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Reinvestigation of Herniaria glabra L. saponins and their biological activity.
Phytochemistry. 2020 Jan; 169:112162.P

Abstract

Twelve undescribed triterpenoid pentacyclic glycosides, medicagenic acid (3-O-β-D-glucuronopyranosyl-28-O-{[β-D-glucopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)]-[α-L-rhamnopyranosyl-(1 → 3)]-4-O-acetyl-β-D-fucopyranosyl-(1→)}-2β,3β-dihydroxyolean-12-ene-23,28-dioic acid, 3-O-β-D-glucuronopyranosyl-28-O-{[α-L-rhamnopyranosyl-(1 → 2)]-[β-D-apiofuranosyl-(1 → 3)]-4-O-acetyl-β-D-fucopyranosyl-(1→)}-2β,3β-dihydroxyolean-12-ene-23,28-dioic acid, 3-O-β-D-glucuronopyranosyl-28-O-{[α-L-rhamnopyranosyl-(1 → 2)]-3,4-O-diacetyl-β-D-fucopyranosyl-(1→)}-2β,3β-dihydroxyolean-12-ene-23,28-dioic acid, 28-O-{[6-O-acetyl-β-D-glucopyranosyl-(1 → 2)]-[2-O-acetyl-α-L-rhamnopyranosyl-(1 → 4)-β-D-glucopyranosyl-(1 → 6)]-β-D-glucopyranosyl-(1→)}-2β,3β-dihydroxyolean-12-ene-23,28-dioic acid, 28-O-{[6-O-acetyl-β-D-glucopyranosyl-(1 → 2)]-[3-O-acetyl-α-L-rhamnopyranosyl-(1 → 4)-β-D-glucopyranosyl-(1 → 6)]-β-D-glucopyranosyl-(1→)}-2β,3β-dihydroxyolean-12-ene-23,28-dioic acid, 28-O-{[6-O-acetyl-β-D-glucopyranosyl-(1 → 2)]-[4-O-acetyl-α-L-rhamnopyranosyl-(1 → 4)-β-D-glucopyranosyl-(1 → 6)]-β-D-glucopyranosyl-(1→)}-2β,3β-dihydroxyolean-12-ene-23,28-dioic acid, 28-O-{[6-O-acetyl-β-D-glucopyranosyl-(1 → 2)]-[β-D-glucopyranosyl-(1 → 6)]-β-D-glucopyranosyl-(1→)}-2β,3β-dihydroxyolean-12-ene-23,28-dioic acid, 28-O-{[β-D-glucopyranosyl-(1 → 2)]-[β-D-glucopyranosyl-(1 → 6)]-β-D-glucopyranosyl-(1→)}-2β,3β-dihydroxyolean-12-ene-23,28-dioic acid), zanhic acid (3-O-β-D-glucuronopyranosyl-28-O-{[β-D-glucopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)]-[α-L-rhamnopyranosyl-(1 → 3)]-4-O-acetyl-β-D-fucopyranosyl-(1→)}2β,3β,16α-trihydroxyolean-12-ene-23,28-dioic acid, 3-O-β-D-glucuronopyranosyl-28-O-{[β-D-glucopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)]-β-D-fucopyranosyl-(1→)}-2β,3β,16α-trihydroxyolean-12-ene-23,28-dioic acid), 29-hydroxy-medicagenic acid (3-O-β-D-glucuronopyranosyl-28-O-{[β-D-glucopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)]-[α-L-rhamnopyranosyl-(1 → 3)]-4-O-acetyl-β-D-fucopyranosyl-(1→)}-2β,3β,29β-trihydroxyolean-12-ene-23,28-dioic acid) and herniaric acid (28-O-{[6-O-acetyl-β-D-glucopyranosyl-(1 → 2)]-[α-L-rhamnopyranosyl-(1 → 4)-β-D-glucopyranosyl-(1 → 6)]-β-D-glucopyranosyl-(1→)}-2β,3β-dihydroxyolean-18-ene-23,28-dioic acid) were isolated from the whole plant extract of Herniaria glabra L. (Caryophyllaceae), wild growing in the Ukraine. In addition, five known triterpenoid saponins; i.e. herniariasaponins 1, 4, 5, 6, and 7 were also isolated. Their structures were elucidated by HRESIMS, 1D and 2D NMR spectroscopy, as well as by comparison with the literature data. Twelve herniariasaponins, the purified crude extract, and the saponin fraction were evaluated in vitro for their xanthine oxidase, collagenase, elastase, and tyrosinase inhibitory activity. Moreover, herniariasaponins 4, 5, and 7 were screened for their cholinesterase inhibitory potential. As a result, no or low inhibition towards the mentioned enzymes was observed.

