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. 2023 Feb 20;23(1):56.
doi: 10.1186/s12906-023-03889-x.

Angiotensin converting enzyme (ACE) inhibitors activity from purified compounds Fructus Phaleria macrocarpa (Scheff) Boerl

Aprilita Rina Yanti Eff  1 , Hasniza Zaman Huri  2 , Maksum Radji  3 , Abdul Mun'im  4 , F D Suyatna  5 , Yonatan Eden  3
Affiliations

Angiotensin converting enzyme (ACE) inhibitors activity from purified compounds Fructus Phaleria macrocarpa (Scheff) Boerl

Aprilita Rina Yanti Eff et al. BMC Complement Med Ther. .

Abstract

Background: Mahkota Dewa [Phaleria macrocarpa (Scheff) Boerl.] fruit in vitro and in- vivo can decrease and prevent elevation of the blood pressure, lower plasma glucose levels, possess an antioxidant effect, and recover liver and kidney damage in rats. This study aimed to determine the structure and inhibitory activity of angiotensin-converting enzyme inhibitors (ACE) from the Mahkota Dewa fruit.

Methods: The fruit powder was macerated using methanol and then partitioned by hexane, ethyl acetate, n-butanol, and water. The fractions were chromatographed on the column chromatography and incorporated with TLC and recrystallization to give pure compounds. The structures of isolated compounds were determined by UV-Visible, FT-IR, MS, proton (1H-NMR), carbon (13C-NMR), and 2D-NMR techniques encompassing HMQC and HMBC spectra. The compounds were evaluated for their ACE inhibitory activity, and the strongest compound was determined by the kinetics enzyme inhibition.

Results: Based on the spectral data, the isolated compounds were determined as 6,4-dihydroxy-4-methoxybenzophenone-2-O-β-D-glucopyranoside (1), 4,4'-dihydroxy-6-methoxybenzophenone-2-O-β-D-glucopyranoside (2) and mangiferin (3). IC50 values of the isolated compounds 1, 2 and 3 were 0.055, 0.07, and 0.025 mM, respectively.

Conclusion: The three compounds have ACE inhibitor and mangiferin demonstrated the best ACE inhibitory activity with competitive inhibition on ACE with the type of inhibition kinetics is competitive inhibition.

Keywords: 4,4′-dihydroxy-6-methoxybenzophenone-2-O-β-D-glucopyranoside; 6,4-dihydroxy-4-methoxybenzophenone–2-O-β-D-glucopyranoside; ACE inhibitor; Mangiferin; Phaleria macrocarpa.

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Conflict of interest statement

The authors declare no competing interests.

Figures

Fig. 1
Fig. 1
Two–dimensional NMR spectrum of compound 1. HSQC: heteronuclear single quantum coherence (red arrow); HMBC: heteronuclear multiple bond correlation (blue arrow)
Fig. 2
Fig. 2
Two–dimensional NMR spectrum of compound 2. HSQC: heteronuclear single quantum coherence (red arrow); HMBC: heteronuclear multiple bond correlation (blue arrow)
Fig. 3
Fig. 3
Two–dimensional NMR spectrum of compound 3. HSQC: heteronuclear single quantum coherence (red arrow); HMBC: heteronuclear multiple bond correlation (blue arrow)
Fig. 4
Fig. 4
Lineaweaver-Burk plot of mangiferin. Description: series 1: Without Inhibitor, series 2: mangiferin
See this image and copyright information in PMC

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