The structure of silybin (silybum substance E6), the first flavonolignan

Pelter, Andrew; Hänsel, Rudolf

doi:10.1016/s0040-4039(00)89610-0

Cited by 106 publications

(81 citation statements)

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“…The latter was isolated for the first time from fruits of the medicinal plant Silybum marianum 80 and its structure has been later revised. [81][82][83] Silybin results from an oxidative coupling of a flavonol (taxifolin) and a monolignol unit (Scheme 5).…”

Section: C H a L C O N E Smentioning

confidence: 99%

Recent advances in the discovery of flavonoids and analogs with high‐affinity binding to P‐glycoprotein responsible for cancer cell multidrug resistance

Boumendjel¹,

Pietro²,

Dumontet³

et al. 2002

Medicinal Research Reviews

158

105

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P-glycoprotein (P-gp) is a plasma membrane glycoprotein that confers multidrug resistance on cells by virtue of its ability to exclude cytotoxic drugs in an ATP-dependent manner. The most commonly considered hypothesis is that P-gp acts as an ATP-driven drug-export pump, the mechanism of which is not understood in detail. Therefore, a tremendous effort is being made to find out modulator molecules to inhibit P-gp. We have been developing flavonoid derivatives as a new class of promising modulators using a new in vitro rational-screening assay based on measurements of the binding-affinity toward the C-terminal nucleotide-binding domain (NBD2) of P-gp. This review is focused on our results obtained with a variety of flavonoids. Structure-activity relationships of flavonoids as potential MDR modulators are reported.

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Section: C H a L C O N E Smentioning

confidence: 99%

Recent advances in the discovery of flavonoids and analogs with high‐affinity binding to P‐glycoprotein responsible for cancer cell multidrug resistance

Boumendjel¹,

Pietro²,

Dumontet³

et al. 2002

Medicinal Research Reviews

158

105

View full text Add to dashboard Cite

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“…6 Anti-angiogenic activity 2.7 MDR pump inhibition activity 2. 8 Anti-cancer activity 2. 9 Anti-oxidant activity 2.10 Additional activities 3 Biosynthesis of 1,4-benzodioxane oxyneolignans 3.…”

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Synthesis and biology of 1,4-benzodioxane lignan natural products

Pilkington

Barker

2015

Nat. Prod. Rep.

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“…Experimental demonstration of the free radical phenolic coupling of taxifolin and coniferyl alcohol to produce silybin was provided by Schrall and Becker (1977). Structural studies (Hansel and SchOpflin, 1967;Pelter and Hansel, 1968; Wagner et aI., 1971e; Bandopadhyay et aI., 1972; Takemoto et aI., 1975; Kaloga, 1981a) led to an appreciation that different products were possible based upon differing modes of condensation, and the nature of the flavonoid precursor. is characterized by linkage through the two B-ring oxygens of dihydroquercetin (taxifolin) and coniferyl alcohol; isosilybin has the veratryl and hydroxymethyl groups reversed.…”

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confidence: 99%

Flavonoids of the Sunflower Family (Asteraceae)

Bohm

Stuessy

2001

119

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This work is subject to copyright. All rights are reserved, whether the whole or part of the material is concerned, specifically those of translation, reprinting, re-use of illustrations, broadcasting, reproduction by photocopying machines or similar means, and storage in data banks. This book is dedicated to:Arthur Cronquist Outstanding plant systematist and major contributor to understanding taxonomic relationships within Asteraceae and Ralph E. Alston (1925Alston ( -1967) Visionary natural products chemist and geneticist who pioneered the use of chemical data in studies of plant systematics and evolution PrefaceCertainly many of the readers of this book will remember the early developments of chemosystematics in the late 1950s. We ourselves remember the excitement of these new data bearing on plant interrelationships. The hopes were high, the techniques were rapidly evolving, the quantities of data were large, and young workers were eagerly enthusiastic. Some even went so far as to predict that chemical data would soon replace morphological information as the basis for plant classification. These overly zealous predictions did not materialize, of course, as the history of plant systematics has amply shown during the past two centuries. If there is any distinct characteristic of systematics it is synthesis, as Lincoln Constance (1964) called it, the "unending synthesis." New tools generate new data and provide insights on additional dimensions of plant relationships. This will never change-we will continue to discover new tools and new data in the years ahead, and they will continue to be incorporated into the predictive general reference system of classification.The earlier efforts in chemosystematics focused on secondary plant products: alkaloids, betacyanins, carbohydrates, cyanogenic glycosides, glucosinolates, lipids, terpenoids, and especialiy flavonoids. The latter were particularly well suited for chemosystematic investigation for several reasons: ease of isolation and characterization, small amounts of plant material needed for analysis, stability of compounds especially through routine preparation of herbarium specimens, and low cost to obtain useful information. As a result of these considerable advantages, literally thousands of studies on use of flavonoids in plant systematics have been published. Although now with the present zest for macromolecular data from DNA restriction sites and sequences, there are fewer workers and laboratories dedicated to flavonoid chemosystematic studies; twenty years ago they were the new currency of exciting data in plant systematics.Because of many workers historically interested in the sunflower family, Asteraceae (or Compositae), in part due to its large size (approximately 23,000 species;Bremer, 1994), and because hundreds of flavonoid compounds were discovered in this family, many chemosystematic investigations have been completed on various taxa. Many studies came from the laboratories of R. A. Alston, B. L. Turner, and T. J. Mabry in the Department of Botany ...

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The structure of silybin (silybum substance E6), the first flavonolignan

Cited by 106 publications

References 5 publications

Recent advances in the discovery of flavonoids and analogs with high‐affinity binding to P‐glycoprotein responsible for cancer cell multidrug resistance

Recent advances in the discovery of flavonoids and analogs with high‐affinity binding to P‐glycoprotein responsible for cancer cell multidrug resistance

Synthesis and biology of 1,4-benzodioxane lignan natural products

Flavonoids of the Sunflower Family (Asteraceae)

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