红松松塔抗癌成分、存在问题及对策的研究进展

辛超; 张艳东; 王振宇

doi:10.13386/j.issn1002-0306.2020040134

红松松塔抗癌成分、存在问题及对策的研究进展

哈尔滨工业大学化工与化学学院, 黑龙江哈尔滨 150090

基金项目:

十三五国家重点研发计划（2016YFC0500307-07）。

详细信息

作者简介:
辛超(1987-),男,博士研究生,研究方向:天然产物化学,E-mail:xinchao198811@126.com。

通讯作者:
王振宇(1957-),男,博士,教授,研究方向:天然产物化学、极端环境营养,E-mail:wzy219000@126.com。

中图分类号: TS255.6
计量
- 文章访问数: 273
- HTML全文浏览量: 44
- PDF下载量: 18
出版历程
- 收稿日期: 2020-04-13
- 网络出版日期: 2021-03-01
- 刊出日期: 2021-02-14

Research Progress of Existing Problems and Countermeasures of Anticancer Components from Pinecones of Pinus koraiensis

School of Chemistry and Chemical Engineering, Harbin Institute of Technology, Harbin 150090, China

摘要

摘要: 红松松仁具有降血压、调节血脂、护肝等多种生物活性，是一类富含营养物质的保健食品。采集松子后的松塔通常被丢弃或焚烧，导致了环境污染及资源浪费。最近的研究表明红松松塔中的多糖、萜类化合物、多酚抗肿瘤活性优异，应用前景良好，但也存在较多的缺陷如效果差、稳定性低、生物利用度低等，为此，本文针对红松松塔抗癌成分的不足提出了两种对策即化学修饰与活性成分纳米递送，以期为实现红松松塔的资源化利用提供参考。
- 红松松塔 /
- 抗癌成分 /
- 化学修饰 /
- 纳米递送
Abstract: Pine nuts of Pinus koraiensis was the health food rich in nutrients,showing various biological activities such as lowering blood pressure,regulating blood fat and protecting liver,etc. As the by-product of picking pine nuts,pinecones were often burned or discarded,resulting in environmental pollution and waste of resources. Recent studies suggested polysaccharides,terpenoids,polyphenols contained in pinecones were some components with superior antitumor activity but there were many defects,such as poor effect,low stability and low bioavailability. In order to provide theoretical reference to the resource utilization of pinecones,research progress of existing problems and countermeasures of anticancer components from pinecones of Pinus koraiensis were summarized in this paper.
- pinecones of Pinus koraiensis /
- anticancer components /
- chemical modification /
- nano-delivery

HTML全文

参考文献(57)

