Investigation of fluorescent molecules from Naematoloma Fasciculare

Background and Significance

Fluorescent molecules are interesting because they have a wide variety of applications in the field of biotechnology. Many of the fluorescent tags used in the chemical industry are based on molecules which are derived from a natural source. Natural fluorescent molecules, such as these, are important because they tend to be biodegradable and environmentally friendly. Because of this, my research group is interested in locating and isolating fluorescent molecules from natural sources. In particular, the mushroom Naematoloma Fasciculare contains a molecule which is highly fluorescent. Naematoloma Fasciculare is a common mushroom which grows in most hardwood forests in Northern California. This mushroom likes to grow out of rotting wood, or stumps and upturned roots. Initial work in our lab has shown that Naematoloma Fasciculare produces a molecule with pronounced light green fluorescence when exposed to UV light, as seen in Figure 1. Although much work has been preformed on the natural products produced by this mushroom, the fluorescent nature of these molecules has yet to be investigated.

Figure 1 The pale green fluorescence of a molecule from Naematoloma Fasciculare.

Specific aims

The specific aim of our group is to isolate and characterize the fluorescent molecule from Naematoloma Fasciculare. Understanding these molecules could lead to applications in the fluorescent labeling industry. Also, we are interested in understanding the structural characteristics which causes these molecules to fluoresce. This would be accomplished through the use of computational chemistry. By building computer models of these molecules, their structural features could be virtually modified to investigate possible improvements in their fluorescence. Once these structural aspects are understood, modifications can be preformed on the basic structure using common organic reactions. If the results are promising, we will then test the molecules capabilities as a fluorescent tag in an actual biomedical imaging situation.

Experimental Design and Methods

The mushroom Naematoloma Fasciculare can be found in the wild throughout Northern California. Initial samples of mushroom will be collected on field trips to local forests. To limit the impact on the environment, the bulk of the mushroom used for this project will be grown in the lab. It has been shown that the fungus can be grown in a peptone/sucrose mixture at room temperature. [1, 2] After this, any organic molecules produced can be isolated through extraction.

References

[1] Suzuki, K; Fujimoto, H; Yamazaki, M. The Toxic Principles of Naematoloma Fasciculare. Chem. Pharm. Bull. 1983, 31, 2176-2178.

[2] Shiono, Y; Matsuzaka, R.; Wakamatsu, H.; Muneta, K.; Murayama, T.; Ikeda, M. Fascicularones A and B from a mycelial culture of Naematoloma Fasciculare. Phytochemistry 2004, 65, 491-496.

[3] Fabian, W.; Niederreiter, K; Uray, G.; Stadlbauer, W.; Substituent effects on absorption and fluorescence spectra of carbostyrils. Journal of Molecular Structure 1999, 477, 209-220.