Castanospermine
Castanospermine is a natural indolizidine alkaloid found in the seeds of the Moreton Bay Chestnut tree (Castanospermum australe). It is a potent inhibitor of some glucosidase enzymes, particularly alpha-glucosidase and beta-glucosidase. This property has led to its investigation for use in the treatment of certain viral diseases and cancers.
Chemical Structure and Properties[edit | edit source]
Castanospermine has a bicyclic structure, with a pyrrolizidine ring fused to a pyranose ring. It is a chiral compound, with four stereocenters, giving rise to 16 possible stereoisomers. However, only one of these, the naturally occurring isomer, has significant biological activity.
The compound is soluble in water and polar organic solvents, but insoluble in nonpolar solvents. It is stable under normal conditions, but can be hydrolyzed under acidic or basic conditions.
Biological Activity[edit | edit source]
Castanospermine inhibits the action of glucosidase enzymes by binding to their active sites, preventing them from breaking down complex sugars into simple sugars. This can interfere with the life cycle of certain viruses, which rely on these enzymes to process the sugars in their glycoprotein coats.
In addition to its antiviral activity, castanospermine has also been found to have anticancer properties. It appears to inhibit the growth of cancer cells by interfering with their metabolism, although the exact mechanism is not yet fully understood.
Medical Applications[edit | edit source]
Due to its biological activity, castanospermine has been investigated for use in the treatment of a number of diseases. These include HIV/AIDS, where it can inhibit the virus's ability to infect new cells, and certain types of cancer, where it can slow the growth of the cancer cells.
However, while laboratory studies have shown promise, clinical trials have so far been less successful. The compound's low bioavailability and high toxicity at therapeutic doses have limited its usefulness. Research is ongoing to develop derivatives of castanospermine with improved properties.
See Also[edit | edit source]
 | This medical article is a stub. You can help WikiMD by expanding it. |
Search WikiMD
Ad.Tired of being Overweight? Try W8MD's physician weight loss program.
Semaglutide (Ozempic / Wegovy and Tirzepatide (Mounjaro / Zepbound) available.
Advertise on WikiMD
|
WikiMD's Wellness Encyclopedia |
| Let Food Be Thy Medicine Medicine Thy Food - Hippocrates |
Translate this page: - East Asian
中文,
日本,
한국어,
South Asian
हिन्दी,
தமிழ்,
తెలుగు,
Urdu,
ಕನ್ನಡ,
Southeast Asian
Indonesian,
Vietnamese,
Thai,
မြန်မာဘာသာ,
বাংলা
European
español,
Deutsch,
français,
Greek,
português do Brasil,
polski,
română,
русский,
Nederlands,
norsk,
svenska,
suomi,
Italian
Middle Eastern & African
عربى,
Turkish,
Persian,
Hebrew,
Afrikaans,
isiZulu,
Kiswahili,
Other
Bulgarian,
Hungarian,
Czech,
Swedish,
മലയാളം,
मराठी,
ਪੰਜਾਬੀ,
ગુજરાતી,
Portuguese,
Ukrainian
Medical Disclaimer: WikiMD is not a substitute for professional medical advice. The information on WikiMD is provided as an information resource only, may be incorrect, outdated or misleading, and is not to be used or relied on for any diagnostic or treatment purposes. Please consult your health care provider before making any healthcare decisions or for guidance about a specific medical condition. WikiMD expressly disclaims responsibility, and shall have no liability, for any damages, loss, injury, or liability whatsoever suffered as a result of your reliance on the information contained in this site. By visiting this site you agree to the foregoing terms and conditions, which may from time to time be changed or supplemented by WikiMD. If you do not agree to the foregoing terms and conditions, you should not enter or use this site. See full disclaimer.
Credits:Most images are courtesy of Wikimedia commons, and templates Wikipedia, licensed under CC BY SA or similar.
Contributors: Prab R. Tumpati, MD
