Eucalyptals A-C with a new skeleton isolated from Eucalyptus globulus

被引:43
作者
Yin, Sheng [1 ]
Xue, Jun-Juan [1 ]
Fan, Cheng-Qi [1 ]
Miao, Ze-Hong [1 ]
Ding, Jian [1 ]
Yue, Jian-Min [1 ]
机构
[1] Chinese Acad Sci, Shanghai Inst Biol Sci, Inst Mat Med, State Key Lab Drug Res, Shanghai 201203, Peoples R China
关键词
D O I
10.1021/ol7025075
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Eucalyptals A-C (1-3) with a new skeleton of 3,5-diformyl-isopentyl phloroglucinol-coupled cadinane were isolated from the fruits of Eucalyptus globulus. Their structures were elucidated by spectroscopic analysis, and that of 1 was confirmed by single-crystal X-ray diffraction. The biosynthetic pathway of 1-3 was also postulated. Compounds 1-3 exhibited selective cytotoxicity against the HL-60 cell line.
引用
收藏
页码:5549 / 5552
页数:4
相关论文
共 12 条
[1]   JENSENONE, A KETONE FROM EUCALYPTUS-JENSENII [J].
BOLAND, DJ ;
BROPHY, JJ ;
FOOKES, CJR .
PHYTOCHEMISTRY, 1992, 31 (06) :2178-2179
[2]   Bioactive acylphloroglucinol derivatives from Eucalyptus species [J].
Ghisalberti, EL .
PHYTOCHEMISTRY, 1996, 41 (01) :7-22
[3]  
*JIANGS NEW MED CO, 1977, DICT TRAD CHIN MED S, P1793
[4]  
KOZUKA M, 1982, CHEM PHARM BULL, V30, P1964
[5]  
KOZUKA M, 1982, CHEM PHARM BULL, V30, P1952
[6]   MACROCARPALS - HIV-RTASE INHIBITORS OF EUCALYPTUS-GLOBULUS [J].
NISHIZAWA, M ;
EMURA, M ;
KAN, Y ;
YAMADA, H ;
OGAWA, K ;
HAMANAKA, N .
TETRAHEDRON LETTERS, 1992, 33 (21) :2983-2986
[7]   Macrocarpals H, I, and J from the leaves of Eucalyptus globulus [J].
Osawa, K ;
Yasuda, H ;
Morita, H ;
Takeya, K ;
Itokawa, H .
JOURNAL OF NATURAL PRODUCTS, 1996, 59 (09) :823-827
[8]   INHIBITORS OF SKIN-TUMOR PROMOTION .8. INHIBITORY EFFECTS OF EUGLOBALS AND THEIR RELATED-COMPOUNDS ON EPSTEIN-BARR-VIRUS ACTIVATION [J].
TAKASAKI, M ;
KONOSHIMA, T ;
FUJITANI, K ;
YOSHIDA, S ;
NISHIMURA, H ;
TOKUDA, H ;
NISHINO, H ;
IWASHIMA, A ;
KOZUKA, M .
CHEMICAL & PHARMACEUTICAL BULLETIN, 1990, 38 (10) :2737-2739
[9]   Total synthesis of (-)-macrocarpal C.: Stereoselective coupling reaction with a novel hexasubstituted benzene Cr(CO)3 complex as a biomimetic chiral benzyl cation equivalent [J].
Tanaka, T ;
Mikamiyama, H ;
Maeda, K ;
Iwata, C ;
In, Y ;
Ishida, T .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (26) :9782-9793
[10]   Five phloroglucinol-monoterpene adducts from Eucalyptus grandis [J].
Umehara, K ;
Singh, IP ;
Etoh, H ;
Takasaki, M ;
Konoshima, T .
PHYTOCHEMISTRY, 1998, 49 (06) :1699-1704