Pseudolaric acid B

Names

[ Name ]:
Pseudolaric acid B

[Synonym ]:
(2E,4E)-5-[(1R,7S,8R,9R)-4,7-Bis(methoxycarbonyl)-9-methyl-11-oxo-10-oxatricyclo[6.3.2.0]tridec-3-en-9-yl]-2-methylpenta-2,4-dienoic acid
(2E,4E)-5-[(1S,7S,8S,9R)-7-Acetoxy-4-(methoxycarbonyl)-9-methyl-11-oxo-10-oxatricyclo[6.3.2.0]tridec-3-en-9-yl]-2-methyl-2,4-pentadienoic acid
1H-4,9a-Ethanocyclohepta[c]pyran-7-carboxylic acid, 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,9aS)-
(2E,4E)-5-[(1R,7S,8R,9R)-4,7-Bis(methoxycarbonyl)-9-methyl-11-oxo-10-oxatricyclo[6.3.2.0]tridec-3-en-9-yl]-2-methyl-2,4-pentadienoic acid
1H-4,9a-Ethanocyclohepta[c]pyran-4a,7(5H)-dicarboxylic acid, 3-[(1E,3E)-4-carboxy-1,3-pentadien-1-yl]-3,4,6,9-tetrahydro-3-methyl-1-oxo-, 4a,7-dimethyl ester, (3R,4R,4aS,9aR)-
PLAB
(2E,4E)-5-[(1S,7S,8S,9R)-7-Acetoxy-4-(methoxycarbonyl)-9-methyl-11-oxo-10-oxatricyclo[6.3.2.0]tridec-3-en-9-yl]-2-methylpenta-2,4-dienoic acid
PseudolaricAcidB
Pseudolarix acid B

Biological Activity

[Description]:

Pseudolaric Acid B is a diterpene isolated from the root of Pseudolarix kaempferi Gorden (pinaceae), has anti-cancer, antifungal, and antifertile activities, and shows immunosuppressive activity on T lymphocytes[1][2][3]. Pseudolaric Acid B inhibits hepatitis B virus (HBV) secretion through apoptosis and cell cycle arrest. Pseudolaric Acid B induces autophagy[4][5].

[Related Catalog]:

Signaling Pathways >> Apoptosis >> Apoptosis

Research Areas >> Cancer

Research Areas >> Infection

Signaling Pathways >> Anti-infection >> HBV

Signaling Pathways >> Anti-infection >> Fungal

Signaling Pathways >> Autophagy >> Autophagy

Research Areas >> Inflammation/Immunology

[References]

[1]. Zhou BN, et al. Some progress on the chemistry of natural bioactive terpenoids from Chinese medicinal plants. Mem Inst Oswaldo Cruz. 1991;86 Suppl 2:219-26.

[2]. 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.

[3]. Wei N, et al. The immunosuppressive activity of pseudolaric acid B on T lymphocytes in vitro. Phytother Res. 2013 Jul;27(7):980-5.

[4]. Yu J, et al. Pseudolaric acid B inhibits the secretion of hepatitis B virus. Oncol Rep. 2017 Jan;37(1):519-525.

[5]. Yu J, et al. Pseudolaric acid B activates autophagy in MCF-7 human breast cancer cells to prevent cell death. Oncol Lett. 2016 Mar;11(3):1731-1737.

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
613.8±55.0 °C at 760 mmHg

[ Melting Point ]:
166°C

[ Molecular Formula ]:
C₂₃H₂₈O₈

[ Molecular Weight ]:
432.464

[ Flash Point ]:
208.8±25.0 °C

[ Exact Mass ]:
432.178406

[ PSA ]:
116.20000

[ LogP ]:
2.78

[ Appearance of Characters ]:
white to off-white

[ Vapour Pressure ]:
0.0±3.8 mmHg at 25°C

[ Index of Refraction ]:
1.565

[ Storage condition ]:
2-8°C

[ Water Solubility ]:
methanol: soluble1mg/mL, clear, colorless

MSDS

Click to get detail MSDS

Safety Information

[ Symbol ]:

GHS06, GHS08

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H301-H361

[ Precautionary Statements ]:
P281-P301 + P310

[ Hazard Codes ]:
T

[ Risk Phrases ]:
25-62

[ Safety Phrases ]:
36/37-45-24/25

[ RIDADR ]:
UN 2811 6.1 / PGIII

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

Newly discovered angiogenesis inhibitors and their mechanisms of action.

Acta Pharmacol. Sin. 33(9) , 1103-11, (2012)

In the past decade, the success of angiogenesis inhibitors in clinical contexts has established the antiangiogenic strategy as an important part of cancer therapy. During that time period, we have dis...

Bcl-2 family proteins were involved in pseudolaric acid B-induced autophagy in murine fibrosarcoma L929 cells.

J. Pharmacol. Sci. 107(3) , 295-302, (2008)

Pseudolaric acid B (PAB) exerted cytostatic activity on murine fibrosarcoma L929 cells. The cytostatic mechanism of PAB on L929 cells was investigated in this paper. At 36 h, after 80 microM PAB treat...

In vitro synergy of pseudolaric acid B and fluconazole against clinical isolates of Candida albicans.

Mycoses 54(5) , e400-6, (2011)

Candida albicans is the most common fungal pathogen in humans. The emergence of resistance to azole antifungals has raised the issue of using such antifungals in combination to optimise therapeutic ou...