日本蛇根草化学成分的提取分离及其抗氧化活性研究

doi:10.3969/j.issn.0253-2417.2023.04.010

Abstract

Abstract:

The Japanese snake root(Ophiorhoza japonica Bl.) was used as the raw material, soaked in anhydrous ethanol and then extracted by organic solvents with different polarities. Based on the preliminary analysis of the antioxidant activities of different extraction parts, the chemical components of each extraction parts were isolated and purified using chromatographic separation techniques including silica gel and Sephadex LH-20 column chromatography, in order to disclose the antioxidant active substances basis of the this plant. The results showed that each extraction part of petroleum ether, ethyl acetate and chloroform from O. japonica Bl. exhibited antioxidant potencies. Among them, the chloroform extraction displayed best activities, with scavenging rates against 1, 1-diphenyl-2-picrylhydrazyl free radical(DPPH·) and 2, 2′-azinobis-3-ethylbenzthiazoline-6-sulfonic acid free radical(·ABTS⁺) of 86% and 89%, respectively. Subsequently, ten compounds were separated and identified as(E)-3-((9H-pyrido[3, 4-b] indol-1-yl) methyl)-2-ethylidenepentane-1, 5-diol(1, deppeaninol), 6-hydroxyharman(2), harman base(3), p-hydroxy benzaldehyde(4), scopoletin(5), 3-oxo-α-ionol(6), loliolide(7), β-sitosterol(8), 3-epi-pomolic acid(9) and 1-monoolein(10). Among them, compounds 1, 4, 6, 7, 9 and 10 were identified from the genus of Ophiorrhiza for the first time. The results of free radical scavenging assays showed that compound 2 exhibited significant antioxidant activity with the half inhibitory concentration(IC₅₀) of DPPH· and ·ABTS⁺ were 0.209 and 0.212 mmol/L, respectively.

Key words: Ophiorrhiza japonica Bl., antioxidant activities, extraction and isolation, chemical constituents, structure elucidation

CLC Number:

TQ35

Mengjuan XU, Qing BU, Hongyang CHEN, Min ZHANG, Lei WU, Linfu LIANG. Extraction and Isolation of Chemical Constituents from Ophiorrhiza japonica Bl. and Their Antioxidant Activities[J]. Chemistry and Industry of Forest Products, 2023, 43(4): 67-73.

