Lucidin
-
Lucidin
structure -
-
CAS No:
478-08-0
-
Formula:
C15H10O5
-
Chemical Name:
Lucidin
-
Synonyms:
9,10-Anthracenedione,1,3-dihydroxy-2-(hydroxymethyl)-;Anthraquinone,1,3-dihydroxy-2-(hydroxymethyl)-;1,3-Dihydroxy-2-(hydroxymethyl)-9,10-anthracenedione;Henine;Lucidin;Lucidin (quinone);1,3-Dihydroxy-2-(hydroxymethyl)anthraquinone;NSC 30546
- Categories:
-
CAS No:
Description
Lucidin (NSC 30546) is a natural component of Rubia tinctorum L. lucidin is mutagenic in bacteria and mammalian cells.IC50 Value:Target: in vitro: Lucidin was mutagenic in five Salmonella typhimurium strains without metabolic activation, but the mutagenicity was increased after addition of rat liver S9 mix. In V79 cells, lucidin was mutagenic at the hypoxanthine-guanine phosphoribosyl transferase gene locus and active at inducing DNA single-strand breaks and DNA-protein cross-links as as
Lucidin is a dihydroxyanthraquinone.
Toxicity
Lucidin has been identified in plants from Rubia (R. tinctorum, R. iberica), Coprosma (C. lucida, C. rotundifolia, C. acerosa), Morinda (M. citrifolia, M. umbellata), Galium (G. fagetorum, G. mollugo, G. dasypodum), Hymenodictyon (H. excelsum) and Commitheca (C. liebrechtsiana) species.
Drug Information
A mutagenic anthraquinone, lucidin, occurring in Rubiaceae plants, reacted with nucleic bases under physiological conditions to form adducts. ... The isolated purine base adducts were identified as condensed reactants at the benzylic position of 1 with a nitrogen atom of a purine base.
Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poison A and B/|Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in respiratory arrest. Positive pressure ventilation techniques with a bag valve mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Consider drug therapy for pulmonary edema ... . For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam (Valium) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poison A and B/
/HUMAN EXPOSURE STUDIES/ The largest outbreak reported to date occurred in the Gulran district of Herat Province in northwest Afghanistan, close to the border of the USSR. ...The outbreak, was estimated to have affected a population of approximately 35,000 in 98 villages. Examination of 7,200 inhabitants of the affected villages showed evidence of disease in 22.6%, which was more serious in 15%. Thus, it was estimated that approximately 8,000 subjects suffered from the disease including 5,000 who were seriously affected. All age groups were affected, but 46% of subjects were below 14 years of age. However, no sign of disease was found in children below 2 years of age. A detailed report concerning the pathological material obtained from 14 liver biopsies and 8 autopsies was made... /although/ the time interval between the onset of symptoms and the biopsy/autopsy was not indicated. Pathological findings were characteristic, ranging from acute disease with characteristic veno-occlusion to non-portal cirrhosis, which was observed in 5 of the above 22 cases. The outbreak was ascribed to massive contamination of wheat, the staple food crop, following 2 years of drought, with the seeds of Heliotropium popovii H. Riedl subsp. gillianum H. Riedl, which had been growing profusely among the wheat crop. The seeds contained pyrrolizidine alkaloids at concentrations reported by 2 laboratories to be 7.2 and 13.2-14.9 g/kg, identified mainly as the N-oxide of heliotrine (74%)..., and one or two other compounds similar in character to lasiocarpine. Samples of wheat from several villages contained an average of 40 seeds/kg, i.e., 0.03% by weight. It was estimated that an adult consumed at least 700 g flour/day, containing approximately 2 mg alkaloid (based on a mean of the seed analyses). /Pyrrolizidine alkaloids/|/HUMAN EXPOSURE STUDIES/ The two main sources of pyrrolizidine alkaloid poisoning reported in human beings are the consumption of cereal grain contaminated by weeds containing the alkaloids and the use of alkaloid-containing herbs for medicinal and dietary purposes. ...Three of the largest outbreaks of the disease have been reported from South Asia, two from the same site in central India and one from North-West