(–)-β-Homoarginine anhydride, a new antioxidant and tyrosinase inhibitor, and further active components from Trichosanthes truncata

Abstract

One new amino acid derivative, (-)-β-homoarginine anhydride 1, as well as nine known compounds were isolated from Trichosanthes truncata. The structures of the isolates were elucidated by spectroscopic methods. Among them, compounds 5 and 11 could notably dose-dependently inhibit ROS productions in HaCaT keratinocyte cells without cytotoxicity in the concentration range of 0.2 to 20 μM. In cell-free mushroom tyrosinase assay, compounds 1-5, 10 and 11 had more potential anti-tyrosinase activities with IC 50 values of 106.9-255.6 μM than arbutin that were similar to predicted values of binding affinity calculated by molecule docking.The most active 2 had hydrogen bonds (Ser77, Glu309, Phe454) and electrostatic charges (Glu309, Glu248) interactions with mushroom tyrosinase, respectively. Our data manifested that T. truncata and its components are potentially to be developed as anti-aging and whitening agents for skin disorders.

Chemical Constituents of the Mushroom Dictyophora indusiata and Their Anti-Inflammatory Activities

“…On the basis of the comprehensive analysis of spectroscopic data from high resolution electrospray ionization mass spectra (HRESIMS), 1D/2D nuclear magnetic resonance (NMR) spectra, ultraviolet (UV) spectra, and comparison with the references, four previously undescribed compounds were named Indusiataines A–D ( 1 – 4 ). Fourteen known compounds were elucidated to be 5-(Methoxymethyl)-1 H -pyrrole-2-carbaldehyde ( 5 ) [ 21 ], nicotinic acid ( 6 ) [ 22 ], dibutyl phthalate ( 7 ) [ 23 ], 5-hydroxymethyl-2-furancarboxaldehyde ( 8 ) [ 24 ], adenosine ( 9 ) [ 25 ], oxindole ( 10 ) [ 26 ], 3-oxo-4-benzyl-3,4-dihydro-1 H -pyrrolo [2,1-c] oxazine-6-methylal ( 11 ) [ 27 ], 2-methyl-3-pyridinol ( 12 ) [ 28 ], linoleic acid ( 13 ) [ 29 ], oleic acid ( 14 ) [ 30 ], 1(10→6)abeo-ergosta-5,7,9,22-tetraen-11β-methoxy-3α-ol ( 15 ) [ 31 ], citreoanthrasteroid ( 16 ) [ 31 ], 5α,6α-epoxy-3β-hydroxy-(22 E )-ergosta-8(14),22-dien-7-one ( 17 ) [ 32 ], and 7-ketositosterol ( 18 ) [ 33 ] ( Figure 1 ). The UV, HRESIMS, and NMR spectra of compounds 1 – 4 are provided in Figure S1 .…”

Chemical constituents of the genus Trichosanthes (Cucurbitaceae) and their biological activities: A review

“…Four cycloartane triterpenoids (46-49) have been isolated from T. kirilowii [30] and T. tricuspidata [31], whereas twenty-one pentacyclic triterpenoids (50-70) have been isolated from T. cucumerina, T. cucumeroides, T. dioica, T. kirilowii and T. truncata (Fig. 3) [19,20,[32][33][34][35][36][37][38][39][40]. Some of these compounds were evaluated for their biological activities.…”

“…Twenty-four other compounds (80-103) have been isolated from T. kirilowii, T. tricuspidata and T. truncata (Fig. 5) [21,40,43,44]. Among them, compounds 87, 89, 92 and 93 showed antiinflammatory activities through inhibition of the activation of NF-κB transcription factors at a concentration of 1 µM [44].…”

“…In the search of new agents from Trichosanthes plants for skin disorders, previous reports revealed that the extracts and their constituents showed anti-tyrosinase activity. For example, compound 98 and 100 had more potential anti-mushroom tyrosinase activities with IC 50 values of 106.9-255.6 µM [40]. In addition, the isolated compounds from T. kirilowii pulps have been reported to exhibit tyrosine acidase inhibitory activity [64].…”

“…a This compound should be the same as "22-dihydro-α-spinasterol" isolated from T. truncata[40]. However, no detailed information was available from[40].www.scienceasia.org…”