参附注射液化学成分研究
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摘要
参附注射液源于古方“参附汤”，由红参、附子两味药物组成，主治元气大亏，阳气暴脱，手足厥冷，头晕气短。现代临床用于保护心肌缺血再灌注损伤，增强心脏收缩功能，抗心力衰竭和心律失常。
为了提高参附注射液的质量标准，保证其安全用药，探明其药效物质基础，本文对参附注射液的化学成分进行了深入研究，并进行了部分活性研究。
本文首先按照参附注射液的制备工艺，分别制备了处方药材红参的提取物和附子的提取物，并对其化学成分进行了分离与鉴定。结果从红参提取物中分离鉴定了十二种常见人参皂苷和十种稀有人参皂苷，它们分别是：人参皂苷Rg_1（ginsenoside Rg_1）、人参皂苷Re（ginsenoside Re）、人参皂苷Rf（ginsenoside Rf）、人参皂苷Rg（2ginsenosideRg_2）、人参皂苷Rb_1（ginsenoside Rb_1）、人参皂苷Rc（ginsenoside Rc）、人参皂苷Rb_2（ginsenoside Rb_2）、人参皂苷Rb_3（ginsenoside Rb_3）、人参皂苷Rd （ginsenoside Rd）、人参皂苷F_1（ginsenoside F_1）、人参皂苷F_3（ginsenoside F_3）、人参皂苷F_5（ginsenosideF_5）、人参皂苷Rk_1（ginsenoside Rk_1）、人参皂苷Rg_5（ginsenoside Rg_5）、人参皂苷Rk_3（ginsenoside Rk_3）、人参皂苷Rh_4（ginsenoside Rh_4）、人参皂苷Rg_6（ginsenoside Rg_6）、人参皂苷F_4（ginsenoside F_4）、人参皂苷Rg_3（ginsenoside Rg_3）、人参皂苷20(R)-Rg_3（ginsenoside20(R)-Rg_3）、人参皂苷Rh1（ginsenoside Rh_1）和人参皂苷20(R)-Rh_1（ginsenoside20(R)-Rh_1）。从附子提取物中分离鉴定了六种乌头类生物碱，它们分别是：苯甲酰脱氧乌头碱（benzoyldeoxyaconitine）、苯甲酰次乌头碱（benzoylhypaconitine）、苯甲酰乌头碱（benzoylaconitine）、苯甲酰新乌头碱（benzoylmesaconitine）、乌头原碱（aconine）和次乌头碱（hypaconine）。
接着本文采用离子液体均匀提取技术结合高效液相色谱法对参附注射液中来自附子的生物碱类成分进行了分析研究，并测定了其中4种单酯型乌头碱：苯甲酰乌头碱（BA）、苯甲酰次乌头碱（BH）、苯甲酰新乌头碱（BM）和苯甲酰脱氧乌头碱（BD）的含量。通过优化离子液体用量，体系最佳pH值，提取时间以及盐浓度等实验条件，最终建立了采用0.058g的[C6Mim][BF4]和0.26g的NH_4PF_6作为提取剂，样品用量为5mL，提取时间为1min，pH为中性，盐浓度为50g·L~(-1)的分析方法。在此条件下测得4种单酯型乌头碱的检出限分别为45.5(BM)，19.8(BA)，26.3(BH)和12.2(BD)μg·L~(-1)。测定结果表明不同批号的参附注射液中4种单酯型乌头碱的含量分别约在0.2~(-1).2μg·mL~(-1)（BM），0.2-0.3μg·mL~(-1)（BA），0.1-0.7μg·mL~(-1)（BH）和0.04-0.1μg·mL~(-1)（BD）的范围内。
此方法具有富集效果好、快速、简便的优点，适宜于测定参附注射液中微量乌头碱的含量。
本文采用固相萃取技术结合高效液相色谱法，对参附注射液中来自人参的皂苷类成分进行了分析研究，并测定了其中20种人参皂苷的含量，包括10种常见人参皂苷（人参皂苷Rg_1、Re、Rb_1、Rb_2、Rb_3、Rc、Rd、Rf、Rg_2、F_1和10种稀有人参皂苷（人参皂苷Rh_1、20(R)-Rh_1、Rk_3、Rh_4、Rg_6、F_4、Rg_3、20(R)-Rg_3、Rk1和Rg_5）。结果表明参附注射液中常见人参皂苷含量较稀有人参皂苷含量略大，且随着生产批号的不同，它们的含量分别约在85~(-1)19（Rg_1）、58-89（Re）、28-31（Rf）、13~(-1)5（Rg_2）、198-227（Rb_1）、97~(-1)14（Rc）、50-64（Rb_2）、8~(-1)4（Rb_3）、3-6（F1）、36-49（Rd）、27-42（Rh_1）、14-25（20(R)-Rh1）、3-6（Rg_6）、4-8（F4）、8~(-1)1（Rk-3）、6~(-1)1（Rh_4）、21-36（Rg_3）、16-30（20(R)-Rg_3）、8~(-1)5（Rk_1）、12-20（Rg_5）μg·mL~(-1)范围内。
本文还考察了三种含有红参的常用中药注射剂参附注射液、参麦注射液和生脉注射液中20种人参皂苷的含量差别。结果表明这三种注射液中无论是常见人参皂苷还是稀有人参皂苷，其总含量相差不大，但具体人参皂苷含量有差别。
