Abstract
A new compound, 2(S)-isobutanol 2-O-β-d-arabinopyranosyl(1→6)-O-β-d-glucopyranoside (1), along with ten known compounds (2–11) were isolated from Piper aduncum L. leaves. The effects of these compounds on soluble epoxide hydrolase and tyrosinase inhibition were evaluated. Among them, compounds 3, 8, and 9 exhibited significant tyrosinase inhibitory activity with IC50 values of 39.3 ± 1.8, 41.3 ± 2.2, and 37.5 ± 2.7 µM, respectively. However, the effects of isolated compounds on soluble epoxide hydrolase inhibition were weak or absent, and compounds 4 and 11 showed the highest inhibitory activity with values of 61.2 ± 4.3 and 60.6 ± 3.7 % at a concentration of 100 μM.
Similar content being viewed by others
Abbreviations
- AUDA:
-
12-(3-Adamantan-1-yl-ureido)-dodecanoic acid
- DHETs:
-
Dihydroxyeicosatrienoic acids
- EETs:
-
Epoxyeicosatrienoic acids
- PHOME:
-
3-Phenyl-cyano(6-methoxy-2-naphthalenyl)methyl ester-2-oxiraneacetic acid
- sEH:
-
Soluble epoxide hydrolase
References
Arroyo-Acevedo J, Chávez-Asmat RJ, Anampa-Guzmán A, Donaires R, Ráez-Gonzáles J (2015) Protective effect of Piper aduncum capsule on DMBA-induced breast cancer in rats. Breast Cancer (Auckl) 9:41–48
Baldoqui DC, Kato MJ, Cavalheiro AJ, Bolzani VdS, Young MCM, Furlan M (1999) A chromene and prenylated benzoic acid from Piper aduncum. Phytochemistry 51:899–902
Chang TS (2009) An updated review of tyrosinase inhibitors. Int J Mol Sci 10:2440–2475
Crout DHG, MacManus DA, Critchley P (1990) Enzymatic synthesis of glycosides using the β-galactosidase of Escherichia coli: regio- and stereo-chemical studies. J Chem Soc Perkin Trans 1:1865–1868
Franzyk H, Olsen CE, Jensen SR (2004) Dopaol 2-keto- and 2,3-diketoglycosides from Chelone obliqua. J Nat Prod 67:1052–1054
Fretland AJ, Omiecinski CJ (2000) Epoxide hydrolases: biochemistry and molecular biology. Chem Biol Interact 129:41–59
Ishimaru K, Nonaka GI, Nishioka I (1987) Phenolic glucoside gallates from Quercus mongolica and Q. acutissima. Phytochemitry 26:1147–1152
Kawahara E, Fujii M, Kato K, Ida Y, Akita H (2005) Chemoenzymatic synthesis of naturally occurring benzyl 6-O-glycosyl-β-d-glucopyranosides. Chem Pharm Bull 53:1058–1061
Khatib S, Nerya O, Musa R, Shmuel M, Tamir SVaya J (2005) Chalcones as potent tyrosinase inhibitors: the importance of a 2,4-substituted resorcinol moiety. Bioorg Med Chem Lett 13:433–441
Matsunami K, Otsuka H, Takeda Y (2010) Structural revisions of blumenol C glucoside and byzantionoside B. Chem Pharm Bull 58:438–441
Mizutani K, Yuda M, Tanaka O, Saruwatari Y, Fuwa T, Jia MR, Ling YK, Pu XF (1988) Chemical studies on chinese traditional medicine, dangshen. I. Isolation of (Z)-3- and (E)-2-hexenyl β-d-glucosides. Chem Pharm Bull 36:2689–2690
Morandim AA, Bergamo DC, Kato MJ, Cavalheiro AJ, Bolzani VS, Furlan M (2005) Circadian rhythm of anti-fungal prenylated chromene in leaves of Piper aduncum. Phytochem Anal 16:282–286
Morandim ADA, Kato MJ, Cavalheiro AJ, Furlan M (2009) Intraspecific variability of dihydrochalcone, chromenes and benzoic acid derivatives in leaves of Piper aduncum L. (Piperaceae). Afr J Biotechnol 8:2157–2162
Okuyama E, Fujimori S, Yamazaki M, Deyama T (1998) Pharmacologically active components of viticis fructus (Vitex rotundifolia). II. The components having analgesic effects. Chem Pharm Bull 46:655–662
Orjala J, Wright AD, Behrends H, Folkers G, Sticher O, Rüegger H, Rali T (1994) Cytotoxic and antibacterial dihydrochalcones from Piper aduncum. J Nat Prod 57:18–26
Sigurskiold BW, Haunstrup I, Bock K (1992) Hydrolysis of substrate analogues catalysed by β-d-glucosidase from Aspergillus niger. Part III. Alkyl and aryl β-d-glucopyranosides. Acta Chem Scand 46:451–458
Spector AA, Norris AW (2007) Action of epoxyeicosatrienoic acids on cellular function. Am J Physiol Cell Physiol 292:C996–C1012
Thao NP, Luyen BTT, Kim JH, Jo AR, Dat NT, Kiem PV, Minh CV, Kim YH (2016a) Identification, characterization, kinetics, and molecular docking of flavonoid constituents from Archidendron clypearia (Jack.) Nielsen leaves and twigs. Bioorg Med Chem 24:3125–3132
Thao NP, Luyen BTT, Widowati W, Fauziah N, Maesaroh M, Herlina T, Manzoor Z, Ali I, Koh YS, Kim YH (2016b) Anti-inflammatory flavonoid C-glycosides from Piper aduncum leaves. Planta Med. doi:10.1055/s-0042-108737
Umehara K, Hattori I, Miyase T, Ueno A, Hara S, Kageyama C (1988) Studies on the constituents of leaves of Citrus unshiu Marcov. Chem Pharm Bull 36:5004–5008
Wang Y, Curtis-Long MJ, Lee BW, Yuk HJ, Kim DW, Tan XF, Park KH (2014) Inhibition of tyrosinase activity by polyphenol compounds from Flemingia philippinensis roots. Bioorg Med Chem 22:1115–1120
Xu ZR, Chai XY, Bai CC, Ren HY, Lu YN, Shi HM, Tu PF (2008) Xylocosides A–G, phenolic glucosides from the stems of Xylosma controversum. Helv Chim Acta 91:1346–1354
Yamano Y, Ito M (2005) Synthesis of optically active vomifolio and roseoside stereoisomer. Chem Pharm Bull 53:541–546
Acknowledgments
This study was supported by Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education (2009–0093815).
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
Conflict of interest
The authors declare that they have no competing interests.
Additional information
Bui Thi Thuy Luyen and Nguyen Phuong Thao have contributed equally to this work.
Electronic supplementary material
Rights and permissions
About this article
Cite this article
Luyen, B.T.T., Thao, N.P., Widowati, W. et al. Chemical constituents of Piper aduncum and their inhibitory effects on soluble epoxide hydrolase and tyrosinase. Med Chem Res 26, 220–226 (2017). https://doi.org/10.1007/s00044-016-1735-3
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00044-016-1735-3