Cytochalasin H

Names

[ 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...

Related Compounds

The content on this webpage is sourced from various professional data sources. If you have any questions or concerns regarding the content, please feel free to contact service1@chemsrc.com.