临床应用证明参附注射液对心肌缺血再灌注损伤具有确切的保护作用。为了探讨这种作用的物质基础与作用机制，本文以AAPH引发的人血红细胞溶血为实验模型，研究了参附注射液、参附注射液中的总皂苷、总生物碱、总皂苷与总生物碱的混合物、10种常见人参皂苷混合物、10种稀有人参皂苷混合物的抗溶血作用。结果表明，参附注射液具有最明显的抗溶血作用，证明其对心肌缺血再灌注损伤具有的保护作用可能与其清除自由基作用有关，且这种作用除了与其中含有的人参皂苷与生物碱有关外还与其他物质有关。另外参附注射液的抗溶血活性在浓度为10%时最为明显，当浓度增大或减小时，其抗溶血活性减弱甚至表现出促溶血活性，说明参附注射液的疗效可能与其临床用量有关。
本文还研究了参附注射液中含有的20种人参皂苷单体的抗AAPH诱导人血红细溶血作用。结果表明，人参皂苷单体的抗溶血活性大小与其结构有密切联系。10种常见人参皂苷和3种稀有人参皂苷自身没有溶血作用且对AAPH诱导的人血红细胞溶血具有保护作用，其作用大小为Rf>20(R)-Rh_1>Rg_1>Rb_1>Rd>Rc>Re>Rh_1>Rg_2~Rb_3~F-1~20(R)-Rg_3>Rb_2；另外7种稀有人参皂苷自身就具有溶血作用，其溶血作用大小为Rg_3~Rk_1~Rg_5>Rg_6~F_4>Rk_3>Rh_4。
Shenfu injection derived from “shenfu tang” which is ancient formula of China. It iscomposed of extracts of Ginseng Radix Et Rhizoma Rubra, and Aconiti Lateralis RadixPraeparata. The injection has the function of protecting against myocardial ischemia-reperfusion injury and improving the systolic function, anti-heart failure andantiarrhythmic.
In order to improve the quality standards, ensure the safety and prove thepharmacodynamic material basis of Shenfu injection, we studied the chemical compositionand the the activity of Shenfu injection in depth.
Firstly, the extracts of Ginseng Radix Et Rhizoma Rubra and Aconiti Lateralis RadixPraeparata were preparated according to the preparation process of the Shenfu injection,and then, the chemical constituents of the two extracts were isolated. Twenty compoundsincluding12kinds major ginsenosides and10kinds rare ginsenosides were separated fromthe extracts of Ginseng Radix Et Rhizoma Rubra and identified as ginsenoside Rg_1,ginsenoside Re, ginsenoside Rf, ginsenoside Rg_2, ginsenoside Rb_1, ginsenoside Rc,ginsenoside Rb_2, ginsenoside Rb_3, ginsenoside Rd, ginsenoside F_1, ginsenoside F_3andginsenoside F_5, ginsenoside Rk_1, ginsenoside Rg_5, ginsenoside Rk_3, ginsenoside Rh4,ginsenoside Rg_6, ginsenoside F_4, ginsenoside Rg_3, ginsenoside20(R)-Rg_3, ginsenoside Rh_1and ginsenoside20(R)-Rh_1. Six compounds were separated and identified from the extractsof Aconiti Lateralis Radix Praeparata, they are benzoylhypaconitine, benzoyldeoxy-aconitine, benzoylmesaconitine, aconine and hypaconine.
