Expression Analysis of Two Chemical-Types of <i>Artemisia Annua</i> L. Terpenoids and Their Related Genes

WANG Ting-ting; DAI Shi-lin; LIU Chan-chan; JIANG Zheng; WU Qi-nan

doi:10.14148/j.issn.1672-0482.2022.0770

Volume 38 Issue 9

Sep. 2022

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WANG Ting-ting, DAI Shi-lin, LIU Chan-chan, JIANG Zheng, WU Qi-nan. Expression Analysis of Two Chemical-Types of Artemisia Annua L. Terpenoids and Their Related Genes[J]. Journal of Nanjing University of traditional Chinese Medicine, 2022, 38(9): 770-779. doi: 10.14148/j.issn.1672-0482.2022.0770

Citation:

WANG Ting-ting, DAI Shi-lin, LIU Chan-chan, JIANG Zheng, WU Qi-nan. Expression Analysis of Two Chemical-Types of Artemisia Annua L. Terpenoids and Their Related Genes[J]. Journal of Nanjing University of traditional Chinese Medicine, 2022, 38(9): 770-779. doi: 10.14148/j.issn.1672-0482.2022.0770

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Expression Analysis of Two Chemical-Types of Artemisia Annua L. Terpenoids and Their Related Genes

doi: 10.14148/j.issn.1672-0482.2022.0770

WANG Ting-ting^{1, 2
,},
DAI Shi-lin^{1, 2},
LIU Chan-chan^{1, 2},
JIANG Zheng¹,
WU Qi-nan^{1, 2, 3
,
,}

1.
School of Pharmacy, Nanjing University of Chinese Medicine, Nanjing 210023, China
2.
Collaborative Innovation Center of Chinese Medicinal Resources Industrialization, Nanjing 210023, China
3.
National and Local Collaborative Engineering Center of Chinese Medicinal Resources Industrialization and Formulae Innovative Medicine, Nanjing 210023, China

Received Date: 2022-01-22
Available Online: 2022-09-19

Abstract

Abstract

OBJECTIVE To investigate the differential metabolites of two chemical-types of Artemisia annua and their possible causes by analyzing the data of terpenoid metabolites and their transcriptome of two chemical-types of Artemisia annua. METHODS The seeds of Artemisia annua were collected from Xuyi County, Jiangsu Province, and Zhongmou County, Henan Province, in China, and grown under the same conditions. The volatile components of Artemisia annua were analyzed by headspace-gas chromatography-triple quadrupole mass spectrometry (HS-GC-QQQ-MS/MS), non-targeted analysis of the differential metabolites of 2 chemical-types of Artemisia annua were performed by ultra-fast liquid chromatography-triple quadrupole-time of flight tandem mass spectrometry (UFLC-Triple TOF-MS/MS), and the expression of the biosynthetic genes of the volatile components was analyzed by transcriptome sequencing. RESULTS Based on the typing of volatile components, Artemisia annua from Xuyi County, Jiangsu Province was classified as artemisia ketone type, and Artemisia annua from Zhongmou County, Henan Province was classified as camphor type. The differential metabolites detected by UFLC-Triple TOF-MS/MS were significantly up-regulated in sesquiterpene, triterpene, and diterpene biosynthesis pathways by Kyoto encyclopedia of genes and genomes (KEGG) database analysis for artemisia ketone type and camphor types of Artemisia annua, respectively. The 2-methyl-D-erythritol-4-phosphate (MEP) pathway leading to terpene skeleton biosynthesis and the mevalonate (MVA) pathway annotated 23 candidate genes for 11 key enzymes that were significantly differential in the transcriptome data. In the monoterpene synthesis pathway, 10 candidate genes were detected for 1, 8-cineole synthase (TPS-Cin). In addition, two borneol dehydrogenase candidates were found to be highly expressed in camphor-type Artemisia annua, and three Artemisia annua alcohol dehydrogenase (ADH2) candidates were highly expressed in artemisia ketone-type Artemisia annua. CONCLUSION This study provides scientific data to reveal the molecular mechanism of Artemisia annua chemical-types formation.
- Artemisia annua L.,
- volatile components,
- chemical type,
- terpenoids,
- biosynthesis

