Phenolic Constituents with Antioxidative, Tyrosinase Inhibitory and Anti-aging Activities from Dendrobium loddigesii Rolfe

Abstract

Aqueous ethanol extracts of powdered stems of Dendrobium loddigesii afforded three new phenolics including threo-7-O-ethyl-9-O-(4-hydroxyphenyl)propionyl-guaiacylglycerol (1), (R)-4,5,4ʹ-trihydroxy-3,3ʹ,α-trimethoxybibenzyl (2) and (S)-5,5′,7-trihydroxy-3′,4′-dimethoxyflavanone (3), together with eleven known analogues. Their structures were determined by extensive spectroscopic analysis. To identify natural antioxidants, whitening, and anti-aging agents, the abilities of these phenolics were assessed to scavenge the 1,2-diphenyl-2-picrylhydrazyl (DPPH) radical, their abilities to inhibit tyrosinase production, and their abilities to stimulate collagen production by human dermal fibroblasts-adult (HDFa) assay. It was found that compounds 1, 4–8, 13 and 14 exhibited significant DPPH radical scavenging activities, compound 10 exhibited tyrosinase inhibitory activity (IC50 37.904 μg/mL), and compound 9 showed significant collagen production with an EC50 value of 3.182 μg/mL. These results suggest that phenolic constituents from D. loddigesii may be candidate antioxidants, skin-whitening and/or anti-aging agents.Graphic Abstract Electronic supplementary materialThe online version of this article (10.1007/s13659-019-00219-y) contains supplementary material, which is available to authorized users.

Antioxidant Activities and Protective Effects of Dendropachol, a New Bisbibenzyl Compound from Dendrobium pachyglossum, on Hydrogen Peroxide-Induced Oxidative Stress in HaCaT Keratinocytes

“…Dendrobium spp. have been reported to possess many secondary metabolites with potent antioxidant activities [ 19 , 25 ], and thus, they appear to be a good source of natural skin rejuvenating and anti-aging agents. In the present study, we investigated the chemical constituents of D. pachyglossum and the biological activities of the isolated compounds, including the new bisbibenzyl named dendropachol ( 1 ), together with 4 known compounds ( 2–5 ).…”

“…The crude extracts from D. sonia “earsakul” (a Dendrobium hybrid) and the bioactive constituents of D. loddigesii have been found to inhibit matrix metalloproteinase enzymes (MMP) and stimulate the production of collagen in human dermal fibroblasts [ 17 , 18 ]. Crude extracts of D. tosaense, D. loddigesii, and D. sonia “earsakul” showed inhibitory effects on melanogenesis [ 17 , 18 , 19 ]. Polysaccharides isolated from D. denneanum, D. officinale, and the crude extracts of D. sabin (a Dendrobium hybrid) and D. moniliforme showed in vitro antioxidant activities [ 20 , 21 , 22 , 23 ].…”

Traditional Uses and Pharmacologically Active Constituents of Dendrobium Plants for Dermatological Disorders: A Review

“…From its stems, threo-7-O-ethyl-9-O-(4-hydroxyphenyl)propionylguaiacylglycerol (113), crepidatin (15), moscatilin (9), 4,5,4′-trihydroxy-3,3′-dimethoxybibenzyl (13), 4′,5-dihydroxy-3,3′-dimethoxybibenzyl (gigantol, 7), tristin (8), dihydroconiferyl dihydro-p-coumarate (114), and p-hydroxyphenethyl trans-ferulate (115) were obtained, and these compounds exhibited significant activities, with DPPH scavenging capacities ranging from 89 to 94% at 100 μg/ mL, as compared with the positive control Trolox, which led to an inhibition of 96% at a concentration of 25 μg/mL. Batatasin III (1) significantly stimulated the collagen production activity of human dermal fibroblasts-adult (HDFa) (EC 50 3.2 μg/mL) and was compared with TGF-β as a positive control, with an inhibition of 66% at a concentration of 0.01 μg/mL [49]. From complete plants, moscatin (45), 9,10-dihydrophenanthrene-2,4,7-triol (56), and crepidatuol B (27) were obtained, and these compounds showed significant activities, with DPPH scavenging capacities ranging from 84 to 95% at 100 μg/mL, as compared with the positive control Trolox, which led to an inhibition of 96% at a concentration of 25 μg/mL [50].…”

Antioxidant Properties of Plant-Derived Phenolic Compounds and Their Effect on Skin Fibroblast Cells

“…A higher fibroblast proliferation rate translates into increased collagen production, as was observed in HDFs treated with geraniin and furosin, an ellagitannin from Phyllanthus muellerianus [ 102 ]. Stimulation of collagen production was also observed in HDFs exposed to batatasin III, a stilbene obtained from Dendrobium loddigesii [ 103 ]. Another phenolic compound, 6-dehydrogingerdione, a phenolic alkenone isolated from the rhizomes of Zingiber officinale , induces both proliferation and migration of HDFs.…”