Changes in Intestinal Toxicity and Component Analysis of Mongolian Medicine Euphorbia Pekinensis Rupr before and after Processing with Milk
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摘要:
目的 探究蒙药京大戟奶制前后肠道毒性变化与成分组成变化的相关性。 方法 小鼠灌胃给予生品京大戟、牛奶浸泡京大戟(奶制)及水浸泡京大戟(水制)的95%乙醇提取物, 以粪便含水量、小鼠各肠段炎症因子TNF-α和IL-1β水平为指标, 考察京大戟奶制前后的泻下作用及肠道致炎毒性变化; 采用LC-MS/MS分析京大戟奶制前后95%醇提取物的成分组成变化。 结果 与空白组相比, 京大戟生品、水制品可导致小鼠粪便含水量及各肠段TNF-α和IL-1β水平显著升高(P < 0.05);与生品组相比, 奶制品组各指标均显著下降(P < 0.05), 水制品组则无显著差异, 表明水制不能起到减毒作用, 辅料牛奶是降低京大戟毒性的关键辅料。质谱分析结果显示, 京大戟中共鉴定出50个成分, 其中萜类成分38个, 酚酸类成分6个, 其它成分6个, 奶制后各成分含量均有不同程度的下降。对生、制品京大戟质谱数据进行主成分分析(Principal component analysis, PCA)及正交偏最小二乘法-判别分析(Partial least squares discriminant analysis, OPLS-DA)发现, 生、制品成分可明显聚为2类, 通过t检验筛选出生、制品的13个差异性成分, 其中11个是萜类成分, 表明京大戟奶制后萜类成分组成发生显著变化。炮制后牛奶辅料残液中检测出来源于京大戟的17个成分, 其中16个为萜类成分, 表明京大戟萜类成分在炮制浸泡过程中转移至辅料牛奶中。 结论 京大戟奶制后毒性降低、泻下作用缓和, 其减毒机制可能与牛奶浸泡炮制过程中, 萜类成分转移至牛奶中, 饮片中毒性成分含量降低有关。 Abstract:OBJECTIVE To explore the correlation between changes in intestinal toxicity and changes in component composition of the Mongolian medicine Euphorbia pekinensis Rupr (EPR) before and after processing with milk. METHODS Mice were given 95% ethanol extract of raw EPR, milk-processed EPR and water-processed EPR by gavage. The purgative effect and intestinal inflammatory toxicity changes of EPR before and after milk processing were investigated using the fecal water content and the levels of inflammatory factors TNF-α and IL-1β in each intestinal segment of mice as indicators; LC-MS/MS was used to analyze the composition changes of the 95% alcohol extract of EPR before and after milk processing. RESULTS Compared with the blank group, the raw and water processed products of EPR could significantly increase the water content of mouse feces and the levels of TNF-α and IL-1β in each intestinal segment (P < 0.05); compared with the raw product group, all indicators in the milk processing group were significantly reduced (P < 0.05), while there was no significant difference in the water processing group, indicating that water processing cannot attenuate toxicity, and the auxiliary material milk is the key auxiliary material to reduce the toxicity of EPR. Mass spectrometry analysis results showed that a total of 50 components were identified in EPR, including 38 terpenoid components, 6 phenolic acid components, and 6 other components. The content of each component decreased to varying degrees after milk processing. Principal component analysis (PCA) and orthogonal partial least squares discriminant analysis (OPLS-DA) were performed on the mass spectrum data of raw materials and products, and it was found that the components of raw materials and products can be obviously clustered into 2 categories. 