Ingenol
belongs to a class of medicinally vital compounds known as terpenes, which are
commonly found in antiseptics, expectorants, gastrointestinal drugs, pain
relievers and antioxidants.1 Ingenol can be further synthesized to ingenol
mutbutate, a gel used to treat actinic keratosis. Actinic keratosis is
described as flat, scaly growths caused by too much sun exposure.2 This
skin condition affects 250 million people worldwide and is a precursor to cancer.3
The treatment is achieved through cell death of the mutated skin cells
through the activation of protein kinase A.4
Ingenol is synthesized from a type of weedy plant known as
spurges. Due to low isomerization, extraction of the compound from the plant
requires 800kg for 1g of the ingenol product which is not an effective method
from commercial production.4 In
2013, Jorgensen et. al. published a
study that gave a more efficient and effective stereocontrolled method. The new
synthesis not only produces higher yields, it also cuts the 37-steps into a
14-step two phase route. It is more cost
effective and will help limit the production with the possibility of consumer
fees. The authors stated that a 1.2% yield can be obtained which is greater
than the previous method.5 This synthesis may open new possibilities
to finding natural-drug products that aid in diseases with business and
consumer spending in mind.
By Christopher Cheng Sources:
1.
Wisegeek.com.http://www.wisegeek.com/what-are-the-medical-uses-of-terpenes.htm
(accessed Apr 6, 2014)
2.
National Library of Medicine. Medline Plus. http://www.nlm.nih.gov/medlineplus/druginfo/meds/a613008.html
(accessed Apr 6, 2014)
3.
Drahl, C. Chemists Find More Efficient Total
Synthesis Route To Ingenol.C&EN.[Online]
2013, 91 , 16.
http://cen.acs.org/articles/91/i51/Chemists-Find-Efficient-Total-Synthesis.html
(accessed Apr 6, 2014)
5.
Jorgensen, L.; McKerrall, S. J.; Kuttruff, C.
A.; Ungeheuer, F.; Felding, J.; Baran, P.S. 14-Step Synthesis of (+)-Ingenol
from (+)-3-Carene. Science. 2013, 341, 878-882
Peplus or Petty
spurge, the plant used for ingenol mutbuate
Source: C&EN
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