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Terpenoid compounds from the fruits of Solanum virginianum

  • Yan Liu , Shuang Liu , Zhen-Peng Xu , Si-Yi Wang , Yi-Kai Jiang , Wei Guan , Juan Pan , Hai-Xue Kuang EMAIL logo and Bing-You Yang EMAIL logo
Published/Copyright: September 27, 2023

Abstract

Eleven compounds were isolated and identified from ethanolic extracts of Solanum virginianum fruits, including two new compounds (12) and nine known compounds (311). Their structures were determined to be melongenaterpene C15-O-β-D-glucopyranoside (1), (9Z)-3,7,11,15-tetramethyl -hexadeca-1,6,10-triene-3,5,14,15-tetraol-5-O-β-D-glucopyranoside (2), actini-dioionoside A (3), byzantionoside B (4), citroside A (5), 7Z-roseoside (6), matenoside A (7), megastigmane (8), dihydrophaseic acid 3′-O-β-D-glucopyranoside (9), taraxerol (10), and huzhangoside C (11). In this paper, NMR spectroscopy was used to study the structures of the compounds, comparing their data with those in the literature. In addition, the potential anti-inflammatory activity of the compounds was also evaluated using the RAW264.7 cell inflammation model induced by lipopolysaccharide (LPS). The terpenoids showed no significant anti-inflammatory activity.


Corresponding authors: Hai-Xue Kuang and Bing-You Yang, Heilongjiang University of Chinese Medicine, Harbin, China, E-mail: (H.-X. Kuang), (B.-Y. Yang)
Key Laboratory of Basic and Application Research of Beiyao (Heilongjiang University of Chinese Medicine), Ministry of Education.

Funding source: Key Research and Development Projects of Heilongjiang Province

Award Identifier / Grant number: GA21D008

Funding source: Heilongjiang Touyan Innovation Team Program

Award Identifier / Grant number: [2019] No.5

Funding source: Heilongjiang Province "Double first-class" discipline collaborative innovation achievement construction project

Award Identifier / Grant number: LJGXCG2022-096

  1. Research ethics: Not applicable.

  2. Author contributions: Yan Liu performed the whole experiment process as a guide, performed the extraction, isolation, structural elucidation of compounds 1–11. Shuang Liu wrote the manuscript. Zhen-Peng Xu and Si-Yi Wang assayed the anti-inflammatory activity of compounds 1–11. Yi-Kai Jiang revised the article and improved the English spelling. Wei Guan measured the HR-ESI-MS spectra. Juan Pan operated the NMR instrument. Hai-Xue Kuang and Bing-You Yang designed the experiments and provided funding for experiments. The authors have accepted responsibility for the entire content of this manuscript and approved its submission.

  3. Competing interests: The authors state no conflict of interest.

  4. Research funding: This work was financed by the Development Projects of Heilongjiang Province (GA21D008), Heilongjiang Touyan Innovation Team Program and Key Research ([2019] No.5) and Heilongjiang Province “Double first-class” discipline collaborative innovation achievement construction project (LJGXCG2022-096).

  5. Data availability: The raw data can be obtained on request from the corresponding author.

References

1. Editorial committee of Chinese flora of Chinese academy of sciences, Flora of China. Beijing: Science Press; 2000.Search in Google Scholar

2. Thenmozhi, V, Elango, V, Sadique, J. Anti-inflammatory activity of some Indian medicinal plants. Ancient Sci Life 1989;8:258–61.Search in Google Scholar

3. Kumar, S, Pandey, AK. Medicinal attributes of Solanum xanthocarpum fruit consumed by several tribal communities as food: an in vitro antioxidant, anticancer and anti HIV perspective. BMC Compl Alternative Med 2014;14:1–8. https://doi.org/10.1186/1472-6882-14-112.Search in Google Scholar PubMed PubMed Central

4. Gupta, SK, Banerjee, AB. Screening of selected West Bengal plants for antifungal activity. Econ Bot 1972;26:255–9. https://doi.org/10.1007/bf02861038.Search in Google Scholar

5. Malik, F, Hussain, S, Mirza, T, Hameed, A, Ahmad, S, Riaz, H, et al.. Screening for antimicrobial activity of thirty-three medicinal plants used in the traditional system of medicine in Pakistan. J Med Plants Res 2011;5:3052–60. https://doi.org/10.5897/JMPR.9001107.Search in Google Scholar

6. Dabur, RK. Antifungal potential of Indian medicinal plants. Fitoterapia 2004;75:389–91. https://doi.org/10.1016/j.fitote.2004.01.015.Search in Google Scholar PubMed

7. Pardhi, P, Jain, AP, Ganeshpurkar, A, Rai, G. Anti-microbial, anti-oxidant and Anthelmintic activity of crude extract of Solanum xanthocarpum. Phcog J 2010;2:400–4. https://doi.org/10.1016/s0975-3575(10)80022-7.Search in Google Scholar

