Silychristin

Silychristin

Silicristin A (2R, 3S)

Silicristin B (2S, 3R)
Names
IUPAC name
Silychristin A = (2R,3R)-3,5,7-trihydroxy-2-((2R,3S)-7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydrobenzofuran-5-yl)chroman-4-one Silychristin B = (2R,3R)-3,5,7-trihydroxy-2-((2S,3R)-7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydrobenzofuran-5-yl)chroman-4-one
Other names
Silichristin, Silicristin, Silycristin
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
EC Number
  • 251-720-9
KEGG
UNII
  • InChI=1S/C25H22O10/c1-33-18-6-10(2-3-15(18)28)23-14(9-26)13-4-11(5-17(30)25(13)35-23)24-22(32)21(31)20-16(29)7-12(27)8-19(20)34-24/h2-8,14,22-24,26-30,32H,9H2,1H3/t14-,22+,23+,24-/m1/s1
    Key: BMLIIPOXVWESJG-LMBCONBSSA-N
  • COC1=C(C=CC(=C1)[C@H]2[C@@H](C3=C(O2)C(=CC(=C3)[C@@H]4[C@H](C(=O)C5=C(C=C(C=C5O4)O)O)O)O)CO)O
Properties
C25H22O10
Molar mass 482.4 g/mol
Hazards
GHS labelling:
GHS07: Exclamation mark
Warning
H302
P264, P270, P301+P312, P330, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Silychristin (also known as silichristin) is a natural product and one of the constituents of silymarin, the standardized, active extract of the fruit of milk thistle, Silybum marianum.[1][2] It is the second most abundant constituent in silymarin, after silybin.[3] Silychristin is a flavonolignan, along with many other silymarin constituents (such as silybin, isosilybin, silydianin, etc.), meaning it is composed up of a flavonoid and a lignan.[3] It is estimated that up to 65–80% of silymarin extract is made up of flavonolignans, like silychristin, which give silymarin its well known potent antioxidant and hepatoprotective properties.[4][5] Silychristin can exist as two stereoisomers, silychristin A (2R, 3S) and silychristin B (2S, 3R). The marianum variety of S. marianum (purple corollas) includes silychristin A as a major flavonolignan constituent, while the lesser known and studied albiflorum variety (white corollas) includes unique flavonolignans, including silyhermin, (–)-silandrin, and (+)-silymonin.[6]

  1. ^ "Silicristin - an overview :ScienceDirect Topics". www.sciencedirect.com. Skin Aging Handbook. Retrieved 2020-11-22.
  2. ^ Johannes, Jörg; Jayarama-Naidu, Roopa; Meyer, Franziska; Wirth, Eva Katrin; Schweizer, Ulrich; Schomburg, Lutz; Köhrle, Josef; Renko, Kostja (2016-04-01). "Silychristin, a Flavonolignan Derived From the Milk Thistle, Is a Potent Inhibitor of the Thyroid Hormone Transporter MCT8". Endocrinology. 157 (4): 1694–1701. doi:10.1210/en.2015-1933. PMID 26910310.
  3. ^ a b Biedermann, D.; Buchta, M.; Holečková, V.; Sedlák, D.; Valentová, K.; Cvačka, J.; Bednárová, L.; Křenková, A.; Kuzma, M.; Škuta, C.; Peikerová, Ž.; Bartůněk, P.; Křen, V., Silychristin: Skeletal Alterations and Biological Activities. Journal of Natural Products 2016, 79 (12), 3086–3092.
  4. ^ Kawaguchi-Suzuki, M.; Frye, R. F.; Zhu, H.-J.; Brinda, B. J.; Chavin, K. D.; Bernstein, H. J.; Markowitz, J. S., The Effects of Milk Thistle (Silybum marianum) on Human Cytochrome P450 Activity. Drug Metabolism and Disposition 2014, 42 (10), 1611–1616.
  5. ^ Zhu, H.-J.; Brinda, B. J.; Chavin, K. D.; Bernstein, H. J.; Patrick, K. S.; Markowitz, J. S., An Assessment of Pharmacokinetics and Antioxidant Activity of Free Silymarin Flavonolignans in Healthy Volunteers: A Dose Escalation Study. Drug Metabolism and Disposition 2013, 41 (9), 1679–1685.
  6. ^ Ahmed, H. S.; Mohamed, W. R.; Moawad, A. S.; Owis, A. I.; Ahmed, R. R.; AbouZid, S. F., Cytotoxic, hepatoprotective and antioxidant activities of Silybum marianum variety albiflorum growing in Egypt. Natural Product Research 2019, 1–5.