林产化学与工业 ›› 2022, Vol. 42 ›› Issue (5): 137-146.doi: 10.3969/j.issn.0253-2417.2022.05.018
• 综述评论 • 上一篇
袁花1,2, 沈红1,2, 颜洋洋1,2, 张昌伟1, 王成章1,*()
收稿日期:
2021-05-06
出版日期:
2022-10-28
发布日期:
2022-11-02
通讯作者:
王成章
E-mail:wangczlhs@sina.com
作者简介:
王成章,研究员,博士生导师,研究领域为天然产物研究与利用;E-mail: wangczlhs@sina.com基金资助:
Hua YUAN1,2, Hong SHEN1,2, Yangyang YAN1,2, Changwei ZHANG1, Chengzhang WANG1,*()
Received:
2021-05-06
Online:
2022-10-28
Published:
2022-11-02
Contact:
Chengzhang WANG
E-mail:wangczlhs@sina.com
摘要:
植物聚戊烯醇是一类天然的类酯化合物,具有抗癌、保肝以及抗病毒等良好的生物活性。但由于聚戊烯醇疏水性较强,导致其在人体内的生物利用度低。针对植物聚戊烯醇含有多个非共轭双键和末端羟基结构特征,总结了聚戊烯醇加氢、氧化、酯化、胺化、烷基化以及格式反应等化学修饰的研究进展,介绍了具有代表性的系列聚戊烯醇衍生物及其生物活性,并重点综述了基于植物聚戊烯醇及其衍生物设计的纳米乳液、脂质体和注射剂等药用剂型最新进展,为进一步研究聚戊烯醇及其衍生物的药品开发提供参考。
中图分类号:
袁花, 沈红, 颜洋洋, 张昌伟, 王成章. 植物聚戊烯醇的化学修饰及药用剂型的研究进展[J]. 林产化学与工业, 2022, 42(5): 137-146.
Hua YUAN, Hong SHEN, Yangyang YAN, Changwei ZHANG, Chengzhang WANG. Review on Structure Modification and Pharmaceutical Formulations of Plant Ployprenol[J]. Chemistry and Industry of Forest Products, 2022, 42(5): 137-146.
1 |
HOFMANN N R . The who, what, and where of plant polyprenol biosynthesis point to thylakoid membranes and photosynthetic performance[J]. Plant Cell, 2017, 29 (7): 1552- 1553.
doi: 10.1105/tpc.17.00559 |
2 |
SAGAMI H , SWIEZEWSKA E , SHIDOJI Y . The history and recent advances in research of polyprenol and its derivatives[J]. Bioscience, Biotechnology, and Biochemistry, 2018, 82 (6): 947- 955.
doi: 10.1080/09168451.2017.1411775 |
3 |
ZHANG C W , LI M F , QI Z W , et al. The construction of a green and efficient system for the separation of polyprenols from ginkgo biloba leaves[J]. Process Biochemistry, 2021, 100, 252- 259.
doi: 10.1016/j.procbio.2020.10.013 |
4 | KUZNECOVS I S , KUZNECOVA G , JOKSTA I . The role of polyprenol in overcoming steroid insensitivity in asthma[J]. World Allergy Organization Journal, 2020, 13 (8): 25- 27. |
5 | VAN GELDER K, VIRTA L K A, EASLICK J, et al. A central role for polyprenol reductase in plant dolichol biosynthesis[J/OL]. Plant Science, 2021, 303: 110773[2021-01-20]. https://doi.org/10.1016/j.plantsci.2020.110773. |
6 |
CAVALLINI G , SGARBOSSA A , PARENTINI I , et al. Dolichol: A component of the cellular antioxidant machinery[J]. Lipids, 2016, 51 (4): 477- 486.
doi: 10.1007/s11745-016-4137-x |
7 |
MUCENIECE R , NAMNIECE J , NAKERTE I , et al. Pharmacological research on natural substances in Latvia: Focus on lunasin, betulin, polyprenol and phlorizin[J]. Pharmacol Research, 2016, 113, 760- 770.
doi: 10.1016/j.phrs.2016.03.040 |
8 | KUZNECOVA G , JOKSTA I , KUZNECOVS I S , et al. Dolichyl phosphate deficiency and polyprenol supplementation in the treatment of atopic dermatitis[J]. World Allergy Organization Journal, 2020, 13 (8): 30- 35. |
9 |
YANG L , WANG C Z , YE J Z , et al. Hepatoprotective effects of polyprenols from Ginkgo biloba L. leaves on CCl4-induced hepatotoxicity in rats[J]. Fitoterapia, 2011, 82 (6): 834- 840.
