Chemical constituents from Trichosanthes cucumeroides

doi:10.5246/jcps.2020.06.041

Journal of Chinese Pharmaceutical Sciences ›› 2020, Vol. 29 ›› Issue (6): 431-438.DOI: 10.5246/jcps.2020.06.041

• Original articles • Previous Articles Next Articles

Chemical constituents from Trichosanthes cucumeroides

Jing Chen¹⁺, Li Cheng¹⁺, Fuqian Wang³, Xuanbin Wang¹, Yonghui Zhang^2*, Xincai Hao^1*

1. Deptment of Traditional Chinese Medicine, Renmin Hospital, Hubei University of Medicine, Shiyan 442008, China
2. Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, China
3. Department of Pharmacy, Wuhan First Hospital, Wuhan 430022, China

Received:2019-09-15 Revised:2019-11-12 Online:2020-06-30 Published:2019-12-19
Contact: Tel.: +86-71-98891124; +86-27-83692311, E-mail: zhangyh@mails.tjmu.edu.cn; hxc_smile@163.com
Supported by:
Hubei Provincial Outstanding Young and Middle-aged Science and Technology Innovation Team Project (Grant No. T201813).

Abstract

Abstract:

One new triterpenoid, 3β-[(E)-caffeoyloxy]-D:C-friedooleana-7,9(11)-dien-29-oic acid (1) and nine known triterpenoidsidentified as cucurbitacin B (2), 23,24-dihydrocucurbitacin B (3), 23,24-dihydrocu-curbitacin D (4), cucurbitacin D (5), cucurbalsaminol A (6), 3-epi-isocucurbitacin D (7), curbitacin G (8), cucurbitacin J (9) and cucurbitacin I (10)were purified from Trichosanthes cucumeroides. Their structures were confirmed by spectroscopic data analysis and comparison with previous literature. All compounds were obtained from T.cucumeroides for the first time.

Key words: Trichosanthes cucumeroides, Chemical constituents, Triterpenoid, Structural identification

CLC Number:

R284

Supporting:

Figure S1. IRspectrum of compound 1.

Figure S2. HRESIMSspectrum of compound 1.

Figure S3. ¹H-NMR spectrum of compound 1 (400MHz CD₃OD).

Figure S4. ¹³C-NMR spectrum of compound 1 (400MHz CD₃OD).

Figure S5. DEPTspectrum of compound 1.

Figure S6. HSQC spectrum of compound 1.

Figure S7. HMBC spectrum of compound 1.

Figure S8. ¹H–¹H COSY spectrum of compound 1.

Figure S9. NOESY spectrum of compound 1.

Jing Chen, Li Cheng, Fuqian Wang, Xuanbin Wang, Yonghui Zhang, Xincai Hao. Chemical constituents from Trichosanthes cucumeroides[J]. Journal of Chinese Pharmaceutical Sciences, 2020, 29(6): 431-438.

References

[1] Akihisa, T.; Tamura, T.; Matsumoto, T.; Eggleston, D.S.; Kokke, W.C.M.C.; Shimizu, N. Karounidiol [D: C-friedo-oleana-7, 9(11)-diene-3α, 29-diol] and its 3-o-benzoate: novel pentacyclic triterpenes from Trichosanthes kirilowii. X-Ray molecular structure of karounidiol diacetate. J. Chem. Soc. Perkin Trans. 1. 1988, 439-443.

[2] Akihisa, T.; Yasukawa, K.; Kimura, Y.; Takido, M.; Kokke, W.C.; Tamura, T. Five D: C-friedo-oleanane triterpenes from the seeds of Trichosanthes kirilowii Maxim. and their anti-inflammatory effects. Chem. Pharm. Bull. 1994, 42, 1101-1105.

[3] Dat, N.T.; Jin, X.J.; Hong, Y.S.; Lee, J.J. An isoaurone and other constituents from Trichosanthes kirilowii seeds inhibit hypoxia-inducible factor-1 and nuclear factor-kappaB. J. Nat. Prod. 2010, 73, 1167-1169.