13 differential components of raw materials and products were screened through t test, and 11 of which were terpene components, indicating that the composition of terpene components changed significantly after milk processing. 17 components derived from EPR were detected in the residual liquid of milk excipients after processing, of which 16 were terpenoids, indicating that the terpenoid components of EPR were transferred to the excipient milk during the soaking and processing processes. CONCLUSION The toxicity of EPR is reduced and the purgative effect is alleviated after milk processing. The attenuation mechanism may be that during the milk soaking and processing processes, terpenoid components are transferred to the milk, and the content of toxic components in the decoction pieces is reduced, thereby reducing the toxicity. -
图 1 京大戟生品、奶制品、水制品对小鼠粪便含水量的影响
注: 与空白组相比, *P < 0.05;与生品组相比, #P < 0.05。x±s, n=10。
Figure 1. Effects of Euphorbia pekinensis Rupr raw products, milk product, and water product on the water content of mouse feces
图 2 京大戟生品、奶制品、水制品对小鼠不同肠段炎症因子TNF-α水平的影响
注: 与空白组相比, *P < 0.05;与生品组相比, #P < 0.05。x±s, n=10。
Figure 2. Effects of Euphorbia pekinensis Rupr raw products, milk product, and water product on the levels of inflammatory factor TNF-α in different intestinal segments of mice
图 3 京大戟生品、奶制品、水制品对小鼠不同肠段炎症因子IL-1β水平的影响
注: 与空白组相比, *P < 0.05;与生品组相比, #P < 0.05。x±s, n=10。
Figure 3. Effects of Euphorbia pekinensis Rupr raw products, milk product, and water product on the levels of inflammatory factor IL-1β in different intestinal segments of mice
图 4 京大戟生品及奶制品95%醇提物的正(ESI+)、负(ESI-)离子模式下的总离子流图
注: A.京大戟生品正离子; B.京大戟奶制品正离子; C.京大戟生品负离子; D.京大戟奶制品负离子
Figure 4. Total ion chromatograms in positive (ESI+) and negative (ESI-) ion modes of 95% alcohol extract of Euphorbia pekinensis Rupr raw product and milk product
图 5 生品京大戟及奶制京大戟的PCA图
注: A.正离子模式; B.负离子模式
Figure 5. PCA scores plot of Euphorbia pekinensis Rupr before and after processing with milk
图 6 生品京大戟及奶制京大戟的OPLS-DA图
注: A.正离子模式; B.负离子模式
Figure 6. OPLS-DA scores plot of Euphorbia pekinensis Rupr before and after processing with milk
表 1 京大戟中化学成分的鉴定结果及奶制前后峰强度变化率
Table 1. Chemical components in Euphorbia pekinensis Rupr and peak intensity change rate before and after milk processing
