林产化学与工业 ›› 2021, Vol. 41 ›› Issue (3): 112-124.doi: 10.3969/j.issn.0253-2417.2021.03.015
杨子颖1,2, 李婧3, 苏洁2, 李惠玲4, 章漳4, 彭锋1,2,*()
收稿日期:
2020-09-15
出版日期:
2021-06-28
发布日期:
2021-07-01
通讯作者:
彭锋
E-mail:fengpeng@bjfu.edu.cn
作者简介:
彭锋, 教授, 博士生导师, 研究领域为植物资源利用; E-mail: fengpeng@bjfu.edu.cn基金资助:
Ziying YANG1,2, Jing LI3, Jie SU2, Huiling LI4, Zhang ZHANG4, Feng PENG1,2,*()
Received:
2020-09-15
Online:
2021-06-28
Published:
2021-07-01
Contact:
Feng PENG
E-mail:fengpeng@bjfu.edu.cn
摘要:
松萝属地衣植物在我国分布广泛,是一种历史悠久的药用植物,但对其化学成分及活性作用的研究少、起步晚、基础资料积淀薄弱,限制了对其进一步的开发与利用。在综述了松萝属植物的初生代谢产物多糖(地衣多糖、异地衣多糖、半乳甘露聚糖、地衣杂多糖)和脂肪酸类化合物,以及次生代谢产物地衣酸(单苯环衍生物、缩酚酸类、缩酚酸环醚类、二苯并呋喃类等)的基础上,进一步介绍了松萝属地衣植物的主要化学成分地衣多糖、地衣酸活性作用的研究进展,其中,地衣多糖具有抗肿瘤、抗氧化作用;地衣酸具有抗菌杀虫,抗癌、抗肿瘤,抗氧化、抗病毒、消炎、保肝解毒以及一定的酶抑制性。
中图分类号:
杨子颖, 李婧, 苏洁, 李惠玲, 章漳, 彭锋. 松萝属地衣植物化学成分及活性作用研究进展[J]. 林产化学与工业, 2021, 41(3): 112-124.
Ziying YANG, Jing LI, Jie SU, Huiling LI, Zhang ZHANG, Feng PENG. Research Progress on Chemical Constituents and Activities of Genus Usnea Lichens[J]. Chemistry and Industry of Forest Products, 2021, 41(3): 112-124.
1 |
RASHID Z M , MORMANN M , STECKHAN K , et al. Polysaccharides from lichen Xanthoria parietina: 1, 4/1, 6-α-D-glucans and a highly branched galactomannan with macrophage stimulating activity via Dectin-2 activation[J]. International Journal of Biological Macromolecules, 2019, 134, 921- 935.
doi: 10.1016/j.ijbiomac.2019.05.056 |
2 |
HONEGGER R . Simon Schwendener(1829-1919) and the dual hypothesis of lichens[J]. The Bryologist, 2000, 103 (2): 307- 313.
doi: 10.1639/0007-2745(2000)103[0307:SSATDH]2.0.CO;2 |
3 |
SPRIBILLE T , TUOVINEN V , RESL P , et al. Basidiomycete yeasts in the cortex of ascomycete macrolichens[J]. Science, 2016, 353 (6298): 488- 492.
doi: 10.1126/science.aaf8287 |
4 | 彭锋. 松萝属植物形态学和五种松萝种多糖的分离纯化及活性研究[D]. 杨凌: 西北农林科技大学, 2007. |
PENG F.Study on the morphology, separation-purification and activities of the Usnea[D]. Yangling: Northwest Agriculture & Forestry University, 2007. | |
5 | 彭锋, 边静, 彭湃, 等. 松萝属地衣植物的研究进展[J]. 林产化学与工业, 2012, 32 (1): 111- 118. |
PENG F , BIAN J , PENG P , et al. Research progress of genus Usnea[J]. Chemistry and Industry of Forest Products, 2012, 32 (1): 111- 118. | |
6 |
SHRESTHA G , ST CLAIR L L . Lichens: A promising source of antibiotic and anticancer drugs[J]. Phytochemistry Reviews, 2013, 12 (1): 229- 244.