In this paper,4kinds of alkaloids and20kinds of ginsenosides in Shenfu injectionwere determined by different approaches. A method for the determination ofbenzoylaconine (BA), benzoylmesaconine (BM), benzoylhypaconine (BH) and benzo-yldeoxyaconine (BD) in Shenfu injection based on homogeneous ionic liquidmicroextraction coupled with high performance liquid chromatographic (HPLC) separationwere developed. The experimental parameters including volume of ionic liquid, pH,extraction time and salt concentration were optimizated when0.058g [C_6Mim][BF_4] and 0.26g NH4PF6were used as extraction solvent，the target compounds can be extracted from5mL of injection, the extraction time is1min, and the concentration of NaCl is50g·L~(-1).The detection limits for BM, BA, BH and BD were45.5,19.8,26.3and12.2μg·L~(-1)respectively. The test of samples purchased from Yaan San-Jiu Pharmaceutical showed thatthe content ranges are0.2~(-1).2(BM),0.2-0.3(BA),0.1-0.7(BH) and0.04-0.1(BD) μg·mL~(-1),respectively, and the values are quite different between samples with different batchnumber. This method was proved to be fast, easy and have good enrichment effect which issuitable for the preconcentration and determination of trace components in traditionalChinese medicine injection.
Twenty kinds of ginsenosides including10kinds major ginsenosides Rg_1, Re, Rb_1,Rb_2, Rb_3, Rc, Rd, Rf, Rg_2, F_1and10kinds rare ginsenosides Rh_1,20(R)-Rh_1, Rk_3, Rh4,Rg6, F_4, Rg_3,20(R)-Rg_3, Rk_1and Rg_5were detected in Shenfu injection by SPE and HPLC.The results showed that the contents of the major ginsenosides are larger than the rare ones.It also found that the amounts of the ginsenosides are different in the samples, the contentschanged in the ranges as follow:85~(-1)19(Rg_1),58-89(Re),28-31(Rf),13~(-1)5(Rg_2),198-227(Rb_1),97~(-1)14(Rc),50-64(Rb_2),8~(-1)4(Rb_3),3-6(F1),36-49(Rd),27-42(Rh_1),14-25(20(R)-Rh_1),3-6(Rg6),4-8(F_4),8~(-1)1(Rk_3),6~(-1)1(Rh4),21-36(Rg_3),16-30(20(R)-Rg_3),8~(-1)5(Rk_1), and12-20(Rg_5) μg·mL~(-1).
In this article, we also investigated the contents of20ginsenosides in the other twocommonly used injections which are also composed of Ginseng Radix Et Rhizoma Rubra,Shenmai injection and Shengmai injection. The results showed that the contents of20ginsenosides are with the same trend in those three kinds of injections but for specificcontent difference.
Shenfu injection was proved to be effective to protect against myocardial ischemia-reperfusion injury clinically. In order to explore the material basis and the mechanism ofthis effect, we studied the protective effects of Shenfu injection, the mixture ofginsenosides and alkaloids, the mixture of ginsenosides, and the mixture of alkaloids onhuman erythrocytes against AAPH-induced hemolysis. The results showed that Shenfuinjection has the most obvious anti-hemolysis effect, which proved that the protective effectof Shenfu injection related with not only the ginsenosides and alkaloids but also other ingredient in it, and the protective effect of Shenfu injection against myocardial ischemia-reperfusion injury may be related to the free radical scavenging effect. The results alsoshowed that the activity of Shenfu injection is closed linked with its concentration, theanti-hemolytic activities is strongest when the concentration is10%(v/v), and weakenedgradually with the increase or decrease of concentration. Shenfu injection showedpro-hemolytic activities until the concentration is higher than50%.
Finally, the effects of monomers of20ginsenosides on human erythrocytes duringAAPH-induced hemolysis were studied. The results showed that the activities ofginsenosides are in relation with their structures.10major ginsenosides and3rareginsenosides can performance anti-hemolytic activity with the order as Rf>20(R)-Rh_1>Rg_1>Rb_1>Rd>Rc>Re>Rh1>Rg_2~Rb_3~F1~20(R)-Rg_3>Rb_2, and other7rare ginsenosides gavehemolytic activity in the order of Rg_3~Rk1~Rg_5>Rg6~F4>Rk3>Rh4.
