Additional Phthalide Derivatives from Meum athamanticum

Kaouadji, Mourad; Pouget, Corinne

doi:10.1021/np50043a041

Cited by 15 publications

(5 citation statements)

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“…Column chromatography is the benchmark method for the isolation of natural products and is prevalent throughout the literature on phthalides, with silica gel being the most widely used adsorbent. 10,26 Other separation media used for column chromatography of phthalides have included alumina, 19 LH-20, 27 polyamide, 28 and reversed-phase (C 18 ) silica gel. 29 common method used for the isolation of phthalides, utilizing both normal-phase 30 and reversed-phase columns.…”

Section: Methods Of Investigationmentioning

confidence: 99%

“…37 This species was investigated in the early 1960s due to its high yield of ligustilide. 38 A later study by Mitsuhashi and co-workers 17 revealed L. officinale to be among the first plants to yield the hydroxylated phthalide derivatives senkyunolide B (7), senkyunolide C (8), senkyunolide E (11), senkyunolide F (27), senkyunolide G (29), senkyunolide D (30), senkyunolide H (39), senkyunolide I (43), and senkyunolide J (46). In this report, compound 7 was originally thought to be 3-butylidene-7-hydroxyphthalide (9).…”

Section: Structural Diversity Of Naturally Occurring Phthalide Deriva...mentioning

confidence: 99%

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The Structural Diversity of Phthalides from the Apiaceae

2007

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Phthalides, and their corresponding dihydro and tetrahydro analogues, are components of several genera of the plant family Apiaceae. These taxa have been reported as exhibiting a wide range of bioactivities against experimental models of several illnesses and physiological conditions, including microbial and viral infections, stroke, tuberculosis, and vasoconstriction. Many of these genera are purported to possess medicinal values, and of these several are considered to be traditional herbal medicines. This review provides an overview of the methods of investigation, the structural diversity, and the bioactivity of phthalides, dihydrophthalides, tetrahydrophthalides, and dimers from plants in the Apiaceae.

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Section: Methods Of Investigationmentioning

confidence: 99%

Section: Structural Diversity Of Naturally Occurring Phthalide Deriva...mentioning

confidence: 99%

The Structural Diversity of Phthalides from the Apiaceae

2007

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“…Celery seed contains a variety of constituents. As a member of the class of bioactive natural products, phthalides occurs widely in umbelliferous plants (Bjeldanes and Kim, 1977;Chulia et al, 1986;Kaouadji et al, 1984;Kaouadji et al, 1986, Banerjee et al, 1982. Earlier studies of A. graveolens led to the isolation of limonene, p-mentha-2,8-dien-1-ol, p-mentha-8(9)-en-1,2diol, 3-n-butylphthalide, sedanolide (Zheng et al, 1994), selinene (Semmler and Risse, 1912), selinenol (Ruzicka and Stoll, 1923) and seselin, isoimperatorin, osthenol, bergapten, isopimpinellin, apigravin, and apiumoside (Grag et al, 1978(Grag et al, , 1979a.…”

Section: Introductionmentioning

confidence: 99%

Bioactive Compounds and 1,3-Di[(cis)-9-octadecenoyl]-2-[(cis,cis)-9,12-octadecadienoyl]glycerol from Apium Graveolens L. Seeds

Momin

Ramsewak

Nair

2000

J. Agric. Food Chem.

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Bioassay-directed isolation and purification of the hexane extract of Apium graveolens L. seeds led to the characterization of three compounds: beta-selinene (1), 3-n-butyl-4,5-dihydrophthalide (2) and 5-allyl-2-methoxyphenol (3). The structures of these compounds were established by using (1)H and (13)C NMR spectral methods. Compounds, 1-3 demonstrated 100% mortality on fourth-instar Aedes aegyptii larvae at 50, 25, and 200 microg mL(-)(1), respectively, in 24 h. Also, 2 inhibited the growth of Candida albicans and Candida kruseii at 100 microg mL(-)(1). It inhibited both topoisomerase-I and -II enzyme activities at 100 microg mL(-)(1). Compound 2 displayed 100% mortality at 12.5 and 50 microg mL(-)(1), respectively, when tested on nematodes, Panagrellus redivivus and Caenorhabditis elegans. The triglyceride, 1,3-di[(cis)-9-octadecenoyl]-2-[(cis,cis)-9, 12-octadecadienoyl]glycerol (4) and 3 were isolated for the first time from A. graveolens seeds, although 4 was not biologically active.

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“…Compounds 9 and 10 were elucidated as 6-hydroxy-senkyunolide B ( 9 ) [19, 20] and senkyunolide C ( 10 ) [21] based on comparisons with published spectroscopic data.…”

Section: Discussionmentioning

confidence: 99%

Novel phthalide derivatives identified from Ligusticum chuanxiong (Chuanxiong)

Yang

et al. 2016

Chin Med

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BackgroundLigusticum chuanxiong Hort. (Chuanxiong) is a well-known Chinese medicine, and studies on its chemical constituents are important for explaining its mechanism of action and quality control. This study aims to investigate the chemical constituents of the dried rhizome of. L. chuanxiong.MethodsThe dried rhizome of L. chuanxiong was extracted with 60 % ethanol, and the concentrated extract was isolated by silica gel, octadecyl silane, and Sephadex LH-20 columns, followed by preparative/semipreparative high-performance liquid chromatography (HPLC) to obtain the pure chemical constituents. The structures of the constituents were elucidated by HR-ESI-MS, UV, IR, 1D NMR, and 2D NMR methods. Enantiomeric separation was achieved by a chiral HPLC method. The absolute configuration was determined by the modified Mosher’s method.ResultsSix novel phthalide derivatives, (+)/(−)-chuanxiongins A–F (1–6), together with four known phthalides (7–10) were isolated from Chuanxiong. All of the new compounds (1–6) were present as pairs of enantiomers. Enantiomeric separation of 1 was successfully achieved by HPLC on a chiral column. The absolute configuration of (−)-1 was determined by a modified Mosher’s method.ConclusionThe six novel phthalide derivatives (1–6) isolated from Chuanxiong were phthalide fatty acid esters that were structurally analogous and characterized by fatty acid acylation at 6-OH or 7-OH.

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Additional Phthalide Derivatives from Meum athamanticum

Cited by 15 publications

References 4 publications

The Structural Diversity of Phthalides from the Apiaceae

The Structural Diversity of Phthalides from the Apiaceae

Bioactive Compounds and 1,3-Di[(cis)-9-octadecenoyl]-2-[(cis,cis)-9,12-octadecadienoyl]glycerol from Apium Graveolens L. Seeds

Novel phthalide derivatives identified from Ligusticum chuanxiong (Chuanxiong)

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