doi: 10.1016/j.fitote.2011.04.009 |
10 |
JONES M B , ROSENBERG J N , BETENBAUGH M J , et al. Structure and synthesis of polyisoprenoids used in N-glycosylation across the three domains of life[J]. Biochimica Et Biophysica Acta, 2009, 1790 (6): 485- 494.
doi: 10.1016/j.bbagen.2009.03.030 |
11 | GOLOVANOVA E V , VINNITSKAIA E V , SHAPOSHNIKOVA N A , et al. Effectiveness of the new plant hepatoprotector-ropren in patients with non-alcoholic steatohepatitis[J]. Experimental and Clinical Gastroenterology, 2010, (7): 97- 102. |
12 | KEIZO U, MASANORI K. Polyprenyl alcohol composition for soft capsules: KR9300048[P]. 1993-05-05. |
13 | SATOSHI S, KIYOMISTU T. Composition for oral with polyprenyl alcohol as active ingredient: JP6072837A[P]. 1994-03-15. |
14 | KEIZO U, NOBUTAKA N. Production of hard capsule prepration containing polyprenyl alcohol: JP2247124A[P]. 1990-10-02. |
15 |
ZHUANG X X , ZANG X , ZHENG G Y , et al. Polyprenols mitigate cognitive dysfunction and neuropathology in the APP/PS1 mouse[J]. Phytotherapy Research, 2018, 32 (6): 1098- 1107.
doi: 10.1002/ptr.6050 |
16 |
TAO R , WANG C Z , LU Y , et al. Characterization and cytotoxicity of polyprenol lipid and vitamin E-TPGS hybrid nanoparticles for betulinic acid and low-substituted hydroxyl fullerenol in MHCC97H and L02 cells[J]. International Journal of Nanomedicine, 2020, 15, 2733- 2749.
doi: 10.2147/IJN.S249773 |
17 |
WANG C Z , YUAN J J , LI W J , et al. In vivo and in vitro toxicity evaluation of polyprenols extracted from Ginkgo biloba L.leaves[J]. Molecules, 2015, 20 (12): 22257- 22271.
doi: 10.3390/molecules201219839 |
18 |
GAWRYS O , POLKOWSKA M , ROSZKOWSKA-CHOJECKA M , et al. Effects of liposomes with polyisoprenoids, potential drug carriers, on the cardiovascular and excretory system in rats[J]. Pharmacological Reports, 2014, 66, 273- 278.
doi: 10.1016/j.pharep.2013.09.009 |
19 |
ZHANG C W , WANG C Z , TAO R , et al. Enzymolysis-based ultrasound extraction and antioxidant activities of polyprenol lipids from Ginkgo biloba leaves[J]. Process Biochemistry, 2016, 51 (3): 444- 451.
doi: 10.1016/j.procbio.2015.12.008 |
20 |
AKHTAR T A , SUROWIECKI P , SIEKIERSKA H , et al. Polyprenols are synthesized by a plastidial cis-prenyltransferase and influence photosynthetic performance[J]. Plant Cell, 2017, 29 (7): 1709- 1725.
doi: 10.1105/tpc.16.00796 |
21 |
EICHLER J , IMPERIALI B . Stereochemical divergence of polyprenol phosphate glycosyltransferases[J]. Trends in Biochemical Sciences, 2018, 43 (1): 10- 17.
doi: 10.1016/j.tibs.2017.10.008 |
22 |
XUE X C , ZHENG R B , KOIZUMI A , et al. Synthetic polyprenol-pyrophosphate linked oligosaccharides are efficient substrates for mycobacterial galactan biosynthetic enzymes[J]. Organic and Biomolecular Chemistry, 2018, 16 (11): 1939- 1957.
doi: 10.1039/C8OB00316E |
23 |
QUELLHORST G J , HALL C W , ROBBINS A R , et al. Synthesis of dolichol in a polyprenol reductase mutant is restored by elevation of cis-prenyl transferase activity[J]. Archives of Biochemistry and Biophysics, 1997, 343 (1): 19- 26.