8. Elizabeth, AM, Soliman, KA. In vitro screening for the tumoricidal properties of international medicinal herbs. Phytother Res 2009;23:385–98. https://doi.org/10.1002/ptr.2636.Search in Google Scholar PubMed PubMed Central

9. Mazzio, E, Soliman, KF. In vitro evaluation of the tumoricidal potency of 370 international herbs. FASEB (Fed Am Soc Exp Biol) J 2007;21:A757. https://doi.org/10.1096/fasebj.21.6.A757.Search in Google Scholar

10. Chauhan, RS, Joshi, A. Anti-cancer properties of herbs in cell culture system. J Immunol Immunopathol 2018;20:107–20. https://doi.org/10.5958/0973-9149.2018.00018.7.Search in Google Scholar

11. Konoshima, T, Takasaki, M, Tokuda, H, Masuda, K, Arai, Y, Shiojima, K, et al.. Anti-tumor-promoting activities of triterpenoids from ferns. I. Biol Pharmaceut Bull 1996;19:962–5. https://doi.org/10.1248/bpb.19.962.Search in Google Scholar PubMed

12. Raja, W, Nosalova, G, Ghosh, K, Sivova, V, Nosal, S, Ray, B. In vivo antitussive activity of a pectic arabinogalactan isolated from Solanum virginianum L. in Guinea pigs. J Ethnopharmacol 2014;156:41–6. https://doi.org/10.1016/j.jep.2014.08.012.Search in Google Scholar PubMed

13. Aziz, M, Khan, A, Adnan, M, Izatullah, I. Traditional uses of medicinal plants reported by the indigenous communities and local herbal practitioners of Bajaur Agency, Federally Administrated Tribal Areas, Pakistan. J Ethnopharmacol 2017;198:268–81. https://doi.org/10.1016/j.jep.2017.01.024.Search in Google Scholar PubMed

14. Javaid, U, Javaid, S, Ashraf, W, Rasool, M, Noman, O, Alqahtani, A, et al.. Chemical profiling and dose-dependent assessment of fear reducing and memory-enhancing effects of Solanum virginianum in rats. Dose Response 2021;19:1559325821998486. https://doi.org/10.1177/1559325821998486.Search in Google Scholar PubMed PubMed Central

15. Verma, S, Kuhad, A, Bhandari, R, Prasad, S, Shakya, A, Prasad, R, et al.. Effect of ethanolic extract of Solanum virginianum Linn. on neuropathic pain using chronic constriction injury rat model and molecular docking studies. Naunyn-Schmiedeberg’s Arch Pharmacol 2020;393:1715–28. https://doi.org/10.1007/s00210-020-01872-8.Search in Google Scholar PubMed

16. Gupta, RK, Hussain, T, Panigrahi, G, Das, A, Singh, GN, Sweety, K, et al.. Hepatoprotective effect of Solanum xanthocarpum fruit extract against CCl4 induced acute liver toxicity in experimental animals. Asian Pac J Tropical Med 2011;4:964–8. https://doi.org/10.1016/s1995-7645(11)60227-7.Search in Google Scholar PubMed

17. Dheeba, B, Sampathkumar, P, Vijay, S. Potential hepatoprotective effect of Solanum xanthocarpum against CCl4 induced hepatotoxicity in albino rats. Asian J Chem 2014;26:230–2. https://doi.org/10.14233/ajchem.2014.15755.Search in Google Scholar

18. Jalali, GB, Ghaffari, H, Prakash, HS, Kini, KR. Antioxidant and hepatoprotective effects of Solanum xanthocarpum leaf extracts against CCl4-induced liver injury in rats. Pharmaceut Biol 2014;52:1060–8. https://doi.org/10.3109/13880209.2013.877490.Search in Google Scholar PubMed

19. Hussain, T, Ramesh, KG, Sweety, K, Eswaran, B, Vijayakumar, M, Rao, CV. Nephroprotective activity of Solanum xanthocarpum fruit extract against gentamicin–induced nephrotoxicity and renal dysfunction in experimental rodents. Asian Pac J Tropical Med 2012;5:686–91. https://doi.org/10.1016/s1995-7645(12)60107-2.Search in Google Scholar PubMed

20. Patel, PK, Saralai, MG, Gandhi, TR. Antiurolithiatic effects of Solanum xanthocarpum fruit extract on ethylene-glycol-induced nephrolithiasis in rats. J Young Pharm 2012;4:164–70. https://doi.org/10.4103/0975-1483.100022.Search in Google Scholar PubMed PubMed Central

21. Demla, M, Verma, H, TanveeR, N. Pharmacognostical investigations on berries of Solanum xanthocarpum. Int J Pol Inf 2011;1:77–85.Search in Google Scholar

22. Evans, CE, Rabiat, UH, Erukainure, OL. Hypoglycemic potency of selected medicinal plants in Nigeria. Hrvatski Asopis ZA Prehrambenu Tehnologiju, Biotehnologiju I Nutricionizam 2014;8:111–4.Search in Google Scholar

