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. 2021 Oct 14;11(1):20452.
doi: 10.1038/s41598-021-99970-x.

Two triterpenoids from Rubus fraxinifolius leaves and their tyrosinase and elastase inhibitory activities

Yesi Desmiaty  1   2 , Muhammad Hanafi  2   3 , Fadlina Chany Saputri  1 , Berna Elya  4 , Eko Aditya Rifai  1 , Rezi Riadhi Syahdi  1
Affiliations

Two triterpenoids from Rubus fraxinifolius leaves and their tyrosinase and elastase inhibitory activities

Yesi Desmiaty et al. Sci Rep. .

Abstract

Numerous therapeutic compounds have been isolated from naturally abundant organic resources, which may offer economical and sustainable sources of compounds with safe and efficacious biological activities. In the cosmetics industry, natural compounds with anti-aging activities are eagerly sought. Thus, we prepared various extracts from Rubus fraxinifolius leaves and used enzyme inhibition assays to isolate compounds with protective effects against skin aging. Two triterpenoids were isolated from Rubus fraxinifolius Poir. leaves. The structures were characterized by spectroscopic analyses (LC-ESI-MS, 1D/2D NMR) and comparison to reported data. Compound 1 and 2 were determined as 2,3-O-ethyleneglycol, 19-hydroxyurs-12-en-23,28-dioic acid and 2,3-O-propanediol,19-hydroxyurs-12-en-28-oic acid. Methanol extract and isolates were assessed for their inhibitory effects on elastase and tyrosinase. Compounds 1 and 2 inhibited elastase with IC50 122.199 µg/mL and 98.22 µg/mL, and also inhibited tyrosinase with IC50 207.79 µg/mL and 221.51 µg/mL, respectively. The molecular docking proved that both compounds have affinities toward the enzymes.

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Conflict of interest statement

The authors declare no competing interests.

Figures

Figure 1
Figure 1
Elastase inhibition by R. fraxinifolius leaf extracts and fractions.
Figure 2
Figure 2
Key HMBC correlations. a = compound 1; b = compound 2.
Figure 3
Figure 3
Structures of compounds 1 and 2. a = 2,3-O-ethylene glycol, 19-hydroxyurs-12-en-23,28-dioic acid; b = 2,3-O-propanediol, 19-hydroxyurs-12-en-28-oic acid.
Figure 4
Figure 4
Anti elastase and anti-tyrosinase activities of extracts and isolates from R. fraxinifolius leaves.
Figure 5
Figure 5
Visualization of elastase binding site using PyMOL. Blue = cocrystal; green = compound 1; yellow = compound 2.
Figure 6
Figure 6
Visualization of tyrosinase binding site using PyMOL. Magenta = cocrystal; green = compound 1; yellow = compound 2.
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