Figures/Tables 2

References 24

1	云博, 吴景东. 氧化应激与相关疾病及其作用机制[J]. 沈阳医学院学报, 2018, 20 (3): 272- 276.
	YUN B , WU J D . Oxidative stress and related diseases and their mechanisms[J]. Journal of Shenyang Medical College, 2018, 20 (3): 272- 276.
2	朱菁, 李春保, 徐幸莲, 等. 膳食蛋白、机体抗氧化调节与健康的关系研究进展[J]. 食品工业科技, 2017, 38 (21): 335- 341.
	ZHU J , LI C B , XU X L , et al. Research progress in the associations of dietary proteins with antioxidant regulation of the body and human health[J]. Science and Technology of Food Industry, 2017, 38 (21): 335- 341.
3	左玉, 张国娟, 惠芳, 等. 食品抗氧化剂的研究进展[J]. 粮食与油脂, 2018, 31 (5): 1- 3. doi: 10.3969/j.issn.1008-9578.2018.05.001
	ZUO Y , ZHANG G J , HUI F , et al. Research progress of food antioxidants[J]. Cereals & Oils, 2018, 31 (5): 1- 3. doi: 10.3969/j.issn.1008-9578.2018.05.001
4	何昶毅, 高潇涵, 李泽文, 等. 向日葵盘精油的化学成分及抗氧化活性[J]. 生物质化学工程, 2020, 54 (1): 43- 48. doi: 10.3969/j.issn.1673-5854.2020.01.007
	HE C Y , GAO X H , LI Z W , et al. Compositions of the essential oil of Helianthus annuus head and its antioxidant activities[J]. Biomass Chemical Engineering, 2020, 54 (1): 43- 48. doi: 10.3969/j.issn.1673-5854.2020.01.007
5	中国科学院中国植物志编辑委员会. 中国植物志: 第71卷. 第1分册[M]. 北京: 科学出版社, 1999: 110- 174.
	Flora of China Editorial Committee . Flora of China: Volume 71. Fascicle 1[M]. Beijing: Science Press, 1994: 110- 174.
6	黄艳丽. 滇南蛇根草和美丽蛇根草的化学成分研究[D]. 北京: 中国科学院研究生院, 2008.
	HUANG Y L. Chemical constituents of Ophiorrhiza austroyunnanensis and Ophiorrhiza rosea[D]. Beijing: Graduate University of Chinese Acadamy of Sciences, 2008.
7	LEKSHMI G M , GANGAPRASAD A . Phytochemical analysis of Ophiorrhiza pectinata ARN.(Rubiaceae) a potential anticancer plant[J]. Journal of Pharmacognosy and Phytochemistry, 2019, 8 (3): 2313- 2315.
8	ADNAN M, CHY M N U, KAMAL A T M M, et al. Investigation of the biological activities and characterization of bioactive constituents of Ophiorrhiza rugosa var. Prostrata(D. Don) & Mondal leaves through in vivo, in vitro, and in silico approaches[J/OL]. Molecules, 2019, 24(7): 1367[2022-03-11]. https://doi.org/10.3390/molecules24071367.
9	ONOZAWA T , KITAJIMA M , KOGURE N , et al. Asymmetric total synthesis and evaluation of antitumor activity of ophiorrhisine A and its derivatives[J]. The Journal of Organic Chemistry, 2018, 83 (24): 15312- 15322. doi: 10.1021/acs.joc.8b02554
10	贾敏如, 张艺. 中国民族药辞典[M]. 北京: 中国医药科技出版社, 2016: 567.
	JIA M R , ZHANG Y . Dictionnary of Chinese Ethinic Medicine[M]. Beijing: China Medicine Science and Technology Press, 2016: 567.
11	SHI B B , AI H L , DUAN K T , et al. Ophiorrhines F and G, key biogenetic intermediates of ophiorrhine alkaloids from Ophiorrhiza japonica and their immunosuppressant activities[J]. Journal of Natural Products, 2022, 85 (2): 453- 457. doi: 10.1021/acs.jnatprod.1c01085
12	FENG T , DUAN K T , HE S J , et al. Ophiorrhines A and B, two immunosuppressive monoterpenoid indole alkaloids from Ophiorrhiza japonica[J]. Organic Letters, 2018, 20 (24): 7926- 7928. doi: 10.1021/acs.orglett.8b03489
13	朱丽丽. 白背清风藤的化学成分研究[D]. 长沙: 中南林业科技大学, 2021.
	ZHU L L. Study on the chemical constituents of Sabia discolor Dunn[D]. Changsha: Central South University of Forestry and Technology, 2021.
14	KAN FAN C , ZUANAZZI J A , QUIRION J C , et al. Deppeaninol, a new β-carboline alkaloid from Deppea blumenaviensis(Rubiaceae)[J]. Natural Product Letters, 1995, 7 (4): 317- 321. doi: 10.1080/10575639508043228
15	HERATH W , MIKELL J R , FERREIRA D , et al. Microbial metabolites of harman alkaloids[J]. Chemical & Pharmaceutical Bulletin, 2003, 51 (6): 646- 648.
16	SEKI H , HASHIMOTO A , HINO T . The ¹H-and ¹³C-nuclear magnetic resonance spectra of harman.Reinvestigation of the assignments by one- and two-dimensional methods[J]. Chemical & Pharmaceutical Bulletin, 1993, 41 (6): 1169- 1172.
17	SHUBINA L K , MAKAR'EVA T N , DENISENKO V A , et al. 4-Hydroxybenzaldehyde from the Baikal sponge Lubomirskia baicalensis[J]. Chemistry of Natural Compounds, 2005, 41 (1): 93- 94. doi: 10.1007/s10600-005-0084-0
18	LI Y H , LUO F , PENG S L , et al. A new dihydroisocoumarin from the rhizomes of Notopterygium forbesii[J]. Natural Product Research, 2006, 20 (9): 860- 865. doi: 10.1080/14786410500463320
19	YAO D , JIN M , ZHANG C , et al. Chemical constituents of the leaves of Juglans mandshurica[J]. Chemistry of Natural Compounds, 2016, 52 (1): 93- 95. doi: 10.1007/s10600-016-1555-1
20	CHEN B N , YANG G E , LI J K , et al. Cytotoxic constituents from Viscum coloratum[J]. Chemistry of Natural Compounds, 2009, 45 (4): 547- 549. doi: 10.1007/s10600-009-9361-7
21	LI W H , CHANG S T , CHANG S C , et al. Isolation of antibacterial diterpenoids from Cryptomeria japonica bark[J]. Natural Product Research, 2008, 22 (12): 1085- 1093. doi: 10.1080/14786410802267510
22	CHIRIBOGA X , GILARDONI G , MAGNAGHI I , et al. New anthracene derivatives from Coussarea macrophylla[J]. Journal of Natural Products, 2003, 66 (7): 905- 909. doi: 10.1021/np030066i
23	肖朝江, 周星利, 韩冰洋, 等. 腺花香茶菜地下根茎化学成分研究[J]. 天然产物研究与开发, 2013, 25 (3): 333- 337. doi: 10.3969/j.issn.1001-6880.2013.03.010
	XIAO C J , ZHOU X L , HAN B Y , et al. Chemical constituents from rhizome of Isodon adenantha[J]. Natural Product Research and Development, 2013, 25 (3): 333- 337. doi: 10.3969/j.issn.1001-6880.2013.03.010
24	刘文武, 蒋晓文, 张帅, 等. 羌活中香豆素类化学成分及其抗氧化活性研究[J]. 中草药, 2019, 50 (6): 1310- 1315.
	LIU W W , JIANG X W , ZHANG S , et al. Chemical constituents of coumarins compounds from Notopterygium incisum and their anti-oxidant activity[J]. Chinese Traditional and Herbal Drugs, 2019, 50 (6): 1310- 1315.

