Lithospermum ruderale: Partial characterization of the principal polyphenol isolated from the roots

Johnson, Gearold R.; Sunderwirth, Stanley; Gibian, Heinz; Coulter, A.W.; Gassner, F. X.

doi:10.1016/s0031-9422(00)82974-x

Cited by 26 publications

(28 citation statements)

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“…Having demonstrated the carbonylative annulationreduction procedure to be a powerful, modular strategy for the synthesis of methyl 2-aryl-2,3-dihydrobenzo[b]furan-3carboxylates, we sought to further highlight the versatility of this approach through the synthesis of lithospermic acid (1). (+)-Lithospermic acid (1) was first isolated from Lithospermum ruderale in 1963 24 and its structure elucidated in 1975. 25 (+)-Lithospermic acid (1) has also been isolated from Salvia miltiorrhiza (Danshen), a popular herb in traditional Chinese medicine, 26 and from many other sources.…”

Section: Ortho-mentioning

confidence: 99%

A Concise Route to Dihydrobenzo[b]furans: Formal Total Synthesis of (+)-Lithospermic Acid

2011

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A sequence of Sonogashira coupling, Pd(II)-catalyzed carbonylative annulation, and benzofuran reduction (Mg, MeOH, NH(4)Cl) provides a convergent and modular synthetic route to trans-2-aryl-2,3-dihydrobenzo[b]furan-3-carboxylates, which are a structural feature of numerous biologically active natural products. This versatile strategy was applied to the formal total synthesis of the anti-HIV natural product (+)-lithospermic acid.

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Section: Ortho-mentioning

confidence: 99%

A Concise Route to Dihydrobenzo[b]furans: Formal Total Synthesis of (+)-Lithospermic Acid

2011

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“…(2)(3)(4)(5)(10)(11)(12)(13)(14)(15)(16)]. A correlation between positive tannin reaction and antigonadotropic activity was reported (6,17,18) and the active compound was assumed to be a polyphenol, lithospermic acid (9,12,13,14,18,19). It was isolated from Lithospermum ruderale L. (9,12,13,14), Lycopus europaeus L., and Symphytum officinale L. (18) and showed antigonadotropic activity only after an enzymatic oxidation (18).…”

Section: Introductionmentioning

confidence: 99%

On the Antigonadotropic Activity ofLithospermumandLycopusSpecies and Some of their Phenolic Constituents¹

Winterhoff¹,

Gumbinger²,

Sourgens³

1988

Planta Med

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The active principle responsible for the antigonadotropic activity of Lirhospermum, Lycopus, and related species is formed from phenolic precursors. For its formation, an oxidation step was found to be essential. It could be shown that several phenolic plant ingredients like caffeic acid, chlorogenic acid, and rosmarinic acid as well as luteolm-7j-glucuronide represent precursors of compounds with such efficacy. During the preparation of aqueous plant extracts, an enzymatical oxidation occurs. This oxidation step can be substituted by treatment with KMnO4.The activity of aqueous plant extracts clearly exceeds the effects expected from its content in phenolic ingredients, e.g. 10 sg FDE of Litospermum off. (77) was found to be more active than 36 g (0.05 smol) rosmannic acid, the most active plant constituent. An evident augmentation in the biological efficacy of such oxidized plant ingredients can be achieved by addition of either Mn2 ions or unoxidized diphenols. Furthermore, the oxidation carried out during the extraction of plant extracts by a very active phenoloxidase of these plants may cause an increased activity. The lack of such auxiliary reactions clearly improving the antigonadotropic activity may explain the poor results gained with plant ingredients till now.

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“…1 It was fully characterized as a trimer of caffeic acid A in 1975 by Carmack et al and Wagner et al independently. 2,3 Lithospermic acid is an active ingredient of the Chinese herb Danshen and showed important biological properties.…”

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confidence: 99%

“…The spectroscopic data of our synthetic (+)-lithospermic acid {[α] D 23 = +75 ( c 0.2, MeOH)}is in complete agreement with those of the natural product. 1,2 …”

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confidence: 99%

Enantioselective Total Synthesis of (+)-Lithospermic Acid

Ghosh

2012

Org. Lett.

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An enantioselective synthesis of (+)-lithospermic acid, a potent anti-HIV agent, has been accomplished in a convergent manner in 9 steps. The synthesis features an enantioselective intramolecular oxa-Michael addition catalyzed by a quinidine derivative, a hypervalent iodine-mediated rearrangement of chromanone to dihydrobenzofuran, an enantioselective α-oxyamination, and an intermolecular C-H olefination.

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Lithospermum ruderale: Partial characterization of the principal polyphenol isolated from the roots

Cited by 26 publications

References 6 publications

A Concise Route to Dihydrobenzo[b]furans: Formal Total Synthesis of (+)-Lithospermic Acid

A Concise Route to Dihydrobenzo[b]furans: Formal Total Synthesis of (+)-Lithospermic Acid

On the Antigonadotropic Activity ofLithospermumandLycopusSpecies and Some of their Phenolic Constituents¹

Enantioselective Total Synthesis of (+)-Lithospermic Acid

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Lithospermum ruderale: Partial characterization of the principal polyphenol isolated from the roots

Cited by 26 publications

References 6 publications

A Concise Route to Dihydrobenzo[b]furans: Formal Total Synthesis of (+)-Lithospermic Acid

A Concise Route to Dihydrobenzo[b]furans: Formal Total Synthesis of (+)-Lithospermic Acid

On the Antigonadotropic Activity ofLithospermumandLycopusSpecies and Some of their Phenolic Constituents1

Enantioselective Total Synthesis of (+)-Lithospermic Acid

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On the Antigonadotropic Activity ofLithospermumandLycopusSpecies and Some of their Phenolic Constituents¹