为了提高参附注射液的质量标准，保证其安全用药，探明其药效物质基础，本文对参附注射液的化学成分进行了深入研究，并进行了部分活性研究。
本文首先按照参附注射液的制备工艺，分别制备了处方药材红参的提取物和附子的提取物，并对其化学成分进行了分离与鉴定。结果从红参提取物中分离鉴定了十二种常见人参皂苷和十种稀有人参皂苷，它们分别是：人参皂苷Rg_1（ginsenoside Rg_1）、人参皂苷Re（ginsenoside Re）、人参皂苷Rf（ginsenoside Rf）、人参皂苷Rg（2ginsenosideRg_2）、人参皂苷Rb_1（ginsenoside Rb_1）、人参皂苷Rc（ginsenoside Rc）、人参皂苷Rb_2（ginsenoside Rb_2）、人参皂苷Rb_3（ginsenoside Rb_3）、人参皂苷Rd （ginsenoside Rd）、人参皂苷F_1（ginsenoside F_1）、人参皂苷F_3（ginsenoside F_3）、人参皂苷F_5（ginsenosideF_5）、人参皂苷Rk_1（ginsenoside Rk_1）、人参皂苷Rg_5（ginsenoside Rg_5）、人参皂苷Rk_3（ginsenoside Rk_3）、人参皂苷Rh_4（ginsenoside Rh_4）、人参皂苷Rg_6（ginsenoside Rg_6）、人参皂苷F_4（ginsenoside F_4）、人参皂苷Rg_3（ginsenoside Rg_3）、人参皂苷20(R)-Rg_3（ginsenoside20(R)-Rg_3）、人参皂苷Rh1（ginsenoside Rh_1）和人参皂苷20(R)-Rh_1（ginsenoside20(R)-Rh_1）。从附子提取物中分离鉴定了六种乌头类生物碱，它们分别是：苯甲酰脱氧乌头碱（benzoyldeoxyaconitine）、苯甲酰次乌头碱（benzoylhypaconitine）、苯甲酰乌头碱（benzoylaconitine）、苯甲酰新乌头碱（benzoylmesaconitine）、乌头原碱（aconine）和次乌头碱（hypaconine）。
接着本文采用离子液体均匀提取技术结合高效液相色谱法对参附注射液中来自附子的生物碱类成分进行了分析研究，并测定了其中4种单酯型乌头碱：苯甲酰乌头碱（BA）、苯甲酰次乌头碱（BH）、苯甲酰新乌头碱（BM）和苯甲酰脱氧乌头碱（BD）的含量。通过优化离子液体用量，体系最佳pH值，提取时间以及盐浓度等实验条件，最终建立了采用0.058g的[C6Mim][BF4]和0.26g的NH_4PF_6作为提取剂，样品用量为5mL，提取时间为1min，pH为中性，盐浓度为50g·L~(-1)的分析方法。在此条件下测得4种单酯型乌头碱的检出限分别为45.5(BM)，19.8(BA)，26.3(BH)和12.2(BD)μg·L~(-1)。测定结果表明不同批号的参附注射液中4种单酯型乌头碱的含量分别约在0.2~(-1).2μg·mL~(-1)（BM），0.2-0.3μg·mL~(-1)（BA），0.1-0.7μg·mL~(-1)（BH）和0.04-0.1μg·mL~(-1)（BD）的范围内。
此方法具有富集效果好、快速、简便的优点，适宜于测定参附注射液中微量乌头碱的含量。
本文采用固相萃取技术结合高效液相色谱法，对参附注射液中来自人参的皂苷类成分进行了分析研究，并测定了其中20种人参皂苷的含量，包括10种常见人参皂苷（人参皂苷Rg_1、Re、Rb_1、Rb_2、Rb_3、Rc、Rd、Rf、Rg_2、F_1和10种稀有人参皂苷（人参皂苷Rh_1、20(R)-Rh_1、Rk_3、Rh_4、Rg_6、F_4、Rg_3、20(R)-Rg_3、Rk1和Rg_5）。结果表明参附注射液中常见人参皂苷含量较稀有人参皂苷含量略大，且随着生产批号的不同，它们的含量分别约在85~(-1)19（Rg_1）、58-89（Re）、28-31（Rf）、13~(-1)5（Rg_2）、198-227（Rb_1）、97~(-1)14（Rc）、50-64（Rb_2）、8~(-1)4（Rb_3）、3-6（F1）、36-49（Rd）、27-42（Rh_1）、14-25（20(R)-Rh1）、3-6（Rg_6）、4-8（F4）、8~(-1)1（Rk-3）、6~(-1)1（Rh_4）、21-36（Rg_3）、16-30（20(R)-Rg_3）、8~(-1)5（Rk_1）、12-20（Rg_5）μg·mL~(-1)范围内。
本文还考察了三种含有红参的常用中药注射剂参附注射液、参麦注射液和生脉注射液中20种人参皂苷的含量差别。结果表明这三种注射液中无论是常见人参皂苷还是稀有人参皂苷，其总含量相差不大，但具体人参皂苷含量有差别。
