- ISOLATION OF DIHYDROXYLUPENE AND DIHYDROXYLUPANE FROM THE BARK OF LAWSONIA INERMIS
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Two pentacyclic triterpenes isolated from the bark of henna were identified as 3β,30-dihydroxylup-20(29)-ene (hennadiol), and (20S)-3β,30-dihydroxylupane.The assignment of the C-20 configuration in the latter compound was supported by the analysis of Eu(fod)3-induced 1H NMR chemical shifts in the two C-20 epimers synthesized from lupeol. - Key Word Index: Lawsonia inermis; Lythraceae; henna; triterpenoids; 30-hydroxylupeol; 30-hydroxylupanol.
- Chakrabartty, Tarakeswar,Poddar, Gurudas,Pyrek, Jan St.
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- Synthesis of lupeol derivatives and their antileishmanial and antitrypanosomal activities
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The natural product lupeol 1 was isolated from aerial parts of Vernonia scorpioides with satisfactory yield, which made it viable to be used as starting material in semisynthetic approach. Ten lupeol derivatives 2–11 were prepared by classical procedures. Including, five new esters derivatives 7–11, which were obtained by structural modifications in the isopropylidene fragment. All semisynthetic compounds and lupeol 1–11 were confirmed by 1H NMR, 13C NMR and HRMS. Their antiprotozoal activity was evaluated in vitro against L. amazonensis and T. cruzi. Derivative 6 showed the best antitrypanosomal activity (IC50?=?12.48?μg/mL) and the lowest cytotoxic derivative (CC50?=?161.50?μg/mL). The mechanism of action of the most active derivatives (4, 6 and 11) is not dependent from the enzyme trypanothione reductase.
- Machado, Vanessa R.,Sandjo, Louis P.,Pinheiro, Giovanni L.,Moraes, Milene H.,Steindel, Mario,Pizzolatti, Moacir G.,Biavatti, Maique W.
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p. 275 - 281
(2017/10/06)
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- Side chain oxidation of lupeol: A reinvestigation
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Oxidation of lupeol with m-chloroperbenzoic acid yields lup-20-norketone-3β-ol (6), lup-20(29)-ene-3β,30-diol (7) and lup-20-al-3β-ol (8).Formation of the compounds 7 and 8 from lupeol is being reported for the first time.
- Roy, Kamal,Bhaduri, A. P.
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p. 823 - 824
(2007/10/03)
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- Lichens and Fungi. XVIII. Extractives from Pseudocyphellaria rubella
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Twenty lupane triterpenoids including five (20RS)-epimeric pairs have been isolated from the chloroform extractives of the lichen Pseudocyphellaria rubella.The utility of g.c.-m.s. procedures in the structural elucidation of the extractives, some of which were complex mixtures is discussed.
- Corbett, R. Edward,Cong, Aimy N. T.,Holland, Patrick T.,Wilkins, Alistair L.
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p. 461 - 468
(2007/10/02)
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- 3-Oxolup-20(29)-en-30-al, a New Lupane from Gymnosporia emarginata (Celastraceae)
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The steam bark of Gymnosporia emarginata (Willd.) Hook f. ex.Thw. (Celastraceae) contains a number of triterpenes including a new oxygenated lupane, 3-oxolup-20(29)-en-30-al (1) and two related lupanes, 3β-hydroxylup-20(29)-en-30-al (2) and 30-hydroxylup-20(29)-en-3-one (3).The structures of these compounds have been established by spectroscopic and chemical methods.
- Wijeratne, Dharmassree B. T.,Kumar, Vijaya,Sultanbawa, M. Uvais S.
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p. 2724 - 2726
(2007/10/02)
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