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References(34)

References

[1]	ROVESTI P. Essential oils of some chemotypes of aromatic Eritrean labiates[J]. Pharm Weekbl, 1957, 92(23): 843-845.
[2]	智亚楠, 陈月华, 马宇明, 等. 河南省黄花蒿挥发油的组分分析及抑菌作用测定[J]. 河南农业科学, 2016, 45(12): 105-109. https://www.cnki.com.cn/Article/CJFDTOTAL-HNNY201612022.htm ZHI YN, CHEN YH, MA YM, et al. The chemical constituents and antifungal activity of essential oil from Artemisia annua linn in Henan Province[J]. J Henan Agric Sci, 2016, 45(12): 105-109. https://www.cnki.com.cn/Article/CJFDTOTAL-HNNY201612022.htm
[3]	SANTOMAURO F, DONATO R, PINI G, et al. Liquid and vapor-phase activity of Artemisia annua essential oil against pathogenic Malassezia spp[J]. Planta Med, 2018, 84(3): 160-167. doi: 10.1055/s-0043-118912
[4]	BILIA AR, SANTOMAURO F, SACCO C, et al. Essential oil of Artemisia annua L. : An extraordinary component with numerous antimicrobial properties[J]. Evid Based Complement Alternat Med, 2014, 2014: 159819.
[5]	赖镇源. 青蒿挥发油抗痤疮病原体及解热作用的实验研究[D]. 广州: 广州中医药大学, 2005. LAI ZY. The experimental study of anti-acne pathogeny and defervescence of Artemisia naphtha[D]. Guangzhou: Guangzhou University of Chinese Medicine, 2005.
[6]	RASHID S, RATHER MA, SHAH WA, et al. Chemical composition, antimicrobial, cytotoxic and antioxidant activities of the essential oil of Artemisia indica Willd[J]. Food Chem, 2013, 138(1): 693-700. doi: 10.1016/j.foodchem.2012.10.102
[7]	SOKTOEVA TE, RYZHOVA GL, DYCHKO KA, et al. Artemisinin content in Artemisia annua L. extracts obtained by different methods[J]. Russ J Bioorg Chem, 2013, 39(7): 761-764. doi: 10.1134/S1068162012070199
[8]	ZHIGZHITZHAPOVA SV, DYLENOVA EP, GULYAEV SM, et al. Composition and antioxidant activity of the essential oil of Artemisia annua L[J]. Nat Prod Res, 2020, 34(18): 2668-2671. doi: 10.1080/14786419.2018.1548461
[9]	FENG XC, CAO SJ, QIU F, et al. Traditional application and modern pharmacological research of Artemisia annua L[J]. Pharmacol Ther, 2020, 216: 107650. doi: 10.1016/j.pharmthera.2020.107650
[10]	张小波, 赵宇平, 黄晓巍, 等. 青蒿道地药材研究综述[J]. 中国中药杂志, 2016, 41(11): 2015-2018. https://www.cnki.com.cn/Article/CJFDTOTAL-ZGZY201611007.htm ZHANG XB, ZHAO YP, HUANG XW, et al. Review on study of Dao-di herbs Artemisiae Annuae Herba[J]. China J Chin Mater Med, 2016, 41(11): 2015-2018. https://www.cnki.com.cn/Article/CJFDTOTAL-ZGZY201611007.htm
[11]	朱亚莹. 热毒宁注射液原料药青蒿的品质评价研究[D]. 南京: 南京中医药大学, 2020. ZHU YY. Study on quality evaluation of artemisiae annuae herba, the raw material of reduning injection[D]. Nanjing: Nanjing University of Chinese Medicine, 2020.
[12]	TSUGAWA H, CAJKA T, KIND T, et al. MS-DIAL: Data-independent MS/MS deconvolution for comprehensive metabolome analysis[J]. Nat Methods, 2015, 12(6): 523-526. doi: 10.1038/nmeth.3393