No. tR/min 化合物 分子式 加和离子峰 预测值 实测值 误差/×10-6 二级碎片 离子强度 炮制前后峰强度变化率/% 类别 生品 奶制品 1 4.91 Quercetin-3-O-β-D-glucopyranoside C21H20O12 [M+COOH]- 509.092 45 509.092 46 -0.2 463.049 8, 300.998 2, 275.019 3, 257.007 5 8 044 1 611 -79.97 其它 2 6.67 Kaempferol-3-O-(2″-O-galloyl)-β-D-glucopyranoside C28H24O15 [M-H]- 599.106 59 599.106 61 4.0 313.055 6, 221.041 3, 169.013 6, 125.023 1 3 448 613 -82.22 其它 3 9.93 Quercetin-3-O-rutinoside C27H30O16 [M-H]- 609.146 88 609.146 89 1.3 609.171 7, 609.140 0, 387.091 3, 301.006 2 1 136 200 -82.00 其它 4 11.46 老鹳草素(Geraniin) C41H28O27 [M-H]- 953.088 65 953.088 64 -0.5 953.089 8, 303.014 0, 277.035, 153.019 4 91 167 91 105 -0.06 酚酸类 5 12.16 鞣花酸(Ellagic acid) C14H6O8 [M-H]- 300.999 3 300.999 31 1.0 300.997 4, 245.008 6, 229.013 2, 173.023 9 401 964 389 476 -3.10 酚酸类 6 13.48 3, 3′-di-O-Methylellagic acid-4′-O-glucopyranoside C22H20O13 [M-H]- 491.081 97 491.081 97 -2.3 491.081 8, 312.998 6, 285.003 3 206 950 61 676 -70.68 酚酸类 7 23.25 3, 3′-di-O-Methylellagic acid-4′-O-β-D-xylopyranoside C21H18O12 [M-H]- 461.071 11 461.071 11 -3.1 461.068 9, 312.997 3, 285.003 2 115 071 4 761 128 -33.85 酚酸类 8 28.35 Geumonid C30H46O5 [M+H]+ 487.340 61 487.340 64 -2.4 203.143 5, 145.102 2, 119.086 7, 95.087 2 9 352 6 647 -28.92 三萜类 9 28.36 覆盆子酸(Fupenzic acid) C30H44O5 [M+H]+ 485.325 43 485.325 41 -1.5 485.324 4, 203.144 8, 187.15, 145.101 7 8 898 8 171 -8.17 三萜类 10 28.85 (3β, 13α)-3-Hydroxypimara-7, 15-diene-2, 12-dione C20H28O3 [M+H]+ 317.211 07 317.211 05 -0.2 317.211 4, 299.197 2, 157.101, 131.085 4 18 270 14 255 -21.97 海松烷型二萜 11 29.55 Ellagic acid 3, 3'-dimethyl ether C16H10O8 [M-H]- 329.030 06 329.030 03 -0.8 298.980 3, 270.986 1, 242.991 5, 214.996 7 1 018 465 973 627 -4.40 酚酸类 12 29.63 Helioscopinolide A C20H28O3 [M+H]+ 317.210 84 317.210 81 -1 299.200 9, 145.102, 143.086 7, 131.086 129 899 56 144 -56.78 松香烷型二萜 13 29.93 Ingol C20H30O6 [M+H]+ 365.196 365.196 02 -2.6 365.194 2, 327.218 3, 181.088 3, 57.037 9 6 935 1 784 -74.27 千金子烷型二萜 14 30.11 Helioscopinolide C20H26O4 [M-H]- 329.175 77 329.175 8 -0.1 329.172 5, 205.124 6, 191.108 6, 139.076 0 16 834 8 493 -49.55 松香烷型二萜 15 30.58 7-羟基香豆素(7-Hydroxycoumarin) C9H6O3 [M+H]+ 163.038 66 163.038 67 -1.8 163.039 7, 135.045 7, 77.043 5 8, 51.030 4 60 601 57 766 -4.68 其它 16 31.48 Helioscopinolide C C20H26O4 [M-H]- 329.175 56 329.175 57 -0.8 298.976 9, 267.175 4, 229.159 0, 201.126 0 27 762 14 593 -47.43 松香烷型二萜 17 31.6 3, 3', 4'-tri-O-Methylellagic acid C17H12O8 [M-H]- 343.045 19 343.045 2 -2.2 343.046 3, 312.997 9, 285.002 8, 257.005 1 29 393 21 838 -25.70 酚酸类 18 32.61 Euphopane A C20H26O4 [M-H]- 329.175 73 329.175 8 -0.1 329.229 7, 329.175 2, 139.076 7, 123.046 2 25 050 10 238 -59.13 海松烷型二萜 19 32.78 Pekinenin E C20H30O4 [M-H]- 333.206 89 333.206 93 -0.6 333.207 0, 289.216 2, 69.036 5, 57.037 4 36 201 13 879 -61.66 卡司烷型二萜 20 32.79 ent-(5β, 8α, 9β, 10α, 11α, 12α)-11-Hydroxyatis-16-ene-3.14-dione C20H28O3 [M+H]+ 317.210 73 