[1]	Fengcheng HU, Rui HAN, Cong GUO, Jiangjiang TANG, Jinming GAO. Chemical Constituents of the Leaves of Eucommia ulmoides and Its Neuroprotective Activity [J]. Chemistry and Industry of Forest Products, 2023, 43(3): 9-15.
[2]	Bin CAO, Jun CHI, Pei WANG, Anqi XIE, Liping DAI, Zhimin WANG. Identification of the Chemical Components in the Milky Sap of Euphorbia helioscopia L. by UPLC-Oribtrap-Exploris-120-MS/NMR [J]. Chemistry and Industry of Forest Products, 2023, 43(3): 49-60.
[3]	Liangjie TANG, Wei LUO, Hulan CHEN. Research Progress of Chemical Constituents and Pharmacological Effects of Euscaphis Plants [J]. Chemistry and Industry of Forest Products, 2023, 43(2): 153-170.
[4]	Wenjuan ZHOU, Yuanwang QIU, Jiayan BEI, Yuzhou WANG, Shiqi RUAN, Lin NI. Separation and Identification of Aqueous Extracts of Cinnamomum longe-paniculatum Leaves and Their Anti-hepatocellular-cancer Activity [J]. Chemistry and Industry of Forest Products, 2022, 42(6): 1-10.
[5]	Meng LIANG, Yafeng WANG, Taojie XIE, Hongjie ZHU, Yonglin HUANG. Chemical Constituents and Tyrosinase Inhibitory Activities from the Pink Flowers of Bauhinia variegata L. [J]. Chemistry and Industry of Forest Products, 2022, 42(4): 68-74.
[6]	Hongdan ZHUANG, Fengqiu LI, Ruilong LUO, Liqin WANG. Research Progress of Chemical Constituents and Pharmacological Activity of Elaeagnus Plants [J]. Chemistry and Industry of Forest Products, 2021, 41(4): 135-146.
[7]	Hongxia CHEN, Hao ZHOU, Jianzhong YE, Ran TAO, Wenjun LI, Chengzhang WANG. Matrix Solid-phase Dispersion Combined with GC-MS for Determination of Chemical Constituents of Essential Oil in Agarwood [J]. Chemistry and Industry of Forest Products, 2021, 41(3): 47-54.
[8]	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.
[9]	Xian CHENG, Liangwu BI, Weixing ZENG, Zhendong ZHAO, Yuxiang CHEN, Zuohui ZHANG. Chemical Constituents of Distillation Residues from Cinnamon Twigs and Leaves by Using UHPLC-QTOF MS [J]. Chemistry and Industry of Forest Products, 2020, 40(6): 50-60.
[10]	Jingxin CHEN,Yuying ZHAN,Yan CHEN,Huiyou XU,Shuangquan ZOU,Lin NI. Chemical Constituents and Anti-inflammatory Activity from the Twigs of Euscaphis konishii Hayata [J]. Chemistry and Industry of Forest Products, 2019, 39(6): 88-94.
[11]	ZHOU Lingyun, LU Bin, YU Xiaohong, ZHANG Mingrui, HUA Yan. Antioxidant Activity of Sesquiterpenes from Cryptoporus volvatus (Peck) Hubbard [J]. Chemistry and Industry of Forest Products, 2018, 38(1): 73-80.
[12]	WEI Qiang, JI Xiao-ying, LONG Xian-shun, LI Qian-rong, YIN Hao. Chemical Constituents Extracted from Leaves of Prunus cerasifera Ehrh.cv. Atropurpurea Jacg. and Their Antioxidant Activities in vitro [J]. Chemistry and Industry of Forest Products, 2015, 35(5): 116-122.
[13]	ZHANG Ni, MU Shu-zhen, WANG Jia-sheng, KONG Qi, YU Zheng-wen. Chemical Constituents of n-Butanol-insoluble Portion from Parochetus communis Buch.Extract [J]. Chemistry and Industry of Forest Products, 2015, 35(3): 121-124.
[14]	JIN Xiao-xi, HE Pei, JIANG Yan, LI Hui-jun. Chemical Constituents from the Stems of Viburnum dilatatum Thunb. var. fulvotomentosum (Hsu) Hsu [J]. Chemistry and Industry of Forest Products, 2014, 34(1): 97-100.
[15]	WAN Chun-peng;ZHOU Shou-ran. Chemical Constituents of Acer rubrum L. and Their Antioxidant Activities [J]. , 2013, 33(5): 93-96.

Extraction and Isolation of Chemical Constituents from Ophiorrhiza japonica Bl. and Their Antioxidant Activities

RichHTML

PDF (PC)

Knowledge

Abstract

Cite this article

share this article

Figures/Tables 2

References 24

Related Articles 15

Recommended Articles

Metrics

Comments