广西师范大学学报（自然科学版） ›› 2022, Vol. 40 ›› Issue (5): 253-270.doi: 10.16088/j.issn.1001-6600.2021123006

• 综述 • 上一篇    下一篇

松香烷型二萜在农药及药学中的研究进展

罗家锱1,2,3,4, 宋习习1,2,3,4, 李梅珊1,2,3,4, 王恒山1,2,3,4*   

  1. 1.广西师范大学 化学与药学学院, 广西 桂林 541004;
    2.省部共建药用资源化学与药物分子工程国家重点实验室(广西师范大学), 广西 桂林 541004;
    3.药用资源化学与药物分子工程教育部重点实验室(广西师范大学),广西 桂林 541004;
    4.广西民族药省部共建协同创新中心 (广西师范大学), 广西 桂林 541004
  • 收稿日期:2021-12-30 修回日期:2022-04-01 出版日期:2022-09-25 发布日期:2022-10-18
  • 通讯作者: 王恒山(1965—), 男, 浙江温州人, 广西师范大学教授, 博导。E-mail: whengshan@163.com
  • 基金资助:
    国家自然科学基金(21977021, 81760626, 22111530012); 广西自然科学基金(AB17292075)

Review on Rosinane Diterpenes in Pesticide and Pharmaceutical Research

LUO Jiazi1,2,3,4, SONG Xixi1,2,3,4, LI Meishan1,2,3,4, WANG Hengshan1,2,3,4*   

  1. 1. School of Chemistry and Pharmaceutical Sciences, Guangxi Normal University, Guilin Guangxi 541004, China;
    2. State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources (Guangxi Normal University), Guilin Guangxi 541004, China;
    3. Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources (Guangxi Normal University), Ministry of Education of China, Guilin Guangxi 541004;
    4. Collaborative Innovation Center for Guangxi Ethnic Medicine (Guangxi Normal University), Guilin Guangxi 541004, China
  • Received:2021-12-30 Revised:2022-04-01 Online:2022-09-25 Published:2022-10-18

PDF (PC)

204

摘要： 松香烷型二萜是具有三环二萜结构的一类化合物,广泛存在于植物、微生物体内,具有广泛的用途,显示出较好的生物利用度。本文从农药科学、药学、药剂学、手性药物检测、活性化合物结构与性质关系5个方面综述松香烷型二萜在农药及药学研究中的应用。

关键词: 松香烷型二萜, 农药, 农药助剂, 药学, 药物制剂, 手性药物检测, 构效关系

Abstract: Rosinane diterpenoids are a class of compounds with a tricyclic diterpene structure, which are widely presented in plants and microorganisms and have a wide range of uses. Due to the in-depth research of natural products and the continuous modification of their structure by organic synthesis, rosinane-type diterpene-type compounds show better bioavailability. This article reviews the application of rosinane-type diterpenes in pesticide and pharmaceutical research from five aspects: pesticide science, pharmacy, chiral drug detection, and research on the relationship between the structure and properties of active compounds.

Key words: rosinane diterpene, pesticides, pesticide co-formulants, pharmacy, pharmaceutic preparation, chiral drug detection, structure-activity relationship

中图分类号: 

