Phenylpropionamides, Piperidine, and Phenolic Derivatives from the Fruit of Ailanthus Altissima

Overview

Journal Molecules

Publisher MDPI

Specialty Biology

Date 2017 Dec 7

PMID 29207525

Citations 9

Authors

Jian-Cheng Ni

Jian-Ting Shi

Qing-Wei Tan

Qi-Jian Chen

Affiliations

Soon will be listed here.

Abstract

Four novel compounds-two phenylpropionamides, one piperidine, and one phenolic derivatives-were isolated and identified from the fruit of a medicinal plant, (Mill.) Swingle (Simaroubaceae), together with one known phenylpropionamide, 13 known phenols, and 10 flavonoids. The structures of the new compounds were elucidated as 2-hydroxy--[(2--β-d-glucopyranosyl)phenyl]propionamide (), 2-hydroxy--[(2--β-d-glucopyranosyl-(1→6)-β-d-glucopyranosyl)phenyl]propionamide (), 2β-carboxyl-piperidine-4β-acetic acid methyl ester (), and 4-hydroxyphenyl-1--[6-(hydrogen-3-hydroxy-3-methylpentanedioate)]-β-d-glucopyranoside () based on spectroscopic analysis. All the isolated compounds were evaluated for their inhibitory activity against (TMV) using the leaf-disc method. Among the compounds isolated, arbutin (), β-d-glucopyranosyl-(1→6)-arbutin (), 4-methoxyphenylacetic acid (), and corilagin () showed moderate inhibition against TMV with IC values of 0.49, 0.51, 0.27, and 0.45 mM, respectively.

Citing Articles

Profiling and Bioactivity of Polyphenols from the Omani Medicinal Plant (syn. ).

Kappen J, Rashan L, Franke K, Wessjohann L Molecules. 2025; 30(4).

PMID: 40005262 PMC: 11858248. DOI: 10.3390/molecules30040952.

Phenolic Composition and Bioactivities of Invasive (Mill.) Swingle Leaf Extracts Obtained by Two-Step Sequential Extraction.

Cocirlea M, Soare A, Petrovici A, Silion M, Calin T, Oancea S Antioxidants (Basel). 2024; 13(7).

PMID: 39061893 PMC: 11273599. DOI: 10.3390/antiox13070824.

In Vitro Screening of Ecotoxic and Cytotoxic Activities of Leaf Extract against Target and Non-Target Plant and Animal Cells.

Cocirlea M, Simionescu N, Petrovici A, Silion M, Biondi B, Lastella L Int J Mol Sci. 2024; 25(11).

PMID: 38891841 PMC: 11171768. DOI: 10.3390/ijms25115653.

Seed Oil-A Valuable Source of Lipid-Soluble Components with DNA Protective and Antiproliferative Activities.

Andonova T, Petkova Z, Teneva O, Antova G, Apostolova E, Naimov S Foods. 2024; 13(8).

PMID: 38672940 PMC: 11048806. DOI: 10.3390/foods13081268.

Antiviral Activity of Ailanthone from on the Rice Stripe Virus.

Tan Q, Zhu J, Ju Y, Chi X, Cao T, Zheng L Viruses. 2024; 16(1).

PMID: 38257773 PMC: 10820994. DOI: 10.3390/v16010073.

References

Wang Y, Wang W, Su C, Zhang D, Xu L, He R . Cytotoxic quassinoids from Ailanthus altissima. Bioorg Med Chem Lett. 2013; 23(3):654-7. DOI: 10.1016/j.bmcl.2012.11.116. View

Sadeghian H, Attaran N, Jafari Z, Saberi M, Seyedi S, Eshghi H . Design and synthesis of 4-methoxyphenylacetic acid esters as 15-lipoxygenase inhibitors and SAR comparative studies of them. Bioorg Med Chem. 2009; 17(6):2327-35. DOI: 10.1016/j.bmc.2009.02.009. View

Du P, Ma Q, Zhu Z, Li G, Wang Y, Li Q . Mechanism of Corilagin interference with IL-13/STAT6 signaling pathways in hepatic alternative activation macrophages in schistosomiasis-induced liver fibrosis in mouse model. Eur J Pharmacol. 2016; 793:119-126. DOI: 10.1016/j.ejphar.2016.11.018. View

Hwang E, Ahn B, Lee H, Kim Y, Lee K, Bok S . Inhibitory activity for chitin synthase II from Saccharomyces cerevisiae by tannins and related compounds. Planta Med. 2001; 67(6):501-4. DOI: 10.1055/s-2001-16487-2. View

