ecdysone

Names

[ Name ]:
ecdysone

[Synonym ]:
MFCD00042683
A-ECDYSONE
[3H]-Ecdysone
Ecdysone
EINECS 222-760-4
(2β,3β,5β,22R)-2,3,14,22,25-pentahydroxycholest-7-en-6-one
Gynostemma Gypenosides
α-Ecdysone

Biological Activity

[Description]:

Ecdysone (α-Ecdysone), a major steroid hormone in insects and herbs, triggers mineralocorticoid receptor (MR) activation and induces cellular apoptosis. Ecdysone plays essential roles in coordinating developmental transitions and homeostatic sleep regulation through its active metabolite 20-hydroxyecdysone (Crustecdysone; 20E; HY-N6979)[1][2].

[Related Catalog]:

Signaling Pathways >> Apoptosis >> Apoptosis

Research Areas >> Metabolic Disease

[Target]

Human Endogenous Metabolite

[In Vitro]

Ecdysone (α-Ecdysone; 100 nM; for 48 hours) causes renal tubular inner medullary collecting duct cells (IMCD) apoptosis[1]. Ecdysone (10, 100 nM; for 48 hours) induces the expression of a-smooth muscle actin (SMA), a standard mesenchymal marker in a dose dependent fashion in inner medullary collecting duct cells (IMCD). Ecdysone elevates the expression of cleaved caspase 3 in a dose dependent fashion[1]. Ecdysone (10, 100 nM; for 12, 24 hours) suppresses cell motility and scratch wound closure to a comparable extent[1]. Ecdysone treatments (100 nM; for 24, 48 hours) induces a branched spindle mesenchymal-like cell shape[1]. Apoptosis Analysis[1] Cell Line: Inner medullary collecting duct cells (IMCD) Concentration: 100 nM Incubation Time: For 48 hours Result: Caused renal tubular cell apoptosis. Western Blot Analysis[1] Cell Line: IMCD cells Concentration: 10, 100 nM Incubation Time: For 48 hours Result: Induced the expression of a-smooth muscle actin (SMA), a standard mesenchymal marker in a dose dependent fashion.

[In Vivo]

Ecdysone (α-Ecdysone; 6 µg/g/day; SC; for 14 days) evidently impaires kidney function marked by a statistically significant increase in BUN levels and amplifies renal expression of α-SMA in male C57BL/6 mice aged 10 weeks. Ecdysone confers an MR dependent nephropathic effect[1].

[References]

[1]. Minglei Lu, et al. Ecdysone Elicits Chronic Renal Impairment via Mineralocorticoid-Like Pathogenic Activities. Cell Physiol Biochem. 2018;49(4):1633-1645.

[2]. Minglei Lu, et al. Activation of Mineralocorticoid Receptor by Ecdysone, an Adaptogenic and Anabolic Ecdysteroid, Promotes Glomerular Injury and Proteinuria Involving Overactive GSK3β Pathway Signaling. Sci Rep. 2018 Aug 15;8(1):12225.

Chemical & Physical Properties

[ Density]:
1.22g/cm3

[ Boiling Point ]:
632ºC at 760mmHg

[ Melting Point ]:
242°C

[ Molecular Formula ]:
C₂₇H₄₄O₆

[ Molecular Weight ]:
464.63500

[ Flash Point ]:
350ºC

[ Exact Mass ]:
464.31400

[ PSA ]:
118.22000

[ LogP ]:
2.73910

[ Index of Refraction ]:
1.582

[ Storage condition ]:
2-8°C

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: FZ8170000

CHEMICAL NAME :: 5-beta-Cholest-7-en-6-one, 2-beta,3-beta,14,22,25-pentahydroxy-, (20S,22R)-

CAS REGISTRY NUMBER :: 3604-87-3

BEILSTEIN REFERENCE NO. :: 2422986

LAST UPDATED :: 199612

DATA ITEMS CITED :: 3

MOLECULAR FORMULA :: C27-H44-O6

MOLECULAR WEIGHT :: 464.71

WISWESSER LINE NOTATION :: L E5 B666 JUTJ A1 E1 FY1&2YQXQ1&1 IQ OQ PQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Amphibian - toad

DOSE/DURATION :: 50 mg/kg/17W-I

TOXIC EFFECTS :: Tumorigenic - equivocal tumorigenic agent by RTECS criteria Liver - tumors Tumorigenic - tumors at site of application

TYPE OF TEST :: Cytogenetic analysis

MUTATION DATA

TEST SYSTEM :: Insect - not otherwise specified

DOSE/DURATION :: 200 ppm

REFERENCE :: EXPEAM Experientia. (Birkhaeuser Verlag, POB 133, CH-4010 Basel, Switzerland) V.1- 1945- Volume(issue)/page/year: 30,279,1974

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Safety Phrases ]:
S22-S24/25

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
FZ8170000

[ HS Code ]:
2937290090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2937290090

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