Anti-tumor promoting activity of polyphenols from Cowania mexicana and Coleogyne ramosissima

Ito, Hideyuki; Miyake, Masaaki; Nishitani, Eisei; Mori, Kazuko; Hatano, Tsutomu; Okuda, Takuo; Konoshima, Takao; Takasaki, Midori; Kozuka, Mutsuo; Mukainaka, Teruo; Tokuda, Harukuni; Nishino, Hoyoku; Yoshida, Takashi

doi:10.1016/s0304-3835(99)00160-3

Cited by 80 publications

(52 citation statements)

References 21 publications

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“…; afterwards, this EEE isomer was isolated successively from Rosaceae, 14) Quercus dentata pollen, 15) anthers of Aphelandra tetraffona and A. chamissoniana (a ZZZ isomer also was isolated concomitantly), 12) sunflower (Helianthus annuus L.) pollen, 16) and Brazilian bee pollen. 17) Pharmacologically, this principal compound has been reported to have anti-human immunodeficiency virus (HIV) infection, 11,18) anti-Helicobacter pylori, 19) anti-tumor, 20,21) anti-fungal, 22) and antioxidant activities. 17) More recently (by the year of 2008), several tri-pcoumaroylspermidines with property of cis-trans conformation such as the ZZZ, EEE, EZE, and EZZ isomer have also been found in safflower [the florets of Carthamus tinctorius (Compositae)].…”

Section: Resultsmentioning

confidence: 99%

Structural Identification of a New Tri-p-coumaroylspermidine with Serotonin Transporter Inhibition from Safflower

Zhao

Qin

Gai

et al. 2010

CHEMICAL & PHARMACEUTICAL BULLETIN

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Safflower (Carthamus tinctorius L.), a member of the family Compositae, geologically distributes in all regions in China, and is utilized for producing herbal medicines for the treatment of inflammatory diseases, hyperlipemia, arteriosclerosis, gynecological disorders, and osteoporosis. 1) To date, it has been known to contain flavonoids, 2) cartharmin, safflower yellow A, quinochalone, safflomin, cartorimine, alkaloids, 3) lignans, fatty acids, 4) triterpene alcohols, 5) and serotonin derivatives.6-8) Additionally, several coumaroylspermidine analogs also were found in safflower, i.e., a principal analog N 1 ,N 5 ,N 10 -(E)-tri-p-coumaroylspermidine (EEE) and its three cis-trans isomers [N 1 ,N 5 9) indicating that that some other geometric isomers of tri-p-coumaroylspermidine could exist in the natural plant. In our previous preliminary screening, we discovered that safflower extracts (especially ethyl acetate extract (HE) and n-butyl alcohol fraction) had regulatory actions on the monoamine transports in transporter-transgenic Chinese hamster ovary (CHO) cells, that is, activations of dopamine (DA)/norepinephrine (NE) uptake and an inhibition of serotonin (5HT) uptake, 10) implying that there may be some constituent(s) acting as serotonin transporter (SERT) blocker(s). In this study, we thereby chose to isolate and characterize the structurally unknown, SERT-targeting compound(s) from the HE fraction by using an activity-directed extraction method and a series of NMR techniques. Finally, one of the active isolates was identified and elucidated as N 1 ,N 5 -(Z)-N 10 -(E)-tri-p-coumaroylspermidine (CX), a new tri-p-coumaroylspermidine as postulated previously by us. Results and DiscussionThe ethyl acetate extract of safflower (Carthamus tinctorius L.) was separated by column chromatography on silica gel and Sephadex LH-20 in combination with a concomitant bioactivity-tracing technique (detailed paradigm described in Supplemental) to afford a bioactive compound CX (designated as carthamide X by us) (Fig. 1). HPLC showed that the purity of CX sample was 95.6% (while the content of CX in HE was only 0.028%). Due to the sensitivity, validity, and feasibility, 10) our screening platform previously established by using isotope-ligand-detection methods is suggested suitable for tracing some structurally unknown/unstable compounds with a sparse content in natural plants when combined with phytochemical techniques, which could, however, be hard to be isolated by traditional phytochemical method alone.The We previously reported that safflower (Carthamus tinctorius L.) ethyl acetate extract (HE) possessed an inhibitory action on serotonin (5HT) uptake in Chinese hamster ovary (CHO) cells expressing 5HT transporter (SERT) (S6 cells). Here, HE was adopted to go through an activity-guided isolation, and then an ingredient with potent SERT inhibitory action was obtained, which was elucidated as N

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Section: Resultsmentioning

confidence: 99%

Structural Identification of a New Tri-p-coumaroylspermidine with Serotonin Transporter Inhibition from Safflower

Zhao

Qin

Gai

et al. 2010

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…The following compounds were isolated from the species indicated in parentheses [15][16][17] : Agrimoniin (Agrimonia japonica); brevifolincarboxylic acid (Phyllanthus flexuosus); gemin A, pedunculagin, and tellimagrandin I (Geum japonicum); geraniin (Geranium thunbergii); procyanidins B2 and C1 (Theobroma cacao); and casuarinin and procyanidin B4 (Cowania mexicana). Pentagalloylglucose was obtained by methanolysis of tannic acid.…”

Section: Samples and Reagentsmentioning

confidence: 99%

Screening of the Inhibitory Effect of Vegetable Constituents on the Aryl Hydrocarbon Receptor-Mediated Activity Induced by 2,3,7,8-Tetrachlorodibenzo-p-dioxin

