Chemical Compounds Isolated from <i>Pleione maculata</i> and Their Bioactive Activity

Yupeng LI; Xinglong CHEN; Shengxing YUAN; Yajuan CHEN; Rongping ZHANG

doi:10.12259/j.issn.2095-610X.S20230312

Volume 44 Issue 3

Mar. 2023

Turn off MathJax

Article Contents

Article Navigation > Journal of Kunming Medical University > 2023 > 44(3): 1-6

Yupeng LI, Xinglong CHEN, Shengxing YUAN, Yajuan CHEN, Rongping ZHANG. Chemical Compounds Isolated from Pleione maculata and Their Bioactive Activity[J]. Journal of Kunming Medical University, 2023, 44(3): 1-6. doi: 10.12259/j.issn.2095-610X.S20230312

Citation:

Yupeng LI, Xinglong CHEN, Shengxing YUAN, Yajuan CHEN, Rongping ZHANG. Chemical Compounds Isolated from Pleione maculata and Their Bioactive Activity[J]. Journal of Kunming Medical University, 2023, 44(3): 1-6. doi: 10.12259/j.issn.2095-610X.S20230312

Citation:

PDF( 588 KB)

Chemical Compounds Isolated from Pleione maculata and Their Bioactive Activity

doi: 10.12259/j.issn.2095-610X.S20230312

1.
School of Pharmaceutical Science and Yunnan Key Laboratory of Pharmacology for Natural Products，Kunming Medical University，Kunming Yunnan 650500
2.
School of Chinese Materia Medica and Yunnan Key Laboratory of Southern Medicine Utilization，Yunnan University of Chinese Medicine，Kunming Yunnan 650500
3.
Dept. of Ultrasound，the First People’s Hospital of Qujing City，Qujing Yunnan 655000
4.
School of Rehabilitation，Kunming Medical University，Kunming Yunnan 650500，China

Received Date: 2022-11-16
Available Online: 2023-03-01
Publish Date: 2023-03-25

Abstract

Abstract

Objective To study the chemical compounds from the medicinal plants of Pleione maculata and find its bioactive compounds. Methods The compounds were extracted by alcohol （95%） and isolated by column chromatography on silica gel and Sephadex LH-20. Their structures were identified by spectroscopic analysis （¹H NMR, ¹³CNMR and EIMS）. The antitumor activity of the compounds was studied by MTT assay in vitro. Results Ten compounds were obtained and identified as 1, 7-dihydroxy-2, 5 -dimethoxyphenanthrene （ 1 ）, 2, 7-dihydroxy-1, 5-dimethoxyphenanthrene （ 2 ）, confusarin （ 3 ）, 4, 7-dihydroxy-2-dimethoxy-9, 10-dihydrophenanthrene （ 4 ）, pleionesin B （ 5 ）, pleionesin C （ 6 ）, flavanthrin （ 7 ）, 2, 2′-dihydroxy-5, 5′, 7, 7′-tetramethoxy-9, 9′, 10, 10′-tetrahydro-3, 3′-biphenanthrene （ 8 ）, 6, 6′, 7, 7′-tetrahy- -droxy-2, 2′, 4, 4′-tetramethoxy -8, 8′-biphenanthrene （ 9 ）, 1, 3′, 5′, 7-tetrahydroxy-4, 7′ -dimethoxy-9, 9′, 10, 10′-tetrahydro-2, 2′- biphenanthrene （1 0 ）; Compounds 3, 7～10 were tested for the inhibitory activity of human lung cancer cell lines （A549）, human breast cancer drug-sensitive cell lines （MCF-7/S）, and human ovarian cancer cell lines （SKOV-3）. The results of anti-tumor activity test of compounds showed that 10 showed good inhibitory activity on three cell lines. Conclusion All compounds were isolated from this plant for the first time. Compound 10 has good inhibitory activity against three tumor cell lines, and with IC₅₀ of 2.45, 6.83, 4.23 μM, respectively.
- Pleione maculata,
- Chemical constituents,
- Bioactive activity

FullText(HTML)

References(23)

