Smilax sieboldii, a climbing tree belonging to Smilacaceae, has been used in traditional oriental medicine for treating arthritis, tumors, leprosy, psoriasis, and lumbago. To evaluate the anti-obesity effects of S. sieboldii (Smilacaceae), we screened methylene chloride (CH2Cl2), ethyl acetate (EtOAc), aqueous-saturated n-butanol, and ethanol (EtOH) extracts of the whole plant at various concentrations to inhibit adipogenesis in adipocytes. The 3T3-L1 cell line with Oil red O staining with the help of fluorometry was used as an indicator of anti-obesity activity. Bioactivity-guided fractionation of the EtOH extract and subsequent phytochemical investigation of the active CH2Cl2- and EtOAc-soluble fractions resulted in the isolation of 19 secondary metabolites (1–19), including a new α-hydroxy acid derivative (16) and two new lanostane-type triterpenoids (17 and 18). The structures of these compounds were characterized using various spectroscopic methods. All the isolated compounds were screened for adipogenesis inhibition at a concentration of 100 μM. Of these, compounds 1, 2, 4–9, 15, and 19 significantly reduced fat accumulation in 3T3-L1 adipocytes, especially compounds 4, 7, 9, and 19, showing 37.05 ± 0.95, 8.60 ± 0.41 15.82 ± 1.23, and 17.73 ± 1.28% lipid content, respectively, at a concentration of 100 μM. These findings provide experimental evidence that isolates from S. sieboldii extracts exert beneficial effects regarding the regulation of adipocyte differentiation.
Veratrum spp. have traditionally been used in folk medicine to treat various pathologies. In this study, nine compounds, comprising one simple phenolic compound (1), three stilbenoids (2–4), and five flavonoids (5–9), were isolated from the aerial parts of Veratrum versicolor f. viride Nakai. The structures of these compounds were elucidated by spectroscopic analyses and comparison with reported data. Together, all reported compounds were isolated from V. versicolor f. viride for the first time in the study. Among them, two flavone aglycone tricetins (7 and 9) have never been isolated from the genus Veratrum or the family Melanthiaceae. The ethanol extract and isolated compounds were assessed for their inhibitory effects on elastase, tyrosinase, and melanin synthesis. Compounds 5 and 7 inhibited elastase (IC50: 292.25 ± 14.39 and 800.41 ± 5.86 μM, respectively), whereas compounds 2–5 inhibited tyrosinase with IC50 values in the range of 6.42 ~ 51.19 μM, respectively. In addition, compounds 3–6 and 8 exhibited dose-dependent inhibition (70.4% ~ 91.0%) of melanogenesis at a concentration of 100 μM.
Jin Gwan Kwon, Yeon Woo Jung, Yun-Hyeok Choi, Ji Eun Lee, Wonsik Jeong, Jung A Lee, Chun Whan Choi, Eun-Kyung Ahn, Yongmun Choi, and Seong Su Hong. Journal of the Korean Society of Food Science and Nutrition 2022;51:1171-7. https://doi.org/10.3746/jkfn.2022.51.11.1171
Two new compounds, including a nor-pimarane diterpenoid (continentanol, 1) and a phenolic derivative (aralianic acid, 2), along with the known diterpenoids (3-11), polyacetylenes (12-15), phenolic components (16-28), and phytosterols (29 and 30), were isolated from roots of Aralia continentalis. The structures of the new compounds were established by spectroscopic data interpretation, particularly HRESIMS, 1 D and 2 D NMR data including HSQC and HMBC. Also, those of the known compounds were identified by spectral comparison with those of the reported values.
Amomum tsao-ko (Zingiberaceae), an important traditional medicinal herb, possesses many biological activities, including anti-inflammatory effects. Though the anti-obesity properties of the crude ethanol extract of A. tsao-ko fruits have been reported, the anti-adipogenic properties of its phytochemical constituents have not been reported. Therefore, in the present study, we isolated the active constituents of A. tsao-ko and investigated their anti-adipogenic effects. The bioassay-guided isolation of the phytochemicals from the ethanol extract of A. tsao-ko fruits identified four bioactive compounds, comprising one fatty acid ( 1 ), one sesquiterpene alcohol ( 2 ), and two phenolic compounds ( 3 and 4 ). Their structures were elucidated by a combination of 1D and/or 2D nuclear magnetic resonance and mass spectrometry. The anti-adipogenic activities of the four compounds evaluated by Oil Red O staining in 3T3-L1 cells revealed that the treatment with the isolated compounds 1 and 3 reduced the lipid accumulation in 3T3-L1 adipocytes more strongly than the compounds 2 and 4 , in a dose-dependent manner.
