(Z)-Hydroxy-5 et (Z)-Dihydroxy-4,5 Butylidène-3 Phthalides, Nouveaux Composés Isolés de Ligusticum wallichii

Puech-Baronnat, Madeleine; Kaouadji, Mourad; Mariotte, Anne‐Marie

doi:10.1055/s-2007-969636

Cited by 14 publications

(12 citation statements)

References 2 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The same observation can be made for 6,7-dihydroxy-3-butylidenephthalide described as the 4,5-dihydroxy isomer in L. wallichii (6) since, in this case, H-8 which is not affected by deshielding induced by hydroxylation in the 4-position is recorded at 5.54 ppm (CD3OD).…”

supporting

confidence: 72%

“…[7-hydroxy-3-butylidenephthalide, cis-and trans-6,7-dihydroxyligustilide (4)], and Cnidium officinale Makino [9-hydroxy-3-butylidenephthalide, 3-(2-hydroxy butylidene)phthalide ( 5)]. 5-Hydroxy-3-butylidenephthalide is present in both of the above species (5,6). relative to 4-hydroxy-3-butylidenephthalide have been wrongly assigned to the 7-hydroxy isomer in C. officinale (5).…”

mentioning

confidence: 99%

See 1 more Smart Citation

Additional Phthalide Derivatives from Meum athamanticum

Kaouadji¹,

Pouget²

1986

J. Nat. Prod.

View full text Add to dashboard Cite

supporting

confidence: 72%

mentioning

confidence: 99%

Additional Phthalide Derivatives from Meum athamanticum

Kaouadji¹,

Pouget²

1986

J. Nat. Prod.

View full text Add to dashboard Cite

“…The material (100 g) was homogenized directly in the solvent mixture (CHCl3-MeOH-H2O (8 : 4 : 3, 150 ml)) and the extract was submitted to the same procedure as described above. Comparison of the column chromatographic fractions from fresh and commercial samples showed virtually the same elution pattern except that the amounts of ferulic acid (3) and hydroxyphthalides (5)(6)(7)(8)(9)(10)(11)(12)(13) obtained from the fresh material were negligible.…”

Section: Glycolation Of Ligustilidementioning

confidence: 77%

“…1-5), hexane-ethyl acetate (3.5 : 6.5, frs. [6][7][8][9][10][11][12][13][14], and 5% MeOH in hexane-ethyl acetate (3.5 : 6.5, frs. 15-19).…”

Section: Methodsmentioning

confidence: 99%

See 1 more Smart Citation

Studies on the constituents of umbelliferae plants. XV Constituents of Cnidium officinale : Occurrence of pregnenolone, coniferylferulate and hydroxyphthalides.

Kobayashi

Fujita

Mitsuhashi

1987

CHEMICAL & PHARMACEUTICAL BULLETIN

View full text Add to dashboard Cite

Pregnenolone (1), coniferylferulate (2) and nine mono-and dihydroxyphthalide derivatives (5-13) were isolated from the commercial C. officinale rhizome. Their structures were determined from the spectroscopic data and the dihydroxyphthalides senkyunolide-H (11) and-1 (12) and senkyunolide-J (13) were synthesized from the major components ligustilide (14) and senkyunolide-A (16), respectively. These oxygenated phthalides were absent in the fresh C. officinale rhizome and they were shown to be derived from the major volatile phthalides during storage of the crude drug. Coniferylferulate (2) also decomposes partly during storage, giving ferulic acid.

show abstract

Phthalides: Distribution in Nature, Chemical Reactivity, Synthesis, and Biological Activity

León

Del-Ángel

Ávila

et al. 2017

Progress in the Chemistry of Organic Natural Products

View full text Add to dashboard Cite

Phthalides are a relatively small group of natural compounds confined to several plant families and some genera of fungi and liverworts. They are divided into two structural groups, the monomeric and dimeric phthalides, and known mainly as bioactive constituents of different plant species used traditionally for medicinal purposes in Asia, Europe, and North America.The first reports on the chemistry of phthalides appeared at the end of the nineteenth century, in which they were identified as the odor constituents of the essential oil of celery (Apium graveolens) by Ciamician and Silber (1897). In the first half of the last century, phthalides were isolated from Cnidium officinale and Ligusticum acutilobum, species widely used in Asian traditional medicine, and from Levisticum officinale, a species used as food and condiment. Throughout the second part of the twentieth century, phthalides have been characterized from several plant families, namely Asteraceae, Leguminosae, Orchidaceae and Rutaceae, among others, but mainly from the Umbelliferae (syn Apiaceae) family, and the major contributors have been the following species used in traditional medicine: Ligusticum chuanxiong (Chinese name: Chuanxiong), Angelica sinensis (Chinese name: Danggui), Cnidium officinale (Japanese name: Senkyu), Angelica acutiloba (Japanese name: Toki), and Ligusticum porteri (Hispanic name: Oshá). Phthalides are also constituents of several genera of fungi, such as Penicillium, Alternaria and Pestalotiopsis, and some liverworts.Different chromatographic, spectrometric, and two-dimensional nuclear magnetic resonance (NMR) techniques have been used for the isolation and structural characterization of phthalides in extracts, and for assessing the quality of plant material containing this type of compound. Isotopic labeling has established the biosynthesis of phthalides via linkage of acetate units forming polyketide intermediates.Chemical transformations of monomeric phthalides have included oxidation, reduction, addition, elimination, and cycloaddition reactions, and treatments with Lewis acids of (Z)-ligustilide have afforded linear dimers. Some intramolecular condensations and differentiated cyclizations of the dimeric phthalides have been carried out, providing evidences for the particular chemical reactivity of these compounds.Several structural modifications of phthalides have been carried out subjecting them to microbial transformations by different species of bacteria, fungi and algae, and these included resolutions of racemic mixtures and oxidations, among others.The [π4s + π2s] and [π2s + π2s] cycloadditions of (Z)-ligustilide for the synthesis of dimeric phthalides have been reported, and different approaches involving cyclizations, Alder-Rickert reactions, Sharpless asymmetric hydroxylations, or Grignard additions have been used for the synthesis of monomeric phthalides. The use of phthalides as building blocks for divergent oriented synthesis has been proven.Many of the naturally occurring phthalides display different biological...

show abstract

(Z)-Hydroxy-5 et (Z)-Dihydroxy-4,5 Butylidène-3 Phthalides, Nouveaux Composés Isolés de Ligusticum wallichii

Abstract: Two new hydroxylated butylidenephthalides were extracted from LIGUSTICUM WALLICHII rhizom and their structures were assigned by spectral analysis.

Cited by 14 publications

References 2 publications

Additional Phthalide Derivatives from Meum athamanticum

Additional Phthalide Derivatives from Meum athamanticum

Studies on the constituents of umbelliferae plants. XV Constituents of Cnidium officinale : Occurrence of pregnenolone, coniferylferulate and hydroxyphthalides.

Phthalides: Distribution in Nature, Chemical Reactivity, Synthesis, and Biological Activity

Contact Info

Product

Resources

About