Anti-Inflammatory and Anti-Tumor-Promoting Effects of 5-Deprenyllupulonol C and Other Compounds from Hop (Humulus lupulus L.)

被引：39

作者：

Akazawa, Hiroyuki ^{[1
,2
]}

Kohno, Hideki ^{[3
]}

Tokuda, Harukuni ^{[4
]}

Suzuki, Nobutaka ^{[2
]}

Yasukawa, Ken ^{[5
]}

Kimura, Yumiko ^{[3
]}

Manosroi, Aranya ^{[2
]}

Manosroi, Jiradej ^{[2
]}

Akihisa, Toshihiro ^{[1
]}

机构：

[1] Nihon Univ, Coll Sci & Technol, Chiyoda Ku, Tokyo 1018308, Japan

[2] Chiang Mai Univ, Fac Pharm, Chiang Mai 50200, Thailand

[3] Nihon Univ, Coll Ind Technol, Narashino, Chiba 2758575, Japan

[4] Kanazawa Univ, Grad Sch Med Sci, Kanazawa, Ishikawa 9208640, Japan

[5] Nihon Univ, Sch Pharm, Funabashi, Chiba 2748555, Japan

来源：

CHEMISTRY & BIODIVERSITY | 2012年 / 9卷 / 06期

关键词：

Hop extracts; Humulus lupulus; Anti-inflammatory activity; Anti-tumor-promoting activity; 5-Deprenyllupulonol C; PRENYLATED FLAVONOIDS; QUANTITATIVE-ANALYSIS; ANGELICA-KEISKEI; BITTER ACIDS; XANTHOHUMOL; PRENYLFLAVONOIDS; CHALCONES; IDENTIFICATION; TRITERPENOIDS; DERIVATIVES;

D O I：

10.1002/cbdv.201100233

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

070307 [化学生物学]; 071010 [生物化学与分子生物学];

摘要：

A new phloroglucinol derivative, 5-deprenyllupulonol C (1), along with four other phloroglucinol derivatives, 25, five chalcones, 610, four flavanones, 1114, two flavonol glycosides, 15 and 16, and five triterpenoids, 1721, were isolated from the female inflorescence pellet extracts of hop (Humulus lupulus L.). Upon evaluation of these compounds against the Epstein-Barr virus early antigen (EBV-EA) activation induced by 12-O-tetradecanoylphorbol 13-acetate (TPA) in Raji cells, twelve compounds, i.e., 14, 1114, 1719, and 21, showed potent inhibitory effects on EBV-EA induction, with IC50 values in the range of 215393 mol ratio/32 pmol TPA. In addition, eleven compounds, i.e., 14, 6, 11, 12, 14, 17, 18, and 20, were found to inhibit TPA-induced inflammation (1 mu g/ear) in mice, with ID50 values in the range of 0.131.06 mu mol per ear. Further, lupulone C (2) and 6-prenylnaringenin (14) exhibited inhibitory effects on skin-tumor promotion in an in vivo two-stage mouse-skin carcinogenesis test based on 7,12-dimethylbenz[a]anthracene (DMBA) as initiator and with TPA as promoter.

引用

页码：1045 / 1054

页数：10

共 41 条

[1]

Chalcones and other compounds from the exudates of Angelica keiskei and their cancer chemopreventive effects [J].

Akihisa, T ;

Tokuda, H ;

Hasegawa, D ;

Ukiya, M ;

Kimura, Y ;

Enjo, F ;

Suzuki, T ;

Nishino, H .

JOURNAL OF NATURAL PRODUCTS, 2006, 69 (01) :38-42

[2]

Chalcones, coumarins, and flavanones from the exudate of Angelica keiskei and their chemopreventive effects [J].

Akihisa, T ;

Tokuda, H ;

Ukiya, M ;

Iizuka, M ;

Schneider, S ;

Ogasawara, K ;

Mukainaka, T ;

Iwatsuki, K ;

Suzuki, T ;

Nishino, H .

CANCER LETTERS, 2003, 201 (02) :133-137

[3]

Akihisa T, 2001, STUD NAT PROD CHEM, V25, P43

[4]

Akihisa T., 2003, Studies in Natural Products Chemistry, P73

[5]

AKIHISA T, 2007, OLEOSCIENCE, V7, P445

[6]

Anti-inflammatory and anti-tumor-promoting effects of triterpene acids and sterols from the fungus Ganoderma lucidum [J].

Akihisa, Toshihiro ;

Nakamura, Yuji ;

Tagata, Masaaki ;

Tokuda, Harukuni ;

Yasukawa, Ken ;

Uchiyama, Emiko ;

Suzuki, Takashi ;

Kimura, Yumiko .

CHEMISTRY & BIODIVERSITY, 2007, 4 (02) :224-231

[7]

Acerogenin M, a cyclic diarylheptanoid, and other phenolic compounds from Acer nikoense and their anti-inflammatory and anti-tumor-promoting effects [J].

Akihisa, Toshihiro ;

Taguchi, Yosuke ;

Yasukawa, Ken ;

Tokuda, Harukuni ;

Akazawa, Hiroyuki ;

Suzuki, Takashi ;

Kimura, Yumiko .

CHEMICAL & PHARMACEUTICAL BULLETIN, 2006, 54 (05) :735-739

[8]

Anti-Inflammatory and Chemopreventive Effects of Triterpene Cinnamates and Acetates from Shea Fat [J].

Akihisa, Toshihiro ;

Kojima, Nobuo ;

Kikuchi, Takashi ;

Yasukawa, Ken ;

Tokuda, Harukuni ;

Masters, Eliot T. ;

Manosroi, Aranya ;

Manosroi, Jiradej .

JOURNAL OF OLEO SCIENCE, 2010, 59 (06) :273-280

[9]

Akihisa T, 2006, BIOMATERIALS FROM AQUATIC AND TERRESTRIAL ORGANISMS, P63

[10]

BENNINI B, 1992, PHYTOCHEMISTRY, V31, P2483, DOI 10.1016/0031-9422(92)83305-I

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