References

[1]	中国科学院中国植物志编辑委员会. 中国植物志 [M], 第18卷, 北京: 科学出版社, 1999: 366-367.
[2]	国家药典委员会. 中华人民共和国药典·一部[S]. 北京: 中国医药科技出版社, 2015: 32 -33.
[3]	Takamiya T,Kitamura S,Suzuki S,et al. Identification of two phenanthrene derivatives from Australasian allied species in genus Dendrobium[J]. Chemical & Pharmaceutical Bulletin,2018,66(6):642-650.
[4]	Majumder P L,Kar A. Confusarin and confusaridin two phenanthrene derivatives of the orchid Eria Confusa[J]. Phytochemistry,1987,26(4):1127-1129. doi: 10.1016/S0031-9422(00)82363-8
[5]	Nanik S A,Ratih H,Mulyadi T. Confusarin and nudol,two phenathrene group compounds,from Dioscorea esculenta L. and their antioxidant activities[J]. Journal of Chemical Technology and Metallurgy,2017,52(6):1135-1139.
[6]	Li C B,Wang C,Fan W W,et al. Chemical components of Dendrobium crepidatum and their neurite outgrowth enhancing activities[J]. Natural Products & Bioprospecting,2013,3(2):70-73.
[7]	Pornprom K,Kesarin B,Pithi C,et al. Cytotoxic and antimigratory activities of phenolic compounds from Dendrobium brymerianum[J]. Evidence-Based Complementary and Alternative Medicine,2015,15(1):1-9. doi: 10.1186/s12906-015-0520-z
[8]	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
[9]	Dong H L,Wang C,Li Y,et al. Complete assignments of 1H and 13C NMR data of three new dihydrophenanthrofurans from Pleione yunnanensis[J]. Magnetic Resonance in Chemistry,2011,48(3):256-260.
[10]	Majumder P L,Banerjee S. Structure of flavanthrin,the first dimeric 9,10-dihydro -phenanthrene derivative from the orchid Eria flava[J]. Tetrahedron,1988,44(23):7303-7308. doi: 10.1016/S0040-4020(01)86102-0
[11]	Li C Y,Liu J,Su X H,et al. New dimeric phenanthrene and flavone from Spiranthes sinensis[J]. Journal of Asian Natural Products Research,2013,15(4):1-5.
[12]	Majumder P L,Lahiri S. Volucrin,a new dimeric phenanthrene derivative from the orchid lusia volucris[J]. Tetrahedron,1990,46(10):3621-3626. doi: 10.1016/S0040-4020(01)81531-3
[13]	Xu J J,Yu H,Qing C,et al. Two new biphenanthrenes with cytotoxic activity from Bulbophyllum odoratissimum[J]. Fitoterapia,2009,80(7):381-384. doi: 10.1016/j.fitote.2009.05.007
[14]	Shao S Y,Wang C,Han S W,et al. Phenanthrenequinone enantiomers with cytotoxic activities from the tubers of Pleione bulbocodioides[J]. Organic & Biomolecular Chemistry,2019,17(3):567-572.
[15]	Shao S Y,Wang C,Han S W,et al. Two new phenanthrenequinones with cytotoxic activity from the tubers of Pleione bulbocodioides[J]. Phytochemistry Letters,2020,35(6):6-9.
[16]	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.
[17]	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.
[18]	Li Y P,Chen Y P,Chen X L,et al. A new phenanthrene derivative with α-Glucosidase inhibitory activity from Pleione maculata[J]. Chemistry of Natural Compounds,2022,58(1):6-8.
[19]	Li Y P,Shao Y T,Zhang R P. A new phenanthrene derivative from Pleione praecox[J]. Chemistry of Natural Compounds,2021,57(3):409-441.
[20]	张伟,王继华,范泽鑫,等. 独蒜兰属植物杂交育种研究进展[J]. 北方园艺,2020,461(14):136-144.
[21]	王中煊,张豪,陈蕾,等. 15种独蒜兰属植物叶表皮微形态特征及分类学意义研究[J]. 西北植物学报,2020,40(9):1527-1538.
[22]	沈立明,戴中武,钟惠,等. 3种独蒜兰属植物的光合特性[J]. 热带作物学报,2021,42(5):1355-1360.
[23]	王跃华,陈芳,鲜俊贤,等. 独蒜兰优质种苗快速培育研究[J]. 成都大学学报(自然科学版),2021,40(3):242-246.

