- Neocrocin A: A novel crocetin glycoside with a unique system for binding sugars isolated from gardenia yellow
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A novel crocetin glycosyl ester, neocrocin A (2), was isolated from gardenia yellow. The structure of 2 was elucidated as that of an all-trans-crocetin β-D-gentiobiosyl β-D-glucopyranosyl-(1→6)-D-2- deoxy-glucopyranos-2-yl diester based on chemical and spectral data. The findings provide evidence that the binding system of crocetin glycosides is not limited to the anomeric position.
- Uekusa, Yoshinori,Sugimoto, Naoki,Sato, Kyoko,Yun, Young Sook,Kunugi, Akira,Yamazaki, Takeshi,Tanamoto, Ken-Ichi
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- Preparation and Anti-Tobacco Mosaic Virus Activities of Crocetin Diesters
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The development of antiviral agents with an original structure and noticeable effect is always in great need. Natural products are important lead compounds in the development of new pesticides. Crocin-1 and crocin-2 were effectively isolated from Gardeniae fructus and found to have higher anti-tobacco mosaic virus (TMV) activity levels than ribavirin. A series of the crocetin diester derivatives were synthesized with separated crocetin-1 as material and evaluated for their anti-TMV activities. They could be dissolved in common organic solvents as dichloromethane, ethyl acetate, tetrahydrofuran, and methanol. Compounds 5, 9, 13, 14, and 15 displayed higher activities in vivo than ribavirin. Compound 14 with significantly higher antiviral activities than lead compounds (crocin-1 and crocin-2) emerged as a new antiviral candidate.
- Chen, Guihua,Deng, Zhaoyang,Li, Ling,Liu, Yuxiu,Wang, Qingmin,Xu, Changjiang,You, Shengyong,Zou, Jiyong
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p. 13637 - 13643
(2021/11/18)
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- Crocetin diester compound as well as preparation method and application thereof
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The invention belongs to the technical field of pesticides, and provides a crocetin diester compound as well as preparation and application thereof in plant protection. It is found for the first timethat natural products crocin-1 and crocin-2 show higher anti-plant virus activity level than commercial variety virazole, can be used as a novel botanical pesticide or used as a lead compound for development, and used as the lead to design and synthesize the crocetin diester compound. An anti-plant virus activity test shows that all the compounds show activity on tobacco mosaic viruses, and particularly, the activity level of the crocetin di (4-fluorophenyl ethyl) ester is higher than that of a lead compound.
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Paragraph 0027-0031
(2021/03/30)
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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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Paragraph 0102; 0142-0146; 0160; 0211-0213; 0216-0217
(2018/10/26)
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- 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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p. 5639 - 5649
(2017/07/26)
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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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Paragraph 0142-0148
(2018/10/31)
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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 35-36; 50-52
(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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- A Short and Efficient Synthesis of Crocetin-dimethylester and Crocetindial
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In this paper we describe an efficient six-step synthesis of crocetin-dimethylester that could be further reduced to a "four-step" synthesis through the use of in situ procedures. The simplicity of the whole process, the ready availability of starting materials, and the high overall yield render this strategy a very attractive synthesis of this very important compound, which is the key intermediate for the synthesis of several carotenoids and other polyene natural products.
- Frederico, Daniel,Marcos Donate, Paulo,Gomes Constantino, Mauricio,Soares Bronze, Erika,Sairre, Mirela I.
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p. 9126 - 9128
(2007/10/03)
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- A Convergent Synthesis of Symmetrical Carotenoids Using the Heck Reaction
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Regioselective Heck-type vinylation of various allylic alcohols with 2, followed by an acidic dehydration, delivers symmetrical carotenoids in good yields. - Key words: Heck vinylation; Palladium; Carotenoids; β-Carotene
- Bienayme, Hugues
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p. 6867 - 6868
(2007/10/02)
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