Abstract
In this study, we isolated and identified cucurbitane triterpene glycosides of Wilbrandia hibiscoides Silva Manso contributing to the phytochemistry of Cucurbitaceae family. Our results show the first phytochemical data of the W. hibiscoides through the identification of three known cucurbitane triterpene glycosides that are chemotaxonomically (chemophenetic) significant constituents in the Cucurbitaceae family, contributing to the chemistry of this species.
Graphical abstract
Change history
13 August 2021
The graphical abstract of this article was corrected to remove unnecessary text.
References
BFG (2015) The Brazil Flora Group. Growing knowledge: an overview of seed plant diversity in Brazil. Rodriguésia 66:1085–1113. https://doi.org/10.1590/2175-7860201566411
Chen XB, Zhuang JJ, Liu JH, Lei M, Ma L, Cheng J, Shen X, HongHu L (2011) Potential AMPK activators of cucurbitane triterpenoids from Siraitia grosvenorii Swingle. Bioorg Med Chem 19:5776–5781. https://doi.org/10.1016/j.bmc.2011.08.030
Correa MP (1978) Dicionário das plantas úteis do Brasil e das exóticas cultivadas. Imprensa Nacional, Rio de Janeiro, Brazil. Available at https://pesquisa.bvsalud.org/portal/resource/pt/biblio-923775. Access date January 22, 2021
González FG, Di Stasi LC (2002) Anti-ulcerogenic activities of the leaves of Wilbrandia ebracteata in mice. Phytomedicine 9:125–134. https://doi.org/10.1078/0944-7113-00096
Gomes-Klein VL, Lima LFP, Gomes-Costa GA, Medeiros ES (2015) Cucurbitaceae In: Lista de Espécies da Flora do Brasil. Jardim Botânico do Rio de Janeiro. Avaiable at http://floradobrasil.jbrj.gov.br/jabot/floradobrasil/FB17036. Access date January 14, 2021
Huang HT, Zhang LJ, Huang HC, Hwang SY, Wu CL, Lin YC, Liaw CC, Cheng YY, Natschke SLM, Huang CY, Lee KH, Kuo YH (2020) Cucurbitane-type triterpenoids from the vines of Momordica charantia and their anti-inflammatory activities. J Nat Prod 83:1400–1408. https://doi.org/10.1021/acs.jnatprod.9b00592
Kasai R, Nie RL, Nashi K, Ohtani K, Zhou J, Tao GD, Tanaka O (1989) Sweet cucurbitane glycosides from fruits of Siraitia siamensis (chi-zi luo-han-guo), a Chinese folk medicine. Agric Biol Chem 53:3347–3349. https://doi.org/10.1080/00021369.1989.10869815
Li D, Ikeda T, Matsuoka N, Nohara T, Zhang H, Sakamoto T, Nonaka G (2006) Cucurbitane glycosides from unripe fruits of Lo Han Kuo (Siraitia grosvenori). Chem Pharm Bull 54:1425–1428. https://doi.org/10.1248/cpb.54.1425
Li QY, Chen HB, Liu ZM, Wang B, Zhao YY (2007) Cucurbitane triterpenoids from Momordica charantia L. Magn Reson Chem 45:451–456. https://doi.org/10.1002/mrc.1989
Li C, Lin L, Luo M, Ma C, Wang Z (2011) A new natural saponin from fruits of Siraitia grosvenorii. Zhongguo Zhong Yao Za Zhi 6:721–724
Li F, Yang F, Liu X, Wang L, Chen B, Li L, Wang M (2017) Cucurbitane glycosides from the fruit of Siraitia grosvenori and their effects on glucose uptake in human HepG2 cells in vitro. Food Chem 228:567–573. https://doi.org/10.1016/j.foodchem.2017.02.018
Liu Y, Zhang L, Xue J, Wang K, Hua H, Yuan T (2020) Norcolocynthenins A and B, two cucurbitane 3-nor-triterpenoids from Citrullus colocynthis and their cytotoxicity. Bioorg Chem 101:104045. https://doi.org/10.1016/j.bioorg.2020.104045
Macleod AJ, Troconis NG (1982) Volatile flavour components of guava. Phytochemistry 21:1339–1342. https://doi.org/10.1016/0031-9422(82)80138-6
Matos MEO, Machado MIL, Craveiro AA, Matos FJA, Braz-Filho R (1991) Nor-cucurbitacin glucosides from Wilbrandia species. Phytochemistry 30:1020–1023. https://doi.org/10.1016/0031-9422(91)85301-F
Nhiem NX, Kiem PV, Minh CV, Ban NK, Cuong NX, Ha LM, Tai BH, Quang TH, Tung NH, Kim YH (2010) Cucurbitane-type triterpene glycosides from the fruits of Momordica charantia. Magn Reson Chem 48:392–396. https://doi.org/10.1002/mrc.2582
Niu B, Ke CQ, Li BH, Li Y, Yi Y, Luo Y, Shuai L, Yao S, Lin LG, Li J, Ye, (2017) Cucurbitane glucosides from the crude extract of Siraitia grosvenorii with moderate effects on PGC-1α promoter activity. J Nat Prod 80:1428–1435. https://doi.org/10.1021/acs.jnatprod.6b01086
Ochi M, Moriyama K, Ohmae K, Fukuyama Y, Nihei K-I, Kubo I (2009) Sweet and bitter constituents of Wilbrandia species. Food Chem 115:61–65. https://doi.org/10.1016/j.foodchem.2008.11.062
Pavan FR, Sato DN, Higuchi CT, Santos ACB, Vilegas W, Leite CQE (2009) In vitro anti-Mycobacterium tuberculosis activity of some Brazilian “Cerrado” plants. Rev Bras Farmacogn 19:204–206. https://doi.org/10.1590/S0102-695X2009000200004
