Safflospermidines from the bee pollen of Helianthus annuus L. exhibit a higher in vitro antityrosinase activity than kojic acid

Abstract

Background: Ozone deterioration in the atmosphere has become a severe problem causing overexposure of ultraviolet light, which results in humans in melanin overproduction and can lead to many diseases, such as skin cancer and melasma, as well as undesirable esthetic appearances, such as freckles and hyperpigmentation. Although many compounds inhibit melanin overproduction, some of them are cytotoxic, unstable, and can cause skin irritation. Thus, searching for new natural compounds with antityrosinase activity and less/no side effects is still required. Here, bee pollen derived from sunflower (Helianthus annuus L.) was evaluated. Materials and methods: Sunflower bee pollen (SBP) was collected from Apis mellifera bees in Lopburi province, Thailand in 2017, extracted by methanol and sequentially partitioned with hexane and dichloromethane (DCM). The in vitro antityrosinase activity was evaluated using mushroom tyrosinase and the half maximal inhibitory concentration (IC 50 ) is reported. The antioxidation activity was determined using the 2,2-diphenyl-1-picrylhydrazyl (DPPH) assay and reported as the half maximal effective concentration. Two pure compounds with antityrosinase activity were isolated by silica gel 60 column chromatography (SG 60 CC) and high performance liquid chromatography (HPLC), and their chemical structure deduced by Nuclear Magnetic Resonance (NMR) analysis. Results:The DCM partitioned extract of SBP (DCMSBP) had an antityrosinase activity (IC 50 , 159.4 μg/mL) and was fractionated by SG 60 CC, providing five fractions (DCMSBP1-5). The DCMSBP5 fraction was the most active (IC 50 ¼ 18.8 μg/mL) and further fractionation by HPLC gave two active fractions, revealed by NMR analysis to be safflospermidine A and B. Interestingly, both safflospermidine A and B had a higher antityrosinase activity (IC 50 of 13.8 and 31.8 μM, respectively) than kojic acid (IC 50 of 44.0 μM). However, fraction DCMSBP5 had no significant antioxidation activity, while fractions DCMSBP1-4 showed a lower antioxidation activity than ascorbic acid. Conclusion: Safflospermidine A and B are potential natural tyrosinase inhibitors.

Phenolamide extract of apricot bee pollen alleviates glucolipid metabolic disorders and modulates the gut microbiota and metabolites in high-fat diet-induced obese mice

“…23,27,35 Previous studies have demonstrated that tri- p -coumaroyl spermidine is a promising active ingredient with great antioxidant, antifungal, and anti-tyrosinase activities. 27,35,36…”

“…Tri-p-coumaroyl spermidine has been detected in Brazilian bee pollen, rape bee pollen, and sunflower bee pollen. 23,27,35 Previous studies have demonstrated that tri-pcoumaroyl spermidine is a promising active ingredient with great antioxidant, antifungal, and anti-tyrosinase activities. 27,35,36 Effects of PAE on body weight, food intake, and organ index HFD-fed mice were treated with PAE for 12 weeks.…”

“…23,27,35 Previous studies have demonstrated that tri-pcoumaroyl spermidine is a promising active ingredient with great antioxidant, antifungal, and anti-tyrosinase activities. 27,35,36 Effects of PAE on body weight, food intake, and organ index HFD-fed mice were treated with PAE for 12 weeks. As shown in Fig.…”

Phytochemical content, especially spermidine derivatives, presenting antioxidant and antilipoxygenase activities in Thai bee pollens

“…The potential of the partitioned extracts was determined as previously described ( Khongkarat et al, 2020 ). Five different concentrations of each sample were prepared in DMSO.…”

“…The in vitro TYRI activity was determined as described ( Khongkarat et al, 2020 ). The reaction mixture contained 120 µL of 2.5 mM L-DOPA in 80 mM phosphate buffer (pH 6.8), 30 µL of 80 mM phosphate buffer (pH 6.8), and 10 µL of partitioned extract or kojic acid (positive control) at different concentrations in DMSO.…”