317.210 72 -1.3 299.199 2, 159.115 1, 155.068 0, 105.074 1 37 246 24 506 -34.20 阿替烷型二萜 21 33.84 (3β, 11α, 13α)-3, 11-Dihydroxy-pimara-7, 15-diene-2, 12-dione C20H28O4 [M+H]+ 333.205 98 333.205 97 -0.2 157.101 8, 145.104 5, 143.085 5, 91.056 1 12 331 9 668 -21.60 海松烷型二萜 22 33.86 (2R, 4αR, 4βS, 7S, 10αR)-7-Ethenyl-1, 2, 4, 4α, 4β, 5, 7, 8, 10, 10α-decahydro-2-hydroxy-1, 1, 4α, 7-tetramethyl-3, 6-phenanthrenedione C20H30O4 [M-H]- 333.207 48 333.207 45 1.0 333.205 6, 289.214 5, 271.202 9, 57.037 5 29 216 13 878 -52.50 海松烷型二萜 23 33.98 Euphorang C C20H32O2 [M+H]+ 305.247 74 305.247 75 0.8 305.247 5, 151.111 4, 137.097 7, 81.074 4 15 699 14 087 -10.26 对映-贝壳松烷型二萜 24 34.47 Euphopane B C21H32O2 [M+COOH]- 361.237 13 361.237 14 -0.5 361.235 5, 233.156 6, 151.077 4, 123.044 5 4 266 3 815 -10.57 海松烷型二萜 25 34.47 (12β)-2, 12-Dihydroxyisopimara-1, 7, 15-trien-3-one C20H28O3 [M+H]+ 317.210 54 317.210 52 -1.9 317.210 6, 299.199 2, 163.074 9, 91.057 6 41 825 25 392 -39.29 海松烷型二萜 26 35.24 月腺大戟素C(Yuexiandajisu C) C19H28O3 [M+H]+ 305.210 92 305.210 90 -0.7 305.209 3, 151.113 3, 137.097 1, 121.103 2 25 392 7 724 -69.58 海松烷型二萜 27 35.81 月腺大戟素B(Yuexiandajisu B) C20H30O2 [M+H]+ 303.231 38 303.231 37 -1.6 303.231 4, 123.082 3, 107.088 3, 91.058 1 570 372 445 576 -21.00 卡司烷型二萜 28 35.89 (5β, 9β, 10α，5β, 9β, 10α)-2-Hydroxypimara-1, 7, 15-trien-3-one C20H28O2 [M+H]+ 301.216 10 301.216 09 -0.4 255.210 9, 131.087 0, 105.073 1, 91.058 2 143 589 127 575 -11.15 海松烷型二萜 29 35.9 Pernambucone C15H18O2 [M+H]+ 231.137 91 231.137 89 -0.3 185.134 0, 157.104 5, 128.063, 91.057 0 15 119 12 356 -18.27 倍半萜类 30 35.9 Pekinenin G C20H30O3 [M-H]- 317.212 44 317.212 42 0.6 317.209 4, 273.220 2, 137.096 7, 123.081 4 482 210 371 448 -23.03 卡司烷型二萜 31 36.08 28-Hudrozylup-20(29)-en-3-one C30H48O2 [M+H]+ 411.372 30 411.372 29 -0.9 441.373 0, 235.169 5, 189.163 8, 133.102 3 45 859 34 120 -25.59 三萜类 32 36.34 Pekinenin A C20H30O2 [M+H]+ 303.231 72 303.231 71 -0.5 303.231 0, 151.112 4, 137.09 7, 91.057 6 629 488 294 671 -53.19 卡司烷型二萜 33 36.35 (5β, 9β, 10α)-2-Hydroxypimara-1, 7, 15-trien-3-one C20H30O2 [M+H]+ 303.231 69 303.231 70 -0.5 303.231 0, 151.112 4, 137.097 2, 91.057 6 389 728 270 106 -30.69 海松烷型二萜 34 36.65 17-nor-7α-Hydroxy-15-oxoabieta-8, 11, 13-triene C20H28O2 [M+H]+ 301.215 88 301.215 90 -1 299.007 0, 283.171 7, 241.119 6, 227.106 7 247 271 144 397 -41.60 海松烷型二萜 35 36.65 Pekinenin D C20H30O3 [M-H]- 317.211 96 317.212 00 -0.7 317.210 1, 273.221 1, 135.081 5, 123.081 2 463 451 351 676 -24.11 卡司烷型二萜 36 37.2 邻苯二甲酸二丁酯(Dibutyl phthalate) C16H22O4 [M+H]+ 279.158 92 279.158 90 -0.7 279.090 3, 149.023 8, 121.029 6, 93.038 0 4 932 4 309 -12.63 其它 37 37.98 