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Cytochalasin H

Names

[ CAS No. ]:
53760-19-3

[ Name ]:
Cytochalasin H

[Synonym ]:
<11>Cytochalasin
paspalin
19-triene-1-one
cytochalasin U
paspalinpi
Paspalin P1
cytochalasinhfromphomopsissp.
kodocytochalasin-1

Biological Activity

[Description]:

Cytochalasin H is a nature product that could be isolated from fungus Phomopsis sp. Cytochalasin H inhibits cell growth and induces apoptosis. Cytochalasin H has anti-angiogenic activity. Cytochalasin H is an antibiotic and has antibacterial activity[1][2][3].

[Related Catalog]:

Signaling Pathways >> Apoptosis >> Bcl-2 Family
Signaling Pathways >> Apoptosis >> Apoptosis
Research Areas >> Cancer
Research Areas >> Infection
Signaling Pathways >> Apoptosis >> Caspase
Signaling Pathways >> Anti-infection >> Bacterial

[In Vitro]

Cytochalasin H (24-72 h) 抑制 A549 细胞的增殖，IC50 值为 159.5 µM[1]。 Cytochalasin H (0-50 µM; 48 h) 在 A549 细胞中诱导细胞凋亡，使细胞周期停滞在 G2/M 期，并影响细胞凋亡相关蛋白的表达[1]。 Cytochalasin H (1-512 μg/mL) 对 MDR 肠道致病菌、革兰氏阳性菌和金黄色葡萄球菌具有抗菌活性[3]。 Apoptosis Analysis[1] Cell Line: A549 cells Concentration: 0, 6.25, 12.5, 25 and 50 µM Incubation Time: 48 h Result: Induced apoptosis in a dose-dependent manner in the A549 cells. Cell Cycle Analysis[1] Cell Line: A549 cells Concentration: 0, 6.25, 12.5, 25 and 50 µM Incubation Time: 48 h Result: Arrested cell cycle at the G2/M phase and sub-G1 peaks. Western Blot Analysis[1] Cell Line: A549 cells Concentration: 0, 6.25, 12.5, 25 and 50 µM Incubation Time: 48 h Result: Increased the protein expression levels of Bax, P53 and cleaved caspase-3 and decreased the protein expression levels of Bcl-xL, Bcl-2 and full-length caspase-3.

[In Vivo]

Cytochalasin H (2.5 mg/kg; i.p.) 可以延迟 Balb/cnu/nu 小鼠中 A549 异种移植肿瘤的生长[2]。 Animal Model: male Balb/cnu/nu mice with A549 xenograft[2] Dosage: 2.5 mg/kg Administration: intraperitoneal injection; 3 injections/week,for 80 days Result: Attenuated tumor growth in vivo.

[References]

[1]. Ma Y, et, al. Cytochalasin H isolated from mangrove‑derived endophytic fungus induces apoptosis and inhibits migration in lung cancer cells. Oncol Rep. 2018 Jun;39(6):2899-2905.  

[2]. Yi JM, et, al. In Vivo Anti-tumor Effects of the Ethanol Extract of Gleditsia sinensis Thorns and Its Active Constituent, Cytochalasin H. Biol Pharm Bull. 2015;38(6):909-12.  

[3]. Jouda JB, et, al. Antibacterial and cytotoxic cytochalasins from the endophytic fungus Phomopsis sp. harbored in Garcinia kola (Heckel) nut. BMC Complement Altern Med. 2016 Nov 14;16(1):462.  

Chemical & Physical Properties

[ Density]:
1.19g/cm3

[ Boiling Point ]:
676.5ºC at 760mmHg

[ Melting Point ]:
252-258ºC

[ Molecular Formula ]:
C30H39NO5

[ Molecular Weight ]:
493.63

[ Flash Point ]:
362.9ºC

[ Exact Mass ]:
493.28300

[ PSA ]:
95.86000

[ LogP ]:
4.06690

[ Index of Refraction ]:
1.591

[ Storage condition ]:
2-8°C

[ Water Solubility ]:
chloroform: 10 mg/mL, clear, colorless

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
HA5306000
CHEMICAL NAME :
(11)Cytochalasa-6(12),13,19-trien-1-one, 21-(acetyloxy)-7,18-dihydroxy-16,18-dimethyl-10- phenyl-, (7S,13E,16S,18S,19E,21R)-
CAS REGISTRY NUMBER :
53760-19-3
LAST UPDATED :
199107
DATA ITEMS CITED :
5
MOLECULAR FORMULA :
C30-H39-N-O5
MOLECULAR WEIGHT :
493.70
WISWESSER LINE NOTATION :
T56-11- 1A R AXVM GY JU PUTJ D1R& F1 GU1 HQ M1 OQ O1 ROV1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
2 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Unreported
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
2 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Bird - chicken
DOSE/DURATION :
12500 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Mammal - species unspecified
DOSE/DURATION :
2341 ug/kg
TOXIC EFFECTS :
Sense Organs and Special Senses (Eye) - ptosis Behavioral - changes in motor activity (specific assay) Behavioral - ataxia

MUTATION DATA

TYPE OF TEST :
Cytogenetic analysis
TEST SYSTEM :
Human Lymphocyte
DOSE/DURATION :
500 ug/L
REFERENCE :
IJEBA6 Indian Journal of Experimental Biology. (Publications & Information Directorate, CSIR, Hillside Rd., New Delhi 110 012, India) V.1- 1963- Volume(issue)/page/year: 16,430,1978

Safety Information

[ Symbol ]:

GHS06, GHS08

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H300-H310-H330-H361

[ Precautionary Statements ]:
P260-P264-P280-P284-P302 + P350-P310

[ Personal Protective Equipment ]:
Eyeshields;Faceshields;full-face particle respirator type N100 (US);Gloves;respirator cartridge type N100 (US);type P1 (EN143) respirator filter;type P3 (EN 143) respirator cartridges

[ Hazard Codes ]:
T+

[ Risk Phrases ]:
26/27/28-63

[ Safety Phrases ]:
28-36/37-45

[ RIDADR ]:
UN 3462 6.1/PG 2

[ WGK Germany ]:
3

[ RTECS ]:
HA5306000

[ Packaging Group ]:
I

[ Hazard Class ]:
6.1(a)

Synthetic Route

Click to get detail synthetic route

Articles

A new fungal isolate from Paspalum scrobiculatum, Linn. with new biologically active metabolites.

Acta Microbiol. Acad. Sci. Hung. 22 , 253, (1975)

A new fungal isolate from the host plant Paspalum scrobiculatum Linn., is reported. It is characterized and designated as a separate species Phomopsis paspali (n. sp.), not only for the different morp...

Effects of cytochalasin H on chick embryo explants cultured in vitro.

Toxicology 33(3-4) , 323-30, (1984)

Effects of the mould metabolite, cytochalasin H (CH) were studied in chick embryos explanted at stages 4, 5 and 8 and cultured in vitro. Morphological and histological observations revealed that the m...

Inhibitory effect of cytochalasin H on cell reaggregation of the fresh water sponge, Ephydatia meyeni Carter.

Exp. Cell Biol. 50(3) , 155-61, (1982)

Cytochalasin H (CH) has been shown to inhibit the reaggregation of dissociated cells of a fresh water sponge. The effect is dose-dependent and reversible. Even after 24 h of CH treatment, the cells sh...


More Articles

Related Compounds