71678-03-0 Usage
Description
Ilimaquinone is a natural sesquiterpene quinone with antimicrobial, anti-HIV, anti-mitotic, and anti-inflammatory properties. It has the ability to reversibly induce vesiculation of Golgi membranes in mammalian cells, blocking the secretory pathway. Ilimaquinone also inhibits the conversion of S-adenosylhomocysteine (SAH) to homocysteine by SAH hydrolase, DNA polymerase β, and dual specificity phosphatase Cdc25B. Additionally, it activates gene expression through hypoxia-inducible factor-1 at a concentration of 10 μM.
Uses
Used in Biological Research:
Ilimaquinone is used as a biological probe for studying intracellular communications and vesicle-mediated transport. Its ability to induce vesiculation of Golgi membranes and block the secretory pathway makes it a valuable tool for understanding these processes.
Used in Pharmaceutical Industry:
Ilimaquinone is used as an ADP-ribosylation factor (ARF) and β-COP to the Golgi membrane inhibitor. Its inhibitory effects on various enzymes and gene expression pathways make it a potential candidate for the development of new drugs targeting these pathways.
Biochem/physiol Actions
Primary TargetInduces a complete and reversible breakdown of Golgi membranes into smaller vesicular structures and causes depolymerization of microtubules.
Check Digit Verification of cas no
The CAS Registry Mumber 71678-03-0 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 7,1,6,7 and 8 respectively; the second part has 2 digits, 0 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 71678-03:
(7*7)+(6*1)+(5*6)+(4*7)+(3*8)+(2*0)+(1*3)=140
140 % 10 = 0
So 71678-03-0 is a valid CAS Registry Number.
InChI:InChI=1/C22H30O4/c1-13-7-6-8-18-21(13,3)10-9-14(2)22(18,4)12-15-19(24)16(23)11-17(26-5)20(15)25/h11,14,18,24H,1,6-10,12H2,2-5H3/t14-,18+,21+,22+/m0/s1
71678-03-0Relevant articles and documents
Unified Synthesis of the Marine Sesquiterpene Quinones (+)-Smenoqualone, (–)-Ilimaquinone, (+)-Smenospongine, and (+)-Isospongiaquinone
Katoh, Takeru,Atsumi, Suguru,Saito, Ryo,Narita, Koichi,Katoh, Tadashi
, p. 3837 - 3849 (2017/07/22)
The marine sesquiterpene quinones (+)-smenoqualone, (–)-ilimaquinone, (+)-smenospongine, and (+)-isospongiaquinone were efficiently synthesized in a unified manner starting from a known trans-decalin derivative, which is accessible from (+)-5-methyl Wiela
Synthesis of (-)-ilimaquinone via a radical decarboxylation and quinone addition reaction.
Ling, Taotao,Poupon, Erwan,Rueden, Erik J,Theodorakis, Emmanuel A
, p. 819 - 822 (2007/10/03)
[reaction: see text] A stereoselective synthesis of (-)-ilimaquinone (4) is presented. The synthetic strategy is based on a novel radical decarboxylation and quinone addition methodology that produces quinone 7 from reaction of thiohydroxamic acid derivat
Efficient total synthesis of (-)-ilimaquinone
Poigny, Stephane,Guyot, Michele,Samedi, Mohammad
, p. 5890 - 5894 (2007/10/03)
The total synthesis of (-)-ilimaquinone, a metabolite isolated from sea sponges, is described. The key step of the synthesis is the attachment of the quinone moiety to the drimane skeleton. Alkylation of enone 11 obtained in four steps from the readily available diketone 8, with tetramethoxybenzyl bromide 15 as the alkylating agent, led to addition product 16 in excellent yield. The presence of the tetramethoxybenzyl group induced stereoselective hydrogenation of the exo olefin 18, leading to the required isomer in a 9:1 ratio. Treatment of compound 21 with ceric ammonium nitrate (CAN) afforded formation of the quinone and deprotection of only one methyl ether in one step to furnish the desired ilimaquinone 1.