doi: 10.1006/abbi.1997.0141 |
24 |
IMPERIALI B , ZIMMERMAN J W . Synthesis of dolichols via asymmetric hydrogenation of plant polyprenols[J]. Tetrahedron Letters, 1988, 29 (42): 5343- 5344.
doi: 10.1016/S0040-4039(00)82862-2 |
25 |
NODA T , TAKE T , WATANABE T , et al. The characterization of malloprenol and its ester with linolenic acid isolated from the leaves of mallotus japonicus[J]. Bulletin of the Chemical Society of Japan, 1970, 43 (7): 2174- 2176.
doi: 10.1246/bcsj.43.2174 |
26 |
SHIBAEV V N , VESELOVSKY V V , LOZANOVA A V , et al. Synthesis of dolichyl phosphate derivatives with fluorescent label at the ω-end of the chain, new tools to study protein glycosylation[J]. Bioorganic and Medicinal Chemistry Letters, 2000, 10 (2): 189- 192.
doi: 10.1016/S0960-894X(99)00662-9 |
27 |
ALLETI R , RAO V , XU L , et al. A solanesol-derived scaffold for multimerization of bioactive peptides[J]. The Journal of Organic Chemistry, 2010, 75 (17): 5895- 5903.
doi: 10.1021/jo101043m |
28 |
KHIDYROVA N K . Modification of polyprenols from cotton leaves acylation by monobasic acid anhydrides[J]. Chemistry of Natural Compounds, 2005, 41 (4): 469- 470.
doi: 10.1007/s10600-005-0181-0 |
29 |
TAO R , WANG C Z , KONG Z W . Antibacterial/antifungal activity and synergistic interactions between polyprenols and other lipids isolated from Ginkgo biloba L.leaves[J]. Molecules, 2013, 18 (2): 2166- 2182.
doi: 10.3390/molecules18022166 |
30 |
QIN B K , LIU L , WU X H , et al. mPEGylated solanesol micelles as redox-responsive nanocarriers with synergistic anticancer effect[J]. Acta Biomaterialia, 2017, 64, 211- 222.
doi: 10.1016/j.actbio.2017.09.040 |
31 |
SWIEZEWSKA E , DANIKIEWICZ W . Polyisoprenoids: Structure, biosynthesis and function[J]. Progress in Lipid Research, 2005, 44 (4): 235- 258.
doi: 10.1016/j.plipres.2005.05.002 |
32 |
MASALOVA O V , LEANOVA E I , ONISHCHUNK A A , et al. Polyprenyl phosphates induce a high humoral and cellular response to immunization with recombinant proteins of the replicative complex of the hepatitis C virus[J]. Doklady Biochemistry and Biophysics, 2018, 482 (1): 261- 263.
doi: 10.1134/S1607672918050083 |
33 |
王成章, 沈兆邦, 郑光耀, 等. 银杏叶聚戊烯基磷酸酯体内外抗肿瘤的生物活性研究[J]. 林产化学与工业, 2006, 26 (3): 13- 16.
doi: 10.3321/j.issn:0253-2417.2006.03.004 |
WANG C Z , SHEN Z B , ZHENG G Y , et al. Antitumor biological activity of polyprenyl phosphate from leaves of Ginkgo biloba L.in vivo and vitro[J]. Chemistry and Industry of Forest Products, 2006, 26 (3): 13- 16.
doi: 10.3321/j.issn:0253-2417.2006.03.004 |
|
34 |
RASADKINA E N , MALENKOVSKAYA M A , PUGASHOVA N M , et al. Phosphorylation of polyprenols by phosphorous acid amides[J]. Russian Journal of Bioorganic Chemistry, 2013, 39 (7): 704- 706.
doi: 10.1134/S1068162013070121 |
35 |
PRONIN A V , NAROYLYANSKY A N , SANIN A V . New approaches to the prevention and treatment of viral diseases[J]. Archivum Immunologiae Et Therapiae Experimentalis, 2021, 69 (1): 10- 21.
doi: 10.1007/s00005-021-00613-w |
36 |
张昌伟, 马余璐, 陶冉, 等. 银杏叶聚戊烯醇的分离纯化及其亲水衍生物的合成[J]. 林产化学与工业, 2019, 39 (1): 41- 45.
