Antiplatelet Activity of Acylphloroglucinol Derivatives Isolated from

Overview

Journal Molecules

Publisher MDPI

Specialty Biology

Date 2019 Jun 16

PMID 31200488

Citations 5

Authors

Nam-Hui Yim

Jung-Jin Lee

BoHyoung Lee

Wei Li

Jin Yeul Ma

Affiliations

Soon will be listed here.

Abstract

Platelets are an important component of the initial response to vascular endothelial injury; however, platelet dysfunction induces the acute clinical symptoms of thrombotic disorders, which trigger severe cardiovascular diseases such as myocardial infarction, ischemia, and stroke. In this study, we investigated the 's antiplatelet activity. A water extract of (WDC) was partitioned into dichloromethane (DCM), ethyl acetate, -butyl alcohol, and water. Among these four fractions, the DCM fraction potently inhibited the collagen-stimulated platelet aggregation in a concentration-dependent manner. From this fraction, five different acylphloroglucinol compounds and one flavonoid were isolated by activity-guided column chromatography. They were identified by comparing their mass, H-, and C-NMR spectral data with those reported in the literature. Quantifying the six compounds in WDC and its DCM fraction by high-performance liquid chromatography (HPLC) revealed that butyryl-3-methylphloroglucinol (compound ) was the most abundant in these samples. Additionally, butyryl-3-methylphloroglucinol showed the strongest inhibitory activity in the collagen- and arachidonic acid (AA)-induced platelet aggregation, with inhibition ratios of 92.36% and 89.51% in the collagen and AA-induced platelet aggregation, respectively, without cytotoxicity. On the active concentrations, butyryl-3-methylphloroglucinol significantly suppressed the convulxin-induced platelet activation. Regarding the structure-activity relationships for the five acylphloroglucinol compounds, our results demonstrated that the functional butanonyl, methoxy, and hydroxy groups in butyryl-3-methylphloroglucinol play important roles in antiplatelet activity. The findings indicate that acylphloroglucinols, including butyryl-3-methylphloroglucinol from , possess an antiplatelet activity, supporting the use of this species for antiplatelet remedies.

Citing Articles

Insights into Chemical Diversity and Potential Health-Promoting Effects of Ferns.

Moussa A, Luo J, Xu B Plants (Basel). 2024; 13(18).

PMID: 39339643 PMC: 11434777. DOI: 10.3390/plants13182668.

Two New Compounds from the Endophytic Fungi of and Their Antimicrobial Activities.

Hai P, Gao Y, Yang L, Chen N, Jia H, Wang M Molecules. 2023; 28(24).

PMID: 38138533 PMC: 10745856. DOI: 10.3390/molecules28248043.

Optimization of Ultrasonic-Assisted Extraction of α-Glucosidase Inhibitors from Using Artificial Neural Network and Response Surface Methodology.

Phong N, Gao D, Kim J, Yang S Metabolites. 2023; 13(4).

PMID: 37110215 PMC: 10145310. DOI: 10.3390/metabo13040557.

Inhibitory Activity of Bioactive Phloroglucinols from the Rhizomes of Dryopteris crassirhizoma on Escherichia coli β-Glucuronidase: Kinetic Analysis and Molecular Docking Studies.

Phong N, Zhao Y, Min B, Yang S, Kim J Metabolites. 2022; 12(10).

PMID: 36295840 PMC: 9610990. DOI: 10.3390/metabo12100938.

Comparison of Constituents and Antioxidant Activity of Above-Ground and Underground Parts of Nakai Based on HS-SPME-GC-MS and UPLC/Q-TOF-MS.

Wang Y, Liu B, Wang X, Fan Y Molecules. 2022; 27(15).

PMID: 35956948 PMC: 9370178. DOI: 10.3390/molecules27154991.

References

Nieswandt B, Schulte V, Bergmeier W, Mokhtari-Nejad R, Rackebrandt K, Cazenave J . Long-term antithrombotic protection by in vivo depletion of platelet glycoprotein VI in mice. J Exp Med. 2001; 193(4):459-69. PMC: 2195902. DOI: 10.1084/jem.193.4.459. View

Majid A, Delanty N, Kantor J . Antiplatelet agents for secondary prevention of ischemic stroke. Ann Pharmacother. 2001; 35(10):1241-7. DOI: 10.1345/aph.10381. View

Ruggeri Z . Platelets in atherothrombosis. Nat Med. 2002; 8(11):1227-34. DOI: 10.1038/nm1102-1227. View

Schulte V, Rabie T, Prostredna M, Aktas B, Gruner S, Nieswandt B . Targeting of the collagen-binding site on glycoprotein VI is not essential for in vivo depletion of the receptor. Blood. 2003; 101(10):3948-52. DOI: 10.1182/blood-2002-10-3242. View