Kamatham S, Kumar N, Gudipalli P . Isolation and characterization of gallic acid and methyl gallate from the seed coats of Griff. and their anti-proliferative effect on human epidermoid carcinoma A431 cells. Toxicol Rep. 2017; 2:520-529. PMC: 5598244. DOI: 10.1016/j.toxrep.2015.03.001. View

Rahman A, Samoylenko V, Jacob M, Sahu R, Jain S, Khan S . Antiparasitic and antimicrobial indolizidines from the leaves of Prosopis glandulosa var. glandulosa. Planta Med. 2011; 77(14):1639-43. PMC: 3700807. DOI: 10.1055/s-0030-1270906. View

Tamura S, Fukamiya N, Okano M, Koyama J, Koike K, Tokuda H . Three new quassinoids, ailantinol E, F, and G, from Ailanthus altissima. Chem Pharm Bull (Tokyo). 2003; 51(4):385-9. DOI: 10.1248/cpb.51.385. View

Park T, Choi K, Park C, Lee S, Kang H, Shon K . Substrate specificity and transglycosylation catalyzed by a thermostable beta-glucosidase from marine hyperthermophile Thermotoga neapolitana. Appl Microbiol Biotechnol. 2005; 69(4):411-22. DOI: 10.1007/s00253-005-0055-1. View

Lee J, Ku C, Baek N, Kim S, Park H, Kim D . Phytochemical constituents from Diodia teres. Arch Pharm Res. 2004; 27(1):40-3. DOI: 10.1007/BF02980043. View

10.

Guo Y, Zhao L, Li X, Mei Y, Zhang S, Tao J . Effect of Corilagin on anti-inflammation in HSV-1 encephalitis and HSV-1 infected microglias. Eur J Pharmacol. 2010; 635(1-3):79-86. DOI: 10.1016/j.ejphar.2010.02.049. View

11.

Shen J, Zhang Z, Wu Z, Ouyang M, Xie L, Lin Q . Antiphytoviral activity of bruceine-D from Brucea javanica seeds. Pest Manag Sci. 2007; 64(2):191-6. DOI: 10.1002/ps.1465. View

12.

Tan Q, Ni J, Fang P, Chen Q . A New Erythrinan Alkaloid Glycoside from the Seeds of Erythrina crista-galli. Molecules. 2017; 22(9). PMC: 6151707. DOI: 10.3390/molecules22091558. View

13.

Tan Q, Ouyang M, Wu Z . A new seco-neolignan glycoside from the root bark of Ailanthus altissima. Nat Prod Res. 2011; 26(15):1375-80. DOI: 10.1080/14786419.2011.587187. View

14.

Xie H, Liang Y, Xue J, Xu Q, Jiang Y, Wei X . Secondary metabolites of the phytopathogen Peronophythora litchii. Nat Prod Commun. 2010; 5(2):245-8. View

15.

Joval E, Kroeger P, Towers N . Hydroquinone: the toxic compound of Agaricus hondensis. Planta Med. 1996; 62(2):185. DOI: 10.1055/s-2006-957852. View

16.

Souleles C, Kokkalou E . A New beta-Carboline Alkaloid from Ailanthus altissima. Planta Med. 1989; 55(3):286-7. DOI: 10.1055/s-2006-962006. View

17.

Dao T, Tran T, Kim J, Nguyen P, Lee E, Park J . Terpenylated coumarins as SIRT1 activators isolated from Ailanthus altissima. J Nat Prod. 2012; 75(7):1332-8. DOI: 10.1021/np300258u. View

18.

Sudjaroen Y, Hull W, Erben G, Wurtele G, Changbumrung S, Ulrich C . Isolation and characterization of ellagitannins as the major polyphenolic components of Longan (Dimocarpus longan Lour) seeds. Phytochemistry. 2012; 77:226-37. DOI: 10.1016/j.phytochem.2011.12.008. View

19.

Hong Z, Xiong J, Wu S, Zhu J, Hong J, Zhao Y . Tetracyclic triterpenoids and terpenylated coumarins from the bark of Ailanthus altissima ("Tree of Heaven"). Phytochemistry. 2012; 86:159-67. DOI: 10.1016/j.phytochem.2012.10.008. View

20.

Pfundstein B, El Desouky S, Hull W, Haubner R, Erben G, Owen R . Polyphenolic compounds in the fruits of Egyptian medicinal plants (Terminalia bellerica, Terminalia chebula and Terminalia horrida): characterization, quantitation and determination of antioxidant capacities. Phytochemistry. 2010; 71(10):1132-48. DOI: 10.1016/j.phytochem.2010.03.018. View