Cytotoxicity of Triterpenes from Green Walnut Husks of Juglans mandshurica Maxim in HepG-2 Cancer Cells

Abstract

Among the classes of identified natural products, triterpenoids, one of the largest families, have been studied extensively for their diverse structures and variety of biological activities, including antitumor effects. In the present study, a phytochemical study of the green walnut husks of Juglans mandshurica Maxim led to the isolation of a new dammarane triterpene, 12β, 20(R), 24(R)-trihydroxydammar-25-en-3-one (6), together with sixteen known compounds, chiefly from chloroform and ethyl acetate extracts. According to their structural characteristics, these compounds were divided into dammarane-type, oleanane-and ursane-type. Dammarane-type triterpenoids were isolated for the first time from the Juglans genus. As part of our continuing search for biologically active compounds from this plant, all of these compounds were also evaluated for their cytotoxic activities against the growth of human cancer cells lines HepG-2 by the MTT assay. The results were shown that 20(S) -protopanaxadiol, 2α,3β,23-trihydroxyolean-12-en-28-oic acid and 2α,3β,23-trihydroxyurs-12-en-28-oic acid exhibited better cytotoxicity in vitro with IC50 values of 10.32 ± 1.13, 16.13 ± 3.83, 15.97 ± 2.47 μM, respectively. Preliminary structure-activity relationships for these compounds were discussed.

Identification of Polar Constituents in the Decoction of Juglans mandshurica and in the Medicated Egg Prepared with the Decoction by HPLC-Q-TOF MS2

“…For the research on the active principles of J. mandshurica , numerous compounds, including tannins [ 7 , 8 ], flavonoids [ 9 , 10 ], naphthalenes [ 11 ], diarylheptanoids [ 12 ], organic acids [ 13 ], anthracenes [ 14 ], triterpenes [ 15 ], lignans [ 16 ] and phenylpropanoids [ 17 ], were isolated from this plant. Some of the compounds isolated have been reported to have growth inhibitory effects on human cancer cell lines (HepG2 hepatoma cells, HL-60 leukemia cells, lung carcinoma cells, SGC-7901 gastric cancer cells, etc.)…”

“…Some of the compounds isolated have been reported to have growth inhibitory effects on human cancer cell lines (HepG2 hepatoma cells, HL-60 leukemia cells, lung carcinoma cells, SGC-7901 gastric cancer cells, etc.) by the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) test in vitro [ 12 , 13 , 15 , 17 ]. Juglone, which is the main naphthoquinone in J. mandshurica , has the most reports of anti-tumor activity.…”

Multiconstituent identification in root, branch, and leaf extracts of Juglans mandshurica using ultra high performance liquid chromatography with quadrupole time‐of‐flight mass spectrometry

“…Chemical constituents of J. mandshurica have been exhaustively explored for its reputation of anti-tumor qualities. As a result, a range of secondary metabolites, including tannins [3,8,9], flavonoids [3,10], naphthalenes [3,11], diarylheptanoids [12,13], organic acids [14], anthracenes [15,16], triterpenes [17], lignans [18,19], and phenylpropanoids [20] were isolated from this plant. Among those compounds isolated, tannins with anti-tumor activity [8] were commonly existed in different plant organs of J. mandshurica.…”

Crystal Structures and Cytotoxicity of ent-Kaurane-Type Diterpenoids from Two Aspilia Species

“…Additional compounds (Figure 1 and Figure 3) isolated from the roots of Aspilia pluriseta include (16 R )-hydroxy- ent -kauran-19-oic acid ( 2 ) [16,17], 9β-hydroxy-15α-angeloyloxy- ent -kaur-16-en-19-oic acid ( 3 ) [18], methyl-9β-hydroxy-15α-angeloyloxy- ent -kaur-16-en-19-oate ( 4 ) [19], 15α-angeloyloxy-16β,17-epoxy- ent -kauran-19-oic acid ( 5 ) [20], ent -kaur-9(11),16-dien-19-oic acid ( 6 ) [21], 15α-angeloyloxy- ent -kaur-16-en-19-oic acid ( 7 ) [22], ent -kaur-9(11),16-dien-12-one ( 9 ) [23] and methyl- ent -kaur-16-en-19-oate ( 10 ) [24]. The aerial part of Aspilia pluriseta contained ent -kaur-16-en-19-oic acid ( 11 ) [21,25], ent -kaur-16-en-19-ol ( 12 ) [26], lanosterol ( 13 ) [27], stigmasta-5,22(E)-dien-3β-ol ( 14 ) [28], 3β-hydroxy-olean-12-en-29-oic acid ( 15 ) [29], and carissone ( 16 ) [30].…”