- Characterization of the Saffron Derivative Crocetin as an Inhibitor of Human Lactate Dehydrogenase 5 in the Antiglycolytic Approach against Cancer
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Inhibition of lactate dehydrogenase (LDH) represents an innovative approach to tackle cancer because this peculiar glycolytic metabolism is characteristic of most invasive tumor cells. An investigation into the biological properties of saffron extracts led to the discover of their LDH-inhibition properties. In particular, the most important saffron components, crocetin, was found to inhibit LDH (IC50 = 54.9 ± 4.7 μM). This carotenoid was independently produced by chemical synthesis, and its LDH-inhibition properties manifested via its antiproliferative activity against two glycolytic cancer cell lines (A549 and HeLa, IC50 = 114.0 ± 8.0 and 113.0 ± 11.1 μM, respectively). The results described in this article suggest that saffron may be a helpful alimentary component in the prevention of cancer that potentially contributes to the efficacy of approved cancer therapies.
- Granchi, Carlotta,Fortunato, Serena,Meini, Serena,Rizzolio, Flavio,Caligiuri, Isabella,Tuccinardi, Tiziano,Lee, Hyang Yeon,Hergenrother, Paul J.,Minutolo, Filippo
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- BIPOLAR TRANS CAROTENOID SALTS AND USES THEREOF
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PROBLEM TO BE SOLVED: To provide compounds useful in improving diffusivity of oxygen between red blood cells and body tissues in mammals including humans. SOLUTION: There is provided a compound which has a structure represented by YZ-TCRO-ZY and is not trans sodium crocetinate [where, Y is a cation; Z is a polar group which is associated with the cation; and TCRO is trans carotenoid skeleton], and preferably, Y is a monovalent metal ion selected from the group consisting of Na+, K+ and Li+, or is an organic cation selected from the group consisting of R4 N+ and R3S+ [R is H, or CnH2n+1(n is 1 to 10)]. SELECTED DRAWING: None COPYRIGHT: (C)2018,JPO&INPIT
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- BIPOLAR TRANS CAROTENOID SALTS AND THEIR USE
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PROBLEM TO BE SOLVED: To provide trans carotenoid salt compounds useful for improving the diffusibility of oxygen between red blood cells and a body tissue in mammalian including human being, a method for producing them, a method for solubilizing them, and a method for using them. SOLUTION: There are provided compounds represented by the following formula, and are compounds not being trans sodium crocetinate: YZ-TCRO-ZY[Y denotes a cation; Z denotes a polar group coupled to the cation; TCRO denotes a trans carotenoid skeleton; preferably, as follows; Y denotes the monovalent metal ion of Na+,K+ or Li+ or R4 N+ or R3S+;R denotes H or CnH2n+1;n denotes the integer of 1 to 10;Z denotes a carboxyl group, a sulfuric acid group, a mono-phosphoric acid group, a di-phosphoric acid group, or a tri-phosphoric acid group; and TCRO denotes a group using isopronoid in which the single bond and double bond of straight chain carbon and carbon as exemplified by the following formula is repeated (X respectively independently denotes H, a straight chain/branched carbon chain substituted/non-substituted with 1 to 10C halogen or a halogen)]. SELECTED DRAWING: None COPYRIGHT: (C)2017,JPO&INPIT
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- BIPOLAR TRANS CAROTENOID SALTS AND THEIR USES
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The invention relates to trans carotenoid salt compounds, methods for making them, methods for solubilizing them and uses thereof. These compounds are useful in improving diffusivity of oxygen between red blood cells and body tissues in mammals including humans.
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Page/Page column 47-48
(2008/06/13)
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- Bipolar trans carotenoid salts and their uses
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The invention relates to trans carotenoid salt compounds, methods for making them, methods for solubilizing them and uses thereof. These compounds are useful in improving diffusivity of oxygen between red blood cells and body tissues in mammals including humans.
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- Synthesis of (7S,15S)- and (7R,15S)-dolatrienoic acid
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The stereospecific synthesis of (7S,15S)- and (7R,15S)-dolatrienoic acids (2) was achieved using an approach consisting of 16 linear steps. The C-11-C-16 unit was prepared in seven steps from ethyl (S)lactate and coupled using a trans-selective Wittig - Schlosser reaction to the C-7-C-10 fragment. Chirality at the C-7 position was introduced using an Evan's-type chiral auxiliary in a cobalt-mediated Reformatsky reaction to give the (3S,11S)-aldehyde 24. Subsequent Wittig reaction with a phosphonium salt derived in three steps from tiglic acid gave (7S,15S)-dolatrienoic acid, one of the four possible diastereoisomers of the nonpeptide portion of the strong Cancer cell growth inhibitory cyclodepsipeptide dolastatin 14 (1). A second diastereoisomer, (7R,15S)-dolatrienoic acid, was synthesized employing chiral oxazolidinone 21 by an analogous synthetic route.
- Duffield, Jonathan J.,Pettit, George R.
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p. 472 - 479
(2007/10/03)
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- 6- and 8?-Ringschlussreaktionen von 2-Oxaheptatrienyl-Dipolen: Synthese von 3-Vinyl-2,3-dihydrofuranen und 2,3(6,7)-Dihydrooxepinen
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The thermally induced ring expansion reactions of several butadienyloxiranes are described.The 3(E)-configurated epoxytrienes 11 are transformed predominantly into cis-3-vinyl-2,3-dihydrofurans 15, the trans-isomers 16 being formed as a minor component only with the derivatives a, c, and h.In contrast, thermolysis of the 3(Z)-butadienyloxiranes 12 leads always to a mixture of fivemembered ring products (15/16) and, additionally, dihyrooxepins (17 and 29, resp.).As mechanism of the ring expansion reactions a multistep sequence is proposed with 2-oxaheptatrienyl dipoles as intermediates, which undergo electrocyclisation with participation of either six or eight electrons leading to dihydrofurans and dihydrooxepins, resp.With relation to 1,7-cyclisation reactions of other extended dipole systems the importance of the stereochemistry in the starting materials is emphasised.
- Eberbach, Wolfgang,Trostmann, Uwe
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p. 2979 - 3003
(2007/10/02)
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