Afghanistan. The first Indian outbreak... occurred in a group of 5 tribal villages in central India in 1972-73. ...Out of a total population of 2,060 in these villages, 71 households with 366 members were investigated. Among these, 39 cases had developed and 19 had died before commencement of the investigations. The incidence rate was 1.1% and the case fatality rate was 50%. All cases occurred among 20 households. In many households, several members were affected. In one household, 4 out of 5 cases died. ...The etiological factor of this outbreak was not established, though dietary contamination with pyrrolizidine alkaloids was considered. A second outbreak occurred at the same site in 1975... . A total population of 486 was affected, 67 cases were reported, of whom 28 (46%) had died. There was a strong family history... . In a later survey, 108 patients were studied and the mortality rate was estimated to be 63%. This time the etiological factor was identified as the plant Crotalaria nana Burm, which had been growing in the fields of millet (Panicum miliare), their staple food crop. The seeds of this plant became mixed with the cereal grain during harvesting. The toxic seeds contained pyrrolizidine alkaloids that were identified as a macrocyclic ester closely similar to monocrotaline. The total alkaloid content was estimated to be 5.3 g/kg of seed, expressed as monocrotaline. The levels of contamination of the millet with seeds were reported to be 0-3.4 g/kg in the unaffected and 0-19 g/kg in the affected households... . /Pyrrolizidine alkaloids/|/SIGNS AND SYMPTOMS/ After intake of madder root, occasional cases of red coloration of the urine, saliva, perspiration, and milk have been observed.
1,3-dihydroxy-2-hydroxymethyl-9,10-anthraquinone
Lucidin Use and Manufacturing
Lucidin has been synthesized from nordamnacanthal.
The /IARC/ Working Group was not aware of any commercial use of purified lucidin.
Lucidin has been identified in plants from Rubia (R. tinctorum, R. iberica), Coprosma (C. lucida, C. rotundifolia, C. acerosa), Morinda (M. citrifolia, M. umbellata), Galium (G. fagetorum, G. mollugo, G. dasypodum), Hymenodictyon (H. excelsum) and Commitheca (C. liebrechtsiana) species.
An HPLC method with isocratic elution has been developed for the separation of anthraquinones with particular attention to the detection of lucidin in commercially available sources of R. tinctorum aglycones.|A reversed-phase HPLC method has been developed for the simultaneous characterization of anthraquinone glycosides and aglycones in extracts of R. tinctorum. The anthraquinones, including lucidin, are separated on a reversed-phase column with a wateracetonitrile gradient as eluent and measured with ultraviolet detection at 250 nm.|Lucidin content in R. tinctorum crude drug powder has been determined using reversed-phase HPLC with methanol/acetic acid as the mobile phase and detection at 225 nm.
Pyrrolizidine alkaloids may be estimated in animal tissues and fluids by removing protein, chromatographing on Florisil and estimating colorimetrically with methyl orange. /Pyrrolizidine Alkaloids/
Computed Properties
Molecular Weight:270.24
XLogP3:2.4
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:1
Exact Mass:270.05282342
Monoisotopic Mass:270.05282342
Topological Polar Surface Area:94.8
Heavy Atom Count:20
Complexity:421
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
Recommended Suppliers of Lucidin
-
CN
5 YRS
Business licensedTrader Supplier of PVC resin,pvc paste resin,melamine
Learn More Other Chemicals
-
Lucidin ω-methyl ether
79560-36-4
-
Lucidin primeveroside
29706-59-0
-
(3S)-1,2,3,4-Tetrahydro-6,7-dimethoxy-3-isoquinolinecarboxylic acid
103733-66-0
-
2-Methoxy-5-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine Formula
1083168-84-6
-
2-iodo-2,3-dihydroinden-1-one Formula
113021-30-0
-
2,2-DIMETHYL-N-[3-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)-PYRIDIN-2-YL]-PROPIONAMIDE Formula
532391-30-3
-
6-Methylbenzoxazole Structure
10531-80-3
-
Methyl N-formylanthranilate Structure
41270-80-8
-
What is 1-(4-amino-3,5-dichlorophenyl)-2-(dimethylamino)ethanol
4812-69-5
-
What is 2,5-Dihydroxy-N-(2-hydroxyethyl)benzamide
61969-53-7