[13]	PANG ZQ, CHONG J, ZHOU GY, et al. MetaboAnalyst 5.0: Narrowing the gap between raw spectra and functional insights[J]. Nucleic Acids Res, 2021, 49(W1): W388-W396. doi: 10.1093/nar/gkab382
[14]	CHEN CJ, CHEN H, ZHANG Y, et al. TBtools: An integrative toolkit developed for interactive analyses of big biological data[J]. Mol Plant, 2020, 13(8): 1194-1202. doi: 10.1016/j.molp.2020.06.009
[15]	SHEN Q, ZHANG LD, LIAO ZH, et al. The genome of Artemisia annua provides insight into the evolution of Asteraceae family and artemisinin biosynthesis[J]. Mol Plant, 2018, 11(6): 776-788. doi: 10.1016/j.molp.2018.03.015
[16]	LOVE MI, HUBER W, ANDERS S. Moderated estimation of fold change and dispersion for RNA-seq data with DESeq2[J]. Genome Biol, 2014, 15(12): 550. doi: 10.1186/s13059-014-0550-8
[17]	UMLAUF D, ZAPP J, BECKER H, et al. Biosynthesis of the irregular monoterpene Artemisia ketone, the sesquiterpene germacrene D and other isoprenoids in Tanacetum vulgare L. (Asteraceae)[J]. Phytochemistry, 2004, 65(17): 2463-2470. doi: 10.1016/j.phytochem.2004.08.019
[18]	李洪梅, 黄璐琦, 周爱香, 等. 不同化学型樟对大鼠佐剂性关节炎模型的影响[J]. 中国中药杂志, 2009, 34(24): 3251-3254. doi: 10.3321/j.issn:1001-5302.2009.24.026 LI HM, HUANG LQ, ZHOU AX, et al. Study on antiinflammatory effect of different chemotype of Cinnamomum camphora on rat arthritis model induced by Freund's adjuvant[J]. China J Chin Mater Med, 2009, 34(24): 3251-3254. doi: 10.3321/j.issn:1001-5302.2009.24.026
[19]	MONTERO-VILLEGAS S, CRESPO R, RODENAK-KLADNIEW B, et al. Cytotoxic effects of essential oils from four Lippia alba chemotypes in human liver and lung cancer cell lines[J]. J Essent Oil Res, 2018, 30(3): 167-181. doi: 10.1080/10412905.2018.1431966
[20]	ACIMOVICM, JEREMICJS, TODOSIJEVIC M, et al. Comparative study of the essential oil and hydrosol composition of sweet wormwood (Artemisia annua L. ) from Serbia[J]. Chem Biodivers, 2022, 19(3): e202100954.
[21]	JUTEAU F, MASOTTI V, BESSIERE JM, et al. Antibacterial and antioxidant activities of Artemisia annua essential oil[J]. Fitoterapia, 2002, 73(6): 532-535. doi: 10.1016/S0367-326X(02)00175-2
[22]	CAVAR S, MAKSIMOVIC M, VIDIC D, et al. Chemical composition and antioxidant and antimicrobial activity of essential oil of Artemisia annua L. from Bosnia[J]. Ind Crops Prod, 2012, 37(1): 479-485. doi: 10.1016/j.indcrop.2011.07.024
[23]	SUGA T, SHISHIBORI T, KOTERA K, et al. The biosynthesis of a non-head to tail monoterpene, Artemisia ketone[J]. Chem Lett, 1972, 1(7): 533-534. doi: 10.1246/cl.1972.533
[24]	ALLEN KG, BANTHORPE DV, CHARLWOOD BV, et al. Biosynthesis of Artemisia ketone in higher plants[J]. Phytochemistry, 1977, 16(1): 79-83. doi: 10.1016/0031-9422(77)83018-5