[4] Yadava, R.N.; Syeda, Y. An isoflavone glycoside from the seeds of Trichosanthes anguina. Phytochemistry. 1994, 36, 1519-1521.

[5] Cheng, L.; Chen, J.; Tan, Y.; Wang, F.Q.; Wang, X.B.; Xue, Y.B.; Hao, X.C.; Zhang, Y.H. Chemical constituents from Teucrium viscidum. J. Chin. Pharm. Sci. 2018, 27, 719-723.

[6] Kimura, Y.; Akihisa, T.; Yasukawa, K.; Takido, M.; Tamura, T. Structures of five hydroxylated sterols from the seeds of trichosanthes kirilowii MAXIM. Chem. Pharm. Bull. 1995, 43, 1813-1817.

[7] Saxena, V.K.; Dave, R.K. A new steroidal saponin from Trichosanthes dioica (Roxb.) Asian J. Chem. 1995, 490-494.

[8] Jang, K.C.; Lee, J.H.; Kim, S.C. Antibacterial and Radical Scavenging Activities of 1-C-(p-Hydroxyphenyl)-Glycerol from Trichosanthes kirilowii. J. Appl. Biol. Chem. 2007, 50, 17-21.

[9] Moon, S.S.; Rahman, A.A.; Kim, J.Y.; Kee, S.H. Hanultarin, a cytotoxic lignan as an inhibitor of actin cytoskeleton polymerization from the seeds of Trichosanthes kirilowii. Bioorg. Med. Chem. 2008, 16, 7264-7269.

[10] Dhiman, K.; Gupta, A.; Sharma, D.K.; Gill, N.S.; Goyal, A. A review on the medicinally important plants of the family Cucurbitaceae. Asian J. Clin. Nutr. 2012, 4, 16-26.

[11] Chao, Z.M.; Shibusawa, Y.; Yanagida, A.; Shimotakahara, S.; Shindo, H. Two new triterpenes from the seeds of Trichosanthes cucumeroides. Nat. Prod. Res. 2005, 19, 211-216.

[12] Che, C.T.; Fang, X.D.; Phoebe, C.H.; Kinghorn, A.D.; Farnsworth, N.R.; Yellin, B.; Hecht, S.M. High-field 1H-NMR spectral analysis of some cucurbitacins. J. Nat. Prod. 1985, 48, 429-434.

[13] Wu, P.L.; Lin, F.W.; Wu, T.S.; Kuoh, C.S.; Lee, K.H.; Lee, S.J. Cytotoxic and anti-HIV principles from the rhizomes of Begonia nantoensis. Chem. Pharm. Bull. 2004, 52, 345-349.

[14] Jacobs, H.; Singh, T.; Reynolds, W.F.; McLean, S. Isolation and 13C-NMR assignments of cucurbitacins from cayaponia angustiloba, cayaponia racemosa, and guraniasubumbellata. J. Nat. Prod. 1990, 53, 1600-1605.

[15] Ramalhete, C.; Mansoor, T.A.; Mulhovo, S.; Molnár, J.; Ferreira, M.J. Cucurbitane-type triterpenoids from the African plant Momordica balsamina. J. Nat. Prod. 2009, 72, 2009-2013.

[16] Halaweish, F.T. Cucurbitacins fromCucurbita texana: Evidence for the role of isocucurbitacins. J. Chem. Ecol. 1993, 19, 29-37.

[17] Sallam, A.A.; Hitotsuyanagi, Y.; Mansour, E.S.S.; Ahmed, A.F.; Gedara, S.; Fukaya, H.; Takeya, K. Phenylpropanoid triesters from Daucus glaber. Phytochem. Lett. 2009, 2, 188-191.

