Structure elucidation and antioxidant activity of (-)-isosilandrin isolated from Silybum marianum L.
A regioisomer of the known flavanolignan (-)-silandrin (3a), named (-)-isosilandrin (8a), was isolated from the fruits of a white-flowered variant of Silybum marianum L. populated in Hungary. Its structure was established both by spectroscopic methods and total synthesis, and its absolute configuration was determined by means of circular dichroism. This compound showed stronger inhibitory activity on the superoxide anion (O2*-) release by human polymorphonuclear leukocytes (PMNL) than (+)-silybin (1a,b).
Samu
Zsuzsanna
Z
Research Institute for Medicinal Plants, P.O. Box 11, H-2011 Budakalász.
Nyiredy
Szabolcs
S
Baitz-Gács
Eszter
E
Varga
Zsuzsa
Z
Kurtán
Tibor
T
Dinya
Zoltán
Z
Antus
Sándor
S
D000975:Antioxidants / Q000737:chemistry* / Q000302:isolation & purification* / Q000494:pharmacology; D005638:Fruit; D006801:Humans; D007962:Leukocytes / Q000187:drug effects / Q000378:metabolism; D020944:Silybum marianum; D010936:Plant Extracts / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D012838:Silymarin / Q000031:analogs & derivatives* / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D013329:Structure-Activity Relationship
D000975:Antioxidants; D010936:Plant Extracts; D012838:Silymarin; C075820:isosilybin