松香树脂酸及其衍生物的分子自组装研究进展

doi:10.3969/j.issn.0253-2417.2019.05.001

Abstract

Abstract: There are many modification sites, such as carboxyl, double bond and benzene ring electric-rich center in the structure of rosin acids. Rosin based derivatives with abundant hydrophilic groups have been obtained by chemical modification. Rosin acids and their derivatives show special self-assembly ability in solutions because they are composed of carboxylic acid, new hydrophilic groups and the unique hydrophobic skeleton, chiral structure of rigid tricyclic terpenes. As a result, rosin and rosin-based derivatives have many functions including high surface activity, smart responsiveness and targeted drug delivery by self-assembly of molecules. According to the structural characteristics of the compounds, the self-assembly of resin acids and their derivatives in small molecules, supramolecules, macromolecules and organic-inorganic hybrid molecules is reviewed. The self-assembly aggregates are analyzed. The self-assembly behaviors and characteristics of resin acids and their derivatives are summarized. The applications in surface activity, smart responsiveness, drug delivery and modification of inorganic nanomaterials are overviewed. Finally, the developments on functional materials and self-assembled aggregates of resin acids and their derivatives are prospected.

Key words: rosin, rigid, terpene, self-assembly, targeted drug delivery, hybrid material

CLC Number:

TQ35

HAN Chunrui, ZHOU Ruonan, HAN Bing, TIAN Chao, XU Pengfei, SONG Xianliang. The Research Progress in Molecular Self-assembly of Rosin Resin Acids and Their Derivatives[J]. Chemistry and Industry of Forest Products, 2019, 39(5): 1-10.

