Abstract
A new oxoaporphine alkaloid, (−)-(6aR,7R)-N-acetylnorushinsunine (1) together with eight known compounds (2–9) had been isolated from the aerial part of Vietnamese Piper hymenophyllum Miq., Piperaceae. The chemical structures of 1–9 were established mainly by spectroscopic, spectrometric, and chiroptical spectra. Their anti-inflammatory activity was evaluated against lipopolysaccharides-induced nitric oxide production in RAW264.7 cells in vitro. Among them, compounds 2–4 showed significant inhibitory activities against the lipopolysaccharide-induced nitric oxide production in RAW264.7 cells with IC50 values of 7.2, 9.3, and 4.5 μM, respectively. In addition, compounds 2 and 4 suppressed both lipopolysaccharides-induced cyclooxygenase-2 and inducible nitric oxide synthase expressions. These results proposed that Piper hymenophyllum and its constituents may exert anti-inflammatory effects.
.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Barrett B (1994) Medicinal plants of Nicaragua’s Atlantic coast. Econ Bot 48:8–20
Chen JJ, Hung HC, Sung PJ, Chen IS, Kuo WL (2011) Aporphine alkaloids and cytotoxic lignans from the roots of Illigera luzonensis. Phytochemistry 72:523–532
Chen S, Huang HY, Cheng MJ, Wu CC, Ishikawa T, Peng CF, Chang HS, Wang CJ, Wong SL, Chen IS (2013) Neolignans and phenylpropanoids from the roots of Piper taiwanense and their antiplatelet and anti-tubercular activities. Phytochemistry 93:203–209
Cuong TD, Hung TM, Na M, Ha DT, Kim JC, Lee D, Ryoo S, Lee JH, Choi JS, Min BS (2011) Inhinbitory effect on NO production of phenolic compounds from Myristica fragrans. Bioorg Med Chem Lett 21:6884–6887
Cuong TD, Hung TM, Kim JC, Kim EH, Woo MH, Choi JS, Lee JH, Min BS (2012) Phenolic compounds from Caesalpinia sappan heartwood and their anti-inflammatory activity. J Nat Prod 75:2069–2075
Cuong TD, Hung TM, Lee JS, Weon KY, Woo MH, Min BS (2015) Anti-inflammatory activity of phenolic compounds from the whole plant of Scutellaria indica. Bioorg Med Chem Lett 25:1129–1134
Dung HV, Cuong TD, Chinh NM, Quyen D, Byeon JS, Kim JA, Woo MH, Choi JS, Min BS (2014) Cholinesterase inhibitors from aerial part of Piper hymenophyllum. Bull Kor Chem Soc 35:655–658
Ekundayo O, Laakso I, Adegbola RM, Oguntimein B, Sofowora A, Hiltunen R (1988) Essential oil constituents of Ashanti pepper (Piper guineense) fruits (berries). J Agric Food Chem 36:880–882
Evans PH, Bowers WS, Funk EJ, Evangeline J (1984) Identification of fungicidal and nematocidal components in the leaves of Piper betle (Piperaceae). J Agric Food Chem 32:1254–1256
Guinaudeau H, Leboeuf M, Cavé A (1988) Aporphinoid alkaloids, IV. J Nat Prod 51:389–474
Guinaudeau H, Leboeuf M, Cavé A (1994) Aporphinoid alkaloids, V. J Nat Prod 57:1033–1135
Marsaioli AJ, Magalhães AF, Rúveda EA, Reis FAM (1980) 13C NMR analysis of some oxoaporphine alkaloids. Phytochemistry 19:995–997
Michel J, Duarte RE, Bolton JL, Huang Y, Caceres A, Veliz M, Soejarto DD, Mahady GB (2007) Medical potential of plants used by the Q’eqchi Maya of Livingston, Guatemala for the treatment of women’s health complains. J Ethnopharmacol 114:92–101
Ringdahl B, Chan RPK, Craig JC, Cava MP, Shamma M (1981) Circular dichroism of aporphines. J Nat Prod 44:80–85
Schmidt HHHW, Kelm M (1996) Determination of nitrite and nitrate by the Griess reaction. In: Feelisch M, Stamler JS (eds) Methods in nitric oxide research. John Wiley and Sons Ltd, New York, p 491497
Simpson B, Ogorzaly M (1995) Economic botany: plants in our world, 2nd edn. McGraw-Hill, New York, p 742
Sun YN, Li W, Yan XT, Yang SY, Kim YH (2014) Chemical constituents from the stems of Acanthopanax divaricatus var. albeofructus. Biochem Syst Ecol 57:164–168
Vaghasiya Y, Nair R, Chanda S (2007) Investigation of some Piper species for anti-bacterial and anti-inflammatory property. Int J Pharmacol 3:400–405
Yao LC, Han CR, Chen GY, Song XP, Chang YH, Zhang WX (2012) A new asymmetric diamide from the seed cake of Jatropha curcas L. Fitoterapia 83:1318–1321
Funding
This work was supported by the Phenikaa University Foundation for Science and Technology Development.
Author information
Authors and Affiliations
Contributions
VDH, PHN, NTH, and HTN contributed laboratory experiments. VDH contributed to collect plant sample. MHT performed anti-inflammatory activity assay. VDH, PHN, NTH, and HTN contributed to isolated and purified compounds, analyzed the NMR data, and prepared the manuscript. DCT and BSM supervised the laboratory work and reviewed the manuscript. All the authors have read the final manuscript and approved the submission.
Corresponding author
Ethics declarations
Conflict of Interest
The authors declare that they have no conflicts of interest.
Protection of Human and Animal Subjects
The authors declare that no experiments were performed on humans or animals for this study.
Confidentiality of Data
The authors declare that they have followed the protocols of their work center on the publication of patient data.
Right to Privacy and Informed Consent
The authors declare that no patient data appear in this article.
Electronic Supplementary Material
ESM 1
(DOC 1084 kb)
Rights and permissions
About this article
Cite this article
Hoang, V.D., Nguyen, P.H., Tran, M.H. et al. Identification of Anti-Inflammatory Constituents from Vietnamese Piper hymenophyllum. Rev. Bras. Farmacogn. 30, 312–316 (2020). https://doi.org/10.1007/s43450-020-00035-3
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s43450-020-00035-3