Chemical Compounds Isolated from <i>Pleione Bulbocodioides</i> and Their Bioactive Activities

Xiaorong ZHOU; Meijun YANG; Yuena YANG; Mingxin XU; Yaping CHEN; Huimin WANG; Meihong LI; Yupeng LI

doi:10.12259/j.issn.2095-610X.S20230528

Volume 44 Issue 5

May 2023

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Xiaorong ZHOU, Meijun YANG, Yuena YANG, Mingxin XU, Yaping CHEN, Huimin WANG, Meihong LI, Yupeng LI. Chemical Compounds Isolated from Pleione Bulbocodioides and Their Bioactive Activities[J]. Journal of Kunming Medical University, 2023, 44(5): 1-5. doi: 10.12259/j.issn.2095-610X.S20230528

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Xiaorong ZHOU, Meijun YANG, Yuena YANG, Mingxin XU, Yaping CHEN, Huimin WANG, Meihong LI, Yupeng LI. Chemical Compounds Isolated from Pleione Bulbocodioides and Their Bioactive Activities[J]. Journal of Kunming Medical University, 2023, 44(5): 1-5. doi: 10.12259/j.issn.2095-610X.S20230528

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Chemical Compounds Isolated from Pleione Bulbocodioides and Their Bioactive Activities

doi: 10.12259/j.issn.2095-610X.S20230528

1.
School of Pharmaceutical Science and Yunnan Key Laboratory of Pharmacology for Natural Products，Kunming Medical University，Kunming Yunnan 650500
2.
Pharmacy Department，The People's Hospital of Lincang，Lincang Yunnan 677000
3.
Women’s Federation of Kunming Medical University ，Kunming Yunnan 650500，China

Received Date: 2023-01-09
Available Online: 2023-05-11
Publish Date: 2023-05-25

Abstract

Abstract

Objective To study the chemical constituents from the herbs of Pleione bulbocodioides and find theirs antitumor bioactive compounds. Methods The constituents were extracted by ethyl acetate and isolated by CC and Sephadex LH-20. Their structures were identified by spectroscopic analysis （¹H NMR, ¹³CNMR and EIMS）. The antitumor activity of the constituents was studied by MTT assay in vitro. Results Twelve compouds were obtained and identified as 4-methoxy-2, 7-dihydroxyphenan- -threne （1）, （8R）-4, 5′-dihydroxy-8-hydroxymehtyl-3′-methoxydeoxybenzoin （2）, 4, 7-dihydroxy-2-methoxy-9, 10-dihydrophenanthrene （3） 2-hydroxy-4, 7-dimethoxy-phenanthrene （4） Ursolic acid （5） β-sitosterol （6） 2-hydroxy-4, 7-dimethoxy-9, 10-dihydrophenanthrene （7） 4- （Benzofuranyl）-phenol （8） Flavanthrinin （9） Coelonin （10） CH₃ （CH₂）₂₇OH （11） and 4-dimethoxy benzaldehyde （12）. The results of anti-tumor activity test of compounds 1～5 showed that 2 expressed good inhibitory activity on SKOV-3 cell line. Conclusion Compounds 2, 5, 8, 11 have been isolated from the herbs for the first time and IC₅₀ of 2 on SKOV-3 cell line is 12.79 μM.
- Pleione bulbocodioides,
- Chemical constituents,
- Bioactive activity

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References(19)

References

[1]	中国科学院中国植物志编辑委员会. 《中国植物志》第十八卷[M]. 北京: 科学出版社, 1999: 364, 377.
[2]	李丹平,陈雨洁,万定荣,等. 鄂西土家族常用兰科植物药[J]. 中南民族大学学报(自然科学版),2009,28(1):52-54.
[3]	国家药典委员会. 中华人民共和国药典一部[M]. 北京: 中国医药科技出版社, 2015: 32-33.
[4]	Teponno R B,Tapondjou A L,Djoukeng J D,et al. Isolation and NMR assignment of a pennogenin glycoside from Dioscorea bulbifera[J]. Natural Product Sciences,2006,12(1):62-66.
[5]	Majumder P L,Lahiri S. Lusianthrin and lusianthridin,two stilbenoids from the orchid Lusia indivisa[J]. Phytochemistry,1990,29(2):621-624. doi: 10.1016/0031-9422(90)85129-4
[6]	Blitzke T,Masaoud M,Jürgen S. Constituents of Eulophia petersii[J]. Fitoterapia,2000,71(5):593-594. doi: 10.1016/S0367-326X(00)00169-6
[7]	Cheng J,Yi X,Chen H,et al. Anti-inflammatory phenylpropanoids and phenolics from Ficus hirta Vahl[J]. Fitoterapia,2017,121(9):229-234.
[8]	Guo X Y,Wang J,Wang N L,et al. New stilbenoids from Pholidota Yunnanensis and their inhibitory effects on nitric oxide production[J]. Chemical & Pharmaceutical Bulletin,2006,54(1):21-25.
[9]	Xue Z,Li S,Wang S,et al. Mono-,Bi-,and triphenanthrenes from the tubers of Cremastra appendiculata[J]. Journal of Natural Products,2006,69(6):907. doi: 10.1021/np060087n
[10]	Yang H,Sung S H,Kim Y C. Antifibrotic phenanthrenes of Dendrobium nobile[J]. Journal of Natural Products,2007,70(12):1925-1929. doi: 10.1021/np070423f
[11]	Zhang P,Yang Y,Zheng X,et al. Synthesis of 2-Phenylbenzofuran derivatives and selective binding activities on estrogen receptor[J]. Chemical & Pharmaceutical Bulletin,2012,60(2):270-274.
[12]	Majumder P L,Banerjee S. Two stilbenoids from the orchid Eria flava[J]. Phytochemistry,1990,29(9):3052-3055. doi: 10.1016/0031-9422(90)87141-G
[13]	Majumder P,Laha S,Datta N. Coelonin,A 9,10-dihydrophenanthrene from the orchids Coelogyne ochracea and Coelogyne elata[J]. Phytochemistry,1982,21(2):478-480. doi: 10.1016/S0031-9422(00)95300-7
[14]	Qin Q,Ling Z,Han S Z,et al. Study on chemical constituents from the petroleum ether extracts of Sauropus rostratus[J]. Journal of Pharmaceutical Sciences,2015,30(3):269-271.
[15]	郭怀宇,王国凯,刘吉开,等. 微酸多年卧孔菌化学成分的研究[J]. 中成药,2018,40(1):129-133.
[16]	Han S,Wang C,Cui B,et al. Hepatoprotective activity of glucosyloxybenzyl succinate derivatives from the pseudobulbs of Pleione bulbocodioides[J]. Phytochemistry,2019,157(1):71-81.
[17]	郝岗平,郝佳丽,李悦,等. 独蒜兰乙酸乙酯萃取物通过内源性线粒体通路诱导白血病K562细胞和HL-60细胞凋亡[J]. 中国病理生理杂志,2018,34(5):769-777.
[18]	李媛,李玉鹏,郑金蓉,等. 云南独蒜兰菲和联苄类化学成分的研究(英文)[J]. 昆明医科大学学报,2021,42(2):29-32.
[19]	王静,肖秋肖,周祖英,等. 基原为云南独蒜兰的山慈菇的化学成分鉴定与分析[J]. 中国药房,2022,33(10):1165-1171.

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