The biosynthesis of shikimate metabolites

Dewick, Paul M.

doi:10.1039/a815017y

Cited by 71 publications

(35 citation statements)

References 331 publications

(306 reference statements)

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“…Me(27), and between Me(25) and Me (26), indicated that Me(27) was a-oriented, whereas Me (25) and Me (26) were both b-oriented. Moreover, from the 1 H-NMR coupling constants, HÀC(18) was assumed to be axial (b-orientation), and considering the biogenetically more reasonable cis junction of rings D and E, the COOH group was placed in equatorial b-position.…”

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confidence: 86%

“…Therefore, madhusalmone (3) was assigned the structure 5,5'',3',3''',4',4''',5',5'''-octamethoxy-6,7'': 7,6''-bis[(methylenedioxy)isoflavone] 1 ). From a biogenetic point of view, madhusalmone (3) may arise from condensation of the isoflavones 4a or 4b, which are formed early in the biosynthetic sequence at the isoflavone oxidation level [26]. Both extracts showed antimicrobial activity against Staphylococcus aureus, S. saprophyticus, S. epidermidis, Streptococcus faecalis, Salmonella typhi para A, Pseudomonas aeruginosa, and Proteus mirabilis.…”

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confidence: 98%

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Chemical Constituents from the Fruits of Madhuca latifolia

Siddiqui

Khan

Kardar

et al. 2004

Helvetica Chimica Acta

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From the fruit coats of the medicinal plant Madhuca latifolia were isolated three new compounds, the triterpenoid madhucic acid ( 3b-(octanoyloxy)-11-oxoolean-12-en-28-oic acid; 1), the untypical isoflavone madhushazone ( 9-methoxy-7-(2,3,6-trimethoxyphenyl)- [1,3]dioxolo [4,5-g][1]benzopyran-8(8H)-one; 2), and a bis(isoflavone) named madhusalmone ( 5,14-dimethoxy-3,12-bis(3,4,5-trimethoxyphenyl)-1,6,8,10,15,17-hexaoxanaphtho[2',3': 6,7]cyclodeca[1,2-b]naphthalene-4,13(4H,13H)-dione; 3), as well as eight known constituents, and their structures were elucidated by spectral analysis, including 2D-NMR techniques.Introduction. ± Madhuca latifolia Syn. M. indica (Sapotaceae) is an important economic plant growing throughout the subtropical region of the Indo-Pak subcontinent [1]. The medicinal properties attributed to this plant are stimulant, demulcent, emollient, heating, and astringent [2]. The bark is a good remedy for itch, swellings, fractures, and snake-bite poisoning, internally employed in diabetes mellitus with much benefit [3]. Mahua oil is used for the treatment of skin diseases, rheumatism, headache, and as a laxative. Fruits are astringent and largely employed as a lotion in chronic ulcer, in acute and chronic tonsillitis and pharyngitis. . In view of the attributed medicinal properties, we investigated the fruit coats of M. indica, which resulted in the isolation and characterization of three new constituents: madhucic acid (1), a pentacyclic triterpenoid, madhushazone (2), an untypical isoflavone, and madhusalmone (3), a bis(isoflavone). Moreover, eight known constituents were isolated and identified by comparison of their physical and spectral data with those reported in the literature. These included b-amyrin acetate, hitherto unreported b-amyrin caprylate, 3b-(capryloxy)ursolic acid, a hydrocarbon (C 29 H 60 ), a triglyceride of palmito-dioleins, and three monoglycerides of stearic, oleic, and arachidic acid, respectively. These glycerides have previously been found in solid seed fats of the same species [15].

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confidence: 86%

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confidence: 98%

Chemical Constituents from the Fruits of Madhuca latifolia

Siddiqui

Khan

Kardar

et al. 2004

Helvetica Chimica Acta

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“…* There are many variations and subtleties in tyrosine and phenylalamine synthesis in different species. lites, including flavanones and napthoquinones [6], and there is an alternative version of the pathway with aminated intermediates that give rise to aminohydroxybenzoate (AHBA), the precursor of the ansamycin antibiotics [7]. Our recent work on apicomplexans has demonstrated a role for the shikimate pathway in the production of PABA and folates in these organisms [1].…”

Section: Overview Of the Shikimate Pathway And Its Branches Derivatimentioning

confidence: 98%

The Shikimate Pathway and Its Branches in Apicomplexan Parasites

et al. 2002

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The shikimate pathway is essential for production of a plethora of aromatic compounds in plants, bacteria, and fungi. Seven enzymes of the shikimate pathway catalyze sequential conversion of erythrose 4-phosphate and phosphoenol pyruvate to chorismate. Chorismate is then used as a substrate for other pathways that culminate in production of folates, ubiquinone, napthoquinones, and the aromatic amino acids tryptophan, phenylalanine, and tyrosine. The shikimate pathway is absent from animals and present in the apicomplexan parasites Toxoplasma gondii, Plasmodium falciparum, and Cryptosporidium parvum. Inhibition of the pathway by glyphosate is effective in controlling growth of these parasites. These findings emphasize the potential benefits of developing additional effective inhibitors of the shikimate pathway. Such inhibitors may function as broad-spectrum antimicrobial agents that are effective against bacterial and fungal pathogens and apicomplexan parasites.

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“…121 The FNS II, firstly isolated from microsomial fraction of Antirrhinum majus, is a cytochrome P450-dependent monooxygenase: the enzyme, membrane-bound, was observed in members of Leguminosae, Verbenaceae, and Asteraceae. 122 FNS I and II accept as substrates only flavanones. Another possible reaction involving flavanones is the hydroxylation on C 3 of the heterocycle with the formation of dihydroflavonols (Figure 2.12).…”

Section: Biosynthesismentioning

confidence: 99%