doi: 10.3969/j.issn.0253-2417.2019.01.006 |
ZHANG C W , MA Y L , TAO R , et al. Separation, purification and hydrophilic derivative synthesis of Ginkgo biloba leaves polyprenol[J]. Chemistry and Industry of Forest Products, 2019, 39 (1): 41- 45.
doi: 10.3969/j.issn.0253-2417.2019.01.006 |
|
37 |
陶冉, 王成章, 叶建中, 等. 银杏叶聚戊烯醇含氮和含卤素衍生物的抑菌活性研究[J]. 林产化学与工业, 2016, 36 (6): 29- 34.
doi: 10.3969/j.issn.0253-2417.2016.06.005 |
TAO R , WANG C Z , YE J Z , et al. Synthesis and antibacterial activity of nitrogenated and haloid derivatives of Ginkgo biloba leaves polyprenol[J]. Chemistry and Industry of Forest Products, 2016, 36 (6): 29- 34.
doi: 10.3969/j.issn.0253-2417.2016.06.005 |
|
38 | WANG J H , WANG C J , GAN Y , et al. Design, synthesis and synergistic effects of novel derivatives of solanesol[J]. Chemical Research in Chinese Universities, 2007, 4, 417- 420. |
39 | GRECKA E, STATKIEWICZ M, GORSKA A, et al. Prenyl ammonium salts-new carriers for gene delivery: A B16-F10 mouse melanoma model[J/OL]. PLOS ONE, 2016, 11(4): e0153633[2021-01-20]. https://doi.org/10.1371/journal.pone.0153633. |
40 | TAKIGAWA T , IBATA K , MIZUNO M . Synthesis of mammalian dolichol from plant polyprenols[J]. Chemistry and Physics of Lipids, 1989, 51 (3/4): 171- 182. |
41 |
ZOKIROVA U T , KHIDIROVA N K , KOROLEVA A A , et al. Alkylation by polyprenols of ortho-and para-cresols: Synthesis of isomeric polyprenylcresols[J]. Chemistry of Natural Compounds, 2020, 56 (1): 39- 43.
doi: 10.1007/s10600-020-02939-x |
42 | 张平. 一种含银杏叶聚戊烯醇的药物组合物及其制备方法: CN1628696[P]. 2005-06-22. |
ZHANG P. A drug composition containing Ginkgo biloba leaves polyprenol and its preparation method: CN1628696[P]. 2005-06-22. | |
43 | 王成章, 杨兰, 叶建中, 等. 抗乙肝病毒的银杏叶聚戊烯醇活性组合物及其制备方法: CN101890059A[P]. 2010-11-24. |
WANG C Z, YANG L, YE J Z, et al. Preparation of polyprenol from Ginkgo biloba leaves against hepatitis B virus: CN101890059A[P]. 2010-11-24. | |
44 |
PRONIN A V , NAROVLYANSKY A N , SHULZHENKO A E , et al. New polyprenyl phosphate based preparation fortepren as promising cytokine regulationg antiviral remedy[J]. Cytokine and Growth Factor Reviews, 2016, 30, 119- 126.
doi: 10.1016/j.cytogfr.2016.04.001 |
45 | DANILOV L L , MALTSEV S D , DEYEVA A V , et al. Phosprenyl: A novel drug with antiviral and immunomodulatory activity[J]. Archivum Immunologiae Et Therapiae Experimentalis, 1996, 44 (5/6): 395- 40. |
46 |
SOULTANOV V , FEDOTOVA J , NIKITINA T , et al. Antidepressant-like effect of ropren© in β-amyloid-(25-35) rat model of alzheimer's disease with altered levels of androgens[J]. Molecular Neurobiology, 2017, 54 (4): 2611- 2621.
doi: 10.1007/s12035-016-9848-8 |
47 | 王成章, 杨兰, 叶建中, 等. 中压柱快速分离聚戊烯醇及其抗H3N2病毒注射剂的制备方法: CN101913992A[P]. 2010-12-15. |
WANG C Z, YANG L, YE J Z, et al. Rapid separation of polyprenols and preparation of anti-H3N2 virus injection by medium pressure column: CN101913992A[P]. 2010-12-15. | |
48 |
GAWRYS O , BARANOWSKA I , GAWARECKA K , et al. Innovative lipid-based carriers containing cationic derivatives of polyisoprenoid alcohols augment the antihypertensive effectiveness of candesartan in spontaneously hypertensive rats[J]. Hypertens Research, 2018, 41 (4): 234- 245.