23. Khanam, S, Sultana, R. Isolation of β-sitosterol & stigmasterol as active immunomodulatory constituents from fruits of Solanum xanthocarpum (Solanaceae). Int J Pharmaceut Sci Res 2012;3:1057–60.Search in Google Scholar

24. Kumud, M, Neha, J. Chemical characterisation of medicinally important Solanaceous plant Solanum xanthocarpum Schrad & Wendl. J. Ultra Chem. 2018;14:22–5. https://doi.org/10.22147/juc/140104.Search in Google Scholar

25. Kumar, S, Sharma, UK, Sharma, AK, Pandey, AK. Protective efficacy of Solanum xanthocarpum root extracts against free radical damage: phytochemical analysis and antioxidant effect. Cell Mol Biol 2012;58:174–81.Search in Google Scholar

26. Enegide, C, Arome, D, Solomon, FA. Phytochemical evaluation of the ethanolic extracts of some nigerian herbal plants. Drug Dev. Therapeut. 2015;6:11–4.10.4103/2394-2002.148882Search in Google Scholar

27. Nithya, M, Ragavendran, C, Natarajan, D. Antibacterial and free radical scavenging activity of a medicinal plant Solanum xanthocarpum. Int J Food Prop 2018;21:328–42. https://doi.org/10.1080/10942912.2017.1409236.Search in Google Scholar

28. Yin, X, Liu, Y, Pan, J, Ye, HL, Sun, Y, Zhao, DY, et al.. Vetispirane-type sesquiterpenoids from the roots of Solanum melongena. J Nat Prod 2019;82:3242–8. https://doi.org/10.1021/acs.jnatprod.9b00206.Search in Google Scholar PubMed

29. Song, MC, Yang, HJ, Kim, DK, Baek, NI. A new acyclic diterpene from Trigonotis peduncularis. Bull Kor Chem Soc 2008;29:2267–9.10.5012/bkcs.2008.29.11.2267Search in Google Scholar

30. Schwindl, S, Kraus, B, Heilmann, J. Phytochemical study of Juglans regia L. leaves. Phytochemistry 2017;144:58–70. https://doi.org/10.1016/j.phytochem.2017.08.012.Search in Google Scholar PubMed

31. Matsunami, K, Otsuka, H, Takeda, Y. Structural revisions of blumenol C glucoside and byzantionoside B. Chem Pharm Bull 2010;58:438–41. https://doi.org/10.1248/cpb.58.438.Search in Google Scholar PubMed

32. Hyun, WK, Taewoong, R, Kee, DY. Phytochemical study of aerial parts of leea asiatica. Molecules 2019;24:1733. https://doi.org/10.3390/molecules24091733.Search in Google Scholar PubMed PubMed Central

33. Wu, JF, Chen, SB, Gao, JC, Wu, LJ, Chen, SL, Tu, PF. Megastigmane glycosides from Polygala hongkongensis Hemsl. Chem Res Chin Univ 2007;23:530–2. https://doi.org/10.1016/s1005-9040(07)60115-9.Search in Google Scholar

34. Xu, GH, Kim, YH, Choo, SJ, Ryoo, IJ, Yoo, JK, Ahn, JS, et al.. Two acetylated megastigmane glycosides from the leaves of Ilex paraguariensis. Arch Pharm Res (Seoul) 2010;33:369–73. https://doi.org/10.1007/s12272-010-0304-4.Search in Google Scholar PubMed

35. Takeda, Y, Okada, Y, Masuda, T, Hirata, E, Shinzato, T, Takushi, A, et al.. New megastigmane and tetraketide from the leaves of Euscaphis japonica. Chem Pharmaceut Bull 2000;48:752–4. https://doi.org/10.1248/cpb.48.752.Search in Google Scholar PubMed

36. Rho, T, Yoon, KD. Chemical constituents of Nelumbo nucifera Seeds. Nat Prod Sci 2017;23:253–7. https://doi.org/10.20307/nps.2017.23.4.253.Search in Google Scholar

37. Qin, HW, Sun, H, Wang, XD, Sun, JY, Zhang, J, Yang, QM, et al.. Chemical constituents of Potentilla discolor. Chin Med Mater 2020;43:339–43. https://doi.org/10.13863/j.issn1001-4454.2020.02.016.Search in Google Scholar

38. Hideki, S, Tsuyoshi, T, Haruhisa, K. Studies on the constituents of Clematis species. VI. the constituents of Clematis stans Sieb. et Zucc. Chem Pharmaceut Bull 1995;43:2187–94.10.1248/cpb.43.2187Search in Google Scholar PubMed


Supplementary Material

This article contains supplementary material (https://doi.org/10.1515/znc-2023-0028).


Received: 2023-02-23
Accepted: 2023-09-06
Published Online: 2023-09-27
Published in Print: 2023-11-27

© 2023 Walter de Gruyter GmbH, Berlin/Boston

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