Relative Articles(20)

Relative Articles

[1]	Zhengde WANG, CUO Raoji PING, Huan BAO, Chunbo QIAN, Junju XU, Meirong HAI. Chemical Compositions of Brassica rapa L.. Journal of Kunming Medical University, 2024, 45(6): 51-56. doi: 10.12259/j.issn.2095-610X.S20240607
[2]	Chenxi ZHUANG, Huimin WANG, Yaping CHEN, Rui ZHANG, Jinrong ZHENG, Meihong LI, Yupeng LI. Chemical Compounds Isolated from Dendrobium crepidatum and Their Bioactive Activities. Journal of Kunming Medical University, 2023, 44(12): 1-5. doi: 10.12259/j.issn.2095-610X.S20231231
[3]	Yupeng LI, Xinglong CHEN, Shengxing YUAN, Yajuan CHEN, Rongping ZHANG. Chemical Compounds Isolated from Cremastra Appendiculata and Their Bioactive Activity. Journal of Kunming Medical University, 2023, 44(2): 1-6. doi: 10.12259/j.issn.2095-610X.S20230209
[4]	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. Journal of Kunming Medical University, 2023, 44(5): 1-5. doi: 10.12259/j.issn.2095-610X.S20230528
[5]	Xiao-zhen WANG, Lu LIU, An-chao WU, Yue-han WANG, Zhi-hong ZHOU, Zhu-ya YANG. Effect of Trillium tschonoskii Maxim. on the Contraction of Uterine Smooth Muscle. Journal of Kunming Medical University, 2021, 42(11): 9-13. doi: 10.12259/j.issn.2095-610X.S20211102
[6]	Fang LIU, Yun-ping GUO, Bo LIU, Chang-qi CHEN, Ya-ni GUO. Isolation and Identification of Chemical Constituents of Ethyl Acetate Extraction Layer from Buddleja Officinalis Maxim. Journal of Kunming Medical University, 2021, 42(8): 31-34. doi: 10.12259/j.issn.2095-610X.S20210806
[7]	Chen Ya Ping , Wu He , Li Mei Hong , Miao Min , Zhao Min , Huang Rong , Tang Qi , Li Yu Peng . . Journal of Kunming Medical University, 2019, 40(06): 39-41.
[8]	Shi Bao Sheng , Chen Ya Ping , Chen Li Jun , Shao Ya Ting , Tao Yong Sheng , Li Yu Peng . Advances in Studies of Chemical Constituents and Pharmacological Effects about Swertia mileensis. Journal of Kunming Medical University, 2017, 38(11): 122-126.
[9]	Shi Bao Sheng , Tao Yong Sheng , Li Wei , Sun Zhong Wen , Shao Ya Ting , Yang Xiao Lin , Li Yu Peng . Advances in Researches of Chemical Components and Pharmacological Effect from Dendrobium nobile Lindl. Journal of Kunming Medical University, 2017, 38(10): 124-129.
[10]	Weng Rui Xuan , Li Yu Peng , Chen Li Jun , Huang Rong , Tao Yong Sheng , Wang Juan , Li Shuang , Wen Xiao Ling , Zhang Gui Hua . . Journal of Kunming Medical University, 2017, 38(02): 6-9.
[11]	Li Yu Peng , Weng Rui Xuan , Tao Yong Sheng , Li Shuang , Wang Juan , Huang Rong , Wen Xiao Ling , Zhang Gui Hua . Study on the Chemical Constituents of Arundina graminifolia. Journal of Kunming Medical University, 2016, 37(11): 5-7.
[12]	Chen Ya Ping . Chemical Constituents from the Flowers of Dendrobium thyrsiflorum. Journal of Kunming Medical University,
[13]	Wu Xue . . Journal of Kunming Medical University, 2015, 36(06): 1-1.
[14]	Li Yu Peng . . Journal of Kunming Medical University,
[15]	Chen Ya Ping . . Journal of Kunming Medical University,
[16]	Weng Rui Xuan . . Journal of Kunming Medical University,
[17]	Wang Hai Ken . . Journal of Kunming Medical University, 2014, 35(01): 1-1.
[18]	Li Yong . . Journal of Kunming Medical University, 2013, 34(11): 1-1.
[19]	Wang Lei . . Journal of Kunming Medical University,
[20]	. The Chemical Composition and Identification of Processing Polygonum Multiflorum. Journal of Kunming Medical University,