Lee S, Na M, An R, Min B, Lee H . Antioxidant activity of two phloroglucinol derivatives from Dryopteris crassirhizoma. Biol Pharm Bull. 2003; 26(9):1354-6. DOI: 10.1248/bpb.26.1354. View

Brass L . Thrombin and platelet activation. Chest. 2003; 124(3 Suppl):18S-25S. DOI: 10.1378/chest.124.3_suppl.18s. View

Born G, Cross M . THE AGGREGATION OF BLOOD PLATELETS. J Physiol. 1963; 168:178-95. PMC: 1359417. DOI: 10.1113/jphysiol.1963.sp007185. View

Chang X, Li W, Koike K, Wu L, Nikaido T . Phenolic constituents from the rhizomes of Dryopteris crassirhizoma. Chem Pharm Bull (Tokyo). 2006; 54(5):748-50. DOI: 10.1248/cpb.54.748. View

Na M, Jang J, Min B, Lee S, Lee M, Kim B . Fatty acid synthase inhibitory activity of acylphloroglucinols isolated from Dryopteris crassirhizoma. Bioorg Med Chem Lett. 2006; 16(18):4738-42. DOI: 10.1016/j.bmcl.2006.07.018. View

10.

Bharate S, Khan S, Yunus N, Chauthe S, Jacob M, Tekwani B . Antiprotozoal and antimicrobial activities of O-alkylated and formylated acylphloroglucinols. Bioorg Med Chem. 2006; 15(1):87-96. DOI: 10.1016/j.bmc.2006.10.006. View

11.

Lee J, Miyashiro H, Nakamura N, Hattori M . Two new triterpenes from the Rhizome of Dryopteris crassirhizoma, and inhibitory activities of its constituents on human immunodeficiency virus-1 protease. Chem Pharm Bull (Tokyo). 2008; 56(5):711-4. DOI: 10.1248/cpb.56.711. View

12.

Shinozaki J, Shibuya M, Masuda K, Ebizuka Y . Dammaradiene synthase, a squalene cyclase, from Dryopteris crassirhizoma Nakai. Phytochemistry. 2008; 69(14):2559-64. DOI: 10.1016/j.phytochem.2008.07.017. View

13.

Lee J, Jin Y, Yu J, Munkhtsetseg T, Park E, Lim Y . Antithrombotic and antiplatelet activities of fenofibrate, a lipid-lowering drug. Atherosclerosis. 2009; 206(2):375-82. DOI: 10.1016/j.atherosclerosis.2009.02.034. View

14.

Lee H, Kim J, Lee S . Antibacterial activity of two phloroglucinols, flavaspidic acids AB and PB, from Dryopteris crassirhizoma. Arch Pharm Res. 2009; 32(5):655-9. PMC: 7091015. DOI: 10.1007/s12272-009-1502-9. View

15.

Singh I, Sidana J, Bharate S, Foley W . Phloroglucinol compounds of natural origin: synthetic aspects. Nat Prod Rep. 2010; 27(3):393-416. DOI: 10.1039/b914364p. View

16.

Chang S, Bae J, Hong D, Choi K, Kim S, Her E . Dryopteris crassirhizoma has anti-cancer effects through both extrinsic and intrinsic apoptotic pathways and G0/G1 phase arrest in human prostate cancer cells. J Ethnopharmacol. 2010; 130(2):248-54. DOI: 10.1016/j.jep.2010.04.038. View

17.

Bae J . Antithrombotic and profibrinolytic activities of phloroglucinol. Food Chem Toxicol. 2011; 49(7):1572-7. DOI: 10.1016/j.fct.2011.04.003. View

18.

Lu C, Zhang H, Ji J, Wang G . In vivo anthelmintic activity of Dryopteris crassirhizoma, Kochia scoparia, and Polygala tenuifolia against Dactylogyrus intermedius (Monogenea) in goldfish (Carassius auratus). Parasitol Res. 2011; 110(3):1085-90. DOI: 10.1007/s00436-011-2592-0. View

19.

Schwartz S, Heimark R, Majesky M . Developmental mechanisms underlying pathology of arteries. Physiol Rev. 1990; 70(4):1177-209. DOI: 10.1152/physrev.1990.70.4.1177. View

20.

Chang M, Chang H, Chan C, Chou H, Chang B, Yeung S . Antiplatelet effect of phloroglucinol is related to inhibition of cyclooxygenase, reactive oxygen species, ERK/p38 signaling and thromboxane A2 production. Toxicol Appl Pharmacol. 2012; 263(3):287-95. DOI: 10.1016/j.taap.2012.06.021. View