Isolation of new poliisoprenyl ketone from silkworm feces

Toyoda, Masanobu; Fukawa, Hideaki; Shimizu, Toru

doi:10.1016/s0040-4039(01)99114-2

Cited by 6 publications

(3 citation statements)

References 2 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The identification of the family corresponding to polyprenols or dolichols was performed in at least three experiments. Bombiprenone (C 43 ) as described by Toyoda et al (1968) and Irvine et al (1972) was purified by the silica-gel chromatography of non-saponifiable lipids of the CHCl 3 / CH 3 OH (2:1) extract of dry perilla leaves and its identity was confirmed by HPLC/MS to have an m/z value [M + Na] + of 625.53183 corresponding to C 43 H 70 O (bombiprenone). Solanesol (C 45 ) standard was prepared as described previously (Kurisaki et al, 1997).…”

Section: Chemicalsmentioning

confidence: 99%

Diversity of polyisoprenoids in ten Okinawan mangroves

et al. 2016

View full text Add to dashboard Cite

The distribution and occurrence of polyisoprenoids (dolichols and polyprenols) in the leaves and roots of nine true Okinawan mangroves and the leaves of one associate mangrove were analyzed using two-dimensional thin layer chromatography. In the leaves, the distribution of three types (I, II, and III) of polyprenols and dolichols were detected. (I) The predominance of dolichols over polyprenols (more than 90%) was observed in Avicennia marina, Bruguiera gymnorrhiza, B. gymnorrhiza (yellow leaves), and Rhizophora stylosa. (II) The occurrence of both polyprenols and dolichols is observed in Excoecaria agallocha, Kandelia obovata, K. obovata (yellow leaves), Lumnitzera racemosa, Pemphis acidula, and Sonneratia alba. (III) The predominance of polyprenols over dolichols (more than 90%) is observed in Heritiera littoralis and Hibiscus tiliaceus. However, in the roots, a type-I distribution was observed in A. marina, B. gymnorrhiza, E. agallocha, H. littoralis and S. alba. A type-II distribution was observed in K. obovata, L. racemosa, P. acidula, and R. stylosa with no type-III distribution. The chain-length distribution of dolichols in the leaves and roots was C 50-C 140 and C 60-C 120 , respectively. A similar chain-length distribution of polyprenols of C 45-C 140 and C 65-C 85 was detected in the leaves and roots respectively. Taken together, sixteen out of twenty-one tissues indicated that dolichols are more abundant than polyprenols in both leaves and roots. The present study is the first to clarify the diversity of polyisoprenoids in both the leaves and roots of mangrove, suggesting the chemotaxonomic significance of polyisoprenoids in the mangrove tree species.

show abstract

Section: Chemicalsmentioning

confidence: 99%

Diversity of polyisoprenoids in ten Okinawan mangroves

et al. 2016

View full text Add to dashboard Cite

show abstract

“…Shorter carbon-chain prenylacetone such as geranyl acetone (C 13 ) or farnesyl acetone (C 18 ) was found as a volatile compound in fruits such as tomatoes and watermelons [53]. A 43-carbon ketone isolated from the unsaponifiable matter of silkworm (Bombyx mori L.) feces was identified as a polyisoprenoid compound (bombiprenone, C 43 ) with 8 isoprene units with each unit having one trans double bond to which an acetonyl residue was attached at the terminal unit [54]. The ketone was also found in the leaves of mulberry trees (M. bombycis K.) [55], which comprises the entire diet of silkworm.…”

Section: Poly-trans Prenylacetonementioning

confidence: 99%

The history and recent advances in research of polyprenol and its derivatives

Sagami

Świeżewska

Shidoji

2018

Bioscience, Biotechnology, and Biochemistry

View full text Add to dashboard Cite

The reduction pathway leading to the formation of dolichol was clarified in 2010 with the identification of SRD5A3, which is the polyprenol reductase. The finding inspired us to reanalyze the length of the major chain of polyprenol and dolichol from several plant leaves, including mangrove plants, as well as from animal and fish livers by 2D-TLC. Polyprenol- and dolichol-derived metabolites such as polyprenylacetone and epoxydolichol were found together with rubber-like prenol. This review focuses on analyses of polyprenol and its derivatives, including recently found epoxypolyprenol and polyprenylacetone. Attention has also been paid to the chromatographic behavior of rubber-like prenol on TLC.

show abstract

“…The mass spectrum of a new' polyisoprenyl ketone from silkworm feces provided essential structural information (485). Mass spectrometry has helped to identify: urinary hippuric acid isolated by anion-exchange chromatography (486); 0-hydroxyisovaleric acid in the urine of a patient with isovaleric acidemia (487); small amounts of methamphetamine after passage through the body (488); 160-hydroxydehydroepiandrosterone in infant urine (489); and pyroglutamic acid as a peak in the gas chromatography of human urine ANALYTICAL CHEMISTRY, VOL.…”

Section: Sulfur-containingmentioning

confidence: 99%

Mass spectrometry

DeJongh¹

1970

Anal. Chem.

View full text Add to dashboard Cite

Isolation of new poliisoprenyl ketone from silkworm feces

Cited by 6 publications

References 2 publications

Diversity of polyisoprenoids in ten Okinawan mangroves

Diversity of polyisoprenoids in ten Okinawan mangroves

The history and recent advances in research of polyprenol and its derivatives

Mass spectrometry

Contact Info

Product

Resources

About