  • O629
[1]钱珊,高成,马兴梅,等. 松香酸及其衍生物的生物活性研究进展[J]. 西华大学学报(自然科学版), 2020, 39(6): 108-114.
[2]吴程宇, 李健. 松香衍生物农用生物活性研究进展[J]. 广州化工, 2020, 48(2):20-24.
[3]RAO X P, SONG Z Q, HAN Z J. Synthesis and insect attractant activity of fluorine-containing Pinus diterpenic amides and imines[J]. Natural Product Research, 2009, 23(9): 851-60. DOI: 10.1080/14786410802155954.
[4]陈乃源, 段文贵, 林桂汕, 等. 去氢枞酸基B环并噻唑-酰胺化合物的合成及抑菌活性[J]. 精细化工, 2016, 33(7): 811-819. DOI: 10.13550/j.jxhg.2016.07.016.
[5]孔祥吉,卜元卿,郭欣妍,等. 不同农药助剂的初级生物降解性研究[J]. 日用化学工业, 2016, 46(9): 511-513,518. DOI: 10.13218/j.cnki.csdc.2016.09.005.
[6]LIU L, YAN X Y, GAO Y Q, et al. Synthesis and antifeedant activities of rosin-based esters against armyworm[J]. Combinatorial Chemistry and High Throughput Screen, 2016, 19(3): 193-199. DOI: 10.2174/1386207319666160121114341.
[7]闫鑫焱,翟兆兰,宋湛谦,等. 松香基梳状高分子表面活性剂的制备及在水相悬浮农药中的应用[C]// 中国化学会第十六届胶体与界面化学会议论文摘要集——第一分会:两亲分子有序组合体. 北京:中国化学会, 2017: 108-110.
[8]张振伟,林宁,詹源菲, 等. 松香及其衍生物在药物制剂中的研究进展[J]. 临床医药文献电子杂志, 2020, 7(2): 196-198. DOI: 10.16281/j.cnki.jocml.2020.02.168.
[9]刘莉. 松香基二萜衍生物的合成、生物活性及定量构效关系研究[D]. 北京: 中国林业科学研究院, 2016.
[10]王恒山, 谢建武, 潘英明, 等. 马来海松酸系列衍生物的合成[J]. 精细化工, 2005,22(11): 878-880. DOI: 10.3321/j.issn:1003-5214.2005.11.023.
[11]岑波, 石贤春, 段文贵, 等. 马来松香基双硫脲-酰胺化合物的合成及抑菌活性[J]. 天然产物研究与开发, 2018, 30(9): 1526-1533. DOI: 10.16333/j.1001-6880.2018.9.009.
[12]翟兆兰,闫鑫焱,许吉,等. 马来海松酸长链烷基酰(亚)胺钠的合成及其对小地老虎的拒食活性研究[J]. 林产化学与工业, 2018, 38(5): 23-29. DOI: 10.3969/j.issn.0253-2417.2018.05.004.
[13]MAO S Y, WU C Y, GAO Y Q, et al. Pine rosin as a valuable natural resource in the synthesis of fungicide candidates for controlling Fusarium oxysporum on cucumber[J]. Journal of Agricultural Food Chemistry, 2021, 69: 6475-6484. DOI: 10.1021/acs.jafc.1c01887.
[14]YAN X Y, ZHAI Z L, SONG Z Q, et al. Synthesis of comb-like polymeric surfactants with a tricyclic rigid core and their use as dispersants in pymetrozine water suspension concentrates[J]. RSC Advances, 2017, 7(88): 55741-55747. DOI: 10.1039/c7ra09992d.
[15]高宏, 许嘉琍, 姚姝凤,等. 一种松香基被膜剂的制备及果蔬保鲜性能初探[J]. 化学研究与应用, 2018, 30(11): 1779-1785.
[16]李修刚,丁谦,吴宜佩,等. 固体超强酸固定床催化裂解松香的研究[J]. 化学试剂, 2019, 41(4): 411-414. DOI:10.13822/j.cnki.hxsj.2019006750.
[17]ZHAO M, ZHOU H J, HAO L, et al. Natural rosin modified carboxymethyl cellulose delivery system with lowered toxicity for long-term pest control[J]. Carbohydrate Polymers, 2021, 259: 117749. DOI: 10.1016/J.CARBPOL.2021.117749.
[18]MA S J, JIA R, LIU L W, et al. The adjuvant effects of rosin and coconut oil on nicosulfuron and mesotrione to control weeds[J]. Ecotoxicology Environmental Safety, 2021, 225:112766. DOI: 10.1016/j.ecoenv.2021.112766.
[19]胡菊芳,申越,韩春蕊. 枞酸型松香树脂酸衍生物及其应用研究进展[J]. 现代化工, 2009, 29(S2): 17-21. DOI: 10.16606/j.cnki.issn0253-4320.2009.s2.011.
[20]陈泳, 林中祥. 树脂酸及其衍生物的生物活性[J]. 天然产物研究与开发, 2009, 21(4): 712-718. DOI: 10.16333/j.1001-6880.2009.04.017.
[21]饶小平,宋湛谦,贾卫红,等. 松香树脂酸及其衍生物的生物活性研究进展[J]. 化学通报, 2008(10): 723-730. DOI: 10.14159/j.cnki.0441-3776.2008.10.005.
[22]罗云龙, 沈明贵, 王丹, 等. 脱氢枞酸及其衍生物生物活性的研究进展[J]. 化学通报, 2018, 81(2): 122-128. DOI: 10.14159/j.cnki.0441-3776.2018.02.004.
