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 configurat...

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Veröffentlicht in:	Chemistry & biodiversity 2004-11, Vol.1 (11), p.1668-1677
Hauptverfasser:	Samu, Zsuzsanna, Nyiredy, Szabolcs, Baitz-Gács, Eszter, Varga, Zsuzsa, Kurtán, Tibor, Dinya, Zoltán, Antus, Sándor
Format:	Artikel
Sprache:	eng
Schlagworte:	Antioxidants - chemistry Antioxidants - isolation & purification Antioxidants - pharmacology Fruit Humans Leukocytes - drug effects Leukocytes - metabolism Plant Extracts - chemistry Plant Extracts - isolation & purification Plant Extracts - pharmacology Silybum marianum Silymarin - analogs & derivatives Silymarin - chemistry Silymarin - isolation & purification Silymarin - pharmacology Structure-Activity Relationship
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Zusammenfassung:	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 ($\rm{ O_2^{ \bullet - }}$) release by human polymorphonuclear leukocytes (PMNL) than (+)‐silybin (1a,b).
ISSN:	1612-1872 1612-1880
DOI:	10.1002/cbdv.200490125