Authors+Show Affiliations

Department of Biochemistry and Crop Quality, Institute of Soil Science and Plant Cultivation, State Research Institute, Ul. Czartoryskich 8, 24-100, Puławy, Poland; Department of Pharmacognosy with Medical Botany, I. Horbachevsky Ternopil National Medical University, Maidan Voli 1, 46001, Ternopil, Ukraine. Electronic address: skozachok@iung.pulawy.pl.Department of Biochemistry and Crop Quality, Institute of Soil Science and Plant Cultivation, State Research Institute, Ul. Czartoryskich 8, 24-100, Puławy, Poland. Electronic address: lpecio@iung.pulawy.pl.Department of Pharmacognosy, Faculty of Pharmacy, Gazi University, 06330, Ankara, Turkey.Department of Pharmacognosy, Faculty of Pharmacy, Gazi University, 06330, Ankara, Turkey.Department of Pharmacognosy with Medical Botany, I. Horbachevsky Ternopil National Medical University, Maidan Voli 1, 46001, Ternopil, Ukraine.Department of Biochemistry and Crop Quality, Institute of Soil Science and Plant Cultivation, State Research Institute, Ul. Czartoryskich 8, 24-100, Puławy, Poland.

Pub Type(s)

Journal Article

Language

eng

PubMed ID

31627115

Citation

Kozachok, Solomiia, et al. "Reinvestigation of Herniaria Glabra L. Saponins and Their Biological Activity." Phytochemistry, vol. 169, 2020, p. 112162.
Kozachok S, Pecio Ł, Orhan IE, et al. Reinvestigation of Herniaria glabra L. saponins and their biological activity. Phytochemistry. 2020;169:112162.
Kozachok, S., Pecio, Ł., Orhan, I. E., Deniz, F. S. S., Marchyshyn, S., & Oleszek, W. (2020). Reinvestigation of Herniaria glabra L. saponins and their biological activity. Phytochemistry, 169, 112162. https://doi.org/10.1016/j.phytochem.2019.112162
Kozachok S, et al. Reinvestigation of Herniaria Glabra L. Saponins and Their Biological Activity. Phytochemistry. 2020;169:112162. PubMed PMID: 31627115.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Reinvestigation of Herniaria glabra L. saponins and their biological activity. AU - Kozachok,Solomiia, AU - Pecio,Łukasz, AU - Orhan,Ilkay Erdogan, AU - Deniz,Fatma Sezer Senol, AU - Marchyshyn,Svitlana, AU - Oleszek,Wiesław, Y1 - 2019/10/15/ PY - 2019/06/24/received PY - 2019/09/26/revised PY - 2019/09/28/accepted PY - 2019/10/19/pubmed PY - 2020/2/27/medline PY - 2019/10/19/entrez KW - Caryophyllaceae KW - Enzyme inhibitory activity KW - GOTCABs KW - Herniaria glabra L. KW - Herniariasaponins KW - Hydroxy-medicagenic acid KW - Medicagenic acid KW - Triterpenoid saponins SP - 112162 EP - 112162 JF - Phytochemistry JO - Phytochemistry VL - 169 N2 - Twelve undescribed triterpenoid pentacyclic glycosides, medicagenic acid (3-O-β-D-glucuronopyranosyl-28-O-{[β-D-glucopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)]-[α-L-rhamnopyranosyl-(1 → 3)]-4-O-acetyl-β-D-fucopyranosyl-(1→)}-2β,3β-dihydroxyolean-12-ene-23,28-dioic acid, 3-O-β-D-glucuronopyranosyl-28-O-{[α-L-rhamnopyranosyl-(1 → 