[23]崔艳杰, 饶小平, 商士斌, 等. 去氢枞酸衍生物生物活性研究新进展[J]. 林产化学与工业, 2012, 32(6): 99-106.
[24]DESBORDES P, GUIGUES F, PEIGNIER R. Pyrazole fungicides 3-substituted by aheterocyclic ring: WO-9429300-Al[P]. 1994-12-22.
[25]陈寒松,赵卫光,李正名, 等. 具有杀菌活性的吡唑联杂环类化合物[J]. 浙江化工, 2000, 31(S1): 27-29.
[26]童碧海,农容丰,王恒山, 等. 两种脱氢松香基喹啉衍生物的合成与表征[J]. 精细化工, 2005,22(5): 398-400.
[27]张业, 潘英明, 王恒山, 等. 脱氢松香酸甲酯喹啉衍生物的合成与表征[J]. 林产化学与工业, 2007,27(2): 25-28.
[28]张中岩,刘诗莹,许金松, 等. 基于苯并呋咱胺类衍生物的碱性荧光探针[J]. 华南师范大学学报(自然科学版), 2021, 53(5): 17-22. DOI: 10.6054/j.jscnun.2021070.
[29]于昊泽,申万洁,周凯悦, 等. 呋咱及二氢卟吩e6缀合物的合成及光动力抗肿瘤活性评价[J]. 精细化工, 2021, 38(9): 1875-1880,1895. DOI: 10.13550/j.jxhg.20210295.
[30]马舵. 呋咱氮氧化物与二苯甲酮类似物拼合分子的合成及抗肿瘤活性研究[D]. 合肥:安徽医科大学, 2021. DOI: 10.26921/d.cnki.ganyu.2021.000681.
[31]RAKHIMOVA E B, KIRSANOV V, MESCHERYAKOVA S, et al. Synthesis and cytotoxic activity of new annulated furazan derivatives[J]. Mendeleev Communications, 2021, 31(3): 362-364. DOI:10.1016/J.MENCOM.2021.04.026.
[32]GHOSH P, TERNAI B, WHITEHOUSE M. Ivestigation of ring and ni-trogen inversion in N-methyl-1,2,3,4-tetra-hydroisoquinoline[J]. Medicinal Research Reviews, 1981, 1(2): 159-165.
[33]张业, 王恒山, 潘英明, 等. 12-溴-13,14-脱氢松香酸甲酯氧化呋咱的合成与表征[J]. 化学试剂, 2005,27(8): 493-494. DOI: 10.13822/j.cnki.hxsj.2005.08.016.
[34]张业,林宁,王恒山, 等. 一些含氮杂环的脱氢松香酸甲酯衍生物的合成[J]. 有机化学, 2008,28(11): 1932-1936.
[35]杨新平,韦京辰,李芳耀, 等. 脱氢松香酸含氮衍生物的合成及其抗肿瘤活性研究[J]. 化学试剂, 2013, 35(1): 21-23,61. DOI: 10.13822/j.cnki.hxsj.2013.01.006.
[36]HUANG X C, WANG M, PAN Y M, et al. Synthesis and antitumor activities of novel α-aminophosphonates dehydroabietic acid derivatives[J]. Bioorganic and Medicinal Chemistry Letters, 2013, 23(19): 5283-5289. DOI: 10.1016/j.bmcl.2013.08.005.
[37]HUANG X C, WANG M, PAN Y M, et al. Synthesis and antitumor activities of novel thiourea α-aminophosphonates from dehydroabietic acid[J]. European Journal of Medicinal Chemistry, 2013, 69: 508-520. DOI: 10.1016/j.ejmech.2013.08.055.
[38]HUANG X C, WANG M, WANG H S, et al. Synthesis and antitumor activities of novel dipeptide derivatives derived from dehydroabietic acid[J]. Bioorganic and Medicinal Chemistry Letters, 2014, 24(6): 1511-1518. DOI: 10.1016/j.bmcl.2014.02.001.
[39]HUANG X C, JIN L, WANG M, Design, synthesis and in vitro evaluation of novel dehydroabietic acid derivatives containing a dipeptide moiety as potential anticancer agents[J]. European Journal of Medicinal Chemistry, 2015, 89: 370-385. DOI: 10.1016/j.ejmech.2014.10.060.
[40]LIU C, LIAO Z X, LIU S J, et al. Two new diterpene derivatives from Euphorbia lunulata Bge and their anti-proliferative activities[J]. Fitoterapia, 2014, 96: 33-38. DOI: 10.1016/j.fitote.2014.03.016.
[41]JIN L, QU H E, HUANG X C, et al. Synthesis and biological evaluation of novel dehydroabietic acid derivatives conjugated with acyl-thiourea peptide moiety as antitumor agents[J]. International Journal of Molecular Sciences, 2015, 16(7): 14571-14593. DOI: 10.3390/ijms160714571.