Orobanone C15H20O [M+H]+ 217.158 59 217.158 56 -0.6 217.156 2, 128.065 1, 105.072 4, 91.058 2 20 828 14 353 -31.09 倍半萜类 38 38.36 豆甾醇(Stigmasterol) C29H48O [M+H]+ 413.377 50 413.377 49 -0.7 413.375 1, 123.082 3, 109.065 4, 97.068 9 13 655 10 121 -25.88 三萜类 39 39.34 沉香螺醇(Agarospirol) C15H26O [M+H]+ 223.205 30 223.205 29 -1.6 223.207 0, 190.999 2, 111.084 2, 55.060 8 14 275 10 558 -25.83 倍半萜类 40 39.53 (12α, 13α)-12-Hydroxypimara-7, 15-dien-3-one C20H30O2 [M+H]+ 303.231 57 303.231 56 -1 257.226 3, 201.164 2, 133.102 7, 81.075 7 129 439 73 310 -43.36 海松烷型二萜 41 39.72 肉豆蔻酸(Myristic acid) C14H28O2 [M-H]- 227.202 47 227.202 49 3.7 222.202 5 1 652 1 724 -43.36 其它 42 39.83 Pekinenin F C20H30O [M+H]+ 287.236 57 287.236 59 -1.2 287.236 4, 151.112 5, 137.097 4, 93.073 7 821 298 658 355 -19.83 卡司烷型二萜 43 39.98 (24R)-9, 19-Cycloart-25-ene-3β, 24-diolh C30H50O2 [M+H]+ 443.387 43 443.387 4 -2.1 443.355 0, 443.331 9, 163.154 7, 95.091 7 187 1 560 -70 三萜类 44 40.12 豆甾-4-烯-3, 6-二醇(Stigmast-4-ene-6β-ol-3-one) C29H48O2 [M+H]+ 429.372 88 429.372 85 0.3 429.386 6, 429.313 6, 165.089 7, 163.111 7 6 134 3 256 -47 三萜类 45 42.06 Ebractenoids P C20H30O [M+H]+ 287.236 68 287.236 70 -0.6 287.236 5, 269.226 5, 119.087 2, 105.072 9 260 457 199 492 -40.66 海松烷型二萜 46 40.67 大戟二烯醇(Euphol) C30H50O [M+H]+ 427.392 88 427.392 90 -1.3 427.390 9, 191.177 7, 135.118 4, 121.102 3 32 706 19 080 -23.41 三萜类 47 42.98 24-亚甲基环阿屯醇(24-Methenecycloartenol) C31H52O [M+H]+ 441.408 77 441.408 78 -0.7 191.180 4, 149.132 3, 135.116 8, 95.088 3 70 346 41 270 -41.33 三萜类 48 46.09 3β, 25-Dihydroxylanosta-8.23-diene C30H50O2 [M+H]+ 443.384 77 443.384 78 -8.1 443.375 3, 149.099 4, 121.102 6, 95.091 9 4 203 3 002 -26.83 三萜类 49 46.1 27-Hydroxy-3-oxolup-12-ene C30H48O2 [M+H]+ 441.371 80 441.371 79 -2.1 441.371 7, 301.253 8, 163.148 6, 161.131 4 89 528 54 120 -39.54 三萜类 50 47.52 表大戟二烯醇(Tirucallol) C30H50O [M+H]+ 427.391 77 427.391 75 -3.9 149.130 8, 123.116 3, 109.100 6, 95.089 3 15 256 12 738 -16.50 三萜类 
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表 2 京大戟奶制前后饮片中主要差异性成分
Table 2. Differential components of Euphorbia pekinensis Rupr before and after processing with milk
化合物 VIP值 类别 炮制前后峰强度变化率/% (12α, 13α)-12-Hydroxypimara-7, 15-dien-3-one 3.525 0 二萜类 -43.36 Pekinenin F 2.749 0 二萜类 -19.83 鞣花酸(Ellagic acid) 2.242 6 酚酸类 -3.10 ent-(5β, 8α, 9β, 10α, 11α, 12α)-11-Hydroxyatis-16-ene-3.14-dione 2.184 0 二萜类 -34.20 17-nor-7α-Hydroxy-15-oxoabieta-8, 11, 13-triene 2.112 2 二萜类 -41.60 Ellagic acid 3, 3'-dimethyl ether 1.824 4 酚酸类 -4.40 Pekinenin A 1.687 6 二萜类 -53.19 月腺大戟素B (Yuexiandajisu B) 1.478 6 二萜类 -21.00 Pekinenin D 1.461 9 二萜类 -24.11 Pekinenin G 1.450 1 二萜类 -23.03 Helioscopinolide A 1.425 1 二萜类 -56.78 (3β, 13α)-3-Hydroxypimara-7, 15-diene-2, 12-dione 1.425 1 二萜类 -21.97 (12β)-2, 12-Dihydroxyisopimara-1, 7, 15-trien-3-one 1.053 3 二萜类 -39.29