References

[1] RIVERA J M, MARTIN T, REBEK J.Chiral spaces:Dissymmetric capsules through self-assembly[J]. Science, 1998, 279(5353):1021-1023.
[2] BAG B G, DASH S S.First self-assembly study of betulinic acid, a renewable nano-sized, 6-6-6-6-5 pentacyclic monohydroxy triterpenic acid[J]. Nanoscale, 2011, 3(11):4564-4569.
[3] LIU Y X, ZHENG D, MA Y Y, et al.A self-assembled nanoparticles platform based on pectin-dihydroartemisinin conjugates for co-delivery of anticancer drugs[J]. ACS Biomaterials Science & Engineering, 2018, 4(5):1641-1650.
[4] KABIN J A, TOLSTEDT S L, SAEZ A E, et al.Removal of organic films from rotating disks using aqueous solutions of nonionic surfactants:Effect of surfactant molecular structure and substrate composition[J]. Journal of Colloid Interface Science, 1998, 206(1):102-111.
[5] YU X N.Novel rosin-based surfactant:The effect of the rigid hydrophobic structure on its self-organization behavior[D]. Wuxi:Jiangnan University, 2016. 余小娜.新型松香基表面活性剂:刚性疏水结构对其自组织行为的影响[D].无锡:江南大学, 2016.
[6] YADAV B K, GIDWANI B, VYAS A.Rosin:Recent advances and potential applications in novel drug delivery system[J]. Journal of Bioactive and Compatible Polymers, 2016, 31:111-126.
[7] MANDAOGADE P M, SATTURWAR P M, FULZELE S V, et al.Rosin derivatives:Novel film forming materials for controlled drug delivery[J]. Reactive and Functional Polymers, 2002, 50(3):233-242.
[8] NAGARAJAN R, RUCKENSTEIN E.Theory of surfactant self-assembly:A predictive molecular thermodynamic approach[J]. Langmuir, 1991, 7:2934-2969.
[9] SHIMIZU T, MASUTOSHI M, MINAMIKAWA H.Supramolecular nanotube architectures based on amphiphilic molecules[J]. Chemical Reviews, 2005, 105:1401-1443.
[10] BEAUDOIN S P, CARBONELL R G, GRANT C S.Dynamic and equilibrium phase behavior in the C₁₂E₅-abietic acid-H₂O system[J]. Journal of Colloid and Interface Science, 1996, 182(2):465-472.
[11] BEAUDOIN S P, GRANT C S, CRABONELL R G.Removal of organic films from solid surfaces using aqueous solutions of nonionic surfactants.2:Theory[J]. Industrial & Engineering Chemistry Research, 1995, 34(10):3318-3325.
[12] KABIN J A, SAEZ A E, GRANT C S, et al.Removal of organic films from rotating disks using aqueous solutions of nonionic surfactants:Film morphology and cleaning mechanisms[J]. Industrial & Engineering Chemistry Research, 1996, 35(12):4494-4509.
[13] KABIN J A, SAEZ A E, GRANT C S, et al.Removal rates of major and trace components of an organic film using aqueous nonionic surfactant solutions[J]. Industrial & Engineering Chemistry Research, 1999, 38(3):683-691.
[14] JAGALSKI V, BARKER R, TOPGAARD D, et al.Biophysical study of resin acid effects on phospholipid membrane structure and properties[J]. Biochimica et Biophysica Acta (BBA)-Biomembranes, 2016, 1858(11):2827-2838.
[15] SAKAMOTO K, SUZUKI Y, YAMAMURA H, et al.Molecular mechanisms underlying pimaric acid-induced modulation of voltage-gated K⁺, channels[J]. Journal of Pharmacological Sciences, 2017, 133(4):223-231.
[16] LI X J, GE S J, YANG J, et al.Synthesis and study the properties of StNPs/gum nanoparticles for salvianolic acid B-oral delivery system[J]. Food Chemistry, 2017, 229:111-119.
[17] ZHOU J Y, YANG Y P, LIANG Y Y, et al.Adsorption behavior of trimethylolpropane-dehydroabietic acid ester at the air-water interface[J]. Journal of Surfactants and Detergents, 2016, 19(6):1143-1151.
[18] LI J, LIN H X, CHEN X Y, et al.Self-assembled structures and excellent surface properties of a novel anionic phosphate diester surfactant derived from natural rosin acids[J]. Journal of Colloid Interface Science, 2017, 486:67-74.
[19] 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 & Surfaces B:Biointerfaces, 2018, 8(1):191-198.
[20] TIAN C, LIANG Y L, LIN H X, et al.Surface properties and doxorubicin delivery in mixed systems comprising a natural rosin-based ester tertiary amine and an anionic surfactant[J]. Journal of Dispersion Science and Technology, 2019, 40(6):892-900.
[21] LIN H X, YANG M S, LI J, et al.A novel bola-type rosin-based functional surfactant and its synergistic effect with natural surfactant saponin[J]. Journal of Surfactants and Detergents, 2017, 20(5):1205-1212.
[22] LIN H X, YANG M S, TIAN C, et al.Self-assembly, mixed system and drug-loading research of rosin-based tertiary amine salt[J]. Chemistry and Industry of Forest Products, 2018, 38(2):59-66. 林海霞, 杨明生, 田超, 等.松香基叔胺盐的自组装、复配及载药性能研究[J].林产化学与工业, 2018, 38(2):59-66.
[23] LEI L, XIE D H, SONG B L, et al.Photoresponsive foams generated by a rigid surfactant derived from dehydroabietic acid[J]. Langmuir, 2017, 33(32):7908-7916.
[24] ZHAI Z L, YAN X Y, SONG Z Q, et al.Annular and threadlike wormlike micelles formed by a bio-based surfactant containing an extremely large hydrophobic group[J]. Soft Matter, 2018, 14(4):499-507.
[25] ZHAI Z L, YAN X Y, XU J, et al.Phase behavior and aggregation in a catanionic system dominated by an anionic surfactant containing a large rigid group[J]. Chemistry:A European Journal, 2018, 24(36):9033-9040.
[26] ZHAI Z L, YAN X Y, XU J, et al.Incorporation and recovery of SWNTs through phase behavior and aggregates transition induced by changes in pH in a catanionic surfactants system[J]. Carbon, 2019, 141:618-625.
[27] ZHAI Z L, YAN X Y, XU J, et al.Reversible dispersion and precipitation of single-walled carbon nanotubes using a pH-responsive rigid surfactant[J]. Chemical Communications, 2018, 54(86):12171-12173.