[42]HUANG R Z, LIANG G B, HUANG X C, et al. Discovery of dehydroabietic acid sulfonamide based derivatives as selective matrix metalloproteinases inactivators that inhibit cell migration and proliferation[J]. European Journal of Medicinal Chemistry, 2017, 138: 979-992. DOI:10.1016/j.ejmech.2017.07.020.
[43]LI F Y, HUANG L, ZHOU X Q, et al. Synthesis and cytotoxicity evaluation of dehydroabielic acid derivatives bearing nitrate moiety[J]. Chinese Journal of Organic Chemistry, 2020, 40(9): 2845-2854. DOI: 10.6023/cjoc202003062.
[44]LI L Y, FEI B L, WANG P P, et al. Discovery of novel dehydroabietic acid derivatives as DNA/BSA binding and anticancer agents[J]. Spectrochim Acta Part A: Molecular Biomolecular Spectroscopy, 2021, 246: 118944. DOI: 10.1016/j.saa.2020.118944.
[45]FEI B L, HUI C N, WEI Z Z, et al. Copper(II) and iron(III) complexes of chiral dehydroabietic acid derived from natural rosin: metal effect on structure and cytotoxicity[J]. Metallomics, 2021, 13(4): mfab014. DOI: 10.1093/mtomcs/mfab014.
[46]CHEN N Y, XIE Y L, LU G D, et al. Synthesis and antitumor evaluation of (aryl)methyl-amine derivatives of dehydroabietic acid-based B ring-fused-thiazole as potential PI3K/AKT/mTOR signaling pathway inhibitors[J]. Molecular Diversity, 2021, 25(2): 967-979. DOI: 10.1007/s11030-020-10081-7.
[47]ZHAO H Y, SU B J, ZHOU W J, et al. Diterpenoids and triterpenoids from Triadica rotundifolia and their effects on microglial nitric oxide production[J]. Bioorganic Chemistry, 2020, 105:104332. DOI: 10.1016/j.bioorg.2020.104332.
[48]雷茜, 冯少波, 王凯, 等. 7-羰基-12-脱氢松香酸甲酯硫醚的合成[J]. 化学试剂, 2008,30(4): 283-284,306. DOI: 10.13822/j.cnki.hxsj.2008.04.011.
[49]王凯, 张业, 梁敏, 等. 7-羰基-12-N-异丙基-13-硝基脱氢松香酸甲酯的合成及其金属离子螯合性[J]. 应用科技, 2010, 37(5): 64-68.
[50]张贵杰,代禄梅,张斌,等. 臭牡丹的化学成分研究[J]. 中国中药杂志, 2017, 42(24): 4788-4793. DOI: 10.19540/j.cnki.cjcmm.2017.0214.
[51]SATTURWAR P M, FULZELE S V, PANYAM J, et al. Evaluation of new rosin derivatives for pharmaceutical coating[J]. International Journal of Pharmaceutics, 2004, 270(1/2): 27-36. DOI: 10.1016/j.ijpharm.2003.10.021.
[52]段文贵,申长茂,方华祥, 等. 马来松香酰化壳聚糖的微波合成、表征及其药控释放行为[J]. 高校化学工程学报, 2008, 22(6): 935-940.
[53]DUAN W G, SHEN C G, FANG H X, et al. Synthesis of dehydroabietic acid-modified chitosan and its drug release behavior[J]. Carbohydrate Research, 2009, 344(1): 9-13. DOI: 10.1016/j.carres.2008.08.007.
[54]SINGH V, JOSHI S, MALVIYA T. Carboxymethyl cellulose-rosin gum hybrid nanoparticles: an efficient drug carrier[J]. International Journal of Biological Macromolecules, 2018, 112: 390-398. DOI: 10.1016/j.ijbiac.2018.01.184.
[55]MORKHADE D M, NANDE V S, BARABDE U V, et al. Design and evaluation of dental films of PEGylated rosin derivatives containing sparfloxacin for periodontitis[J]. Drug Development and Industrial Pharmacy, 2018, 44(6): 914-922. DOI: 10.1080/03639045.2017.1421660.
[56]LIN H X, YANG M S, TIAN C, et al. Design of diversified self-assembly systems based on a natural rosin-based tertiary amine for doxorubicin delivery and excellent emulsification[J]. Colloids and Surfaces B:Biointerfaces, 2018, 165: 191-198. DOI: 10.1016/j.colsurfb.2018.01.049.