doi: 10.1007/s11101-013-9283-7 |
7 | NASH T H . Lichen Biology[M]. Cambridge: Cambridge University Press, 2008. |
8 |
HONEGGER R , HAISCH A . Immunocytochemical location of the (1→3)-(1→4)-β-glucan lichenin in the lichen-forming ascomycete Cetraria islandica(icelandic moss)[J]. New Phytologist, 2001, 150 (3): 739- 746.
doi: 10.1046/j.1469-8137.2001.00122.x |
9 | SMITH A L . Lichens[M]. Cambridge: Cambridge University Press, 1921: 55- 65. |
10 | SHIBATA S . Polysaccharides of lichens[J]. Journal of the National Science Council of Sri Lanka, 1973, 1, 183- 188. |
11 | NISHIKAWA Y , OHKI K , TAKAHASHI K , et al. Studies on the water-soluble constituents of lichens.II: Antitumor polysaccharides of Lasallia, Usnea and Cladonia species[J]. Chemical & Pharmaceutical Bulletin, 1974, 22 (11): 2692- 2702. |
12 |
IACOMINI M , GORIN P A J , BARON M , et al. Novel D-glucans obtained by dimethyl sulphoxide extraction of the lichens Letharia vulpina, Actinogyra muehlenbergii and an Usnea sp[J]. Carbohydrate Research, 1988, 176 (1): 117- 126.
doi: 10.1016/0008-6215(88)84063-1 |
13 | GORIN P A J , IACOMINI M . Structural diversity of galactomannan components isolated from lichens having ascomycetous mycosymbionts[J]. Carbohydrate Research, 1986, 142 (2): 253- 267. |
14 |
PENG F , REN J L , XU F , et al. Structural analysis of a fraction of polysaccharides from Usnea montis-fuji[J]. Journal of Biobased Materials and Bioenergy, 2010, 4 (1): 12- 15.
doi: 10.1166/jbmb.2010.1058 |
15 |
SHRESTHA G , ST CLAIR L L , O'NEILL K L . The immunostimulating role of lichen polysaccharides: A Review[J]. Phytotherapy Research, 2015, 29 (3): 317- 322.
doi: 10.1002/ptr.5251 |
16 |
OLAFSDOTTIR E S , INGÓIFSDOTTIR K . Polysaccharides from lichens: Structural characteristics and biological activity[J]. Planta Medica, 2001, 67 (3): 199- 208.
doi: 10.1055/s-2001-12012 |
17 | PERIERA E C , NASCIMENTO S C , LIMA R C , et al. Analysis of Usnea fasciata crude extracts with antineoplastic activity[J]. Tokai Journal of Experimental and Clinical Medicine, 1994, 19 (1/2): 47- 52. |
18 | 丁东宁, 靳菊情, 张莉, 等. 长松萝多糖的研究[J]. 天然产物研究与开发, 1992, (4): 3- 7. |
DING D N , JIN J Q , ZHANG L , et al. Research of Usnea longissimi polysaccharides[J]. Natural Product Research and Development, 1992, (4): 3- 7. | |
19 |
PRATEEKSHA P , PALIYAA B S , BAJPAI R , et al. The genus Usnea: A potent phytomedicine with multifarious ethnobotany, phytochemistry and pharmacology[J]. RSC Advances, 2016, 6 (26): 21672- 21696.
doi: 10.1039/C5RA24205C |
20 | 拉喜那木吉拉. 长松萝化学成分与药理活性研究[D]. 长春: 吉林农业大学, 2013. |
LA X N M J L.Research on the chemical components and pharmacological activities of Usnea longissimi[D]. Changchun: Jilin Agricultural University, 2013. | |
21 |
ULLAH M , UDDIN Z , SONG Y H , et al. Bacterial neuraminidase inhibition by phenolic compounds from Usnea longissima[J]. South African Journal of Botany, 2019, 120, 326- 330.
doi: 10.1016/j.sajb.2018.10.020 |
22 | 于学龙, 杨鑫瑶, 高小力, 等. 长松萝中酚类化学成分研究[J]. 中国中药杂志, 2016, 41 (10): 1864- 1869. |
YU X L , YANG X Y , GAO X L , et al. Phenolic constituents from lichen Usnea longissimi[J]. China Journal of Chinese Materia Medica, 2016, 41 (10): 1864- 1869. | |
23 |
CHOUDHARY M I , AZIZUDDIN , JALIL S , et al. Bioactive phenolic compounds from a medicinal lichen, Usnea longissima[J]. Phytochemistry, 2005, 66 (19): 2346- 2350.