Chemical constituents from Trichosanthes cucumeroides

RichHTML

PDF (PC)

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Lei Jiang, Yujiao Tu, Weihua Dai, Lin Yuan. Chemical constituents from the calli of Maytenus hookeri [J]. Journal of Chinese Pharmaceutical Sciences, 2023, 32(4): 283-290.
[2]	Jingling Tan, Juan Lu, Guohua Zheng. Chemical constituents from the stem of Embelia laeta [J]. Journal of Chinese Pharmaceutical Sciences, 2022, 31(4): 264-269.
[3]	Chengneng Mi, Wenli Mei, Jingzhe Yuan, Wenxing Long, Haofu Dai. Chemical constituents from agarwood of Aquilaria filaria [J]. Journal of Chinese Pharmaceutical Sciences, 2021, 30(6): 505-517.
[4]	Tong Wu, Xiao Du, Jiannong Wang, Liangyu Liu, Yuke Yang. Two new glycoalkaloids from Solanum lyratum Thunb. [J]. Journal of Chinese Pharmaceutical Sciences, 2021, 30(6): 518-523.
[5]	Caicai Xi, Yunling Xu, Kang Feng, Renzhao Wu, Shihong Luo. Chemical constituents from the seeds of Capparis masaikai [J]. Journal of Chinese Pharmaceutical Sciences, 2021, 30(11): 924-931.
[6]	Huinan Wang, Jingzhen Zhang, Yuexin Cui, Siyu Wang, Hui Gao, Yao Zhang, Xinjie Wang, Ziye Yang, Mengyu Chen, Peihua Wang, Guimei Zhang, Yingzi Wang, Chao Zhang. Chemical comparison of Semen Euphorbiae and Semen Euphorbiae Pulveratum by UPLC-Q-TOF/MS coupled with multivariate statistical techniques [J]. Journal of Chinese Pharmaceutical Sciences, 2020, 29(7): 470-479.
[7]	Yunling Xu, Yuji Wang, Shiping Jiang, Tingting Cai, Nannan Wang, Xia Liu, Wanping Zhu. Chemical constituents from the fruit of Schisandra Chinensis [J]. Journal of Chinese Pharmaceutical Sciences, 2020, 29(7): 480-486.
[8]	Fangfang Xu, Biao Sun, Xiaoqi Zhang, Bo Liu. Flavonoid C-glycosides from the seeds of Hovenia dulcis Thunb. [J]. Journal of Chinese Pharmaceutical Sciences, 2020, 29(11): 813-818.
[9]	Xiaolu Yang, Xingyang Xue, Yan Lin, Qiyun Huang, Maoyan Mo, Shumei Wang, Jiang Meng. Chemical constituents from the Moutan Cortex charcoal and their potential coagulation activities [J]. Journal of Chinese Pharmaceutical Sciences, 2018, 27(9): 608-616.
[10]	Chuanjun Huang, Xiaorui Liu, Mi Zhang, Qiong Bie, Fanrong Zeng, Yanyan Wang, Chunmei Chen, Hucheng Zhu, Yonghui Zhang. A new alkaloid from Chaetomium globosum [J]. Journal of Chinese Pharmaceutical Sciences, 2018, 27(9): 617-622.
[11]	Qian Li, Shuding Sun, Meiying Wang, Caifeng Li, Dan Yuan, Hongzheng Fu. Chemical constituents and analgesic activity of Aconitum kusnezoffii Reichb. [J]. Journal of Chinese Pharmaceutical Sciences, 2018, 27(12): 855-863.
[12]	Li Cheng, Jing Chen, Yan Tan, Fuqian Wang, Xuanbin Wang, Yongbo Xue, Xincai Hao, Yonghui Zhang. Chemical constituents from Teucrium viscidum [J]. Journal of Chinese Pharmaceutical Sciences, 2018, 27(10): 719-723.
[13]	Xintao Chen, Hong Lan, Tao Zheng, Yongcheng Dong, Jun Liang, Chen Li. Chemical constituents isolated from the endophytic fungus Penicillium commune [J]. Journal of Chinese Pharmaceutical Sciences, 2017, 26(2): 156-160.
[14]	Ying Zhou, Wenguang Wang, Pengfei Tu, Yong Jiang . Chemical constituents from Murraya tetramera Huang [J]. Journal of Chinese Pharmaceutical Sciences, 2016, 25(3): 201-205.
[15]	Chen Chen, Guandi Luo, Rong Hu, Hongzheng Fu. Chemical constituents from Paliurus ramosissimus [J]. Journal of Chinese Pharmaceutical Sciences, 2016, 25(2): 111-115.