3-oxododecanal

Description

Houttuynin is one of the main ingredients in the volatile oil derived from jicai 蕺菜 (Houttuynia cordata Thunb), which belongs to the family Saururaceae, and is also named as yuxingcao 鱼腥草 because of its fishlike smells when grated. H. cordata has been widely used in traditional Chinese medicines and is recorded in Grand Compendium of Materia Medica. H. cordata is used in the treatment of skin diseases, hemorrhoids, and certain diseases of women, relieving fever, resolving toxicity, reducing swelling, draining pus, and promoting urination. H. cordata is available in China and India.

Physical properties

Appearance: aromatic oil with a volatile odor, yellow oily liquid. Solubility: soluble in methanol, ethanol, ether, and petroleum ether; insoluble in water; easily polymerizable

History

In 1952, houttuynin was firstly found in the volatile oil extracted from Houttuynia by steam distillation. The chemical structure was named decanoyl acetaldehyde. However, houttuynin is easy to polymerize and became invalid. In 1971, Chinese scholars synthesized sodium houttuyfonate (houttuyninum, HOU), which is an addition compound of sodium bisulfite and houttuynin. HOU is more stable and maintains the original antibacterial activity. HOU possessed broad-spectrum antibacterial and anti-inflammatory activities, diuretic swelling, rapid antifebrile, antivirus and antitumor proliferation, increased immunity, and other pharmacological effects.
Neo-houttuyninum as the other derivative of houttuynin possesses more obvious inhibitory effect on a variety of bacteria and is used for the treatment of infectious diseases.
Since houttuynin was found 60? years ago, Houttuynia injection preparations have been developed, such as Houttuynia injection, neo-houttuyfonate sodium chloride injection, neo-houttuyfonate injection, etc. These drugs are commonly used in clinical antimicrobial drugs. However, these injection preparations were withdrawed for serious adverse reactions in 2006, and continued to be used in clinic since 2008.

Indications

Houttuynin is recorded in the Pharmacopoeia of the People’s Republic of China (1995).
Houttuynin preparations include Houttuynia injection, sodium neo-houttuyfonate injection, sodium neo-houttuyfonate and sodium chloride injection, sodium houttuyfonate tablets, and tabellae natrii houttuyfonatis. These preparations are mainly used to treat chronic bronchitis, pediatric pneumonia, and other respiratory inflammatory diseases; cervicitis, annex inflammation, pelvic inflammatory disease, chronic cervicitis, and other gynecological inflammation; and also other skin diseases such as psoriasis. Houttuynin preparations also include sodium houttuyfonate suppository and compound Houttuynia tablets. The former is used to treat cervical erosion, and the latter is used to treat acute pharyngitis and acute tonsillitis.

Definition

ChEBI: Decanoyl acetaldehyde is a fatty aldehyde.

Pharmacology

Houttuynin is reported as a major antibacterial constituent in the volatile oil of H. cordata. Houttuynin exhibits significant inhibitory effects on Staphylococcus aureus, pneumococcus, and other bacteria as well as certain fungi and also has certain antiviral and anti-inflammatory effects. It is reported that houttuynin could reduce cardiomyocyte cross-section area and collagen deposition. Houttuynin attenuates ventricular remodeling in coronary artery ligation rats by restricting the excessive activation of rennin-angiotensin-aldosterone system (RAAS) and peroxidation . Houttuynin also shows hypolipidemic and anti-atherosclerotic effects.
Houttuyninum has a significant inhibitory effect on Candida albicans, Cryptococcus neoformans, and Brochothrix thermosphacta. Houttuyninum has anti-inflammatory and analgesic effects, and the inhibition of inflammation is related to NF-κB and MCP-1. In recent years, studies have shown that intragastric administration of houttuyninum can increase apoptosis of the rheumatoid arthritis synovial cell and reduce joint index and inflammation factor levels in rheumatoid arthritis rat model

Clinical Use

Houttuynin and its derivatives are used to treat milk moths, lung carbuncle, leaching disease, carbuncle swollen sore, and other infectious diseases. Currently it is used mainly for the treatment of gynecological diseases and respiratory system, especially upper respiratory tract infection. However, there are side effects associated with the use of these injection preparations, mainly involving the cardiovascular system, gastrointestinal system, blood system, and skin or kidney.

Raw materials

Preparation Products