γ-Lactam alkaloids from the flower buds of daylily

被引:25
作者
Matsumoto, Takahiro [1 ]
Nakamura, Seikou [1 ]
Nakashima, Souichi [1 ]
Ohta, Tomoe [1 ]
Yano, Mamiko [1 ]
Tsujihata, Junichiro [1 ]
Tsukioka, Junko [1 ]
Ogawa, Keiko [1 ]
Fukaya, Masashi [1 ]
Yoshikawa, Masayuki [1 ]
Matsuda, Hisashi [1 ]
机构
[1] Kyoto Pharmaceut Univ, Dept Pharmacognosy, Yamashina Ku, Kyoto 6078412, Japan
基金
日本学术振兴会;
关键词
Daylily; Alkaloids; Alzheimer's diseases; PC12; cell; A beta 42 aggregation; OLEANANE-TYPE; 2,5-DIHYDROFURYL-GAMMA-LACTAM DERIVATIVES; TRITERPENE OLIGOGLYCOSIDES; CANANGA-ODORATA; ADENOSINE; C-13;
D O I
10.1007/s11418-015-0963-z
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Four new alkaloids, hemerocallisamines IV-VII, were isolated from the methanol extract of flower buds of daylily. The chemical structures of the new compounds were elucidated on the basis of chemical and physicochemical evidence. The absolute stereochemistry of the hemerocallisamines IV-VI was elucidated by the application of the modified Mosher's method, HPLC analysis, and optical rotation. In the present study, the isolated alkaloids significantly inhibited the aggregation of A beta 42 in vitro. This is the first report about bioactive alkaloids with a gamma-lactam ring from daylily. In addition, isolated nucleosides showed accelerative effects on neurite outgrowth under the non-fasting condition.
引用
收藏
页码:376 / 383
页数:8
相关论文
共 20 条
[1]   Complete 1H and 13C NMR spectral assignment of α- and β-adenosine, 2'-deoxyadenosine and their acetate derivatives [J].
Ciuffreda, P. ;
Casatii, S. ;
Manzocchi, A. .
MAGNETIC RESONANCE IN CHEMISTRY, 2007, 45 (09) :781-784
[2]   Medicinal Flowers. XXXV. Nor-Oleanane-Type and Acylated Oleanane-Type Triterpene Saponins from the Flower Buds of Chinese Camellia japonica and Their Inhibitory Effects on Melanogenesis [J].
Fujimoto, Katsuyoshi ;
Nakamura, Seikou ;
Nakashima, Souichi ;
Matsumoto, Takahiro ;
Uno, Kaoru ;
Ohta, Tomoe ;
Miura, Tomoko ;
Matsuda, Hisashi ;
Yoshikawa, Masayuki .
CHEMICAL & PHARMACEUTICAL BULLETIN, 2012, 60 (09) :1188-1194
[3]   NOVEL 2,5-DIHYDROFURYL-GAMMA-LACTAM DERIVATIVES FROM HEMEROCALLIS-FULVA L VAR KWANZO REGEL [J].
INOUE, T ;
IWAGOE, K ;
KONISHI, T ;
KIYOSAWA, S ;
FUJIWARA, Y .
CHEMICAL & PHARMACEUTICAL BULLETIN, 1990, 38 (11) :3187-3189
[4]  
INOUE T, 1994, CHEM PHARM BULL, V42, P154, DOI 10.1248/cpb.42.154
[5]   Structure of constituents isolated from the flower buds of Cananga odorata and their inhibitory effects on aldose reductase [J].
Matsumoto, Takahiro ;
Nakamura, Seikou ;
Fujimoto, Katsuyoshi ;
Ohta, Tomoe ;
Ogawa, Keiko ;
Yoshikawa, Masayuki ;
Matsuda, Hisashi .
JOURNAL OF NATURAL MEDICINES, 2014, 68 (04) :709-716
[6]   A Rare Glutamine Derivative from the Flower Buds of Daylily [J].
Matsumoto, Takahiro ;
Nakamura, Seikou ;
Ohta, Tomoe ;
Fujimoto, Katsuyoshi ;
Yoshikawa, Masayuki ;
Ogawa, Keiko ;
Matsuda, Hisashi .
ORGANIC LETTERS, 2014, 16 (11) :3076-3078
[7]   Lignan Dicarboxylates and Terpenoids from the Flower Buds of Cananga odorata and Their Inhibitory Effects on Melanogenesis [J].
Matsumoto, Takahiro ;
Nakamura, Seikou ;
Nakashima, Souichi ;
Fujimoto, Katsuyoshi ;
Yoshikawa, Masayuki ;
Ohta, Tomoe ;
Ogawa, Keiko ;
Matsuda, Hisashi .
JOURNAL OF NATURAL PRODUCTS, 2014, 77 (04) :990-999
[8]   Protective effects of caffeoylquinic acids on the aggregation and neurotoxicity of the 42-residue amyloid β-protein [J].
Miyamae, Yusaku ;
Kurisu, Manami ;
Murakami, Kazuma ;
Han, Junkyu ;
Isoda, Hiroko ;
Irie, Kazuhiro ;
Shigemori, Hideyuki .
BIOORGANIC & MEDICINAL CHEMISTRY, 2012, 20 (19) :5844-5849
[9]   Palladium-Catalyzed Direct Hydroxymethylation of Aryl Halides and Triflates with Potassium Acetoxymethyltrifluoroborate (vol 14, pg 1281, 2012) [J].
Murai, Norio ;
Yonaga, Masahiro ;
Tanaka, Keigo .
ORGANIC LETTERS, 2012, 14 (14) :3812-3813
[10]   Alkaloid constituents from flower buds and leaves of sacred lotus (Nelumbo nucifera, Nymphaeaceae) with melanogenesis inhibitory activity in B16 melanoma cells [J].
Nakamura, Seikou ;
Nakashima, Souichi ;
Tanabe, Genzo ;
Oda, Yoshimi ;
Yokota, Nami ;
Fujimoto, Katsuyoshi ;
Matsumoto, Takahiro ;
Sakuma, Rika ;
Ohta, Tomoe ;
Ogawa, Keiko ;
Nishida, Shino ;
Miki, Hisako ;
Matsuda, Hisashi ;
Muraoka, Osamu ;
Yoshikawa, Masayuki .
BIOORGANIC & MEDICINAL CHEMISTRY, 2013, 21 (03) :779-787