Acetylenic Compounds Isolated from Cultured Cells of Asparagus officinalis.

Terada, Kinuko; Honda, Chie; Suwa, Kiyoko; Takeyama, Shizuyo; Oku, Hisae; Kamisako, Wasuke

doi:10.1248/cpb.43.564

Cited by 23 publications

(39 citation statements)

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“…Phytochemical study of green asparagus led to the isolation of 23 compounds, including 7 steroids (1−7), 2 esters (8, 11), 3 arynes (9, 25 aurantiamide acetate (17), 26 neoechinulin A (18), 27 3-pyridinecarboxylic acid, 1,6-dihydro-6-oxo-methyl ester (19), 2-(2-hydroxytetracosanoylmino)-1,3,4-octadecanetriol (20), 28 hexadecanoic acid, 2,3-dihydroxypropyl ester (21), 29 12,13,15-trihydroxy-9-octadecenoic acid (22), 30 and 2-octadecendioic acid (23). 31 The known compounds 1−23 ( Figure 2) were identified by comparison of their NMR data with those reported in the literature.…”

Section: ■ Materials and Methodsmentioning

confidence: 99%

“…Signals were detected by an enhanced chemiluminescence technique (Amersham Life Science, USA).Quantification of the Active Compounds from Green Asparagus. For HPLC analysis, the top four active compounds(3,4,10,12) were analyzed using a HPLC system (LC3000, Beijing ChuangXinTongHeng Science & Technology Co., Ltd., Beijing, China) equipped with a UV lamp (Beijing ChuangXinTongHeng Science & Technology Co., Ltd.) and a C18 reversed-phase analytical column (Agilent HC-C18, 4.6 × 250 mm, 5 μm; Agilent Technologies Inc., Santa Clara, CA, USA). The HPLC mobile phase was composed of methanol (solvent A) and water (solvent B).…”

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confidence: 99%

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Antihepatic Fibrosis Effect of Active Components Isolated from Green Asparagus (Asparagus officinalis L.) Involves the Inactivation of Hepatic Stellate Cells

Zhong

Jiang²,

Xia

et al. 2015

J. Agric. Food Chem.

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Green asparagus (Asparagus officinalis L.) is a vegetable with numerous nutritional properties. In the current study, a total of 23 compounds were isolated from green asparagus, and 9 of these compounds were obtained from this genus for the first time. Preliminary data showed that the ethyl acetate (EtOAc)-extracted fraction of green asparagus exerted a stronger inhibitory effect on the growth of t-HSC/Cl-6 cells, giving an IC50 value of 45.52 μg/mL. The biological activities of the different compounds isolated from the EtOAc-extracted fraction with respect to antihepatic fibrosis were investigated further. Four compounds, C3, C4, C10, and C12, exhibited profound inhibitory effect on the activation of t-HSC/Cl-6 cells induced by TNF-α. The activation t-HSC/Cl-6 cells, which led to the production of fibrotic matrix (TGF-β1, activin C) and accumulation of TNF-α, was dramatically decreased by these compounds. The mechanisms by which these compounds inhibited the activation of hepatic stellate cells appeared to be associated with the inactivation of TGF-β1/Smad signaling and c-Jun N-terminal kinases, as well as the ERK phosphorylation cascade.

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Section: ■ Materials and Methodsmentioning

confidence: 99%

mentioning

confidence: 99%

Antihepatic Fibrosis Effect of Active Components Isolated from Green Asparagus (Asparagus officinalis L.) Involves the Inactivation of Hepatic Stellate Cells

Zhong

Jiang²,

Xia

et al. 2015

J. Agric. Food Chem.

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“…24). Diaryl metabolites 20A-C are produced by Asparagus officinalis (Liliaceae) [261,262]. Analysis of "No Nuclear Overhauser Effect" (NNE) 13 Phenylalanine decarboxylation provides the acetylenic C 6 -C 2 unit.…”

Section: Biosynthesis Of Acetylenes Originating From the Shikimate Pamentioning

confidence: 99%

“…Biosynthesis of polyacetylenes via the shikimate pathway. While it is rare that acetylenic metabolites result from only shikimate intermediates, the aryl ethers 20A-C have been proposed to arise from two such fragments via the hypothetical cyclic ether 20D [261,262]. Proposed biosynthesis of acetylenic spiroketals found in Asteraceae species.…”

Section: Future Directionsmentioning

confidence: 99%

Biosynthesis and function of polyacetylenes and allied natural products

Minto

Blacklock

2008

Progress in Lipid Research

296

228

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Polyacetylenic natural products are a substantial class of often unstable compounds containing a unique carbon-carbon triple bond functionality, that are intriguing for their wide variety of biochemical and ecological functions, economic potential, and surprising mode of biosynthesis. Isotopic tracer experiments between 1960 and 1990 demonstrated that the majority of these compounds are derived from fatty acid and polyketide precursors. During the past decade, research into the metabolism of polyacetylenes has swiftly advanced, driven by the cloning of the first genes responsible for polyacetylene biosynthesis in plants, moss, fungi, and actinomycetes, and the initial characterization of the gene products.The current state of knowledge of the biochemistry and molecular genetics of polyacetylenic secondary metabolic pathways will be presented together with an up-to-date survey of new terrestrial and marine natural products, their known biological activities, and a discussion of their likely metabolic origins.

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“…Bioassay-directed fractionation of the dried roots of Asparagus cochinchinensis (Asparagaceae) led to the isolation of some active compounds (130)(131)(132), including a new acetylenic derivative, 3′′-methoxyasparenydiol (92), and asparenydiol (93). These compounds demonstrated moderate cytotoxicities in a panel comprised of KB, Col-2, LNCaP, Lu-1, and human umbilical vein endothelial cells (HUVEC) cells, with IC 50 values ranging from 4 to 20 µg/mL ( Table 9).…”

Section: Acetylenic Metabolites From Plant Speciesmentioning

confidence: 99%

Anticancer activity of natural and synthetic acetylenic lipids

Dembitsky¹

2006

Lipids

129

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This review is a comprehensive survey of acetylenic lipids and their derivatives, obtained from living organisms, that have anticancer activity. Acetylenic metabolites belong to a class of molecules containing triple bond(s). They are found in plants, fungi, microorganisms, and marine invertebrates. Although acetylenes are common as components of terrestrial plants, fungi, and bacteria, it is only within the last 30 years that biologically active polyacetylenes having unusual structural features have been reported from plants, cyanobacteria, algae, invertebrates, and other sources. Naturally occurring aquatic acetylenes are of particular interest since many of them display important biological activities and possess antitumor, antibacterial, antimicrobial, antifouling, antifungal, pesticidal, phototoxic, HIV-inhibitory, and immunosuppressive properties. There is no doubt that they are of great interest, especially for the medicinal and/or pharmaceutical industries. This review presents structures and describes cytotoxic and anticancer activities only for more than 300 acetylenic lipids and their derivatives isolated from living organisms.

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Acetylenic Compounds Isolated from Cultured Cells of Asparagus officinalis.

Cited by 23 publications

References 1 publication

Antihepatic Fibrosis Effect of Active Components Isolated from Green Asparagus (Asparagus officinalis L.) Involves the Inactivation of Hepatic Stellate Cells

Antihepatic Fibrosis Effect of Active Components Isolated from Green Asparagus (Asparagus officinalis L.) Involves the Inactivation of Hepatic Stellate Cells

Biosynthesis and function of polyacetylenes and allied natural products

Anticancer activity of natural and synthetic acetylenic lipids

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