doi: 10.1038/s41440-018-0011-y |
49 |
VANAGA I , GUBERNATOR J , NAKURTE I , et al. Identification of Abies sibirica L.polyprenols and characterisation of polyprenol-containing liposomes[J]. Molecules, 2020, 25 (8): 1801- 1813.
doi: 10.3390/molecules25081801 |
50 |
MADEJA Z , RAK M , RALSKA E , et al. New cationic polyprenyl derivative proposed as a lipofecting agent[J]. Acta Biochimica Polonica, 2007, 54 (4): 873- 876.
doi: 10.18388/abp.2007_3191 |
51 |
GAWRYS O , RAK M , BARANOWSKA I , et al. Polyprenol-based lipofecting agents for in vivo delivery of therapeutic DNA to treat hypertensive rats[J]. Biochemical Genetics, 2021, 59 (1): 62- 82.
doi: 10.1007/s10528-020-09992-9 |
52 |
STACHYRA A , RAK M , REDKIEWICZ P , et al. Effective usage of cationic derivatives of polyprenols as carriers of DNA vaccines against influenza virus[J]. Virology Journal, 2017, 14 (1): 168- 177.
doi: 10.1186/s12985-017-0838-x |
53 | ZHANG C W , LI M F , TAO R , et al. Physiochemical property and antibacterial activity of formulation containing polyprenol extracted from Ginkgo biloba leaves[J]. Industrial Crops and Products, 2020, 147, 112- 213. |
54 | 陶冉, 王成章, 叶建中, 等. 银杏叶聚戊烯醇纳米乳液联合抗生素抗菌活性研究[J]. 林产化学与工业, 2017, 37 (1): 81- 86. |
TAO R , WANG C Z , YE J Z , et al. Antibacterial activity of Ginkgo biloba leaves polyprenols nanoemulsion in combination with antibiotics[J]. Chemistry and Industry of Forest Products, 2017, 37 (1): 81- 86. | |
55 |
WANG C Z , LI W J , TAO R , et al. Antiviral activity of a nanoemulsion of polyprenols from Ginkgo leaves against influenza A H3N2 and hepatitis B virus in vitro[J]. Molecules, 2015, 20 (3): 5137- 5151.
doi: 10.3390/molecules20035137 |
56 |
TAO R , WANG C Z , ZHANG C W , et al. Characterization, cytotoxicity, and genotoxicity of TiO2 and folate-coupled chitosan nanoparticles loading polyprenol-based nanoemulsion[J]. Biological Trace Element Research, 2018, 184 (1): 60- 74.
doi: 10.1007/s12011-017-1184-y |
57 |
QIN B K , LIU L , PAN Y Y , et al. PEGylated solanesol for oral delivery of coenzyme Q10[J]. Journal of Agricultural and Food Chemistry, 2017, 65 (16): 3360- 3367.
doi: 10.1021/acs.jafc.7b00165 |
58 | XIONG Y, HOU T, LIU L, et al. Solanesol derived therapeutic carriers for anticancer drug delivery[J/OL]. International Journal of Pharmaceutics, 2019, 572: 118823[2021-01-20]. https://doi.org/10.1016/j.ijpharm.2019.118823. |
[1] | 夏继林, 谭中标, 朱小燕, 时号, 李相前. 双催化域糖苷水解酶研究进展[J]. 林产化学与工业, 2018, 38(2): 11-20. |
[2] | 王兴达, 李蕾, 韩泳平. 大黄酸衍生物的合成及其抑菌活性研究[J]. 林产化学与工业, 2018, 38(2): 105-111. |
[3] | 陶冉, 王成章, 叶建中, 周昊, 陈虹霞. 银杏叶聚戊烯醇含氮和含卤素衍生物的抑菌活性研究[J]. 林产化学与工业, 2016, 36(6): 29-34. |
[4] | 刘延成;陈振锋;彭艳;梁宏. 鹅掌楸碱的研究进展[J]. 林产化学与工业, 2011, 31(4): 109-116. |
[5] | 敬璞;张晓光;董英. 紫玉米花青苷的研究进展[J]. 林产化学与工业, 2010, 30(1): 103-110. |
阅读次数 | ||||||
全文 |
|
|||||
摘要 |
|
|||||