| Identification | Back Directory | [Name]
PSEUDOLARIC ACID B | [CAS]
82508-31-4 | [Synonyms]
PLAB
Pseudolaric acid
PSEUDOLARIC ACID B
Pseudolarix acid B
(-)-Pseudolaric Acid B
Pseudolaric Acid B(PBA)
Pseudolaric Acid B
(PAB)
pha(1e,3e),4-alpha,4a-alpha,9a-alpha)-(-)-(9ci)
Pseudolaric acid B, 98%, from Pseudolarix amabilis (J. Nelson) Rehder
-1,3-pentadienyl)3,4,4a,5,6,9-hexahydro-3-methyl-1-oxo-,7-methylester,(3-al
1h-4,9a-ethanocyclohepta(c)pyran-7-carboxylicacid,4a-(acetyloxy)-3-(4-carboxy
(2E,4E)-5-((3R,4S,4aS,9aS)-4a-acetoxy-7-(methoxycarbonyl)-3-methyl-1-oxo-3,4,4a,5,6,9-hexahydro-1H-4,9a-ethanocyclohepta[c]pyran-3-yl)-2-methylpenta-2,4-dienoic acid
1H-4,9a-Ethanocyclohepta[c]pyran-7-carboxylicacid,4a-(acetyloxy)-3-[(1E,3E)-4-carboxy-1,3-pentadien-1-yl]-3,4,4a,5,6,9-hexahydro-3-methyl-1-oxo-,7-methyl ester, (3R,4S,4aS,9aR)- | [EINECS(EC#)]
231-291-4 | [Molecular Formula]
C23H28O8 | [MDL Number]
MFCD01746346 | [MOL File]
82508-31-4.mol | [Molecular Weight]
432.46 |
| Chemical Properties | Back Directory | [Melting point ]
166°C | [Boiling point ]
466.14°C (rough estimate) | [density ]
1.2108 (rough estimate) | [refractive index ]
1.4480 (estimate) | [storage temp. ]
2-8°C | [solubility ]
methanol: soluble1mg/mL, clear, colorless | [form ]
powder or crystals | [pka]
4.52±0.19(Predicted) | [color ]
white to off-white | [InChIKey]
VDGOFNMYZYBUDT-YCONPBHISA-N | [SMILES]
C1(=O)O[C@@](/C=C/C=C(/C(O)=O)\C)(C)[C@]2([H])CC[C@@]31CC=C(C(OC)=O)CC[C@@]32OC(C)=O |
| Hazard Information | Back Directory | [Description]
Pseudolaric acid B (PAB) is a diterpene acid isolated from the bark of P. kaempferi, a traditional Chinese medicinal plant. It has reported antifungal activities, consistent with its traditional use in the treatment of dermatological fungal infections.1 Moreover, PAB has diverse effects that are relevant to cancer therapy, including inducing apoptosis of cancer cells (IC50 = ~1 μM), preventing angiogenesis, and inhibiting tumor growth in vivo.2,3,4 | [Chemical Properties]
White crystalline powder, soluble in chloroform, acetone and methanol, derived from the bark of the Chinese thorn tree and the golden pine. | [Uses]
Activates PPARα and the phospholipase C (PLC) signalling pathway. Stimulates peroxisomal fatty acyl-CoA oxidase activity. These effects can be blocked by staurosporine . Exhibits significant cytotoxic activities against numerous tumor cell lines. Binds tubulin. Inhibits angiogenesis. Reduces HIF-1α protein levels. Induces apoptosis. Antifungal. | [Definition]
ChEBI: Pseudolaric acid B is a diterpene lactone. | [in vivo]
Pseudolaric Acid B (Oral gavage; 10-20 mg/kg; 3 days) has anti-fertility ability in rats, which may be related to the maternal vascular system[4]. | [IC 50]
HIF-1α | [References]
[1] ERGUANG LI Charles D H Alice M Clark. Antifungal Evaluation of Pseudolaric Acid B, a Major Constituent of Pseudolarix kaempferi[J]. Journal of Natural Products , 1995, 58 1: 57-67. DOI: 10.1021/np50115a007
[2] XIANFENG GONG. Involvement of JNK-initiated p53 accumulation and phosphorylation of p53 in pseudolaric acid B induced cell death[J]. Experimental and Molecular Medicine, 2006, 38 4: 428-434. DOI: 10.1038/emm.2006.50
[3] VINCENT K W WONG. Pseudolaric acid B, a novel microtubule-destabilizing agent that circumvents multidrug resistance phenotype and exhibits antitumor activity in vivo.[J]. Clinical Cancer Research, 2005, 11 16: 6002-6011. DOI: 10.1158/1078-0432.ccr-05-0209
[4] MEI-HONG LI. Pseudolaric acid B inhibits angiogenesis and reduces hypoxia-inducible factor 1alpha by promoting proteasome-mediated degradation.[J]. Clinical Cancer Research, 2004, 10 24: 8266-8274. DOI: 10.1158/1078-0432.ccr-04-0951 |
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