植物聚戊烯醇的化学修饰及药用剂型的研究进展

doi:10.3969/j.issn.0253-2417.2022.05.018

Abstract

Abstract:

Plant polyprenols were a class of natural compound of esters with good biological activity, such as anticancer, hepatoprotective and antiviral. However, the strong hydrophobic of polyprenols resulted in the low bioavailability in the human body. In view of the structural characteristics of plant polyprenols containing multiple unconjugated double bonds and terminal hydroxyl groups, the research progress of polyprenols chemical modifications, such as addition, oxidation, esterification, amination, alkylation and grignard reaction were summarized, and a series of representative polyprenols derivatives and their biological activities were introduced. Meanwhile, the latest design and development of nanoemulsions, liposomes and injections based on plant polyprenols and their derivatives were reviewed, which provide a reference for further research into the development of pharmaceutical drugs of polyprenols and their derivatives.

Key words: plant ployprenol, ployprenol derivatives, structural modification, pharmacological activity

CLC Number:

TQ35

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.

Figures/Tables 15

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References 58

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.

结构类型 structure type	结构式 structure	主要分布及链长 main distribution and chain length
茄尼醇 solanesol		茄科植物(n=6-9) solanaceae
桦木醇 betulaprenol		裸子植物(12≤ n≤120) gymnosperm
菲卡醇 ficaprenol		被子植物(n=6-40) angiosperm

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Review on Structure Modification and Pharmaceutical Formulations of Plant Ployprenol

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