Peters RR, Farias MR, Ribeiro-Do-Valle RM (1997) Anti-inflammatory and analgesic effects of cucurbitacins from Wilbrandia ebracteata. Planta Med 63:525–528. https://doi.org/10.1055/s-2006-957755
Peters RR, Saleh TF, Lora M, Patry C, Brum-Fernandes AJ, Farias MR, Ribeiro-Do-Valle RM (1999) Anti-inflammatory effects of the products from Wilbrandia ebracteata on carregeenan-induced pleurisy in mice. Life Sci 64:2429–2437. https://doi.org/10.1016/S0024-3205(99)00200-3
Recio MC, Prieto M, Bonucelli M, Orsi C, Máñez S, Giner MR, Cerdá-Nicolás M, Ríos JL (2004) Anti-inflammatory activity of two cucurbitacins isolated from Cayaponia tayuya roots. Planta Med 70:414–420. https://doi.org/10.1055/s-2004-818968
Salehi B, Capanoglu E, Adrar N, Catalkaya G, Shaheen S, Jaffer M, Giri L, Suyal R, Jugran AK, Calina D, Docea AO, Kamiloglu S, Kregiel D, Antolak H, Pawlikowska E, Sen S, Acharya K, Selamoglu Z, Sharifi-Rad J, Martorell M, Rodrigues CF, Sharopov F, Martins N, Capasso R (2019) Cucurbits plants: a key emphasis to its pharmacological potential. Molecules 24:1854. https://doi.org/10.3390/molecules24101854
Schaefer H, Renner SS (2011) Phylogenetic relationships in the order Cucurbitales and a new classification of the gourd family (Cucurbitaceae). Taxon 60:122–138. https://doi.org/10.1002/tax.601011
Siqueira JM Jr, Peters RR, Gazola AC, Krepsky PB, Farias MR, Rae GA, de Brum-Fernandes AJ, Ribeiro-do-Valle RM (2007) Anti-inflammatory effects of a triterpenoid isolated from Wilbrandia ebracteata Cogn. Life Sci 80:1382–1387. https://doi.org/10.1016/j.lfs.2006.12.021
Stuppner H, Müller EP (1994) Structure revision of gratioside. Phytochemistry 37:1483–1485. https://doi.org/10.1016/S0031-9422(00)90439-4
Torres MH, Ianni F, Zepeda RER, Romero JCL, Gutiérrez MV, Durán MDJ, Galarini R, Camaioni E, Sardella R, Marcotullio MC (2020) Quantitative analysis of cucurbitane-type triterpenes in Ibervillea sonorae extracts: relationship study with their antiproliferative activity. Steroids 161:108676. https://doi.org/10.1016/j.steroids.2020.108676
Ukiya M, Akihisa T, Yasukawa K, Tokuda H, Toriumi M, Koike K, Kimura Y, Nikaido T, Aoi W, Nishino H, Takido M (2002) Anti-inflammatory and anti-tumor-promoting effects of cucurbitane glycosides from the roots of Bryonia dioica. J Nat Prod 65:179–183. https://doi.org/10.1021/np010423u
Xu F, Li DP, Huang ZC, Lu FL, Huang YL, Wang RF, Liu GX, Shang MY, Cai SQ (2015) Exploring in vitro, in vivo metabolism of mogroside V and distribution of its metabolites in rats by HPLC-ESI-IT-TOF-MSn. J Pharm Biomed 115:418–430. https://doi.org/10.1016/j.jpba.2015.07.024
Zidorn C (2019) Plant chemophenetics − a new term for plant chemosystematics/plant chemotaxonomy in the macro-molecular era. Phytochemistry 163:147–148. https://doi.org/10.1016/j.phytochem.2019.02.013
Acknowledgements
The authors thank Silvia H. T. Contini and Adriana A. Lopes for their support.
Funding
This work was supported by the São Paulo Research Foundation (FAPESP) [grant numbers 2012/14408- 9, 2014/50265–3 and 2014/18052–0], the University of São Paulo NPPNS [grant number 2012.1.17587.1.1.].
Author information
Authors and Affiliations
Contributions
AMSP collected plant material and VLCK was responsible for the identification. GMLF designed the study and performed the laboratory work. DPD contributed to chromatographic and spectra analysis and interpretation. AMSP, VLCK, and NPL contributed to the critical reading of the manuscript and analyzing and interpreting results. All the authors have read the final manuscript and approved the submission.
Corresponding author
Ethics declarations
Conflict of Interest
The authors declare no competing interest.
Additional information
This article is part of a Special Issue to celebrate the 35th anniversary of the Brazilian Journal of Pharmacognosy
Supplementary Information
Supplementary Material includes information HPCL chromatograms, MS/MS, RMN spectra data of the isolated compounds and description of general experimental procedures and reagents used to perform the study
Below is the link to the electronic supplementary material.
Rights and permissions
About this article
Cite this article
Fiori, G.M.L., Demarque, D.P., Pereira, A.M.S. et al. Cucurbitane Triterpene Glycosides from the Roots of Wilbrandia hibiscoides. Rev. Bras. Farmacogn. 31, 715–719 (2021). https://doi.org/10.1007/s43450-021-00172-3
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s43450-021-00172-3