doi: 10.1016/j.phytochem.2005.06.023 |
24 |
SULTANA N , AFOLAYAN A J . A new depsidone and antibacterial activities of compounds from Usnea undulata Stirton[J]. Journal of Asian Natural Products Research, 2011, 13 (12): 1158- 1164.
doi: 10.1080/10286020.2011.622720 |
25 |
冯洁, 杨秀伟, 苏思多, 等. 长松萝化学成分研究[J]. 中国中药杂志, 2009, 34 (6): 708- 711.
doi: 10.3321/j.issn:1001-5302.2009.06.016 |
FENG J , YANG X W , SU S D , et al. Research on the chemical components of Usnea longissimi[J]. China Journal of Chinese Materia Medica, 2009, 34 (6): 708- 711.
doi: 10.3321/j.issn:1001-5302.2009.06.016 |
|
26 |
QI H Y , JIN Y P , SHI Y P . A new depsidone from Usnea diffracta[J]. Chinese Chemical Letters, 2009, 20 (2): 187- 189.
doi: 10.1016/j.cclet.2008.10.032 |
27 |
MOREIRA A S N , FERNANDES R O S , LEMOS F J A , et al. Larvicidal activity of Ramalina usnea lichen against Aedes aegypti[J]. Revista Brasileira De Farmacognosia-Brazilian Journal of Pharmacognosy, 2016, 26 (4): 530- 532.
doi: 10.1016/j.bjp.2016.03.006 |
28 |
SALGADO F , ALBORNOZ L , CORTÉZ C , et al. Secondary metabolite profiling of species of the genus Usnea by UHPLC-ESI-OT-MS-MS[J]. Molecules, 2017, 23 (1): 1- 16.
doi: 10.3390/molecules23010001 |
29 | ATALAY F , HALICI M B , CAKIR A , et al. Antioxidant phenolics from Lobaria pulmonaria(L.) Hoffm.and Usnea longissima Ach.lichen species[J]. Turkish Journal of Chemistry, 2011, 35 (4): 647- 661. |
30 | 拉喜那木吉拉, 梁鸿, 巴根那, 等. 蒙药长松萝的化学成分研究(II)[J]. 中药材, 2015, 38 (12): 2541- 2542. |
LA X N M J L , LIANG H , BA G N , et al. Chemical constituents from Usnea longgisima, a traditional mongolian medicine(Ⅱ)[J]. Journal of Chinese Medicinal Materials, 2015, 38 (12): 2541- 2542. | |
31 |
NGUYEN K V , DUONG T H , NGUYEN K P P , et al. Chemical constituents of the lichen Usnea baileyi(Stirt.) Zahlbr[J]. Tetrahedron Letters, 2018, 59 (14): 1348- 1351.
doi: 10.1016/j.tetlet.2018.02.007 |
32 | RAWAT M S M , SHUKLA V , NEGI S , et al. Chemical study on Garhwal Himalayan lichen: Usnea emidotteries[J]. Indian Journal of Chemistry Section B: Organic Chemistry Including Medicinal Chemistry, 2006, 45 (11): 2566- 2570. |
33 | NUGRAHA A S , WANGCHUK T , WILLIS A C , et al. Phytochemical and pharmacological studies on four indonesian epiphytic medicinal plants: Drynaria rigidula, Hydnophytum formicarum, Usnea misaminensis, and Calymperes schmidtii[J]. Natural Product Communications, 2019, 14 (6): 1- 6. |
34 | REDDY S D, SIVA B, KUMAR K, et al. Comprehensive analysis of secondary metabolites in Usnea longissima(Lichenized Ascomycetes, Parmeliaceae) using UPLC-ESI-QTOF-MS/MSand pro-apoptotic activity of barbatic acid[J/OL]. Molecules, 2019, 24(12): 1-19[2020-01-10]. https://pubmed.ncbi.nlm.nih.gov/31216770/. DOI:10.3390/molecules24122270. |
35 |
JIN Y R , MA Y H , XIE W W , et al. UHPLC-Q-TOF-MS/MS-oriented characteristiccomponents dataset and multivariate statistical techniques for the holistic quality control of Usnea[J]. RSC Advances, 2018, 8 (28): 15487- 15500.
