Cytotoxic Phenylpropanoids from Carrot

Abstract

Carrot is widely used as a foodstuff. The active components such as beta-carotene and panaxynol have been studied by many researchers. In this investigation of nonpolar active components from carrot, a new phenylpropanoid, epilaserine oxide ( 3), was isolated along with six known compounds, laserine ( 1), 2-epilaserine ( 2), panaxynol ( 4), ginsenoyne K ( 5), (8 E)-1,8-heptadecadiene-4,6-diyne-3,10-diol ( 6), and vaginatin ( 7). Their structures were deduced on the basis of spectroscopic methods. Significant cytotoxicity of 2-epilaserine against HL-60 cells was observed, which implied that phenylpropanoids were cytotoxic compounds in carrot. Laserine and 2-epilaserine in carrots from diverse locations in China were quantified by HPLC.

Phytochemical Investigation of Rhus parviflora Fruit from Nepal

“…The compounds were elucidated from interpretation of their spectroscopic data, including NMR, MS, and IR, and by comparison of their spectroscopic data with literature values as vaginatin (1) (4) [12], 7E-methoxy-E-sitosterol (5) [12], ergosterol peroxide (6) [13], D-amyrin (7) [14], lupeol (8) [14], linolenic acid methyl ester (9) [11], glycerol (10) [15], 1,2-dioleoyl-3-linolein (11) [16], isoliquirtigenin (12) [17], quercetin (13) [17], (-)-syringaresinol (14) [18], (-)-pinoresinol-4c-O-E-D-glucopyranoside (15) [18], (+)-5,5c-dimethoxylariciresinol (16) [19], (+)-isolariciresinol-9c-O-D-L-rhamnopyranoside (17) [20], and methyl-E-D-fructofuranose (18) [21]. All compounds are reported here for the first time from the fruits of R. parviflora.Although the 13 C NMR are similar in CDCl 3 and pyridine-d 5 , some signals in the 1 H NMR that have been previously reported as overlapped for H-6, H-7, 13-CH 3 , and 15-CH 3 in CDCl 3 [10] showed better resolution in pyridine-d 5 , so we have dealt here the structure determination of compound 1. The IR spectrum indicated hydroxyl (3454 cm -1 ), cyclopentanone (1748 cm -1 ), conjugated aromatic ester (1685 cm -1 ), and double bond (1610 cm -1 ).…”

“…Although the 13 C NMR are similar in CDCl 3 and pyridine-d 5 , some signals in the 1 H NMR that have been previously reported as overlapped for H-6, H-7, 13-CH 3 , and 15-CH 3 in CDCl 3 [10] showed better resolution in pyridine-d 5 , so we have dealt here the structure determination of compound 1. The IR spectrum indicated hydroxyl (3454 cm -1 ), cyclopentanone (1748 cm -1 ), conjugated aromatic ester (1685 cm -1 ), and double bond (1610 cm -1 ).…”

“…The compounds were elucidated from interpretation of their spectroscopic data, including NMR, MS, and IR, and by comparison of their spectroscopic data with literature values as vaginatin (1) [10], E-sitosterol (2) [11], daucosterol (3) [11], 7D-methoxy-E-sitosterol (4) [12], 7E-methoxy-E-sitosterol (5) [12], ergosterol peroxide (6) [13], D-amyrin (7) [14], lupeol (8) [14], linolenic acid methyl ester (9) [11], glycerol (10) [15], 1,2-dioleoyl-3-linolein (11) [16], isoliquirtigenin (12) [17], quercetin (13) [17], (-)-syringaresinol (14) [18], (-)-pinoresinol-4c-O-E-D-glucopyranoside (15) [18], (+)-5,5c-dimethoxylariciresinol (16) [19], (+)-isolariciresinol-9c-O-D-L-rhamnopyranoside (17) [20], and methyl-E-D-fructofuranose (18) [21]. All compounds are reported here for the first time from the fruits of R. parviflora.…”

Two New Guaiane-Type Sesquiterpene Glycosides from the Fruits of Daucus carota L.

“…1) Pharmacological studies on the plant of D. carota have demonstrated antibacterial, 2) antifungal, 3) anthelmintic, hepatoprotective 4) and cytotoxic 5) activities. The previous research on chemical constituents of D. carota has carried out the presence of sesquiterpenes, [6][7][8] chromones, 9) flavonoids, 10,11) coumarins 6,12) and anthocyanins.…”

Two New Guaiane Sesquiterpenes from the Fruits of Daucus carota

“…[1]. In modern pharmacological research, it has exhibited a wide range of pharmacological effects, including antibacterial [2], antifungal [3], anthelmintic, hepatoprotective [4], and cytotoxic [5] activities. Previous chemical investigations on the plant of D. carota have demonstrated the occurrence of sesquiterpenes [6], chromones [7], flavonoids [8], coumarins [6a] [9], and anthocyanins [10].…”