New Acetylenes Isolated from the Bark of<i>Heisteria acuminata</i>

Kraus, Christina M.; Neszmélyi, András; Holly, S.; Wiedemann, B.; Nenninger, A.; Torssell, Kurt; Bohlin, Lars; Wagner, Hildebert

doi:10.1021/np970357p

Cited by 28 publications

(23 citation statements)

References 24 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…2007) but not in other plants. In comparison, octadeca‐8,10,12‐triynoic acid, which is structurally similar to octadeca‐9,11,13‐triynoic acid, has also been found in several plant species, such as the bark of Heisteria acuminata (Kraus et al. 1998) and Scurrula atropurpurea (Ohashi et al.…”

Section: Discussionmentioning

confidence: 99%

Effect of polyacetylenic acids from Prunella vulgaris on various plant pathogens

Yoon

Choi

et al. 2010

Letters in Applied Microbiology

View full text Add to dashboard Cite

Aims: This study is aiming at characterizing antifungal substances from the methanol extract of Prunella vulgaris and at investigating those substances’ antifungal and antioomycete activities against various plant pathogens. Methods and Results: Two polyacetylenic acids were isolated from P. vulgaris as active principles and identified as octadeca‐9,11,13‐triynoic acid and trans‐octadec‐13‐ene‐9,11‐diynoic acid. These two compounds inhibited the growth of Magnaporthe oryzae, Rhizoctonia solani, Phytophthora infestans, Sclerotinia sclerotiorum, Fusarium oxysporum f. sp. raphani, and Phytophthora capsici. In addition, these two compounds and the wettable powder‐type formulation of an n‐hexane fraction of P. vulgaris significantly suppressed the development of rice blast, tomato late blight, wheat leaf rust, and red pepper anthracnose. Conclusions: These data show that the extract of P. vulgaris and two polyacetylenic acids possess antifungal and antioomycete activities against a broad spectrum of tested plant pathogens. Significance and Impact of the Study: This is the first report on the occurrence of octadeca‐9,11,13‐triynoic acid and trans‐octadec‐13‐ene‐9,11‐diynoic acid in P. vulgaris and their efficacy against plant diseases. The crude extract containing the two polyacetylenic acids can be used as a natural fungicide for the control of various plant diseases.

show abstract

Section: Discussionmentioning

confidence: 99%

Effect of polyacetylenic acids from Prunella vulgaris on various plant pathogens

Yoon

Choi

et al. 2010

Letters in Applied Microbiology

View full text Add to dashboard Cite

show abstract

“…Acid 26I has also been identified in two related Lauraceae species [310,311]. Enediynoic acids with C-8,10 acetylenic bonds, and a triynoic acid with the additional triple bond at C-12 (26M-O) and 6-acetylenic acid (26L) were found in Heisteria acuminata bark cyclooxygenase bioassay-guided purification [312]. These compounds may be related through α-and β-oxidation chainshortening, although 26L appears to be derived from a C 17 precursor.…”

Section: New Natural Productsmentioning

confidence: 99%

Biosynthesis and function of polyacetylenes and allied natural products

Minto

Blacklock

2008

Progress in Lipid Research

296

228

View full text Add to dashboard Cite

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.

show abstract

“…ssp campylotheca (Compositae) [194], or 11(S),16(R)-dihydroxy-octadeca-9Z,17-diene-12,14-diyn-1-yl acetate from Angelica pubescens f. biserrata [52] are more efficient. Potent derivatives are cis-hexadec-11-ene-7,9-diynoic acid 108 and cis-octadec-12-ene-7,9-diynoic acid 109 [195], falcarindol 110 and panaxynol 111 from Saposhnikoviae [52], [196] that block 5-LO product synthesis with IC 50 values of 2 ± 10 mM. All these compounds lack substantial antioxidant activities, and it is assumed that polyacetylenes bind to the active site of 5-LO, thereby competing with AA as substrate.…”

Section: Alkaloidsmentioning

confidence: 99%

Inhibition of 5-Lipoxygenase Product Synthesis by Natural Compounds of Plant Origin

Werz¹

2007

Planta Med

155

135

View full text Add to dashboard Cite

The biosynthesis of leukotrienes (LTs) is initiated by the transformation of free arachidonic acid to LTA 4 by 5-lipoxygenase (5-LO). Subsequent enzymatic conversion of LTA 4 yields LTB 4 and the cysteinyl-LTs C 4 , D 4 and E 4 . LTs have prominent functions in pathophysiology and are connected to numerous disorders including bronchial asthma, allergic rhinitis, inflammatory bowel and skin diseases, rheumatoid arthritis, cancer, osteoporosis and cardiovascular diseases. Pharmacological and genetic interruption of the 5-LO pathway or blockade of LT receptors, serving as means for intervention with LTs, may be of therapeutic value for certain related disorders. Natural or plant-derived substances were among the first 5-LO inhibitors identified in the early 1980 s. To date, a huge number of diverse plant-derived compounds have been reported to interfere with 5-LO product synthesis. However, many investigations have addressed the efficacy of a given compound solely in cellular test systems and analysis of direct interference with 5-LO has been neglected. In the first part of this review, the biology and molecular pharmacology of the 5-LO pathway is summarized in order to understand its overall regulation and complexity as well as to comprehend the possible points of attack of compounds that eventually lead to inhibition of 5-LO product formation in intact cells. In the second part, natural compounds that interfere with 5-LO product formation are compiled and grouped into structural classes, and the underlying molecular mechanisms and structureactivity relationships are discussed.

show abstract

New Acetylenes Isolated from the Bark ofHeisteria acuminata

Cited by 28 publications

References 24 publications

Effect of polyacetylenic acids from Prunella vulgaris on various plant pathogens

Effect of polyacetylenic acids from Prunella vulgaris on various plant pathogens

Biosynthesis and function of polyacetylenes and allied natural products

Inhibition of 5-Lipoxygenase Product Synthesis by Natural Compounds of Plant Origin

Contact Info

Product

Resources

About