Rugulosin((+)-Rugulosin)

Names

[ Name ]:
Rugulosin((+)-Rugulosin)

[Synonym ]:
(5aS:17S:20S)-1.7.9.15.17.20-hexahydroxy-5.8.13.16-tetraoxo-5.8.13.16-tetrahydro-6H.14H-6c.13ac.!5ar.14c-[1.2.3.4]butanetetrayl-cycloocta[1.2-b:5.6-b']dinaphthalene
(+)-Rugulosin,(1S,1S,2R,2R,3S,3S,9aR,9aR)-Rugulosin,(2R,2R)-Rugulosin
5H,6H-6,13A,5A,14-[1,2,3,4]Butanetetraylcycloocta[1,2-B:5,6-B']dinaphthalene-5,8,13,16(14H)-tetrone,1,7,9,15,17,20-hexahydroxy-3,11-dimethyl-,[5as-(5ar*,6S*,13ar*,14S*,17R*,18S*,19S*,20R*)]
(+)-rugulosin
(5aS:17S:20S)-1.7.9.15.17.20-Hexahydroxy-5.8.13.16-tetraoxo-5.8.13.16-tetrahydro-6H.14H-6c.13ac.!5ar.14c-[1.2.3.4]butantetryl-cycloocta[1.2-b:5.6-b']dinaphthalin
5H,6H-6,13A,5A,14-[1,2,3,4]Butanetetraylcycloocta[1,2-B:5,6-B']dinaphthalene-5,8,13,16(14H)-tetrone,1,7,9,15,17,20-hexahydroxy-3,11-dimethyl

Biological Activity

[Description]:

Rugulosin is a crystalline colouring matter of Penicillium rugulosum Thom. Rugulosin shows markedly specific antibacterial activity and moderately antifungal activity[1].

[Related Catalog]:

Research Areas >> Infection

Signaling Pathways >> Anti-infection >> Fungal

Signaling Pathways >> Anti-infection >> Bacterial

[In Vitro]

Rugulosin is very highly antibacterial active against certain bacilli, streptococci and corynebacteria, but is much less active against Gram-negative organisms[1]. Rugulosin completely inhibits the growth of Pythium intermedium de Bary at a concentration of 1: 50000[1].

[References]

[1]. BREEN J, et al. Studies in the biochemistry of micro-organisms. 95. Rugulosin, a crystalline colouring matter of Penicillium rugulosum Thom. Biochem J. 1955 Aug;60(4):618-26.

Chemical & Physical Properties

[ Density]:
1.87g/cm3

[ Boiling Point ]:
980ºC at 760mmHg

[ Molecular Formula ]:
C₃₀H₂₂O₁₀

[ Molecular Weight ]:
542.49000

[ Flash Point ]:
560.3ºC

[ Exact Mass ]:
542.12100

[ PSA ]:
189.66000

[ LogP ]:
2.01080

[ Vapour Pressure ]:
0mmHg at 25°C

[ Index of Refraction ]:
1.868

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: VM1610000

CHEMICAL NAME :: Rugulosin

CAS REGISTRY NUMBER :: 23537-16-8

LAST UPDATED :: 199510

DATA ITEMS CITED :: 14

MOLECULAR FORMULA :: C30-H22-O10

MOLECULAR WEIGHT :: 542.52

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 44 mg/kg

TOXIC EFFECTS :: Behavioral - tremor Behavioral - coma Nutritional and Gross Metabolic - body temperature decrease

TYPE OF TEST :: LD - Lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >4 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 55 mg/kg

TOXIC EFFECTS :: Behavioral - tremor Behavioral - coma Nutritional and Gross Metabolic - body temperature decrease

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1100 mg/kg/22D-C

TOXIC EFFECTS :: Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - hepatic microsomal mixed oxidase (dealkylation, hydroxylation, etc.) Related to Chronic Data - death

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 4400 mg/kg/1Y-C

TOXIC EFFECTS :: Tumorigenic - equivocal tumorigenic agent by RTECS criteria Liver - tumors

MUTATION DATA

TYPE OF TEST :: Mutation in microorganisms

TEST SYSTEM :: Yeast - Saccharomyces cerevisiae

DOSE/DURATION :: 100 umol/L

REFERENCE :: CPBTAL Chemical and Pharmaceutical Bulletin. (Japan Pub. Trading Co., USA, 1255 Howard St., San Francisco, CA 94103) V.6- 1958- Volume(issue)/page/year: 22,2258,1974 *** REVIEWS *** IARC Cancer Review:Animal Inadequate Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 40,99,1986 IARC Cancer Review:Human No Adequate Data IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 40,99,1986 IARC Cancer Review:Group 3 IMSUDL IARC Monographs, Supplement. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) No.1- 1979- Volume(issue)/page/year: 7,56,1987 TOXICOLOGY REVIEW LLOYA2 Lloydia. (Cincinnati, OH) V.1-41, 1938-78. For publisher information, see JNPRDF. Volume(issue)/page/year: 38,21,1975 TOXICOLOGY REVIEW ARMIAZ Annual Review of Microbiology. (Annual Reviews, Inc., POB 10139, Palo Alto, CA 94303) V.1- 1947- Volume(issue)/page/year: 26,279,1972

Related Compounds

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