Chinese Star Anise

Description

"a spice that closely resembles anise in flavor, obtained from the star-shaped pericarp of Illicium verum, a small native evergreen tree of southwest China. The star shaped fruits are harvested just before ripening. It is widely used in Chinese cuisine, in Indian cuisine where it is a major component of garam masala, and in Malay–Indonesian cuisine. It is widely grown for commercial use in China, India, and most other countries in Asia. Star anise is an ingredient of the traditional five-spice powder of Chinese cooking. It is also a major ingredient in the making of phở, a Vietnamese noodle soup. In northern India, where it is used as an ingredient of Masala Chai, it is also known as badian khatai (ਬਾਦੀਆਂ ਖਟਾਈ in Punjabi), which leads to its European name badiane. It is used as a spice in preparation of Biryani in Andhra Pradesh, a state of southern India. In Marathi, it is called BarDan (बारदान) which literally means 'spice with twelve (बारा) seeds (दाणे)'."^[3]

Research

"Merrilactone A was found to exhibit a significant neurotrophic activity, such as greatly promoting neurite outgrowth in the primary cultures of fetal rat cortical neurons at concentrations from 10 to 0.1 μmol/L. It was also found that this compound had a property of neuroprotection at same concentration."^[1]

"Merrilactone A is one of the four sesquiterpenes that were newly discovered from the fruit of Illicium merrillianum in 2000[1]. Members of the genus Illicium include Chinese star anise, widely used as a spice for flavouring food and beverages, and also poisonous plants such as Japanese star anise[2]. Chemical studies of Illicium have developed rapidly over the last 20 years, and merrilactone A has been shown to have neurotrophic activity in fetal rat cortical neuron cultures.[3] This has led researchers to believe that Merrilactone A may hold therapeutic potential in the treatment of neuro-degenerative diseases such as Alzheimer’s and Parkinson’s disease.[4]"^[1]

"(-)-Merrilactone A [(-)-1], isolated from Illicium merrillianum in 2000, possesses neurite outgrowth activity in cultures of fetal rat cortical neurons, and, therefore, is expected to show therapeutic potential for the treatment of neurodegeneration associated with Alzheimer's and Parkinson's diseases. Apart from its biological aspects, the caged pentacyclic skeleton of 1 poses interesting synthetic challenges. Here, we report the total synthesis of the unnatural enantiomer of merrilactone A [(+)-1], based on a novel desymmetrization strategy. The chiral lithium amide 16g promoted an enantioselective transannular aldol reaction of eight-membered meso-diketone 3d, establishing the absolute stereochemistries of four chiral centers of the cis-bicyclo[3.3.0]octane framework of 1 in a single step. The obtained compound 4d served as a platform for the subsequent functional group manipulations necessary for the construction of (+)-1. Surprisingly, both the natural and unnatural enantiomers of synthetic merrilactone A equally promoted neurite outgrowth in primary neuronal cultures."^[2]

"Star anise has been used in a tea as a remedy for rheumatism, and the seeds are sometimes chewed after meals to aid digestion. As a warm and moving herb, star anise is used to assist in relieving cold-stagnation in the middle jiao, according to Traditional Chinese medicine.

Shikimic acid, a primary feedstock used to create the anti-flu drug Tamiflu, is produced by most autotrophic organisms, but star anise is the industrial source. In 2005, there was a temporary shortage of star anise due to its use in making Tamiflu. Late in that year, a way was found of making shikimic acid artificially. Roche now derives some of the raw material it needs from fermenting E. coli bacteria. The 2009 swine flu outbreak led to another series of shortages as stocks of Tamiflu were built up around the world, sending prices soaring."^[3]

References
^[1] Wikipedia: Merrilactone A

^[2] Total synthesis and bioactivity of an unnatural enantiomer of merrilactone a: development of an enantioselective desymmetrization strategy.

^[3] Wikipedia: Star Anise