Polyglycerol fatty acid ester contributes to the improvement and maintenance of water solubility of amorphous curcumin by suppressing the intermolecular interaction and the diffusion rate of curcumin

Kazuya Nagano; Tomohiro Nakao; Mariko Takeda; Haruna Hirai; Hikaru Maekita; Michiko Nakamura; Naoki Imakawa; Ayako Egawa; Toshimichi Fujiwara; Jian-Qing Gao; Keigo Kinoshita; Makoto Sakata; Masayuki Nishino; Takuya Yamashita; Takuya Yoshida; Kazuo Harada; Keisuke Tachibana; Takefumi Doi; Kazumasa Hirata; Hirofumi Tsujino; Kazuma Higashisaka; Yasuo Tsutsumi

doi:10.1016/j.foodchem.2023.137866

Polyglycerol fatty acid ester contributes to the improvement and maintenance of water solubility of amorphous curcumin by suppressing the intermolecular interaction and the diffusion rate of curcumin

Food Chem. 2024 Mar 30;437(Pt 2):137866. doi: 10.1016/j.foodchem.2023.137866. Epub 2023 Oct 28.

Authors

Kazuya Nagano¹, Tomohiro Nakao², Mariko Takeda³, Haruna Hirai³, Hikaru Maekita³, Michiko Nakamura³, Naoki Imakawa³, Ayako Egawa⁴, Toshimichi Fujiwara⁴, Jian-Qing Gao⁵, Keigo Kinoshita⁶, Makoto Sakata⁶, Masayuki Nishino⁶, Takuya Yamashita⁷, Takuya Yoshida³, Kazuo Harada⁸, Keisuke Tachibana³, Takefumi Doi³, Kazumasa Hirata⁹, Hirofumi Tsujino¹⁰, Kazuma Higashisaka¹¹, Yasuo Tsutsumi¹²

Affiliations

¹ Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamadaoka, Suita, Osaka 565-0871, Japan; School of Pharmaceutical Sciences, Wakayama Medical University, 25-1 Shichibancho, Wakayama, Wakayama 640-8156, Japan. Electronic address: knagano@phs.osaka-u.ac.jp.
² Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamadaoka, Suita, Osaka 565-0871, Japan; San-Ei Gen F. F. I., Inc, 1-1-11 Sanwa-cho, Toyonaka, Osaka 561-8588, Japan.
³ Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamadaoka, Suita, Osaka 565-0871, Japan.
⁴ Institute for Protein Research, Osaka University, 3-2 Yamadaoka, Suita, Osaka 565-0871, Japan.
⁵ Institute of Pharmaceutics, College of Pharmaceutical Sciences, Zhejiang University, 866 Yuhangtang Road, Hangzhou 310058, PR China.
⁶ San-Ei Gen F. F. I., Inc, 1-1-11 Sanwa-cho, Toyonaka, Osaka 561-8588, Japan.
⁷ School of Pharmaceutical Sciences, Wakayama Medical University, 25-1 Shichibancho, Wakayama, Wakayama 640-8156, Japan.
⁸ Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamadaoka, Suita, Osaka 565-0871, Japan; Graduate School of Medicine, Osaka University, 2-2 Yamadaoka, Suita, Osaka 565-0871, Japan.
⁹ Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamadaoka, Suita, Osaka 565-0871, Japan; School of Pharmaceutical Sciences, Wakayama Medical University, 25-1 Shichibancho, Wakayama, Wakayama 640-8156, Japan.
¹⁰ Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamadaoka, Suita, Osaka 565-0871, Japan; The Museum of Osaka University, 1-13 Machikaneyama, Toyonaka, Osaka 560-0043, Japan.
¹¹ Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamadaoka, Suita, Osaka 565-0871, Japan; Institute for Advanced Co-Creation Studies, Osaka University, 1-6 Yamadaoka, Suita, Osaka 565-0871, Japan.
¹² Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamadaoka, Suita, Osaka 565-0871, Japan; Graduate School of Medicine, Osaka University, 2-2 Yamadaoka, Suita, Osaka 565-0871, Japan; Global Center for Medical Engineering and Informatics, Osaka University, 1-6, Yamadaoka, Suita, Osaka 565-0871, Japan. Electronic address: ytsutsumi@phs.osaka-u.ac.jp.

PMID: 37931447
DOI: 10.1016/j.foodchem.2023.137866

Abstract

Curcumin (CUR), a polyphenol, is an attractive component of functional foods, owing to various physiological activities. However, CUR is highly hydrophobic, insoluble in water, and difficult to absorb in the body. Here, we report an amorphous CUR formulation containing the dispersant polyglycerol fatty acid ester (PGFE), demonstrating high and stable water solubility. Improved water solubility enhanced the absorbability of CUR in our amorphous formulation along with enhanced triglyceride inhibition, compared to that in a commercial formulation. Nuclear Overhauser effect spectroscopy (NOESY) analysis revealed that PGFE reduced CUR-CUR interaction, resulting in higher dispersion and improved solubility of CUR. Taylor dispersion analysis showed a lower diffusion coefficient of CUR in the highly water-soluble formulation (with PGFE) than that in the low water-soluble formulation (without PGFE), which prevents recontact and recrystallization of CUR, which is trapped by PGFE. Overall, the amorphous CUR with high solubility could be used as a promising functional food.

Keywords: Absorption; Amorphous; Curcumin; Dyslipidemia; Polyglycerol fatty acid ester; Water solubility.

MeSH terms

Curcumin* / chemistry
Esters
Solubility
Water / chemistry

Substances

polyglycerol
Curcumin
Water
Esters