An ellagic compound and iridoids from Cornus capitata root cultures

Tanaka, Norie; Tanaka, Takashi; Fujioka, Toshihiro; Fujii, Hiroko; Mihashi, Kunihide; Shimomura, Koichiro; Ishimaru, Kanji

doi:10.1016/s0031-9422(01)00179-0

Cited by 36 publications

(17 citation statements)

References 16 publications

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“…In agreement with our results, similar classes of metabolites have been reported in the leaves and fruits of Cornus mas and the sarcocarp of C. officinalis (Cao et al 2011;Badalica-Petrescu et al 2014). Moreover, the ellagic and iridoid compounds have been detected in the roots of C. capitata (Tanaka et al 2001). Our study further correlates phenolic acids (quinic acid derivatives) and flavan-3-ol (epicatechin and cinchonain I) specifically to the Rosaceae, confirming earlier reports where quinic acids derivatives were identified in the fruits of Prunus domestica and in the leaves of Crataegus species (C. laevigata, C. monogyna, C. nigra, and C. pentagyna) (Cádiz-Gurrea et al 2014; Kuczkowiak et al 2014).…”

Section: Plant Cell Repsupporting

confidence: 92%

Metabolite fingerprinting, pathway analyses, and bioactivity correlations for plant species belonging to the Cornaceae, Fabaceae, and Rosaceae families

et al. 2016

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A multi-parallel approach gauging the mass spectrometry-based metabolite fingerprinting coupled with bioactivity and pathway evaluations could serve as an efficacious tool for inferring plant taxonomic orders. Thirty-four species from three plant families, namely Cornaceae (7), Fabaceae (9), and Rosaceae (18) were subjected to metabolite profiling using gas chromatography-time-of-flight-mass spectrometry (GC-TOF-MS) and ultrahigh performance liquid chromatography-linear trap quadrupole-ion trap-mass spectrometry (UHPLC-LTQ-IT-MS/MS), followed by multivariate analyses to determine the metabolites characteristic of these families. The partial least squares discriminant analysis (PLS-DA) revealed the distinct clustering pattern of metabolites for each family. The pathway analysis further highlighted the relatively higher proportions of flavonols and ellagitannins in the Cornaceae family than in the other two families. Higher levels of phenolic acids and flavan-3-ols were observed among species from the Rosaceae family, while amino acids, flavones, and isoflavones were more abundant among the Fabaceae family members. The antioxidant activities of plant extracts were measured using ABTS, DPPH, and FRAP assays, and indicated that extracts from the Rosaceae family had the highest activity, followed by those from Cornaceae and Fabaceae. The correlation map analysis positively links the proportional concentration of metabolites with their relative antioxidant activities, particularly in Cornaceae and Rosaceae. This work highlights the pre-eminence of the multi-parallel approach involving metabolite profiling and bioactivity evaluations coupled with metabolic pathways as an efficient methodology for the evaluation of plant phylogenies.

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Section: Plant Cell Repsupporting

confidence: 92%

Metabolite fingerprinting, pathway analyses, and bioactivity correlations for plant species belonging to the Cornaceae, Fabaceae, and Rosaceae families

et al. 2016

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“…Thus, the iridoid part of 2 bears a loganin skeleton, on the other hand, dihydrocornin and secologanin were also obtained in this phytochemical study which shared the same relative configuration. Dihydrocornin [10] and secologanin [11] were identified by comparison of their NMR data and the physical properties with those reported in the literature. From a biogenetic view, HÀC (15) and HÀC(20) of 2 should be b-oriented, while HÀC (14) and HÀC(21) have a-orientation.…”

Section: Results Andmentioning

confidence: 99%

“…[2]. Our phytochemical investigation on the 95% EtOH extract of the title plant led to the isolation of 13 compounds, comprising seven alkaloids, i.e., mappine A (1), mapposidic acid (2), 1-methyl-b-carboline [3], strictosidine [4], strictosidine acid [4], 5-carboxystrictosidine [5], and lyalosidic acid (3) [6], three lignans, i.e., pinoresinol [7], (þ)-(1R,2S,5R,6S)-2,6-bis(4-hydroxyphenyl)-3,7-dioxabicyclo[3.3.0]octane [8], and pinoresinol dimethyl ether [9], two iridoid glycosides, i.e., dihydrocornin [10] and secologanin [11], and one phenolic glycoside, i.e., 3,4,5-trimethoxyphenol [12]. The above compounds were reported for the first time from this genus.…”

mentioning

confidence: 99%

Two New Cytotoxic Alkaloids from Mappianthus iodoidesHand.‐Mazz.