[1]	Cortes J,Perez-García J M,Llombart-Cussac A,et al. Enhancing global access to cancer medicines[J]. CA:A Cancer Journal for Clinicians,2020,70(2):105-124.
[2]	Hou K X,Bao M L,Wang L,et al. Aqueous enzymatic pretreatment ionic liquid-lithium salt based microwave-assisted extraction of essential oil and procyanidins from pinecones of Pinus koraiensis[J]. Journal of Cleaner Production,2019,236:117581.
[3]	Qu H,Gao X,Zhao H T,et al. Structural characterization and in vitro hepatoprotective activity of polysaccharide from pine nut(Pinus koraiensis Sieb.et Zucc.)[J]. Carbohydrate Polymers,2019,223:115056.
[4]	Parisi O I,Puoci F,Restuccia D,et al. Polyphenols and their formulations[M]//Polyphenols in human health and disease. Amsterdam:Elsevier,2014:29-45.
[5]	Yang C S,Lee M J,Chen L,et al. Polyphenols as inhibitors of carcinogenesis[J]. Environmental Health Perspectives,1997,105(Suppl 4):971-976.
[6]	Amatori S,Mazzoni L,Alvarez-Suarez J M,et al. Polyphenol-rich strawberry extract(PRSE)shows in vitro and in vivo biological activity against invasive breast cancer cells[J]. Scientific Reports,2016,6:30917.
[7]	Pieme C A,Ngogang J,Costache M.Polyphenol contents of five of medicinal plants from Cameroon and effects of their extracts on antioxidant capacities of human breast cancer cells[J].Toxicological & Environmental Chemistry,2014,96(7):1120-1130.
[8]	Ko Y S,Lee W S,Joo Y N,et al. Polyphenol mixtures of Euphorbia supina the inhibit invasion and metastasis of highly metastatic breast cancer MDA-MB-231 cells[J]. Oncology Reports,2015,34(6):3035-3042.
[9]	Kubatka P,Kapinová A,Kello M,et al. Fruit peel polyphenols demonstrate substantial anti-tumour effects in the model of breast cancer[J]. European Journal of Nutrition,2016,55(3):955-965.
[10]	Liu S M,Ou S Y,Huang H H.Green tea polyphenols induce cell death in breast cancer MCF-7 cells through induction of cell cycle arrest and mitochondrial-mediated apoptosis[J]. Journal of Zhejiang University-Science B,2017,18(2):89-98.
[11]	Abdal Dayem A,Choi H,Yang G M,et al. The anti-cancer effect of polyphenols against breast cancer and cancer stem cells:Molecular mechanisms[J]. Nutrients,2016,8(9):581.
[12]	Yi J J,Wang Z Y,Bai H N,et al. Optimization of purification,identification and evaluation of the in vitro antitumor activity of polyphenols from Pinus koraiensis pinecones[J]. Molecules,2015,20(6):10450-10467.
[13]	Yi J J,Wang Z Y,Bai H N,et al. Polyphenols from pinecones of Pinus koraiensis induce apoptosis in colon cancer cells through the activation of caspase in vitro[J]. RSC Advances,2016,6(7):5278-5287.
[14]	Yi J J,Cheng C L,Li X Y,et al. Protective mechanisms of purified polyphenols from pinecones of Pinus koraiensis on spleen tissues in tumor-bearing S180 mice in vivo[J]. Food & Function,2017,8(1):151-166.
[15]	Yi J J,Qu H,Wu Y Z,et al. Study on antitumor,antioxidant and immunoregulatory activities of the purified polyphenols from pinecone of Pinus koraiensis on tumor-bearing S180 mice in vivo[J]. International Journal of Biological Macromolecules,2017,94:735-744.
[16]	Ohsaki Y,Gazdar A F,Chen H C,et al. Antitumor activity of Magainin analogues against human lung cancer cell lines[J]. Cancer Research,1992,52(13):3534-3538.
[17]	Zhang Y D,Xin C,Qiu J Q,et al. Essential oil from Pinus koraiensis pinecones inhibits gastric cancer cells via the HIPPO/YAP signaling pathway[J]. Molecules,2019,24(21):3851.
[18]	苏晓雨. 红松松塔萜类成分及生物活性研究[D]. 哈尔滨:哈尔滨工业大学,2006.
[19]	杨鑫,张英春,张华,等.一种红松松塔提取物及其应用和提取方法:CN101066916A[P].2007-11-07.
