Sporopollenin is a natural biomacromolecule which can be found in the outer wall (exine) of spores or pollens that it can be performed with clever designing in a lot of innovative and scientific areas. In this paper, a novel sporopollenin reformed with a recently synthesized pillar[5]arene molecule were elucidated by FT-IR spectroscopy, TGA and SEM techniques. This study is the first report leading to a comprehensive investigation of the biological applications of a functionalized bio-microcapsule including antioxidant and anticancer properties. Two in vitro assays (DPPH and FRAP) were used to determine the antioxidant activities of sporopollenin and functionalized microcapsules. Furthermore, the anticancer activities of these microcapsules were tested on 2 different cancer cell lines (HT-29 and MCF-7), and a fibroblast cell line (L929) by the Alamar blue assay. Among the samples tested in the antioxidant capacity results, especially Sp-P[5] exhibited higher antioxidant capacity and stood out with IC50: 101.98 ± 4.32 μg/mL in DPPH assay and IC50: 87.97 ± 3.14 μg/mL in FRAP assay. Similar to the antioxidant result, Sp-P[5] bio-microcapsule had greater cell inhibition on HT-29 (IC50: 132.31 ± 5.38 μg/mL), MCF-7 (IC50: 107.30 ± 8.28 μg/mL), and L929 (IC50: 255.80 ± 4.91 μg/mL) cell lines than Sp and Sp-APTMS. The analysis results in the study show promise for the development of sporopollenin-based microcapsules to deliver and enhance the biological activity of compounds with therapeutic potential.