Xiao

Lin

Gong

et al. 2011

Helvetica Chimica Acta

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Two new alkaloids, mappine A (1) and mapposidic acid (2), together with eleven known compounds, were isolated from the stems of Mappianthus iodoides Hand.-Mazz. Their structures were elucidated by means of spectroscopic and mass-spectrometric analyses, particularly 1D-and 2D-NMR spectroscopy. The cytotoxic activities of the two new alkaloids were also evaluated.Introduction. -The genus Mappianthus (Icacinaceae family) consists of three species which are distributed in subtropical and tropical zone. Mappianthus iodoides Hand.-Mazz., one species occurring in China, is used by local people for the treatment of traumatic injury, rheumatalgia, arthralgia, etc.[1].There were no phytochemical studies on this genus except that a sesquiterpene named (À)-cedrol had been reported from Mappianthus iodoides Hand.-Mazz.[2]. Our phytochemical investigation on the 95% EtOH extract of the title plant led to the isolation of 13 compounds, comprising seven alkaloids, i.e., mappine A (1), mapposidic acid (2) . The above compounds were reported for the first time from this genus. Here, we report on the isolation and structure elucidation of the two new alkaloids 1 and 2, and the evaluation of their cytotoxic activities.

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“…Table 4). The sugar moiety was determined The other constituents isolated from E. humifusa were identified as diisobutyl phthalate 7, 4 bis-(2-ethylhexyl) phthalate 8, 5 kaempferol-3-O-a-L-arabinofuranoside 9, 6 avicularin 10, 6 3,3 0 -di-O-methyl ellagic acid 11, 7 stenophyllin H 12, 8 Compounds 1-6 were tested for their cytotoxic activity against P388 and HL-60 leukemia, A-549 human lung adenocarcinoma, and SGC-7901 gastric adenocarcinoma tumor cell lines in vitro, but the inhibition was less than 50% (10 25 mol/l).…”

Section: Resultsmentioning

confidence: 99%

New α-pyrrolidinonoids and glycosides from Euphorbia humifusa

Dèng

Tang

et al. 2008

Journal of Asian Natural Products Research

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A phytochemical investigation on the constituents from Euphorbia humifusa Willd. has resulted in the isolation of three new alpha-pyrrolidinonoidal compounds, 5beta-methoxy-4beta-hydroxy-3-methylene-alpha-pyrrolidinone (1), 5beta-methoxy-4alpha-hydroxy-3-methylene-alpha-pyrrolidinone (2), and 5beta-butoxy-4alpha-hydroxy-3-methylene-alpha-pyrrolidinone (3), and three new glycosides including an indole glycoside, 3-(2-hydroxyethyl)-5-(1-O-beta-glucopyranosyloxy)-indole (4), an ionone glycoside, 3-oxo-7,8-dihydro-alpha-ionone-11-O-beta-glucoside (5), and a hemiterpene glycoside, 1-(4-hydroxy-2-methyl-2-buten-1-yl)-6- (3,4,5-trihydroxybenzoyl)-beta-d-glucose (6), along with 10 known compounds. Their structures were elucidated by analysis of 1D and 2D NMR spectral data. The structure of 1 was further confirmed by a single-crystal X-ray diffraction analysis.

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An ellagic compound and iridoids from Cornus capitata root cultures

Cited by 36 publications

References 16 publications

Metabolite fingerprinting, pathway analyses, and bioactivity correlations for plant species belonging to the Cornaceae, Fabaceae, and Rosaceae families

Metabolite fingerprinting, pathway analyses, and bioactivity correlations for plant species belonging to the Cornaceae, Fabaceae, and Rosaceae families

Two New Cytotoxic Alkaloids from Mappianthus iodoidesHand.‐Mazz.

New α-pyrrolidinonoids and glycosides from Euphorbia humifusa

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