Pseudolaric Acid A

Names

[ Name ]:
Pseudolaric Acid A

[Synonym ]:
(2E,4E)-5-[(1R,7S,8S,9R)-7-Acetoxy-4,9-dimethyl-11-oxo-10-oxatricyclo[6.3.2.0]tridec-3-en-9-yl]-2-methyl-2,4-pentadienoic acid
(2E,4E)-5-[(1R,7S,8S,9R)-7-Acetoxy-4,9-dimethyl-11-oxo-10-oxatricyclo[6.3.2.0]tridec-3-en-9-yl]-2-methylpenta-2,4-dienoic acid
2,4-Pentadienoic acid, 5-[(3R,4S,4aS,9aR)-4a-(acetyloxy)-3,4,4a,5,6,9-hexahydro-3,7-dimethyl-1-oxo-1H-4,9a-ethanocyclohepta[c]pyran-3-yl]-2-methyl-, (2E,4E)-
(2E,4E)-5-[(1R,7R,8S,9S)-7-Acetoxy-4,9-dimethyl-11-oxo-10-oxatricyclo[6.3.2.0]tridec-3-en-9-yl]-2-methyl-2,4-pentadienoic acid
(2E,4E)-5-[(3R,4S,4aS,9aR)-4a-(acetyloxy)-3,7-dimethyl-1-oxo-3,4,4a,5,6,9-hexahydro-4,9a-ethanocyclohepta[c]pyran-3(1H)-yl]-2-methylpenta-2,4-dienoic acid
pseudolaric acid A
2,4-Pentadienoic acid, 5-[(3S,4S,4aR,9aR)-4a-(acetyloxy)-3,4,4a,5,6,9-hexahydro-3,7-dimethyl-1-oxo-1H-4,9a-ethanocyclohepta[c]pyran-3-yl]-2-methyl-, (2E,4E)-
PseudolaricAcid A

Biological Activity

[Description]:

Pseudolaric Acid A is a diterpene acid isolated from Pseudolarix kaempferi, has antifungal, cytotoxic and antifertile activities[1][2][3].

[Related Catalog]:

Research Areas >> Infection

Signaling Pathways >> Anti-infection >> Fungal

[References]

[1]. Zhang J, et al,. Antifungal activity of compounds extracted from Cortex Pseudolaricis against Colletotrichum gloeosporioides. J Agric Food Chem. 2014 May 28;62(21):4905-10.

[2]. Pan DJ, et al. The cytotoxic principles of Pseudolarix kaempferi: pseudolaric acid-A and -B and related derivatives. Planta Med. 1990 Aug;56(4):383-5.

[3]. Wang WC, et al. [Endocrine activity of pseudolaric acids A and B and their effects on sex hormones, prostaglandins, uteri, and fetuses]. Zhongguo Yao Li Xue Bao. 1991 Mar;12(2):187-90.

Chemical & Physical Properties

[ Density]:
1.23

[ Boiling Point ]:
571.5±50.0 °C at 760 mmHg

[ Melting Point ]:
206-207 ºC

[ Molecular Formula ]:
C₂₂H₂₈O₆

[ Molecular Weight ]:
388.454

[ Flash Point ]:
196.6±23.6 °C

[ Exact Mass ]:
388.188599

[ PSA ]:
89.90000

[ LogP ]:
3.49

[ Vapour Pressure ]:
0.0±3.4 mmHg at 25°C

[ Index of Refraction ]:
1.563

[ Storage condition ]:
2-8C

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: RZ2473800

CHEMICAL NAME :: 2,4-Pentadienoic acid, 5-(4a-(acetyloxyl)-3,4,4a,5,6,9-hexahydro-3,7-dimethy l-1-oxo- 1H-4,9a-ethanocyclohepta(c)pyran-3-yl)-2-methyl-, (3-alpha(2E,4E),4-alpha,9a-alpha)-(-)- (9CI)

CAS REGISTRY NUMBER :: 82508-32-5

LAST UPDATED :: 199309

DATA ITEMS CITED :: 5

MOLECULAR FORMULA :: C22-H28-O6

MOLECULAR WEIGHT :: 388.50

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 219 mg/kg

TOXIC EFFECTS :: Behavioral - food intake (animal) Gastrointestinal - hypermotility, diarrhea

REFERENCE :: CYLPDN Zhongguo Yaoli Xuebao. Acta Pharmacologica Sinica. Chinese Journal of Pharmacology. (China International Book Trading Corp., POB 2820, Beijing, Peop. Rep. China) V.1- 1980- Volume(issue)/page/year: 9,445,1988

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 397 mg/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold Behavioral - muscle weakness

REFERENCE :: CYLPDN Zhongguo Yaoli Xuebao. Acta Pharmacologica Sinica. Chinese Journal of Pharmacology. (China International Book Trading Corp., POB 2820, Beijing, Peop. Rep. China) V.1- 1980- Volume(issue)/page/year: 9,445,1988

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

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 486 mg/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold Behavioral - muscle weakness

REFERENCE :: CYLPDN Zhongguo Yaoli Xuebao. Acta Pharmacologica Sinica. Chinese Journal of Pharmacology. (China International Book Trading Corp., POB 2820, Beijing, Peop. Rep. China) V.1- 1980- Volume(issue)/page/year: 9,445,1988 ** REPRODUCTIVE DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 24600 ug/kg

SEX/DURATION :: female 7-9 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - pre-implantation mortality (e.g. reduction in number of implants per female; total number of implants per corpora lutea)

REFERENCE :: CYLPDN Zhongguo Yaoli Xuebao. Acta Pharmacologica Sinica. Chinese Journal of Pharmacology. (China International Book Trading Corp., POB 2820, Beijing, Peop. Rep. China) V.1- 1980- Volume(issue)/page/year: 9,445,1988

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 200 mg/kg

SEX/DURATION :: female 7-11 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - pre-implantation mortality (e.g. reduction in number of implants per female; total number of implants per corpora lutea) Reproductive - Effects on Embryo or Fetus - fetal death

REFERENCE :: CYLPDN Zhongguo Yaoli Xuebao. Acta Pharmacologica Sinica. Chinese Journal of Pharmacology. (China International Book Trading Corp., POB 2820, Beijing, Peop. Rep. China) V.1- 1980- Volume(issue)/page/year: 9,445,1988