Esculentoside A

Names

[ Name ]:
Esculentoside A

[Synonym ]:
Esculentoside
4-O-(2,23,28-Trihydroxy-29-methoxy-28,29-dioxoolean-12-en-3-yl)pentopyranosyl hexopyranoside
EsculentosideA
(2β,3β)-3-{[4-O-(β-D-Glucopyranosyl)-β-D-xylopyranosyl]oxy}-2,23-dihydroxy-30-methoxy-30-oxoolean-12-en-29-oic acid
Phytolacaponin E
Hexopyranoside, 4-O-(2,23,28-trihydroxy-29-methoxy-28,29-dioxoolean-12-en-3-yl)pentopyranosyl
Olean-12-ene-29,30-dioic acid, 3-[(4-O-β-D-glucopyranosyl-β-D-xylopyranosyl)oxy]-2,23-dihydroxy-, 30-methyl ester, (2β,3β)-

Biological Activity

[Description]:

Esculentoside A (EsA), a kind of triterpene saponin isolated from roots of Phytolacca esculenta[1].Esculentoside A (EsA) possesses anti-inflammatory activity in acute and chronic experimental models[2], has selective inhibitory activity towards cyclooxygenase-2 (COX-2)[1].Esculentoside A (EsA) suppresses inflammatory responses in LPS-induced acute lung injury (ALI) through inhibition of the nuclear factor kappa B (NF-ΚB) and mitogen activated protein kinase (MAPK) signaling pathways[3].

[Related Catalog]:

Research Areas >> Inflammation/Immunology

Signaling Pathways >> Immunology/Inflammation >> COX

[In Vitro]

Esculentoside A (0-10 μM; 24 hours) reduced the release of TNF concentration in primed macrophages [4].

[In Vivo]

Esculentoside A (EsA) (intraperitoneal injection; 20 mg/kg; once a day; 4 weeks) plays significant roles in the treatment of BXSB mice through modulation of inflammatory cytokines, inhibition of renal cell proliferation and induction of apoptosis [2]. Esculentoside A (EsA) (injected intraperitoneally; 5, 10 and 20 mg/kg; once a day; 7 days) dose-dependently decreases the TNF, IL-1 and IL-6 levels in the sera of mice following LPS challenge[4]. Animal Model: BXSB mice[2] Dosage: 20 mg/kg Administration: Intraperitoneal injection; 20 mg/kg; once a day; 4 weeks Result: Alleviated the renal damage of LN.

[References]

[1]. Wu F, et al. Synthesis, in vitro inhibitory activity towards COX-2 and haemolytic activity of derivatives of esculentoside A. Bioorg Med Chem Lett. 2007 Dec 1;17(23):6430-3. Epub 2007 Oct 5.

[2]. Ma H, et al. The effect of esculentoside A on lupus nephritis-prone BXSB mice. Arch Med Sci. 2013 Apr 20;9(2):354-60.

[3]. Zhong WT, et al. Protective effect of esculentoside A on lipopolysaccharide-induced acute lung injury in mice. J Surg Res. 2013 Nov;185(1):364-72.

[4]. Ju DW, et al. Esculentoside A inhibits tumor necrosis factor, interleukin-1, and interleukin-6 production induced by lipopolysaccharide in mice. Pharmacology. 1998 Apr;56(4):187-95

Chemical & Physical Properties

[ Density]:
1.4±0.1 g/cm3

[ Boiling Point ]:
935.8±65.0 °C at 760 mmHg

[ Molecular Formula ]:
C₄₂H₆₆O₁₆

[ Molecular Weight ]:
826.964

[ Flash Point ]:
275.1±27.8 °C

[ Exact Mass ]:
826.435059

[ PSA ]:
262.36000

[ LogP ]:
3.01

[ Vapour Pressure ]:
0.0±0.6 mmHg at 25°C

[ Index of Refraction ]:
1.620

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: RK0177530

CHEMICAL NAME :: Olean-12-ene-28,29-dioic acid, 2,23-dihydroxy-3-((4-O-beta-D-glucopyranosyl-beta-D- xylopyranosyl)oxy)-, 29-methyl ester, (2-beta,3-beta,4-alpha,20-beta)-

CAS REGISTRY NUMBER :: 65497-07-6

LAST UPDATED :: 198706

DATA ITEMS CITED :: 4

MOLECULAR FORMULA :: C42-H66-O16

MOLECULAR WEIGHT :: 827.08

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

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

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 42300 ug/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Lungs, Thorax, or Respiration - respiratory depression Nutritional and Gross Metabolic - weight loss or decreased weight gain

REFERENCE :: SYHJAM Saengyak Hakhoechi. Journal of the Society of Pharmacognosy. (Hanguk Saengyak Hakhoe, c/o Natural Products Institute, Seoul National Univ., 28 Yunkeon-Dong, Chong-ro-ku, Seoul 110, Korea) 1970- Volume(issue)/page/year: 10,73,1979

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1200 mg/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Skin and Appendages - hair Nutritional and Gross Metabolic - body temperature decrease

REFERENCE :: SHZAAY Shoyakugaku Zasshi. Journal of Pharmacognosy. (Nippon Shoyaku Gakkai, c/o Nippon Gakkai Jimu Senta, 2-4-16 Yayoi, Bunkyo-ku, Tokyo 113, Japan) V.6- 1952- Volume(issue)/page/year: 33,111,1979

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 486 mg/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Skin and Appendages - hair Nutritional and Gross Metabolic - body temperature decrease

REFERENCE :: SHZAAY Shoyakugaku Zasshi. Journal of Pharmacognosy. (Nippon Shoyaku Gakkai, c/o Nippon Gakkai Jimu Senta, 2-4-16 Yayoi, Bunkyo-ku, Tokyo 113, Japan) V.6- 1952- Volume(issue)/page/year: 33,111,1979

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

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 23600 ug/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Lungs, Thorax, or Respiration - respiratory depression Nutritional and Gross Metabolic - weight loss or decreased weight gain

REFERENCE :: SYHJAM Saengyak Hakhoechi. Journal of the Society of Pharmacognosy. (Hanguk Saengyak Hakhoe, c/o Natural Products Institute, Seoul National Univ., 28 Yunkeon-Dong, Chong-ro-ku, Seoul 110, Korea) 1970- Volume(issue)/page/year: 10,73,1979

Safety Information

[ Safety Phrases ]:
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