doi: 10.1039/C8RA00081F |
36 | DIN L B , ZAKARIA Z , SAMSUDIN M W , et al. Chemical profile of compounds from lichens of Bukit Larut, Peninsular Malaysia[J]. Sains Malaysiana, 2010, 39 (6): 901- 908. |
37 |
DÉVÉHAT F , TOMASI S , JOHN E , et al. Stictic acid derivatives from the lichen Usnea articulata and their antioxidant activities[J]. Journal of Natural Products, 2007, 70 (7): 1218- 1220.
doi: 10.1021/np070145k |
38 |
KATHIRGAMANATHAR S , WILLIAMS D E , ANDERSEN R J , et al. β-Orcinol depsidones from the lichen Usnea sp. from Sri Lanka[J]. Natural Product Research, 2005, 19 (7): 695- 701.
doi: 10.1080/14786410512331330639 |
39 |
MILLOT M , DIEU A , TOMASI S . Dibenzofurans and derivatives from lichens and ascomycetes[J]. Natural Product Reports, 2016, 33 (6): 801- 811.
doi: 10.1039/C5NP00134J |
40 | 靳菊情, 石娟, 葛萍, 等. 长松萝多糖对小鼠免疫功能的影响[J]. 中国药学杂志, 2003, 38 (6): 31- 33. |
JIN J Q , SHI J , GE P , et al. Effects of Usnea longissima polysaccharide on immunologic function in mice[J]. Chinese Pharmaceutical Journal, 2003, 38 (6): 31- 33. | |
41 |
边晓丽, 靳菊情, 丁东宁, 等. 长松萝多糖清除氧自由基和抗脂质过氧化反应的研究[J]. 中药材, 2002, 25 (3): 188- 189.
doi: 10.3321/j.issn:1001-4454.2002.03.018 |
BIAN X L , JIN J Q , DING D N , et al. Study on the scavenging action of polysaccharide of Usnea longissimi to oxygen radical and its anti-lipidperoxidation effects[J]. Journal of Chinese Medicinal Materials, 2002, 25 (3): 188- 189.
doi: 10.3321/j.issn:1001-4454.2002.03.018 |
|
42 |
GUPTA V K , VERMA S , GUPTA S , et al. Membrane-damaging potential of natural L-(-)-usnic acid in Staphylococcus aureus[J]. European Journal of Clinical Microbiology & Infectious Diseases, 2012, 31 (12): 3375- 3383.
doi: 10.1007/s10096-012-1706-7 |
43 |
MACIAG-DORSZYNSKA M , WEGRYN G , GUZOW-KRZEMINSKA B . Antibacterial activity of lichen secondary metabolite usnic acid is primarily caused by inhibition of RNA and DNA synthesis[J]. Fems Microbiology Letters, 2014, 353 (1): 57- 62.
doi: 10.1111/1574-6968.12409 |
44 | BAZARNOVA Y , POLITAEVA N , LYSKOVA N . Research for the lichen Usnea barbata metabolites[J]. Zeitschrift Fur Naturforschung Section C: A Journal of Biosciences, 2018, 73 (7/8): 291- 296. |
45 | DO T , NGUYEN T T H , HA T N , et al. Identification of anti-helicobacter pylori compounds from Usnea undulate[J]. Natural Product Communications, 2019, 14 (7): 1934578. |
46 |
BEHERA B C , VERMA N , SONONE A , et al. Antioxidant and antibacterial activities of lichen Usnea ghattensis in vitro[J]. Biotechnology Letters, 2005, 27 (14): 991- 995.
doi: 10.1007/s10529-005-7847-3 |
47 |
BILEN S , SIRTIYAH A M A , TERZI E . Therapeutic effects of beard lichen, Usnea barbata extract against Lactococcus garvieae infection in rainbow trout(Oncorhynchus mykiss)[J]. Fishand Shellfish Immunology, 2019, 87, 401- 409.