[25]	吕宗友. 抑制青蒿素合成竞争支路及水杨酸调控青蒿中青蒿素合成的研究[D]. 上海: 上海交通大学, 2016. LYU ZY. The study of regulating artemisinin biosynthesis in Artemisia annua by branch pathway blocking and salicylic acid[D]. Shanghai: Shanghai Jiao Tong University, 2016.
[26]	POLICHUK DR, ZHANG YS, REED DW, et al. A glandular trichome-specific monoterpene alcohol dehydrogenase from Artemisia annua[J]. Phytochemistry, 2010, 71(11/12): 1264-1269.
[27]	YAMAGUCHI S. Gibberellin metabolism and its regulation[J]. Annu Rev Plant Biol, 2008, 59: 225-251. doi: 10.1146/annurev.arplant.59.032607.092804
[28]	DAVIERE JM, ACHARD P. Gibberellin signaling in plants[J]. Development, 2013, 140(6): 1147-1151. doi: 10.1242/dev.087650
[29]	COLEBROOK EH, THOMAS SG, PHILLIPS AL, et al. The role of gibberellin signalling in plant responses to abiotic stress[J]. J Exp Biol, 2014, 217(Pt 1): 67-75.
[30]	DU Q, LI CL, LI DQ, et al. Genome-wide analysis, molecular cloning and expression profiling reveal tissue-specifically expressed, feedback-regulated, stress-responsive and alternatively spliced novel genes involved in gibberellin metabolism in Salvia miltiorrhiza[J]. BMC Genomics, 2015, 16: 1087. doi: 10.1186/s12864-015-2315-5
[31]	MA TY, GAO H, ZHANG D, et al. Transcriptome analyses revealed the ultraviolet B irradiation and phytohormone gibberellins coordinately promoted the accumulation of artemisinin in Artemisia annua L[J]. Chin Med, 2020, 15: 67. doi: 10.1186/s13020-020-00344-8
[32]	张铁军, 王于方, 刘丹, 等. 天然药物化学史话: 青蒿素——中药研究的丰碑[J]. 中草药, 2016, 47(19): 3351-3361. doi: 10.7501/j.issn.0253-2670.2016.19.001 ZHANG TJ, WANG YF, LIU D, et al. Historical story on natural medicinal chemistry: Artemisinin, a milestone of traditional Chinese medicine study[J]. Chin Tradit Herb Drugs, 2016, 47(19): 3351-3361. doi: 10.7501/j.issn.0253-2670.2016.19.001
[33]	彭琼辉, 刘琼, 刘成高, 等. 热毒宁注射液治疗AECOPD的疗效及对TLR4/NF-κB炎症信号通路的影响[J]. 湖南中医杂志, 2021, 37(12): 1-4, 20. https://www.cnki.com.cn/Article/CJFDTOTAL-HNZO202112001.htm PENG QH, LIU Q, LIU CG, et al. Clinical effect of Reduning injection in treatment of acute exacerbation of chronic obstructive pulmonary disease and its effect on the Toll-like receptor 4/nuclear factor-kappa B inflammatory signaling pathway[J]. Hunan J Tradit Chin Med, 2021, 37(12): 1-4, 20. https://www.cnki.com.cn/Article/CJFDTOTAL-HNZO202112001.htm
[34]	罗杰平, 黄胜贤, 陈丽珍, 等. 甘草酸苷联合热毒宁治疗手足口病患儿的临床疗效及对免疫反应的影响[J]. 川北医学院学报, 2022, 37(1): 35-38. https://www.cnki.com.cn/Article/CJFDTOTAL-NOTH202201008.htm LUO JP, HUANG SX, CHEN LZ, et al. Clinical efficacy of Reduning combined with glycyrrhizin in the treatment of children with hand-foot-mouth disease and its effect on inflammatory immune reaction[J]. J North Sichuan Med Coll, 2022, 37(1): 35-38. https://www.cnki.com.cn/Article/CJFDTOTAL-NOTH202201008.htm