Chemical investigation of Hyptis suaveolens seed, a potential antihyperuricemic nutraceutical, with assistance of HPLC-SPE-NMR

Abstract

The seed of Hyptis suaveolens , commonly known as wild flour ball (san fen yuan) in Taiwan, serves as a main refreshing drink substance in several regions. This study investigated firstly its secondary metabolites, leading to the isolation of five major caffeoylquinic acid derivatives ( 1–5 ) from the ethanol extract. In addition, ten minors, including three caffeoylquinic acid derivatives ( 12–14 ), were characterized via assistance of HPLC-SPE-NMR. Of these isolates, sodium 4,5-dicaffeoylquinate ( 2 ) and methyl 3,5-dicaffeoylquinate ( 4 ) showed moderate inhibitory activity against xanthine oxidase with the respective IC 50 values of 69.4 μM and 92.1 μM ( c.f. allopurinol IC 50 28.4 μM). Quantitative HPLC analysis of the EtOH extract indicates the content of sodium 3,5-dicaffeoylquinate ( 1 ) and sodium 4,5-dicaffeoylquinate ( 2 ) to be 0.1% and 0.08% (w/w, dry seed), respectively. This study not only discloses the bioactive constituents, but also demonstrates the potential of H. suaveolens seed as an antihyperuricemic nutraceutical.

Validation of in Silico Docking Analysis of Oligophenylpropanoids to Xanthine Oxidase by Correlation with in Vitro Bioassay and Its Application to Phlorotannins

“…These amino acid residues form H-bond or/and ionic interaction with the active ligands, which play critical roles against XO. Using the refinement (Forcefield−Affinity ∆G) mode, the docking results of either phenylpropanoids 1−7 or three phlorotannins (9,12,13) were more consistent with the bioassay results than those obtained by the refinement (Forcefield−London) mode. Thus the London (trimatch)−refinement (Forcefield−Affinity ∆G) docking method is recommended for virtual screening of the related phenolic compounds.…”

“…Thus the London (trimatch)−refinement (Forcefield−Affinity ∆G) docking method is recommended for virtual screening of the related phenolic compounds. As 6,6'-bieckol (12) and dieckol (13) showed inhibitory activity against XO comparable to the positive control allopurinol, three phlorotannins (11,14,15) having better docking score than 12 and 13 deserve further study. Since these phlorotannins are rich in Ecklonia cava and E. stolonifera, these common edible seaweeds should be beneficial to persons suffering hyperuricemia.…”

“…The method used for this assay was adopted from a recent report [13]. In a 96-well plate, MeOH-H 2 O (10 µL, 1:9, v/v) or sample in MeOH-H 2 O (10 µL, 1:9, v/v), and 2 mM xanthine solution (60 µL) was added to each well.…”

Subtribe Hyptidinae (Lamiaceae): A promising source of bioactive metabolites

“…Hyptis suaveolens ) allowed the identification of rosmarinic acid ( 222 ) and methyl rosmarinate ( 229 ) ( Prawatsri et al, 2013 ; Abedini et al, 2013 ; Tang et al, 2019 ). More recently, a study carried out with the later species led to the isolation of five caffeoylquinic acid derivatives, identified as 3,5-dicaffeoylquinate ( 230 ), 4,5-dicaffeoylquinate ( 231 ), 3,4-dicaffeoylquinate ( 232 ), methyl-3,5- dicaffeoylquinate ( 233 ), methyl-3,4- dicaffeoylquinate ( 234 ) ( Hsu et al, 2019 ).…”

Thermal and emulsifying properties of globulins from chan ( Hyptis suaveolens L. Poit) seeds

“…Chan ( Hyptis suaveolens L. Poit) is a dicotyledonous plant from the Lamiaceae family that was used by pre‐Colombian people as food in addition to maize ( Zea mays ), beans ( Phaseolus vulgaris ), amaranth, and chia (Aguirre, Torres, Mendoza‐Hernández, Garcia‐Gasca, & Blanco‐Labra, 2012). This plant is well adapted with worldwide distribution in the tropical regions; in the South and along the Pacific Coast of Mexico, it is not only a component of natural vegetation, but also is produced in short scale for the elaboration of a typical regional beverage called “bate” (Hsu, Tsai, & Lee, 2019; Sanchez‐Aguirre, Cruz‐Navarro, Guevara‐Valencia, Rengifo‐Salgado, & Vargas‐Arana, 2020; Vergara‐Santana, Lemus‐Juárez, & Bayardo‐Parra, 2005). Chan seed is considered as pseudocereal and contains around 14% of protein content on a dry weight basis, similar to other pseudocereals such as amaranth (13.5%), buckwheat ( Fagopyrum esculentum ) (13.1%), and quinoa (16.3%) (Aguirre et al., 2012; Mota et al., 2016).…”