[57]QIU S F, GAO F, LIANG Z J. Rosin modified aminated mesoporous silica adsorbed tea tree oil sustained-release system for improve synergistic antibacterial and long-term antibacterial effects[J]. Nanotechnology, 2021, 32(27):275707. DOI: 10.1088/1361-6528/abf26c.
[58]宋路杰,吴友平,邓建平. 手性药物的对映体选择性释放[J]. 化学进展, 2021, 33(9): 1550-1559.
[59]农容丰,吴强, 王恒山, 等. 溴代脱氢松香酸结构和构象的NMR研究[J]. 广西师范大学学报(自然科学版), 2004,22(3): 58-61.
[60]王恒山, 谢建武, 潘英明, 等. 脱氢松香酸合成新型手性荧光衍生试剂的研究[C]// 第三届全国有机化学学术会议论文集(上册). 北京: 中国化学会, 2004: 103.
[61]ZHAO S L, ZHANG R C, WANG H S, et al. Capillary electrophoresis enantioselective separation of vigabatrin enantiomers by precolumn derivatization with dehydroabiety lisothiocyante and UV-visdetection[J].Journal of Chromatography B, 2006, 833(2): 186-190. DOI: 10.1016/j.jchromb.2006.01.018.
[62]WANG H S, ZHANG R C, ZHAO S L, et al. Synthesis and application of dehydroabietylisothiocyante as a new chiral derivatizing agent for the enantiomeric separation of chiral compounds by capillary electrophoretic[J]. Analytica Chimica Acta, 2006, 560(1): 64-68. DOI: 10.1016/j.aca.2005.12.041.
[63]王迎春,刘陆智,吴秀荣,等. 12-苯甲酰基脱氢松香异硫氰酸酯的合成与光谱性质[J]. 化学试剂, 2010, 32(9): 769-773. DOI: 10.13822/j.cnki.hxsj.2010.09.004.
[64]冯少波, 雷茜, 赵书林, 等. 三类脱氢松香基手性衍生试剂的合成及性能对比[J]. 广西师范大学学报(自然科学版), 2008,26(2): 56-59.
[65]JIANG X X, CAO Y M, WANG Y Q, et al. A unique approach to the concise synthesis of highly optically active spirooxazolines and the discovery of a more potent oxindole-type phytoalexin analogue[J]. Journal of the American Chemical Society,2010, 132(43): 15328-15333. DOI: 10.1021/ja106349m.
[66]吴强, 姚贵阳, 朱永涛, 等. 用于芳香胺和醇NMR对映体检测的松香基膦试剂的合成[J]. 有机化学, 2012, 32(5): 900-906.
[67]杨达, 苏春华, 赵志才, 等. 脱氢松香酰二胺表面活性剂的合成及性能研究[J]. 广西师范大学学报(自然科学版), 2012, 30(1): 55-59. DOI: 10.16088/j.issn.1001-6600.2012.01.006.
[68]王恒山, 吴强, 姚贵阳, 等. 马来松香手性膦试剂的合成及其手性识别的31P NMR研究[J]. 广西师范大学学报(自然科学版), 2012, 30(3): 207-213. DOI: 10.16088/j.issn.1001-6600.2012.03.019.
[69]姚贵阳,韦京辰,戴伟龙, 等. 马来海松酸三甲酯区域选择性格氏加成反应研究[J]. 有机化学, 2013, 33(1): 138-142.
[70]韦京辰, 姚贵阳, 叶鳗仪, 等. 双苯基马来海松酸内酯的合成和手性识别特性[J]. 化学试剂, 2013, 35(3): 209-212,222. DOI: 10.13822/j.cnki.hxsj.2013.03.018.
[71]黄国保, 雷茜, 黄胜梅, 等. 6-溴-7-异丙基-1,10-二甲基-1,2,3,4-四氢蒽-1-羧酸的合成[J]. 合成化学, 2013, 21(4): 476-478. DOI: 10.15952/j.cnki.cjsc.2013.04.023.
[72]花世鲜, 王迎春, 李亚军, 等. 脱氢松香基12位芳基取代衍生物的合成与光学性质[J]. 广西师范大学学报(自然科学版), 2013, 31(2): 64-68. DOI: 10.16088/j.issn.1001-6600.2013.02.017.
[73]黄胜梅, 张荣江, 黄国保, 等. 基于脱氢松香酸的酰氯的合成[J]. 天然产物研究与开发, 2013, 25(7): 889-891. DOI: 10.16333/j.1001-6880.2013.07.020.
[74]陈华妮,叶鳗仪,姚贵阳, 等.N-芳基马来海枞酸单甲酯二酰亚胺位阻异构化反应及其动力学特性[J]. 高等学校化学学报, 2014, 35(4): 839-846.
[75]金乐, 朱永涛, 姚贵阳, 等. N-芳基马来海松酸二酰亚胺位阻异构化研究[J]. 广西师范大学学报(自然科学版), 2014, 32(1): 81-86. DOI: 10.16088/j.issn.1001-6600.2014.01.017.
[76]王恒山, 李剑飞, 覃坚妹, 等. 马来海松酸二酰亚胺的合成及其构象[J].吉首大学学报(自然科学版), 2014, 35(1): 63-67.
[1] 蒋庆科, 邹品田, 罗勇为, 陆海南, 覃江克, 邹华红. QuEChERS-LC-MS/MS法测定黄皮果中30种常用农药残留[J]. 广西师范大学学报（自然科学版）, 2016, 34(3): 109-115.
Viewed
Full text