[20]	Lee T K,Roh H S,Yu J S,et al. Pinecone of Pinus koraiensis inducing apoptosis in human lung cancer cells by activating caspase-3 and its chemical constituents[J]. Chemistry & Biodiversity,2017,14(4):e1600412.
[21]	Lee T K,Park J Y,Yu J S,et al. 7α,15-Dihydroxydehydroabietic acid from Pinus koraiensis inhibits the promotion of angiogenesis through downregulation of VEGF,p-Akt and p-ERK in HUVECs[J]. Bioorganic & Medicinal Chemistry Letters,2018,28(6):1084-1089.
[22]	张曜武,高原.红松松塔残渣多糖的抗氧化活性研究[J].化学与生物工程,2015,32(7):41-43.
[23]	杨鑫,王鑫淼,高星烨,等.红松松塔多糖提取工艺优化及其含量测定[J]. 中成药,2011,33(2):351-353.
[24]	张桢,孙帮燕,郭贵唐,等.华山松松塔提取物抗HIV活性部位中铅含量的测定[J]. 安徽农业科学,2015,43(11):1-2.
[25]	Sakagami H,Kushida T,Oizumi T,et al. Distribution of lignin-carbohydrate complex in plant kingdom and its functionality as alternative medicine[J]. Pharmacology & Therapeutics,2010,128(1):91-105.
[26]	安巍巍,唐雅莉,赵莲花,等.红松松塔提取物多聚苯丙素-多糖复合物诱导人乳腺癌MCF-7细胞凋亡[J]. 实用肿瘤学杂志,2019,33(4):289-293.
[27]	Zou P,Yang X,Huang W W,et al. Characterization and bioactivity of polysaccharides obtained from pine cones of Pinus koraiensis by graded ethanol precipitation[J]. Molecules,2013,18(8):9933-9948.
[28]	Wang L,Li X Y,Wang H C.Physicochemical properties,bioaccessibility and antioxidant activity of the polyphenols from pine cones of Pinus koraiensis[J]. International Journal of Biological Macromolecules,2019,126:385-391.
[29]	Sanna V,Lubinu G,Madau P,et al. Polymeric nanoparticles encapsulating white tea extract for nutraceutical application[J]. Journal of Agricultural and Food Chemistry,2015,63(7):2026-2032.
[30]	Rao X P,Song Z Q,He L,et al. Synthesis,structure analysis and cytotoxicity studies of novel unsymmetrically N,N'-substituted ureas from dehydroabietic acid[J]. Chemical & Pharmaceutical Bulletin,2008,56(11):1575-1578.
[31]	Huang X C,Wang M,Pan Y M,et al. Synthesis and antitumor activities of novel α-aminophosphonates dehydroabietic acid derivatives[J]. Bioorganic & Medicinal Chemistry Letters,2013,23(19):5283-5289.
[32]	Pertino M W,Verdugo V,Theoduloz C,et al. Synthesis and antiproliferative activity of some novel triazole derivatives from dehydroabietic acid[J]. Molecules,2014,19(2):2523-2535.
[33]	Huang X C,Wang M,Wang H S,et al. Synthesis and antitumor activities of novel dipeptide derivatives derived from dehydroabietic acid[J]. Bioorganic & Medicinal Chemistry Letters,2014,24(6):1511-1518.
[34]	李军,李玉明,申利群,等.脱氢枞酸磺酰脲类化合物的合成及抗肿瘤活性[J]. 中国新药杂志,2019,28(14):1778-1783.
[35]	Huang X C,Huang R Z,Liao Z X,et al. Synthesis and pharmacological evaluation of dehydroabietic acid thiourea derivatives containing bisphosphonate moiety as an inducer of apoptosis[J]. European Journal of Medicinal Chemistry,2016,108:381-391.
[36]	Wang Y Y,He Y,Yang L F,et al. Synthesis of novel diterpenoid analogs with in-vivo antitumor activity[J]. European Journal of Medicinal Chemistry,2016,120:13-25.
[37]	Zheng Y,Tang Q,Wang T,et al. Synthesis of a green fuel additive over cation resins[J]. Chemical Engineering & Technology,2013,36(11):1951-1956.
[38]	Zhang L F,Radovic-Moreno A,Alexis F,et al. Co-delivery of hydrophobic and hydrophilic drugs from nanoparticle-aptamer bioconjugates[J]. Chem Med Chem,2007,2(9):1268-1271.
[39]	Hu C M,Zhang L F.Therapeutic nanoparticles to combat cancer drug resistance[J]. Current Drug Metabolism,2009,10(8):836-841.
[40]	Stojadinovic M,Radosavljevic J,Ognjenovic J,et al. Binding affinity between dietary polyphenols and β-lactoglobulin negatively correlates with the protein susceptibility to digestion and total antioxidant activity of complexes formed[J]. Food Chemistry,2013,136(3/4):1263-1271.
