Isolation of new isoprenyl alcohols from silkworm feces

Fukawa, Hideaki; Toyoda, Masanobu; Shimizu, Toru; Murohashi, Masao

doi:10.1016/s0040-4039(00)70167-5

Cited by 12 publications

(3 citation statements)

References 7 publications

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“…Farnesyl-type prenol (di-trans poly-cis) include betulaprenol of Betula verrucosa [25,26], rubber-like poly-cis prenol of L. racemosa [10], and undecaprenol of Lactobacillus plantarum [27]. Geranygeranyl-type prenol (tri-trans poly-cis) include ficaprenol from Ficus elastica [28], malloprenol from Mallotus japonicus [29], moraprenol from Morus bombycis K. (mulberry) [30,31], castaprenol from Aesculus hippocastanum (horse chestnut) [32], and cleomeprenol detected on the first silica gel thin-layer plate. In the 2D-TLC of the unsaponifiable lipids of perilla leaves, there were compounds that remained on the first silica gel plate, as indicated with an arrow in Figure 1, implying the presence of rubber-like prenol in perilla.…”

Section: Poly-cis Prenolmentioning

confidence: 99%

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

Sagami

Świeżewska

Shidoji

2018

Bioscience, Biotechnology, and Biochemistry

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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.

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Section: Poly-cis Prenolmentioning

confidence: 99%

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

Sagami

Świeżewska

Shidoji

2018

Bioscience, Biotechnology, and Biochemistry

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“…Three polyisoprenoid alcohols, undeca-and dodecaprenols and solanesol, were isolated from silk-worm cocoons and leaves of M. alba [2]. Solanesol was not observed in the leaves.…”

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confidence: 97%

“…Mainly two species grow in Uzbekistan, M. alba and M. nigra. These species also include little studied varieties such as khasak-tut (used to feed silk worms), balkhi-tut (for fruit), ilon-tut and plakuchaya (as decorative plants), and shotut (M. nigra, for fruit) [1].Three polyisoprenoid alcohols, undeca-and dodecaprenols and solanesol, were isolated from silk-worm cocoons and leaves of M. alba [2]. Solanesol was not observed in the leaves.…”

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confidence: 99%

Polyisoprenoids from leaves of Morus alba and M. nigra

et al. 2012

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Trees or bushes of the genus Morus (mulberry) have been cultivated since antiquity. Mainly two species grow in Uzbekistan, M. alba and M. nigra. These species also include little studied varieties such as khasak-tut (used to feed silk worms), balkhi-tut (for fruit), ilon-tut and plakuchaya (as decorative plants), and shotut (M. nigra, for fruit) [1].Three polyisoprenoid alcohols, undeca-and dodecaprenols and solanesol, were isolated from silk-worm cocoons and leaves of M. alba [2]. Solanesol was not observed in the leaves. Moraprenols (polyprenols) from leaves of M. alba growing in Fergan Oblast were studied [3]. However, the quantitative composition of the polyprenologs was not reported. Polyprenols from M. nigra have not been reported.Recently a rather large number of preparations based on the use of polyprenols has appeared. In particular, the preparation gamapren (OOO GamaVetFarm, Russia) based on moraprenols is manufactured by phosphorylation of polyprenols isolated from Morus spp. The preparation exhibits antiviral action against Herpes viruses by suppressing the synthesis of viral proteins and stimulating the production of interferons [4].In continuation of research on plant polyprenols [5][6][7][8] and in order to compare the quantitative contents of M. alba and M. nigra polyprenols, we present results from a study of polyisoprenols from these two mulberry varieties growing in Tashkent Oblast.Total polyisoprenoids were isolated by the previously published method [9]. Dried and ground leaves (10 g) produced total polyisoprenoids in 2.6 and 3.2% yields. The content of total polyprenols was 1.37 and 1.97%, respectively, of the airdried leaf mass. The qualitative and quantitative compositions of the total polyisoprenoids were determined by high-performance TLC (HPTLC, Camag), by densitometry with UV detection at 210 nm, and by other alternate methods. HPTLC analysis used Sorbfil HPTLC-AF-UV plates (10 u 10). Plates were rinsed in distilled CHCl 3 and dried in air at 20-25°C for 10 min. The eluent was toluene:EtOAc (19:1). Compounds (1.0 mg) were dissolved in solvent (1 mL) and sampled (5 PL). The distance from the origin to the solvent front was 70.0 mm. The distance between tracks was 7.7 mm. Plates were dried in air at 20-25°C for 15 min.The standards were authentic samples of polyprenols from leaves of Asimina triloba (at least 96% pure) and those isolated by us from cotton leaves (at least 95% pure) of composition C 50 -C 65 . Standard samples of D-tocopherol and sitosterol were obtained from cotton leaves. Standard samples were prepared as described before [9]. Table 1 presents the results.According to the results, total polyisoprenoids contained polyprenols and D-tocopherol and sitosterol. The sitosterol contents in M. nigra and M. alba were almost identical. However, the amount of D-tocopherol was almost 13 times greater in leaves of M. nigra than in those of M. alba. The homologous composition of polyprenols from both M. nigra and M. alba included deca-, undeca-, and dodecaprenols with undecaprenol do...

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Polyterpenoids

Connolly¹,

Hill²

1991

Dictionary of Terpenoids

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Isolation of new isoprenyl alcohols from silkworm feces

Cited by 12 publications

References 7 publications

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

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

Polyisoprenoids from leaves of Morus alba and M. nigra

Polyterpenoids

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