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表 3 辅料牛奶残液中成分鉴定结果
Table 3. Identification of chemical components in residual milk
No. tR/min 英文名 分子式 加和离子峰 预测值 实测值 误差/×10-6 二级碎片 离子强度 类别 11 30.34 Ellagic acid 3, 3'-dimethyl ether C16H10O8 [M-H]- 329.028 8 329.028 8 -4.4 298.981 0, 270.986 3, 242.991 4, 214.996 8 1 572 990 b 12 30.43 Helioscopinolide A C20H28O3 [M+H]+ 317.210 1 317.210 0 -1.0 299.200 9, 145.102 0, 143.086 7, 131.086 0 74 639 a 16 30.89 Helioscopinolide C C20H26O4 [M-H]- 329.175 3 329.174 8 -3.1 329.173 8, 298.982 6, 270.986 8, 187.113 7 34 259 a 19 32.78 Pekinenin E C20H30O4 [M-H]- 333.205 4 333.206 0 -2.3 333.206 0, 271.204 0, 69.037 5, 57.039 2 35 931 a 20 33.08 ent-(5β, 8α, 9β, 10α, 11α, 12α)-11-Hydroxyatis-16-ene-3.14-dione C20H28O3 [M+H]+ 317.219 7 317.219 9 -4.0 253.194 6, 143.089 2, 141.072 4, 131.088 6 9 789 a 23 33.98 Euphorang C C20H32O2 [M+H]+ 305.247 8 305.247 5 -4.7 305.247 5, 151.111 4, 137.097 7, 81.074 4 5 338 a 26 36.21 月腺大戟素B (Yuexiandajisu B) C20H30O2 [M+H]+ 303.231 03 303.231 08 -3.7 303.230 6, 123.088 1, 107.089 3, 91.072 1 100 060 a 28 36.95 (5β, 9β, 10α, 5β, 9β, 10α)-2-Hydroxypimara-1, 7, 15-trien-3-one C20H28O2 [M+H]+ 301.215 2 301.215 03 -3.9 255.210 8, 143.085 8, 131.086 7, 91.058 1 137 395 a 30 36.95 Pekinenin G C20H30O3 [M-H]- 317.211 2 317.211 1 -3.5 317.209 5, 273.220 6, 137.096 2, 135.080 7 313 159 a 32 36.21 Pekinenin A C20H30O2 [M+H]+ 303.231 1 303.230 8 -3.7 303.230 6, 123.083 1, 107.089 3, 93.074 2 100 061 a 34 36.65 17-nor-7α-Hydroxy-15-oxoabieta-8, 11, 13-triene C20H28O2 [M+H]+ 301.214 8 301.215 0 -3.9 255.210 8, 143.085 8, 131.086 7, 91.058 1 137 395 a 35 36.65 Pekinenin D C20H30O3 [M-H]- 317.211 2 317.211 1 -3.5 317.219 5, 273.220 6, 137.096 2, 135.080 7 313 159 a 38 38.93 豆甾醇(Stigmasterol) C29H48O [M+H]+ 413.374 4 413.374 3 -0.7 413.399 1, 413.378 1, 109.063 9, 71.089 8 1 214 a 39 39.51 沉香螺醇(Agarospirol) C15H26O [M+H]+ 223.204 8 223.204 7 -4.4 207.031 8, 190.999 7, 115.003 7, 111.085 6 2 111 a 40 39.53 (12α, 13α)-12-Hydroxypimara-7, 15-dien-3-one C20H30O2 [M+H]+ 303.230 8 303.230 9 -3.7 303.230 6, 123.083 1, 107.089 3, 93.074 2 100 060 a 42 40.00 Pekinenin F C20H30O [M+H]+ 287.236 5 287.236 6 -4.1 287.237 0, 151.113 2, 137.098 0, 93.074 2 331 589 a 49 46.15 27-Hydroxy-3-oxolup-12-ene C30H48O2 [M+H]+ 441.370 1 441.370 2 -5.7 441.370 5, 301.253 3, 161.134 6, 121.104 1 16 368 a 注: a.倍半萜类成分; b.二萜类成分; c.三萜类成分; d.酚酸类成分。
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