To promote its use in nutraceutical and functional food ingredients, jiaogulan (Gynostemma pentaphyllium) of different sources, genotypes and parts of the plant were investigated for their chemical profiles and biological properties. The first part of this research studied five commercial jiaogulan for their phytochemical profiles, and antioxidant, anti-proliferative and anti-inflammatory effects. It was found that individual jiaogulan samples significantly differed in their chemical and biological properties. The second part of this research further investigated phytochemical compositions and biological activities in different genotypes and parts of jiaogulan. The results indicated that different genotypes or plant parts of jiaogulan may have different biological activities. The results led to the third study to develop chromatographic fingerprinting techniques for differentiating genotypes and plant parts of jiaogulan using LC/MS. LC-MS fingerprints combined with PCA were able to differentiate diploid and tetraploid, and the leaf and whole botanical jiaogulan. The results from this research suggest the potential use of selected jiaogulan to improve human health while enhancing food agriculture economy, and indicate that HPLC fingerprinting may be a useful controlling the quality of jiaogulan.