Amakura

Tsutsumi

Sasaki

et al. 2003

Biological & Pharmaceutical Bulletin

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“…These acyl groups were consistent with the appearance of ten ester carbonyl carbon signals in 13 C-NMR (see text) and chemically confirmed by the production of methyl tri-O-methylgallate (7) and dimethyl hexamethoxydiphenate (8) upon methanolysis of the methylated derivative of 1. The odd number of aromatic 1H singlets in the 1 H-NMR spectrum of 1 suggested that one of the HHDP groups may participate in C-C bond formation with an anomeric carbon of open-chain glucose residue as characterized by C-glucosidic ellagitannins such as casuarinin (2) and stachyurin (3). The presence of two open-chain glucose residues was indicated by the coupling patterns and chemical shifts of aliphatic proton signals which were assigned by 1 C-NMR resonances of glucose and catechin residues of 1, which were assigned by the heteronuclear multiple quantum connectivity (HMQC) spectrum, indicated a close resemblance to those of stachyuranin A (6) 6) and stenophyllanin B (5) 7) rather than stenophyllanin A (4) as shown in Table 1.…”

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confidence: 99%

“…Inhibitory effect on EBV-EA activation induced by TPA according to the reported method 3) was tested for cowaniin in order to compare with the previously reported effects 3) of the co-existing anti-tumor promoting polyphenols, alienanin B and stenophyllanin A (4); however the potency (44.9% inhibition) of 1 was much weaker than those of alienanin B (81.5% inhibition) and 4 (79.1% inhibition) at a concentration of 500 mol ratio per TPA. …”

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confidence: 99%

Cowaniin, a C-Glucosidic Ellagitannin Dimer Linked through Catechin from Cowania mexicana

Ito

Miyake

Nishitani

et al. 2007

CHEMICAL & PHARMACEUTICAL BULLETIN

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Cowania mexicana D. DON (Rosaceae) is distributed in western North America, and its aerial parts have been used as a cough suppressant and a remedy for respiratory disease by America Indians. As chemical constituents of this plant, the presence of triterpenoids, such as ursolic acid 1) and cucurbitan-type triterpenes 2) as inhibitors of Epstein-Barr virus early antigen (EBV-EA) activation were reported. We reported the isolation and characterization of nine tannins and related polyphenols [casuarinin (2), stachyurin (3), pterocarinin A, stenophyllanin A (4), alienanin B, casuglaunin A, (Ϫ)-epicatechin, procyanidin B-4 and ellagic acid] along with two nitrile glucosides (menisdaurin and lithospermoside) from the leaves and stems of C. mexicana. Their inhibitory effects on in vitro EBV-EA activation induced by 12-O-tetradecanoylphorbol-13-acetate (TPA) and on in vivo two-stage carcinogenesis on mouse back-skin were also reported.3) Further chemical investigation on a polar fraction of the plant extract has resulted in the isolation of a new complex tannin dimer named cowaniin (1) and a known nitrile glucoside. This paper describes the isolation and structure elucidation of the new tannin, along with five known polyphenols from a non-polar fraction.A concentrated 70% aqueous acetone homogenate of the dried aerial parts of C. mexicana was extracted with Et 2 O, EtOAc and water-saturated n-BuOH to give the respective extracts and the water-soluble portion. The Et 2 O extract was chromatographed over polyvinyl gels to afford five known compounds, quercetin 3-O-a-L-arabinofuranoside, 4) and pcoumaric, p-hydroxybenzoic, protocatechuic and gallic acids. The separation and purification of the n-BuOH and watersoluble portion by polystylene and/or polyvinyl gels gave cowaniin (1) and a known nitrile glucoside, purshianin.5) The known compounds were identified by direct comparison with authentic samples and/or by their spectral comparisons with data reported in the literature.Cowaniin (1) was obtained as an off-white amorphous powder and exhibited an [MϩNH 4 ] ϩ ion peak at m/z 2162 in electrospray ionization (ESI)-MS. The molecular formula was determined to be C 97 H 68 O 57 by elemental analysis and NMR spectra along with MS data. The 1 H-NMR spectrum of 1 exhibited two 2H singlets (d 7.09, 7.06) and seven 1H singlets (d 6.83, 6.72, 6.62, 6.55, 6.53, 6.51, 6.25), which were assignable to two galloyl and four hexahydroxydiphenoyl (HHDP) groups. These acyl groups were consistent with the appearance of ten ester carbonyl carbon signals in C-NMR resonances of glucose and catechin residues of 1, which were assigned by the heteronuclear multiple quantum connectivity (HMQC) spectrum, indicated a close resemblance to those of stachyuranin A (6) 6) and stenophyllanin B (5) 7) rather than stenophyllanin A (4) as shown in Table 1. These NMR spectral features and MS data, taking the absence of A-ring protons of catechin into consideration, suggested the dimeric structure of cowaniin, in which the 6-and 8-positions of the catechin u...

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Anti-tumor promoting activity of polyphenols from Cowania mexicana and Coleogyne ramosissima

Cited by 80 publications

References 21 publications

Structural Identification of a New Tri-p-coumaroylspermidine with Serotonin Transporter Inhibition from Safflower

Structural Identification of a New Tri-p-coumaroylspermidine with Serotonin Transporter Inhibition from Safflower

Screening of the Inhibitory Effect of Vegetable Constituents on the Aryl Hydrocarbon Receptor-Mediated Activity Induced by 2,3,7,8-Tetrachlorodibenzo-p-dioxin

Cowaniin, a C-Glucosidic Ellagitannin Dimer Linked through Catechin from Cowania mexicana

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