[41]	Chung J E,Tan S,Gao S J,et al. Self-assembled micellar nanocomplexes comprising green tea catechin derivatives and protein drugs for cancer therapy[J]. Nature Nanotechnology,2014,9(11):907-912.
[42]	Qiao H Z,Fang D,Zhang L,et al. Nanostructured peptidotoxins as natural pro-oxidants induced cancer cell death via amplification of oxidative stress[J]. ACS Applied Materials & Interfaces,2018,10(5):4569-4581.
[43]	Liang K,Chung J E,Gao S J,et al. Highly augmented drug loading and stability of micellar nanocomplexes composed of doxorubicin and poly(ethylene glycol)-green tea catechin conjugate for cancer therapy[J]. Advanced Materials,2018,30(14):1706963.
[44]	Cheng T J,Liu J J,Ren J,et al. Green tea catechin-based complex micelles combined with doxorubicin to overcome cardiotoxicity and multidrug resistance[J]. Theranostics,2016,6(9):1277-1292.
[45]	Qiu J Q,Zhang H,Wang Z Y,et al. Response surface methodology for the synthesis of an Auricularia auriculajudae polysaccharides-CDDP complex[J]. International Journal of Biological Macromolecules,2016,93:333-343.
[46]	Qiu J Q,Zhang H,Wang Z Y,et al. The antitumor effect of folic acid conjugated-Auricularia auricular polysaccharide-cisplatin complex on cervical carcinoma cells in nude mice[J]. International Journal of Biological Macromolecules,2018,107(Pt B):2180-2189.
[47]	Lai W F,Rogach A L.Hydrogel-based materials for delivery of herbal medicines[J]. ACS Applied Materials & Interfaces,2017,9(13):11309-11320.
[48]	Choi W,No R H,Kwon H S,et al. Enhancement of skin anti-inflammatory activities of Scutellaria baicalensis extract using a nanoencapsulation process[J]. Journal of Cosmetic and Laser Therapy,2014,16(6):271-278.
[49]	Lee S Y,Cho H J.Dopamine-conjugated poly(lactic-co-glycolic acid)nanoparticles for protein delivery to macrophages[J]. Journal of Colloid and Interface Science,2017,490:391-400.
[50]	Pereira F,Baptista R,Ladeiras D,et al. Production and characterization of nanoparticles containing methanol extracts of Portuguese Lavenders[J]. Measurement,2015,74:170-177.
[51]	Bhattacharyya S S,Paul S,Khuda-Bukhsh A R.Encapsulated plant extract(Gelsemium sempervirens)poly(lactide-co-glycolide)nanoparticles enhance cellular uptake and increase bioactivity in vitro[J]. Experimental Biology and Medicine(Maywood,N.J.),2010,235(6):678-688.
[52]	Hill L E,Taylor T M,Gomes C.antimicrobial efficacy of poly(dl-lactide-co-glycolide)(plga)nanoparticles with entrapped cinnamon bark extract against Listeria monocytogenes and Salmonella typhimurium[J]. Journal of Food Science,2013,78(4):N626-N632.
[53]	Das J,Das S,Samadder A,et al. Poly(lactide-co-glycolide)encapsulated extract of Phytolacca decandra demonstrates better intervention against induced lung adenocarcinoma in mice and on A549 cells[J]. European Journal of Pharmaceutical Sciences,2012,47(2):313-324.
[54]	Xin C,Ma J H,Tan C J,et al. Preparation of melanin from Catharsius molossus L.and preliminary study on its chemical structure[J]. Journal of Bioscience and Bioengineering,2015,119(4):446-454.
[55]	Ye M,Guo G Y,Lu Y,et al. Purification,structure and anti-radiation activity of melanin from Lachnum YM404[J]. International Journal of Biological Macromolecules,2014,63:170-176.
[56]	Wang X Y,Zhang J S,Wang Y T,et al. Multi-responsive photothermal-chemotherapy with drug-loaded melanin-like nanoparticles for synergetic tumor ablation[J]. Biomaterials,2016,81:114-124.
[57]	Chu M Q,Hai W X,Zhang Z Y,et al. Melanin nanoparticles derived from a homology of medicine and food for sentinel lymph node mapping and photothermal in vivo cancer therapy[J]. Biomaterials,2016,91:182-199.