-H), 5.97(d, 1H, J=15.6 Hz, 7'-H), 5.74—5.72(m, 1H, 4-H), 5.36—5.31(m, 1H, 10-H), 4.75—4.73(m, 1H, 15a-H), 4.63—4.60(m, 1H, 2'-H), 4.41—4.38(m, 1H, 5'a-H), 4.14—4.11(m, 1H, 15b-H), 3.96—3.92(m, 1H, 5'b-H), 3.79(d, 1H, J=4.8 Hz, 2-H), 3.49(d, 1H, J=4.8 Hz, 11-H), 3.05(d, 1H, J=3.6 Hz, 13a-H), 2.75(d, 1H, J=3.6 Hz, 13b-H), 2.43—2.39(m, 1H, 3a-H), 2.37—2.31(m, 1H, 3'-H), 2.18—2.14(m, 1H, 3b-H), 1.98—1.93(m, 1H, 14'a-H), 1.90—1.85(m, 1H, 14'b-H), 1.85—1.80(m, 2H, 8-H), 1.80—1.75(m, 1H, 7a-H), 1.80—1.75(m, 1H, 4'a-H), 1.67(s, 3H,16-H), 1.65—1.62(m, 1H, 4'b-H), 1.62—1.60(m, 1H, 7b-H), 0.97(d, 3H, J=6.6 Hz, 12'-H), 0.94—0.91(m, 2H, 15'-H), 0.90—0.83(m, 3H, 16'-H), 0.81—0.77(m, 3H, 14-H)	172.49(C1'), 168.01(C6'), 165.18(C13'), 164.32(C11'), 140.65(C9), 137.86(C8'), 137.86(C9'), 126.31(C7'), 124.99(C10'), 116.64(C10), 77.91(C2), 74.88(C4), 74.76(C2'), 66.01(C11), 64.27(C12), 61.78(C15), 59.78(C5'), 48.49(C5), 46.85(C13), 43.24(C6), 34.83(C14'), 33.91(C3), 31.91(C3'), 29.80(C4'), 28.68(C8), 26.22(C16), 22.33(C7), 17.39(C15'), 12.54(C16'), 10.46(C12'), 6.34(C14)

Table 3 Experimental and calculated 13C NMR(150 MHz) data of compound 6

C Position	Shielding constant	δ_C(exp.)	δ_C(calcd.)	C Position	Shielding constant	δ_C(exp.)	δ_C(calcd.)
2	83.33	95.24	93.42	1'	6.41	174.70	171.02
3	138.00	41.29	38.25	2'	102.17	76.36	74.40
4	92.98	78.73	83.67	3'	143.79	33.42	32.41
5	115.21	61.54	61.25	4'	144.94	32.18	31.25
6	132.39	48.26	43.91	5'	116.80	63.25	59.64
7	157.72	22.76	18.35	6'	9.53	165.36	167.88
8	151.07	27.39	25.06	7'	48.16	127.60	128.90
9	34.03	140.56	143.16	8'	36.44	140.56	140.73
10	56.66	117.57	120.32	9'	38.05	139.19	139.10
11	111.52	62.03	64.97	10'	50.30	124.81	126.74
12	102.55	67.34	74.02	11'	11.94	165.01	165.45
13	96.85	73.64	79.77	12'	163.41	13.37	12.61
14	157.59	11.92	18.48	13'	5.02	171.00	172.43
15	113.35	64.50	63.12	14'	161.80	20.99	14.24
16	159.42	23.29	16.63

Fig.2 Relative errors of 13C NMR between the experimental and calculated NMR spectra for compound 6[δC(exp.)- δC(calcd.)]

Table 4 Half maximal inhibitory concentration(IC50) of compounds 1—9 on different tumor cell lines

Compd.	IC₅₀/(μmol·L^-1)
Compd.	HeLa	MGC-803	MCF-7	A549	HL-60	SMMC-7721	SW480
1	0.0034	0.0015	0.0027	0.0010	0.00010	0.00073	0.0072
2	0.033	0.043	0.035	0.014	0.0012	0.00074	0.063
3	0.045	0.041	0.066	0.030	0.0086	0.00085	0.075
4	0.033	0.025	0.0073	0.00013	0.00016	0.00013	0.026
5	0.057	0.039	0.057	0.042	0.0080	0.00094	0.056
6	1.38	2.17	29.29	29.29	27.42	25.58	27.45
7	3.19	3.93	14.62	4.65	19.35	18.15	21.23
8	6.77	2.84	21.72	5.87	13.67	22.43	32.37
9	3.59	3.77	37.29	9.05	15.21	13.87	20.47
Cisplatin	3.98	11.32	7.53	2.67	2.29	11.87	16.42
Taxinol	<0.008	<0.008	<0.008	<0.008	<0.008	<0.008	<0.008

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