New Phenylethanoid Glycosides and Sugar Esters from Ku‐Ding‐Cha, a Herbal Tea Produced from Ligustrum purpurascens

Abstract

Ku-Ding-Cha is a kind of herbal tea used commonly in China for its effects on hypertension, fatness, inflammation, and diuresis. The chlorophyll removal fraction from 60% aqueous acetone extract of Ku-Ding-Cha produced from the leaves of Ligustrum purpurascens (Oleaceae) exhibited observable antioxidant activity on 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging assay (SC50 = 45 microg/mL). Further detailed phytochemical investigation on this fraction led to the isolation of 2 new phenylethanoid glycosides, ligupurpurosides C-D (1 and 2), and 2 new sugar esters, ligupurpurosides E-F (3 and 4), together with 15 known compounds (5 to 19). All of them, except for 7, 8, 9, 11, and 12, were isolated from Ku-Ding-Cha and its original plants for the first time. The chemical structures were elucidated based on the analysis of spectroscopic data, including 1D, 2D NMR, and FABMS. In addition, the isolated compounds were evaluated for their antioxidant activities by DPPH assay.

Evaluation of the antioxidant activity of five endemic Ligustrum species leaves from Taiwan flora in vitro

“…The IC 50 values for L. morrisonense, L. liukiuense, L. pricei, L. sinense, and L. lucidum in the DPPH assay were 0.48, 0.94, 1.38, 1.47, and 2.06 mg/ml, respectively. The results obtained from the DPPH assay is similar to recent reports of other Ligustrum species, including L. lucidum and L. robustum (Chen, Wong, Leung, He, & Huang, 2002;Katsube et al, 2004;Nagy et al, 2006;She, Wang, Zeng, Yang, & Zhang, 2008;Zhu et al, 2009). For the TEAC assay, the IC 50 values for L. morrisonense, L. liukiuense, L. pricei, L. sinense, and L. lucidum were 0.21, 0.24, 0.37, 0.52, and 1.40 mg/ml, respectively.…”

Phenylethanoid and secoiridoid glycosides from the leaves of Ligustrum purpurascens

“…The fourteen known phenylethanoid glycosides were identified as acteoside (1) (He et al, 1992), ligupurpuroside A (3) (He et al, 1992), syringalide A 3 0 -a-L-rhamnopyranoside (4) (Zhang et al, 2013), lipedoside A-I (5) (He et al, 1994), kankanoside G (6) (Yoshikawa et al, 2006), lipedoside A-II (7) (He et al, 1994), isoacteoside (8) (Lu and Shen, 2008), osmanthuside B (9) (He et al, 1992), ligupurpuroside C (10) (She et al, 2008), cis-lipedoside A-I (11) (He et al, 1992), ligurobustoside N (12) (He et al, 2003), (E)-ligupurpuroside B (13) (He et al, 1992), angoroside A (14) (Li et al, 2011), and (Z)-ligupurpuroside B (15) (Wong et al, 2001) by comparison of their spectroscopic data with those reported in the literature.…”

“…The leaves of L. purpurascens have long been used as a traditional Chinese tea known as Ku-Ding-Cha (He et al, 1992). Phytochemical investigations have revealed that the main chemical constituents of this plant are flavonoids, monoterpenoids, iridoids and phenylethanoid glycosides (He et al, 1992;He et al, 2003;Wong et al, 2001;She et al, 2008;Tian et al, 1998Tian et al, , 1997Li et al, 2010;Tian and Sun, 1999;Tian et al, 1996;Xiong et al, 2007). Among them, phenylethanoid glycosides exhibited antioxidative and immunomodulatory activities, while iridoids showed antiviral properties (Wong et al, 2001;He et al, 2003;She et al, 2008;Song et al, 2012;Ma et al, 2001).…”

Immunomodulatory effects of crude phenylethanoid glycosides from Ligustrum purpurascens

“…1C). In these spectra, the parent ions and product ions of these five constituents were compared with literature (Li et al, 2010She et al, 2008). The structures Table 2 Effects of CPGs on mouse peritoneal MF phagocytosis of chicken RBCs and NK cell activity.…”