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Chemotaxonomic and biosynthetic relationships between flavonolignans produced by Silybum marianum populations.
Fitoterapia 2017; 119:175-184F

Abstract

Flavonolignans constitute an important class of plant secondary metabolites formed by oxidative coupling of one flavonoid and one phenylpropanoid moiety. The standardized flavonolignan-rich extract prepared from the fruits of Silybum marianum is known as silymarin and has long been used medicinally, prominently as an antihepatotoxic and as a chemopreventive agent. Principal component analysis of the variation in flavonolignan content in S. marianum samples collected from different locations in Egypt revealed biosynthetic relationships between the flavonolignans. Silybin A, silybin B, and silychristin are positively correlated as are silydianin, isosilychristin, and isosilybin B. The detection of silyamandin in the extracts of S. marianum correlates with isosilychristin and silydianin content. The positive correlation between silydianin, isosilychristin, and silyamandin was demonstrated using quantitative 1H nuclear magnetic resonance spectroscopy (qHNMR). These correlations can be interpreted as evidence for the involvement of a flavonoid radical in the biosynthesis of the flavonolignans in S. marianum. The predominance of silybins A & B over isosilybin A & B in the silybin-rich samples is discussed in light of the relative stabilities of their respective radical flavonoid biosynthetic intermediates.

Authors+Show Affiliations

Department of Pharmacognosy, Faculty of Pharmacy, Beni-Suef University, Beni-Suef 62111, Egypt. Electronic address: sameh.zaid@pharm.bsu.edu.eg.Department of Pharmacognosy, Faculty of Pharmacy, Beni-Suef University, Beni-Suef 62111, Egypt.Department of Pharmacognosy, Faculty of Pharmacy, Beni-Suef University, Beni-Suef 62111, Egypt.Department of Pharmacognosy, Faculty of Pharmacy, Beni-Suef University, Beni-Suef 62111, Egypt.UIC/NIH Center for Botanical Dietary Supplements Research, College of Pharmacy, University of Illinois at Chicago, 833 S. Wood St., M/C 781, Chicago, IL 60612, United States; Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago, 833 S. Wood St., M/C 781, Chicago, IL 60612, United States.Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago, 833 S. Wood St., M/C 781, Chicago, IL 60612, United States.Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago, 833 S. Wood St., M/C 781, Chicago, IL 60612, United States.Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago, 833 S. Wood St., M/C 781, Chicago, IL 60612, United States; Physical Sciences Department, Rosary College of Arts and Sciences, Dominican University, 7900 West Division Street, River Forest, IL 60305, United States.UIC/NIH Center for Botanical Dietary Supplements Research, College of Pharmacy, University of Illinois at Chicago, 833 S. Wood St., M/C 781, Chicago, IL 60612, United States; Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago, 833 S. Wood St., M/C 781, Chicago, IL 60612, United States.

Pub Type(s)

Journal Article

Language

eng

PubMed ID

28392269

Citation

AbouZid, Sameh F., et al. "Chemotaxonomic and Biosynthetic Relationships Between Flavonolignans Produced By Silybum Marianum Populations." Fitoterapia, vol. 119, 2017, pp. 175-184.
AbouZid SF, Ahmed HS, Moawad AS, et al. Chemotaxonomic and biosynthetic relationships between flavonolignans produced by Silybum marianum populations. Fitoterapia. 2017;119:175-184.
AbouZid, S. F., Ahmed, H. S., Moawad, A. S., Owis, A. I., Chen, S. N., Nachtergael, A., ... Pauli, G. F. (2017). Chemotaxonomic and biosynthetic relationships between flavonolignans produced by Silybum marianum populations. Fitoterapia, 119, pp. 175-184. doi:10.1016/j.fitote.2017.04.002.
AbouZid SF, et al. Chemotaxonomic and Biosynthetic Relationships Between Flavonolignans Produced By Silybum Marianum Populations. Fitoterapia. 2017;119:175-184. PubMed PMID: 28392269.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Chemotaxonomic and biosynthetic relationships between flavonolignans produced by Silybum marianum populations. AU - AbouZid,Sameh F, AU - Ahmed,Hayam S, AU - Moawad,Abeer S, AU - Owis,Asmaa I, AU - Chen,Shao-Nong, AU - Nachtergael,Amandine, AU - McAlpine,James B, AU - Brent Friesen,J, AU - Pauli,Guido F, Y1 - 2017/04/06/ PY - 2017/03/01/received PY - 2017/03/28/revised PY - 2017/04/04/accepted PY - 2017/4/11/pubmed PY - 2017/6/16/medline PY - 2017/4/11/entrez KW - Biosynthesis KW - Flavonolignans KW - Principal component analysis KW - Silybum marianum KW - qHNMR SP - 175 EP - 184 JF - Fitoterapia JO - Fitoterapia VL - 119 N2 - Flavonolignans constitute an important class of plant secondary metabolites formed by oxidative coupling of one flavonoid and one phenylpropanoid moiety. The standardized flavonolignan-rich extract prepared from the fruits of Silybum marianum is known as silymarin and has long been used medicinally, prominently as an antihepatotoxic and as a chemopreventive agent. Principal component analysis of the variation in flavonolignan content in S. marianum samples collected from different locations in Egypt revealed biosynthetic relationships between the flavonolignans. Silybin A, silybin B, and silychristin are positively correlated as are silydianin, isosilychristin, and isosilybin B. The detection of silyamandin in the extracts of S. marianum correlates with isosilychristin and silydianin content. The positive correlation between silydianin, isosilychristin, and silyamandin was demonstrated using quantitative 1H nuclear magnetic resonance spectroscopy (qHNMR). These correlations can be interpreted as evidence for the involvement of a flavonoid radical in the biosynthesis of the flavonolignans in S. marianum. The predominance of silybins A & B over isosilybin A & B in the silybin-rich samples is discussed in light of the relative stabilities of their respective radical flavonoid biosynthetic intermediates. SN - 1873-6971 UR - https://www.unboundmedicine.com/medline/citation/28392269/Chemotaxonomic_and_biosynthetic_relationships_between_flavonolignans_produced_by_Silybum_marianum_populations_ L2 - https://linkinghub.elsevier.com/retrieve/pii/S0367-326X(17)30333-7 DB - PRIME DP - Unbound Medicine ER -