[28] CHEN J, SONG B L, PEI X, et al.Rheological behavior of environmentally friendly viscoelastic solutions formed by a rosin-based anionic surfactant[J]. Journal of Agricultural and Food Chemistry, 2019, 67(7):2004-2029.
[29] FENG L, XIE D, SONG B L, et al.Aggregate evolution in aqueous solutions of a Gemini surfactant derived from dehydroabietic acid[J]. Soft Matter, 2018, 14(7):1210-1218.
[30] YAN X Y, ZHAI Z L, SONG Z Q, et al.Synthesis and properties of polyester-based polymeric surfactants from diterpenic rosin[J]. Industrial Crops and Products, 2017, 108:371-378.
[31] ZHOU J Y, ZHANG X, ZHAO Y Z, et al.Surface properties and structural transformation behaviors of mPEG-Maleic rosin copolymer in water[J]. Polymers, 2017, 9(10):466-478.
[32] ZHANG H B, HUANG X, JIANG J X, et al.Hydrogels with high mechanical strength cross-linked by a rosin-based crosslinking agent[J]. RSC Advances, 2017, 7(67):42541-42548.
[33] WANG J, YAO K J, WANG C Z, et al.Synthesis and drug delivery of novel amphiphilic block copolymers containing hydrophobic dehydroabietic moiety[J]. Journal of Materials Chemistry B, 2013, 1(17):2324-2332.
[34] AN S Y, HONG S H, TANG C B, et al.Rosin-based block copolymer intracellular delivery nanocarriers with reduction-responsive sheddable coronas for cancer therapy[J]. Polymer Chemistry, 2016, 7(29):4751-4760.
[35] YU C L, REN P, WANG X L, et al.Preparation and characterization of magnetic polystyrene/Fe₃O₄ microspheres with rosin moiety[J]. Chemistry and Industry of Forest Products, 2015, 35(5):37-44. 余彩莉, 任鹏, 王孝磊, 等.含松香的聚苯乙烯/Fe₃O₄磁性微球的制备与表征[J].林产化学与工业, 2015, 35(5):37-44.
[36] ATTA A M, ELMAHDY G A, ALLOHEDAN H A, et al.Synthesis of environmentally friendly highly dispersed magnetite nanoparticles based on rosin cationic surfactants as thin film coatings of steel[J]. International Journal of Molecular Sciences, 2014, 15(4):6974-6989.
[37] JINDAL R, SHARMA R, MAITI M, et al.Synthesis and characterization of novel reduced gum rosin-acrylamide copolymer-based nanogel and their investigation for antibacterial activity[J]. Polymer Bulletin, 2016, 74(8):1-20.
[38] HUANG J F, SHI Q S, FENG J, et al.Facile pyrolysis preparation of rosin-derived biochar for supporting silver nanoparticles with antibacterial activity[J]. Composites Science and Technology, 2017, 145:89-95.
[39] YANG M S, TIAN C, HAN C R, et al.Hierarchical self-assembled hollow hydroxyapatite flower microspheres containing terpene functional groups for efficient drug loading and pH-responsive drug release[J]. Ceramics International, 2018, 44(17):20913-20920.
[40] ZHAN S H, JIANG X H, LI J, et al.Controlled synthesis of hydroxyapatite using a novel natural rosin-based surfactant[J]. Nano, 2017, 12(8):1750098-1750104.
[41] YANG M S, XU P F, ZHAO X Y, et al.Systematic studies of hydroxyapatite/terpene hybrid microspheres:Natural rosin-based phosphorus sources and chemical structure of coordination compounds[J/OL]. Materials Research Express, 2019, 6:1-27[2019-05-13].https://doi.org/10.1088/2053-1591/ab208f.
[42] ZHANG Z K, DU J H, ZHANG D D, et al.Rosin-enabled ultraclean and damage-free transfer of graphene for large-area flexible organic light-emitting diodes[J]. Nature Communications, 2017, 8:14560-14568.
[43] HAN C R, ZHU L W, LIU L J, et al.Controlled aythesis of Ni(OH)₂ materials with rosin-based surfactant by microwave solvothermal method[J].Chemistry and Industry of Forest Products, 2009, 29(supplement):149-153. 韩春蕊, 朱莉伟, 刘六军, 等.微波溶剂热法松香基表面活性剂控制合成氢氧化镍材料[J].林产化学与工业, 2009, 29(增刊):149-153.
[44] XU Y X, LI B T, LI J, et al.Controlled hydrothermal synthesis of ball-flower Ni(OH)₂/NiOOH composites assisted by rosin-based betaine zwitterionic surfactant[J]. Journal of Materials Science:Materials in Electronics, 2015, 26(10):8040-8046.
[45] SONG F, WANG P, CHEN S X, et al.Ordered lamellar supermicroporous titania templating by rosin-derived quaternary ammonium salt[J]. Plos One, 2017, 12(6):e0180178-e0180189.
[46] LI W K, XIE D H, SONG B L, et al.Synthesis and characterization of ordered mesoporous silica using rosin-based Gemini surfactants[J]. Journal of Materials Science, 2018, 53:2434-2442.
[47] HAN S Y, SONG Z Q, YU F D, et al.Preparation and photocatalytic activity of nanometer TiO₂ using gemini surfactant as a template[J]. Journal of Functional Materials, 2011, 42(11):2064-2067. 韩世岩, 宋湛谦, 余方丹, 等.双子表面活性剂为模板纳米二氧化钛的制备及光催化活性[J].功能材料, 2011, 42(11):2064-2067.
[48] YANG M S, CHEN X Y, LIN H X, et al.Preparation of wood with better water-resistance properties by a one-step impregnation of maleic rosin[J]. Journal of Adhesion Science and Technology, 2018, 32(21):2381-2393.
[49] YANG M S, CHEN X Y, LIN H X, et al.A simple fabrication of superhydrophobic wood surface by natural rosin based compound via impregnation at room temperature[J]. European Journal of Wood and Wood Products, 2018, 76(5):1417-1425.
[50] YU X Y, BIAN P W, XUE Y X, et al.Combination of microsized mineral particles and rosin as a basis for converting cellulosic fibers into "sticky" superhydrophobic paper[J]. Carbohydrate Polymers, 2017, 174:95-102.
[51] MOUSTAFA H, EL K N, ABOU-KANDIL A I, et al.PLA/PBAT bionanocomposites with antimicrobial natural rosin for green packaging[J]. ACS Applied Materials & Interfaces, 2017, 9(23):20132-20141.

The Research Progress in Molecular Self-assembly of Rosin Resin Acids and Their Derivatives

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