2)]-[β-D-apiofuranosyl-(1 → 3)]-4-O-acetyl-β-D-fucopyranosyl-(1→)}-2β,3β-dihydroxyolean-12-ene-23,28-dioic acid, 3-O-β-D-glucuronopyranosyl-28-O-{[α-L-rhamnopyranosyl-(1 → 2)]-3,4-O-diacetyl-β-D-fucopyranosyl-(1→)}-2β,3β-dihydroxyolean-12-ene-23,28-dioic acid, 28-O-{[6-O-acetyl-β-D-glucopyranosyl-(1 → 2)]-[2-O-acetyl-α-L-rhamnopyranosyl-(1 → 4)-β-D-glucopyranosyl-(1 → 6)]-β-D-glucopyranosyl-(1→)}-2β,3β-dihydroxyolean-12-ene-23,28-dioic acid, 28-O-{[6-O-acetyl-β-D-glucopyranosyl-(1 → 2)]-[3-O-acetyl-α-L-rhamnopyranosyl-(1 → 4)-β-D-glucopyranosyl-(1 → 6)]-β-D-glucopyranosyl-(1→)}-2β,3β-dihydroxyolean-12-ene-23,28-dioic acid, 28-O-{[6-O-acetyl-β-D-glucopyranosyl-(1 → 2)]-[4-O-acetyl-α-L-rhamnopyranosyl-(1 → 4)-β-D-glucopyranosyl-(1 → 6)]-β-D-glucopyranosyl-(1→)}-2β,3β-dihydroxyolean-12-ene-23,28-dioic acid, 28-O-{[6-O-acetyl-β-D-glucopyranosyl-(1 → 2)]-[β-D-glucopyranosyl-(1 → 6)]-β-D-glucopyranosyl-(1→)}-2β,3β-dihydroxyolean-12-ene-23,28-dioic acid, 28-O-{[β-D-glucopyranosyl-(1 → 2)]-[β-D-glucopyranosyl-(1 → 6)]-β-D-glucopyranosyl-(1→)}-2β,3β-dihydroxyolean-12-ene-23,28-dioic acid), zanhic acid (3-O-β-D-glucuronopyranosyl-28-O-{[β-D-glucopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)]-[α-L-rhamnopyranosyl-(1 → 3)]-4-O-acetyl-β-D-fucopyranosyl-(1→)}2β,3β,16α-trihydroxyolean-12-ene-23,28-dioic acid, 3-O-β-D-glucuronopyranosyl-28-O-{[β-D-glucopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)]-β-D-fucopyranosyl-(1→)}-2β,3β,16α-trihydroxyolean-12-ene-23,28-dioic acid), 29-hydroxy-medicagenic acid (3-O-β-D-glucuronopyranosyl-28-O-{[β-D-glucopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)]-[α-L-rhamnopyranosyl-(1 → 3)]-4-O-acetyl-β-D-fucopyranosyl-(1→)}-2β,3β,29β-trihydroxyolean-12-ene-23,28-dioic acid) and herniaric acid (28-O-{[6-O-acetyl-β-D-glucopyranosyl-(1 → 2)]-[α-L-rhamnopyranosyl-(1 → 4)-β-D-glucopyranosyl-(1 → 6)]-β-D-glucopyranosyl-(1→)}-2β,3β-dihydroxyolean-18-ene-23,28-dioic acid) were isolated from the whole plant extract of Herniaria glabra L. (Caryophyllaceae), wild growing in the Ukraine. In addition, five known triterpenoid saponins; i.e. herniariasaponins 1, 4, 5, 6, and 7 were also isolated. Their structures were elucidated by HRESIMS, 1D and 2D NMR spectroscopy, as well as by comparison with the literature data. Twelve herniariasaponins, the purified crude extract, and the saponin fraction were evaluated in vitro for their xanthine oxidase, collagenase, elastase, and tyrosinase inhibitory activity. Moreover, herniariasaponins 4, 5, and 7 were screened for their cholinesterase inhibitory potential. As a result, no or low inhibition towards the mentioned enzymes was observed. SN - 1873-3700 UR - https://www.unboundmedicine.com/medline/citation/31627115/Reinvestigation_of_Herniaria_glabra_L__saponins_and_their_biological_activity_ L2 - https://linkinghub.elsevier.com/retrieve/pii/S0031-9422(19)30583-7 DB - PRIME DP - Unbound Medicine ER -