Inhibitory Effect of Di- and Trihydroxy Triterpenes from the Flowers of Compositae on 12-.OMICRON.-Tetradecanoylphorbol-13-acetate-Induced Inflammation in Mice.

Yasukawa, Ken; Akihisa, Toshihiro; Oinuma, Hirotoshi; Kasahara, Yoshiyuki; Kimura, Yumiko; Yamanouchi, Sakae; Kumaki, Kunio; Tamura, Toshitake; Takido, Michio

doi:10.1248/bpb.19.1329

Cited by 38 publications

(32 citation statements)

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“…Its flowers contain essential oil, sesquiterpenes, flavonoids, and their glycosides. 1,2) It has been reported that these flowers have various biological activities, such as anti-oxidation, 3) anti-inflammation, 4,5) oncogenic suppression, 6) anti-mutagenicity, 7) and anti-HIV. 8) We developed chrysanthemum flower oil (CFO; Kaneka Chrysflavone TM ) as an oily fraction containing polyphenols derived from chrysanthemum flowers.…”

mentioning

confidence: 99%

Administered chrysanthemum flower oil attenuates hyperuricemia: mechanism of action as revealed by DNA microarray analysis

Honda

Kawamoto

Tanaka

et al. 2014

Bioscience, Biotechnology, and Biochemistry

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confidence: 99%

Administered chrysanthemum flower oil attenuates hyperuricemia: mechanism of action as revealed by DNA microarray analysis

Honda

Kawamoto

Tanaka

et al. 2014

Bioscience, Biotechnology, and Biochemistry

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“…sinense MAKINO forma esculentum MAKINO; Japanese name: Ryourigiku) and other Asteraceae plants (pot marigold, cosmos, sunflower, burdock, etc.) possess remarkable anti-inflammatory activity on 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced ear edema in mice, [2][3][4][5] inhibitory effects on trypsin and chymotrypsin, 6) anti-tumor promoting effects, [7][8][9] and cytotoxic activity against human cancer cell lines. 7) Various types of triterpenoids from plants have recently been reported to exhibit antitubercular activity.…”

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confidence: 99%

Antitubercular Activity of Triterpenoids from Asteraceae Flowers

Akihisa

Franzblau

Ukiya

et al. 2005

Biological & Pharmaceutical Bulletin

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The flowers of Chrysanthemum morifolium RAMAT. and related chrysanthemum plants (Asteraceae) are used as a Chinese natural medicine. Florists Chrysanthemum Flower (Ju Hua) is prescribed for anti-inflammatory, analgesic, and antipyretic purposes and for the treatment of eye disease in Chinese traditional preparations. 1) In the course of our studies on bioactive principles of natural medicines and medicinal foodstuffs, we found that the triterpene alcohols isolated from the non-saponifiable lipid (NSL) fraction of the extract of chrysanthemum (C. morifolium RAMAT. var. sinense MAKINO forma esculentum MAKINO; Japanese name: Ryourigiku) and other Asteraceae plants (pot marigold, cosmos, sunflower, burdock, etc.) possess remarkable anti-inflammatory activity on 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced ear edema in mice, [2][3][4][5] inhibitory effects on trypsin and chymotrypsin, 6) anti-tumor promoting effects, [7][8][9] and cytotoxic activity against human cancer cell lines. 7) Various types of triterpenoids from plants have recently been reported to exhibit antitubercular activity. 10,11) In this paper, we describe the antitubercular activity against Mycobacterium tuberculosis of twenty-nine 3-hydroxy triterpenoids: twentyeight (1-16, 18-29) were isolated from the NSL fraction of the extract of chrysanthemum flowers and one (17) was chemically derived from compound 16. MATERIALS AND METHODSChemicals Twenty-seven triterpenoids (1-16, 18-26, 28, 29) (Chart 1) were isolated from the NSL fraction of the methanol extract of chrysanthemum flowers.2,3,5) Triterpenoid 27, which had previously been isolated from the extract of sunflower pollen, 12) was isolated from the NSL fraction of the methanol extract of chrysanthemum flower, 13) and triterpenoid 17 was prepared from 16 by oxidation with CrO 3 -pyridine followed by NaBH 4 reduction of the oxidation product. 14)Determination of Antitubercular Activity Antitubercular activity of compounds in DMSO was determined against Mycobacterium tuberculosis H 37 Rv (ATCC 27294) in Middlebrook 7H12 medium using the Microplate Alamar Blue Assay (MABA) as previously described.15) The MIC is defined as the lowest concentration effecting a reduction in fluorescence of 90% relative to controls.Cytotoxicity Assay Toxicity against Vero cells (ATCC CCL-81) was determined as described earlier.16) After 72 h exposure, cell viability was measured using the CellTiter 96 aqueous non-radioactive cell proliferation assay. The IC 50 is defined as the reciprocal dilution resulting in 50% inhibition of the Vero cells. RESULTS AND DISCUSSIONThe MIC values of 1-29 against M. tuberculosis are shown in Table 1. Among the compounds tested, fifteen of them: five taraxastanes (2, 4-7), two oleananes (9, 11), two ursanes (13, 15), two lupanes (17, 18), two cycloartanes (22, 24), one tirucallane (27), and one dammarane (29), exhibited activity with MIC values of 4-64 mg/ml, among which maniladiol (9; MIC 4 mg/ml) and 3-epilupeol (17; 4 mg/ml) followed by 4,5a-epoxyhelianol (27; 6 mg/ml) showed the ...

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“…The methanol and water extracts of T. japonicum inhibited tumor promotion by TPA or fumonisin B1 in DMBA-initiated mice (Takasaki, et al, 1999a). Several triterpenoids have been isolated from the flowers of T. officinale and T. platycarpum (Akihisa, et al, 1996;Yasukawa, et al, 1996d), taraxasterol and faradiol inhibited tumor promotion by DMBA/TPA in mouse skin (Yasukawa, et al, 1996c). Furthermore, taraxasterol and taraxerol inhibited same experiment (Takasaki, et al, 1999b).…”

Section: Compositae Plants and Their Active Componentsmentioning

confidence: 98%

“…It is used in folk medicine for hypertension, coronary artery disease, angina, feverish colds, and liver-related disorders. Triterpenoids were isolated from edible chrysanthemum flowers, and heliantriol C was found to be the major compound (Yasukawa, et al, 1996d). The activity of heliantriol C was ten times greater than other pentacyclic triterpenes against TPA-induced tumor promotion in mouse skin (Yasukawa, et al, 1998b).…”

Section: Compositae Plants and Their Componentsmentioning

confidence: 99%