doi: 10.1016/j.fsi.2019.01.046 |
48 | 于大永, 郭秀磊, 高鸿雁, 等. 松萝酸对3种肿瘤细胞增殖和凋亡的影响[J]. 天津师范大学学报(自然科学版), 2020, 40 (4): 39- 43. |
YU D Y , GUO X L , GAO H Y , et al. Effects of usnic acid on the proliferation and apoptosis of three kinds of tumor cells[J]. Journal of Tianjin Normal University(Natural Science Edition), 2020, 40 (4): 39- 43. | |
49 | 郝凯华, 韩涛, 胡鹏斌. 松萝酸抑制小鼠H22肿瘤生长及作用机制研究[J]. 中国药师, 2019, 19 (1): 29- 32. |
HAO K H , HAN T , HU P B . Growth inhibitory effect of usnic acid on H22 tumor cells in mice and underlying mechanism[J]. China Pharmacist, 2019, 19 (1): 29- 32. | |
50 | MAULIDIYAH , CAHYANA A H , SUWARSO W P , et al. Isolation and structure elucidation of Eumitrin A1 from lichen Usnea blepharea Motyka and its cytotoxic activity[J]. International Journal of PharmTech Research, 2015, 8 (4): 782- 789. |
51 | MAULIDIYAH , AZIS T , SABARWATI S , et al. Isolation and identification of (-)-usnic acid compound from lichen Usnea sp. and its cytotoxic activity onmurine leukemia P388 cell[J]. Journal Ilmu Kefarmasian Indonesia, 2015, 13 (1): 40- 44. |
52 | TANG J Y, WU K H, WANG Y Y, et al.Methanol extract of Usnea barbata induces cell killing, apoptosis, and DNA damage against oral cancer cells through oxidative stress[J/OL]. Antioxidants(Basel), 2020, 9(8): 1-18[2020-01-10].https://pubmed.ncbi.nlm.nih.gov/32756347/.DOI: 10.3390/antiox9080694. |
53 | ZUGIC A, JEREMIC I, ISAKOVIC A, et al.Evaluation of anticancer and antioxidant activity of a commercially available CO2 supercritical extract of old man's beard(Usnea barbata)[J/OL]. Plos One, 2016, 11(1): e0146342.DOI: 10.1371/journal.pone.0146342. |
54 | TRUONG T L, AREE T, DO L T M, et al.Dimeric tetrahydroxanthones from the lichen Usnea aciculifera[J/OL]. Fitoterapia, 2019, 137: 1-7.[2020-01-20].https://doi.org/10.1016/j.fitote.2019.104194. |
55 |
AYDIN S , KINALIOG∨LU K , SÖKMEN B B . Antioxidant, anti-urease and anti-elastase activities of Usnea Longissima Ach[J]. Bangladesh Journal of Botany, 2018, 47 (3): 429- 435.
doi: 10.3329/bjb.v47i3.38680 |
56 | LONDONE-BAILON P, SANCHEZ-ROBINET C, ALVAREZ-GUZMAN G.In vitro antibacterial, antioxidant and cytotoxic activity of methanol-acetone extracts from Antarctic lichens(Usnea antarctica and Usnea aurantiaco-atra)[J/OL]. Polar Science, 2019, 22: 1-7[2020-01-20].https://doi.org/10.1016/j.polar.2019.08.003. |
57 |
BEHERA B C , VERMA N , SONONE , et al. Evaluation of antioxidant potential of the cultured mycobiont of a lichen Usnea ghattensis[J]. Phytotherapy Research, 2005, 19 (1): 58- 64.
doi: 10.1002/ptr.1607 |
58 |
PEYRAT-MAILLARD M N , CUVELIER M E , BERSET C . Antioxidant activity of phenolic compounds in 2, 2'-azobis (2-amidinopropane) dihydrochloride (AAPH)-induced oxidation: Synergistic and antagonistic effects[J]. Journal of the American Oil Chemists Society, 2003, 80 (10): 1007- 1012.