临床应用证明参附注射液对心肌缺血再灌注损伤具有确切的保护作用。为了探讨这种作用的物质基础与作用机制，本文以AAPH引发的人血红细胞溶血为实验模型，研究了参附注射液、参附注射液中的总皂苷、总生物碱、总皂苷与总生物碱的混合物、10种常见人参皂苷混合物、10种稀有人参皂苷混合物的抗溶血作用。结果表明，参附注射液具有最明显的抗溶血作用，证明其对心肌缺血再灌注损伤具有的保护作用可能与其清除自由基作用有关，且这种作用除了与其中含有的人参皂苷与生物碱有关外还与其他物质有关。另外参附注射液的抗溶血活性在浓度为10%时最为明显，当浓度增大或减小时，其抗溶血活性减弱甚至表现出促溶血活性，说明参附注射液的疗效可能与其临床用量有关。
本文还研究了参附注射液中含有的20种人参皂苷单体的抗AAPH诱导人血红细溶血作用。结果表明，人参皂苷单体的抗溶血活性大小与其结构有密切联系。10种常见人参皂苷和3种稀有人参皂苷自身没有溶血作用且对AAPH诱导的人血红细胞溶血具有保护作用，其作用大小为Rf>20(R)-Rh_1>Rg_1>Rb_1>Rd>Rc>Re>Rh_1>Rg_2~Rb_3~F-1~20(R)-Rg_3>Rb_2；另外7种稀有人参皂苷自身就具有溶血作用，其溶血作用大小为Rg_3~Rk_1~Rg_5>Rg_6~F_4>Rk_3>Rh_4。
Shenfu injection derived from “shenfu tang” which is ancient formula of China. It iscomposed of extracts of Ginseng Radix Et Rhizoma Rubra, and Aconiti Lateralis RadixPraeparata. The injection has the function of protecting against myocardial ischemia-reperfusion injury and improving the systolic function, anti-heart failure andantiarrhythmic.
In order to improve the quality standards, ensure the safety and prove thepharmacodynamic material basis of Shenfu injection, we studied the chemical compositionand the the activity of Shenfu injection in depth.
Firstly, the extracts of Ginseng Radix Et Rhizoma Rubra and Aconiti Lateralis RadixPraeparata were preparated according to the preparation process of the Shenfu injection,and then, the chemical constituents of the two extracts were isolated. Twenty compoundsincluding12kinds major ginsenosides and10kinds rare ginsenosides were separated fromthe extracts of Ginseng Radix Et Rhizoma Rubra and identified as ginsenoside Rg_1,ginsenoside Re, ginsenoside Rf, ginsenoside Rg_2, ginsenoside Rb_1, ginsenoside Rc,ginsenoside Rb_2, ginsenoside Rb_3, ginsenoside Rd, ginsenoside F_1, ginsenoside F_3andginsenoside F_5, ginsenoside Rk_1, ginsenoside Rg_5, ginsenoside Rk_3, ginsenoside Rh4,ginsenoside Rg_6, ginsenoside F_4, ginsenoside Rg_3, ginsenoside20(R)-Rg_3, ginsenoside Rh_1and ginsenoside20(R)-Rh_1. Six compounds were separated and identified from the extractsof Aconiti Lateralis Radix Praeparata, they are benzoylhypaconitine, benzoyldeoxy-aconitine, benzoylmesaconitine, aconine and hypaconine.