Abstract

Cited
  Shared   
  Discussed   
[1] 张喜龙, 韩萌, 陈志强, 武红鑫, 李慕航. 面向复杂数据流的集成分类综述[J]. 广西师范大学学报（自然科学版）, 2022, 40(4): 1 -21 .
[2] 童凌晨, 李强, 岳鹏鹏. 基于CiteSpace的喀斯特土壤有机碳研究进展[J]. 广西师范大学学报（自然科学版）, 2022, 40(4): 22 -34 .
[3] 帖军, 隆娟娟, 郑禄, 牛悦, 宋衍霖. 基于SK-EfficientNet的番茄叶片病害识别模型[J]. 广西师范大学学报（自然科学版）, 2022, 40(4): 104 -114 .
[4] 翁烨, 邵德盛, 甘淑. 等式约束病态最小二乘的主成分Liu估计解法[J]. 广西师范大学学报（自然科学版）, 2022, 40(4): 115 -125 .
[5] 覃城阜, 莫芬梅. C3-和C4-临界连通图的结构[J]. 广西师范大学学报（自然科学版）, 2022, 40(4): 145 -153 .
[6] 贺青, 刘剑, 韦联福. 微弱电磁信号的物理极限检测:单光子探测器及其研究进展[J]. 广西师范大学学报（自然科学版）, 2022, 40(5): 1 -23 .
[7] 田芮谦, 宋树祥, 刘振宇, 岑明灿, 蒋品群, 蔡超波. 逐次逼近型模数转换器研究进展[J]. 广西师范大学学报（自然科学版）, 2022, 40(5): 24 -35 .
[8] 张师超, 李佳烨. 知识矩阵表示[J]. 广西师范大学学报（自然科学版）, 2022, 40(5): 36 -48 .
[9] 梁钰婷, 罗玉玲, 张顺生. 基于压缩感知的混沌图像加密研究综述[J]. 广西师范大学学报（自然科学版）, 2022, 40(5): 49 -58 .
[10] 郝雅茹, 董力, 许可, 李先贤. 预训练语言模型的可解释性研究进展[J]. 广西师范大学学报（自然科学版）, 2022, 40(5): 59 -71 .
版权所有 © 广西师范大学学报（自然科学版）编辑部
地址：广西桂林市三里店育才路15号　邮编：541004
电话：0773-5857325　E-mail: gxsdzkb@mailbox.gxnu.edu.cn
本系统由北京玛格泰克科技发展有限公司设计开发