doi: 10.1007/s11746-003-0812-z |
59 | ORANA S , SAHINB S , SAHINTURKC P , et al. Antioxidant and antimicrobial potential, and HPLC analysis of stictic and usnic acids of three Usnea species from Uludag Mountain(Bursa, Turkey)[J]. Iranian Journal of Pharmaceutical Research, 2016, 15 (2): 527- 535. |
60 | AZIZUDDIN , IMRAN S , CHOUDHARY M I . In vivo anti-inflammatory and anti-platelet aggregation activities of longissiminone A, isolated from Usnea longissimi[J]. Pakistan Journal of Pharmaceutical Sciences, 2017, 30 (4): 1213- 1217. |
61 | 双荣, 韩晓静, 白梅荣, 等. 蒙药长松萝抗急性肝损伤活性部位的筛选研究[J]. 时珍国医国药, 2017, 28 (9): 2067- 2068. |
SHUANG R , HAN X J , BAI M R , et al. Screening of active parts of Mongolian medicine Usnea longissima against acute liver injury[J]. Lishizhen Medicine and Materia Medica Research, 2017, 28 (9): 2067- 2068. | |
62 | VIJAYAN P , RAGHU C , ASHOK G , et al. Antiviral activity of medicinal plants of Nilgiris[J]. Indian Journal of Medical Research, 2004, 120 (1): 24- 29. |
[1] | 陈虹霞, 周昊, 叶建中, 陶冉, 李文君, 王成章. 基质固相分散-气相色谱质谱联用法测定沉香中精油的化学成分[J]. 林产化学与工业, 2021, 41(3): 47-54. |
[2] | 程贤, 毕良武, 曾维星, 赵振东, 陈玉湘, 张笮晦. 基于UHPLC-QTOF MS的肉桂枝叶蒸油剩余物化学成分研究[J]. 林产化学与工业, 2020, 40(6): 50-60. |
[3] | 朱华,吴珽,房桂干,梁龙,朱北平,佘光辉. 五种海南常见速生材种制化学机械浆性能评估[J]. 林产化学与工业, 2020, 40(2): 63-68. |
[4] | 戴天歌,王亚凤,何瑞杰,李典鹏,黄永林. 饭甑青冈叶的化学成分研究[J]. 林产化学与工业, 2020, 40(2): 99-103. |
[5] | 陈景新,詹玉莹,陈燕,徐会有,邹双全,倪林. 圆齿野鸦椿枝条化学成分及其抗炎活性研究[J]. 林产化学与工业, 2019, 39(6): 88-94. |
[6] | 郑红富,廖圣良,范国荣,王宗德,陈尚钘,司红燕. 水蒸气蒸馏提取芳樟精油及其抑菌活性研究[J]. 林产化学与工业, 2019, 39(3): 108-114. |
[7] | 陈超, 虞宇翔, 韩利平, 邢靖晨, 常建民. 落叶松热解油防霉抑菌特性研究[J]. 林产化学与工业, 2018, 38(1): 81-86. |
[8] | 刘建群, 伍秋珊, 余昭芬. 雷公藤化学成分及其热稳定性研究[J]. 林产化学与工业, 2017, 37(2): 72-78. |
[9] | 周凌云, 余小红, 耿圆圆, 华燕. 小远志中口山酮类化学成分及生物活性研究[J]. 林产化学与工业, 2017, 37(2): 121-128. |
[10] | 欧阳婷, 杨琼梁, 颜红, 钟理峰, 杨仁义. 不同产地香茅挥发油的化学成分比较研究[J]. 林产化学与工业, 2017, 37(1): 141-148. |
[11] | 余小红, 李盼盼, 耿圆圆, 黄艳杰, 华燕. 小远志化学成分研究[J]. 林产化学与工业, 2017, 37(1): 149-154. |
[12] | 崔贺帅, 杨淑敏, 刘杏娥, 马建锋, 田根林. 杞柳的化学成分及其木质素微区分布的研究[J]. 林产化学与工业, 2016, 36(5): 120-126. |
[13] | 宋孝周, 苑一丹, 张强, 赵泾峰. 软木细胞壁结构及其主要化学成分研究进展[J]. 林产化学与工业, 2016, 36(5): 133-138. |
[14] | 卫强, 纪小影, 龙先顺, 李前荣, 尹浩. 红叶李叶化学成分及其体外抗氧化活性研究[J]. 林产化学与工业, 2015, 35(5): 116-122. |
[15] | 张妮, 穆淑珍, 王家胜, 孔琪, 余正文. 金雀花提取物正丁醇沉淀部分化学成分研究[J]. 林产化学与工业, 2015, 35(3): 121-124. |
阅读次数 | ||||||
全文 |
|
|||||
摘要 |
|
|||||