In this paper,4kinds of alkaloids and20kinds of ginsenosides in Shenfu injectionwere determined by different approaches. A method for the determination ofbenzoylaconine (BA), benzoylmesaconine (BM), benzoylhypaconine (BH) and benzo-yldeoxyaconine (BD) in Shenfu injection based on homogeneous ionic liquidmicroextraction coupled with high performance liquid chromatographic (HPLC) separationwere developed. The experimental parameters including volume of ionic liquid, pH,extraction time and salt concentration were optimizated when0.058g [C_6Mim][BF_4] and 0.26g NH4PF6were used as extraction solvent，the target compounds can be extracted from5mL of injection, the extraction time is1min, and the concentration of NaCl is50g·L~(-1).The detection limits for BM, BA, BH and BD were45.5,19.8,26.3and12.2μg·L~(-1)respectively. The test of samples purchased from Yaan San-Jiu Pharmaceutical showed thatthe content ranges are0.2~(-1).2(BM),0.2-0.3(BA),0.1-0.7(BH) and0.04-0.1(BD) μg·mL~(-1),respectively, and the values are quite different between samples with different batchnumber. This method was proved to be fast, easy and have good enrichment effect which issuitable for the preconcentration and determination of trace components in traditionalChinese medicine injection.
Twenty kinds of ginsenosides including10kinds major ginsenosides Rg_1, Re, Rb_1,Rb_2, Rb_3, Rc, Rd, Rf, Rg_2, F_1and10kinds rare ginsenosides Rh_1,20(R)-Rh_1, Rk_3, Rh4,Rg6, F_4, Rg_3,20(R)-Rg_3, Rk_1and Rg_5were detected in Shenfu injection by SPE and HPLC.The results showed that the contents of the major ginsenosides are larger than the rare ones.It also found that the amounts of the ginsenosides are different in the samples, the contentschanged in the ranges as follow:85~(-1)19(Rg_1),58-89(Re),28-31(Rf),13~(-1)5(Rg_2),198-227(Rb_1),97~(-1)14(Rc),50-64(Rb_2),8~(-1)4(Rb_3),3-6(F1),36-49(Rd),27-42(Rh_1),14-25(20(R)-Rh_1),3-6(Rg6),4-8(F_4),8~(-1)1(Rk_3),6~(-1)1(Rh4),21-36(Rg_3),16-30(20(R)-Rg_3),8~(-1)5(Rk_1), and12-20(Rg_5) μg·mL~(-1).
In this article, we also investigated the contents of20ginsenosides in the other twocommonly used injections which are also composed of Ginseng Radix Et Rhizoma Rubra,Shenmai injection and Shengmai injection. The results showed that the contents of20ginsenosides are with the same trend in those three kinds of injections but for specificcontent difference.
Shenfu injection was proved to be effective to protect against myocardial ischemia-reperfusion injury clinically. In order to explore the material basis and the mechanism ofthis effect, we studied the protective effects of Shenfu injection, the mixture ofginsenosides and alkaloids, the mixture of ginsenosides, and the mixture of alkaloids onhuman erythrocytes against AAPH-induced hemolysis. The results showed that Shenfuinjection has the most obvious anti-hemolysis effect, which proved that the protective effectof Shenfu injection related with not only the ginsenosides and alkaloids but also other ingredient in it, and the protective effect of Shenfu injection against myocardial ischemia-reperfusion injury may be related to the free radical scavenging effect. The results alsoshowed that the activity of Shenfu injection is closed linked with its concentration, theanti-hemolytic activities is strongest when the concentration is10%(v/v), and weakenedgradually with the increase or decrease of concentration. Shenfu injection showedpro-hemolytic activities until the concentration is higher than50%.
Finally, the effects of monomers of20ginsenosides on human erythrocytes duringAAPH-induced hemolysis were studied. The results showed that the activities ofginsenosides are in relation with their structures.10major ginsenosides and3rareginsenosides can performance anti-hemolytic activity with the order as Rf>20(R)-Rh_1>Rg_1>Rb_1>Rd>Rc>Re>Rh1>Rg_2~Rb_3~F1~20(R)-Rg_3>Rb_2, and other7rare ginsenosides gavehemolytic activity in the order of Rg_3~Rk1~Rg_5>Rg6~F4>Rk3>Rh4.
引文
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