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Cyclovirobuxin D

CAS No.860-79-7
Chemical Name:Cyclovirobuxin D
CBNumber:CB3663206
Molecular Formula:C26H46N2O
Formula Weight:402.66
MOL File:860-79-7.mol

Cyclovirobuxin D Property

Melting point 220-221 °C (decomp)(Solv: acetone (67-64-1))
Boiling point 524.75°C (rough estimate)
Density 0.9815 (rough estimate)
refractive index 1.5300 (estimate)
storage temp. Store at -20°C
solubility Soluble to 20 mg/mL (49.66 mM) in Ethanol
form cryst.
pka 15.12±0.70(Predicted)
color White
LogP 4.635 (est)
CAS DataBase Reference 860-79-7(CAS DataBase Reference)
FDA UNII 51GY352868
UNSPSC Code 51111800
NACRES NA.77

Safety

Safety Statements :24/25
HS Code :29420000
Toxicity :LD50 oral in mouse: 293mg/kg

NFPA 704:

	0
2		0

Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal wordDanger
Hazard statements H301
Precautionary statements P264-P270-P301+P310-P321-P330-P405-P501

Cyclovirobuxin D Chemical Properties,Usage,Production

Description A Buxus alkaloid of the steroidal class, this base has been found in the strong base fraction of the alkaloidal extract from Buxus microphylla Sieb. et Zucco var. suffruticosa and B. microphylla Sieb. et Zucco var. suffruticosa Makino forma major. It is dextrorotatory having a specific rotation of [α]²³_D + 98° (c 4.40,CHC13)and yields a series of salts and derivatives including the dihydrobromide, m.p. 288-292°C (dec.); dihydriodide, m.p. 276-8°C (dec.); diperchlorate, m.p. 244- 5°C (dec.); dioxalate as an amorphous powder, m.p. 264-7°C (dec.): the N:Ndiacetyl derivative, m.p. 278-281°C (dec.) with [α]²⁴_D + 10° (c 1.94, CHC13) and the O,N,N-triacetyl derivative, m.p. 246-8°C with [α]²⁴_D - 12° (c 2.40, CHCI3)·
The structure and stereochemistry of the base have been elucidated from chemical analysis, spectroscopic evidence and comparison with other alkaloids of this class.
Physical properties Appearance: colorless needle crystals. Solubility: sparingly soluble in acetone; slightly soluble in water; freely soluble in chloroform; soluble in methanol and ethanol. Melting point: 219–222?°C.
History Cyclovirobuxine in the treatment of coronary heart disease began in 1969 . The medical teams of Chinese People’s Liberation Army No.86489 explored a treatment of coronary heart disease named Guo, prescription composed of Buxus microphylla (huangyangmu), Salvia miltiorrhiza Bge. (danshen), Ligustici Chuanxiong Rhizoma (chuanxiong), Belamcandae Rhizoma (shegan), Radix Aristolochiae (qingmuxiang) and Asari Radix et Rhizoma (xixin).
In 1978, the Anhui Huangyang Research Cooperation Group carried out systematic experiments to determine the chemical structure and the separation and identification method of cyclovirobuxine by melting point determination, thin-layer chromatography, infrared spectroscopy, mass spectrometry and NMR . Three studies containing more than 300 cases of coronary heart disease patients treated with cyclovirobuxine showed that this drug can significantly improve angina, chest tightness, arrhythmia and other symptoms caused by coronary heart disease.
Uses Cyclovirobuxine D is a potential preventative agent of cardiac dysfunction.
Indications It is mainly used for the treatment of cardiovascular and cerebrovascular diseases in China, such as the coronary heart disease, arrhythmia, cerebral arteriosclerosis, cerebral embolism and brain vascular accident which are caused by insufficiency of cerebral blood supply.
Pharmacology Pharmacological studies have shown that cyclovirobuxine has a positive inotropic effect on the heart that may predominantly be due to the inhibition of cardiomyocyte membrane Na+-K+-ATPase activity and promotion of myocardial extracellular Ca2+ influx and cardiomyocyte Ca2+ release. Moreover, cyclovirobuxine could markedly reduce myocardial oxygen consumption and increase coronary blood flow, suggesting that it has definite anti-myocardial ischemia effect. Experiments also showed that cyclovirobuxine could induce marked inhibition of myocardial ischemia infarction and enhancement of anoxia tolerance in mice .
Besides, cyclovirobuxine could have protective effect on the acute experimental cerebral ischemia in mice by bilateral ligation of common carotid arteries, prolong the life span of mice, increase blood flow and decrease the formation of thrombus during cerebral ischemia . In vitro experiments have also shown that cyclovirobuxine has neuroprotective effects on neurons and restrains PC12 cells from excitatory amino acid-induced injury .
Clinical Use After decades of clinical observation, cyclovirobuxine has the therapeutic role of anti-myocardial ischemia and antiarrhythmia and protects against acute cerebral ischemia. In addition, cyclovirobuxine can cross the blood-brain barrier and improve brain microcirculation and oxygen supply to treat cerebral arteriosclerosis insufficiency.
References Nakano, Terao, Tetrahedron Lett., 1035, 1045, (1964)
Brown, Kupchan, J. Amer. Chem. Soc., 86, 4414, 4424 (1964)
Nakano, Terao,J. Chem. Soc., 4512, 4537 (1965)
Nakano, Hasegawa, ibid, 6688 (1965)