In our search for novel plant-derived inhibitors of nitric oxide (NO) with potential for treating inflammatory diseases, the phytochemicals of Amomum tsao-ko fruits were investigated, leading to the isolation of one bicyclic nonane (1), three menthene skeleton monoterpenoids (2–4), and two acyclic monoterpenoids (5 and 6). Their structures were identified using one- and two-dimensional nuclear magnetic resonance spectroscopy, and mass spectrometry. To the best of our knowledge, compounds 2–5 were obtained from the genus Amomum for the first time. All isolates were tested for their ability to inhibit lipopolysaccharide-stimulated NO overproduction in RAW264.7 cells. Compound 4 was found to inhibit NO production. Western blotting analysis indicated that active compound 4 can regulate inducible NO synthase expression. In addition, lipopolysaccharide-induced interleukin 1 beta and interleukin-6 overproduction was reduced in a concentration-dependent manner.
Gnetum species have been traditionally consumed as food and used as folk medicine to treat various pathological conditions. Ten compounds including three simple phenolic compounds (1–3), five stilbenoids (4, 5, 8–10), and two C-glycosyl flavanones (6 and 7), were isolated from the stems of Gnetum macrostachyum Hook. f. The structures of these compounds were elucidated by the analysis of spectroscopy data and their comparison with the reported values. This is the first report of the isolation of compounds 1–4 and 6–9 from G. macrostachyum. Compounds 1–3, 6, and 7 have not been previously reported from the genus Gnetum. The C-glycosyl flavanones in G. macrostachyum can be used as chemotaxonomic markers.
In the course of screening for cosmetic ingredients by measuring antioxidant and antiwrinkle and whitening and anti-inflammatory activities, skin-related activity was tested using 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging, 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) radical scavenging, elastase inhibition, tyrosinase inhibition, and nitric oxide assay. Several Polygonaseae extracts were found to show potent activity. The results showed that the Persicaria senticosa methanolic extract has the 1,1diphenyl-2picrylhydrazyl (DPPH) and ABTS radical scavenging activities (IC50 61.0 and 17.5 μg/mL). In the elastase inhibition assay and nitric oxide assay, the IC50 of methanolic extract of Persicaria senticosa was 739.7 μg/mL and 71.8 μg/mL. The Persicaria senticosa 70% ethanolic extract partitioned with n-hexane, CH2Cl2, EtOAc, n-BuOH, and aqueous fractions. The purification of EtOAc soluble layer was by column chromatography separation and MPLC analysis of Compounds 1-7. It was identified as loliolide (1), quercetin-3-O-glucoside (2), quercetin-3-O-glucuronide (3), 4-methoxy caftraric acid (4), kaempferol-3-(6-methylglucuronide) (5), quercetin-3-(6-methylglucuronide) (6), and quercetin (7). Structure was elucidated by a combination of 1D and 2D NMR and MS spectrometry as well as comparison with reported literatures. Radical scavenging effect on DPPH, tyrosinase inhibition, and nitric oxide assay on several compounds from Persicaria senticosa was found to show potent activity. The results showed that Compound 7 has the NO assay (IC5029.7 μM). For DPPH, the IC50 of Compounds 2, 3, 5, and 7 was 39.6, 31.2, 37.0, and 22.7 μM. In tyrosinase inhibitory activity, the IC50 of Compound 7 was 14.3 μM.
Four new β-carboline alkaloids, siliendines A–D (1‒4), and four known metabolites (5–8) were isolated from the ethanolic extract of the aerial parts of Silene seoulensis using various chromatographic methods. The structures of the new compounds were established using multiple spectroscopic approaches, with techniques such as HRESIMS and NMR, which included HSQC and HMBC. The known compounds were identified by comparing their spectra with those of the reported compounds.
The ethanolic extract obtained from the stems of Glycosmis pentaphylla was found to suppress antigen-mediated degranulation of rat basophilic leukemia (RBL-2H3) cells. Four new geranylated 2-quinolone alkaloids, named glycopentanolones A-D (1-4), and 12 known metabolites (5-16) were isolated from the ethanolic extract from the stems of G. pentaphylla using bioassay-guided fractionation. Their structures were elucidated by a combination of 1D and 2D NMR, and HRESI-MS. The inhibitory effects of the isolated constituents on beta-hexosaminidase release from RBL-2H3 cells were examined, and compounds 1, 5, 8 and 11 exhibited potent inhibitory activity with IC50, values between 0.05 and 4.28 mu M.