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The study of flavonolignan association patterns in fruits of diverging Silybum marianum (L.) Gaertn. chemotypes provides new insights into the silymarin biosynthetic pathway.
Phytochemistry 2017; 144:9-18P

Abstract

Silymarin is the phytochemical with medicinal properties extracted from Silybum marianum (L.) Gaertn. fruits. Yet, little information is available about silymarin biosynthesis. Moreover, the generally accepted pathway, formulated thus far, is not in agreement with actual experimental measurements on flavonolignan contents. The present work analyses flavonolignan and taxifolin content in 201 S. marianum samples taking into consideration a wide phenotypic variability. Two stable chemotypes were identified: one characterized by both high silychristin and silybin content (chemotype A) and another by a high silydianin content (chemotype B). Through the correlation analysis of samples divided according to chemotype, it was possible to construct a simplified silymarin biosynthetic pathway that is sufficiently versatile in explaining experimental results responding to the actually unresolved questions about this process. The proposed pathway highlights that three separate and equally sized metabolite pools exist, namely: diastereoisomers A (silybin A plus isosilybin A), diastereoisomers B (silybin B plus isosilybin B) and silychristin. In both A and B diastereoisomers pools, isosilybin A and isosilybin B always represent a given amount of the metabolite flux through the specific metabolite pool suggesting the possible involvement of dirigent protein-like enzymes. We suggest that chemotype B possesses a complete silymarin biosynthetic pathway in which silydianin biosynthesis is enzymatically controlled. On the contrary, chemotype A is probably a natural mutant unable to biosynthesize silydianin. The present simplified pathway for silymarin biosynthesis will constitute an important tool for the further understanding of the reactions that drive flavonolignan biosynthesis in S. marianum.

Authors+Show Affiliations

Council for Agricultural Research and Economics - Research Centre for Cereal and Industrial Crops (CREA-CI), Bologna, Italy. Electronic address: tommaso.martinelli@crea.gov.it.University of Florence, Department of Agrifood Production and Environmental Sciences (DISPAA), Firenze, Italy.University of Florence, Department of Agrifood Production and Environmental Sciences (DISPAA), Firenze, Italy.Council for Agricultural Research and Economics - Research Centre for Cereal and Industrial Crops (CREA-CI), Bologna, Italy.Department of Agrotechnology, University of Science and Technology, Bydgoszcz, Poland.

Pub Type(s)

Journal Article

Language

eng

PubMed ID

28863306

Citation

Martinelli, Tommaso, et al. "The Study of Flavonolignan Association Patterns in Fruits of Diverging Silybum Marianum (L.) Gaertn. Chemotypes Provides New Insights Into the Silymarin Biosynthetic Pathway." Phytochemistry, vol. 144, 2017, pp. 9-18.
Martinelli T, Whittaker A, Benedettelli S, et al. The study of flavonolignan association patterns in fruits of diverging Silybum marianum (L.) Gaertn. chemotypes provides new insights into the silymarin biosynthetic pathway. Phytochemistry. 2017;144:9-18.
Martinelli, T., Whittaker, A., Benedettelli, S., Carboni, A., & Andrzejewska, J. (2017). The study of flavonolignan association patterns in fruits of diverging Silybum marianum (L.) Gaertn. chemotypes provides new insights into the silymarin biosynthetic pathway. Phytochemistry, 144, pp. 9-18. doi:10.1016/j.phytochem.2017.08.013.
Martinelli T, et al. The Study of Flavonolignan Association Patterns in Fruits of Diverging Silybum Marianum (L.) Gaertn. Chemotypes Provides New Insights Into the Silymarin Biosynthetic Pathway. Phytochemistry. 2017;144:9-18. PubMed PMID: 28863306.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - The study of flavonolignan association patterns in fruits of diverging Silybum marianum (L.) Gaertn. chemotypes provides new insights into the silymarin biosynthetic pathway. AU - Martinelli,Tommaso, AU - Whittaker,Anne, AU - Benedettelli,Stefano, AU - Carboni,Andrea, AU - Andrzejewska,Jadwiga, Y1 - 2017/09/01/ PY - 2017/06/10/received PY - 2017/08/06/revised PY - 2017/08/22/accepted PY - 2017/9/2/pubmed PY - 2017/12/22/medline PY - 2017/9/2/entrez KW - Asteraceae KW - Correlation analysis KW - Flavonolignans KW - Isosilybin KW - Isosilybin A (PubChem CID: 11059920) KW - Isosilybin B (PubChem CID: 10885340) KW - Milk thistle KW - Silybin KW - Silybin A (PubChem CID: 16211710) KW - Silybin B (PubChem CID: 1548994) KW - Silybum marianum KW - Silychristin KW - Silychristin (PubChem CID: 441764) KW - Silydianin KW - Silydianin (PubChem CID: 11982272) KW - Silymarin KW - Taxifolin (PubChem CID: 439533) SP - 9 EP - 18 JF - Phytochemistry JO - Phytochemistry VL - 144 N2 - Silymarin is the phytochemical with medicinal properties extracted from Silybum marianum (L.) Gaertn. fruits. Yet, little information is available about silymarin biosynthesis. Moreover, the generally accepted pathway, formulated thus far, is not in agreement with actual experimental measurements on flavonolignan contents. The present work analyses flavonolignan and taxifolin content in 201 S. marianum samples taking into consideration a wide phenotypic variability. Two stable chemotypes were identified: one characterized by both high silychristin and silybin content (chemotype A) and another by a high silydianin content (chemotype B). Through the correlation analysis of samples divided according to chemotype, it was possible to construct a simplified silymarin biosynthetic pathway that is sufficiently versatile in explaining experimental results responding to the actually unresolved questions about this process. The proposed pathway highlights that three separate and equally sized metabolite pools exist, namely: diastereoisomers A (silybin A plus isosilybin A), diastereoisomers B (silybin B plus isosilybin B) and silychristin. In both A and B diastereoisomers pools, isosilybin A and isosilybin B always represent a given amount of the metabolite flux through the specific metabolite pool suggesting the possible involvement of dirigent protein-like enzymes. We suggest that chemotype B possesses a complete silymarin biosynthetic pathway in which silydianin biosynthesis is enzymatically controlled. On the contrary, chemotype A is probably a natural mutant unable to biosynthesize silydianin. The present simplified pathway for silymarin biosynthesis will constitute an important tool for the further understanding of the reactions that drive flavonolignan biosynthesis in S. marianum. SN - 1873-3700 UR - https://www.unboundmedicine.com/medline/citation/28863306/The_study_of_flavonolignan_association_patterns_in_fruits_of_diverging_Silybum_marianum__L___Gaertn__chemotypes_provides_new_insights_into_the_silymarin_biosynthetic_pathway_ L2 - https://linkinghub.elsevier.com/retrieve/pii/S0031-9422(17)30288-1 DB - PRIME DP - Unbound Medicine ER -