Yaoshanenolides A and B: New Spirolactones from the Bark of Machilus yaoshansis

被引：46

作者：

Liu, Mingtao ^{[1
,2
]}

Lin, Sheng ^{[1
,2
]}

Gan, Maoluo ^{[1
,2
]}

Chen, Minghua ^{[1
,2
]}

Li, Li ^{[1
,2
]}

Wang, Sujuan ^{[1
,2
]}

Zi, Jiachen ^{[1
,2
]}

Fan, Xiaona ^{[1
,2
]}

Liu, Ying ^{[1
,2
]}

Si, Yikang ^{[1
,2
]}

Yang, Yongchun ^{[1
,2
]}

Chen, Xiaoguang ^{[1
,2
]}

Shi, Jiangong ^{[1
,2
]}

机构：

[1] Chinese Acad Med Sci, State Key Lab Bioact Subst & Funct Nat Med, Inst Mat Med, Beijing 100050, Peoples R China

[2] Peking Union Med Coll, Beijing 100050, Peoples R China

来源：

ORGANIC LETTERS | 2012年 / 14卷 / 04期

关键词：

ELECTRONIC CIRCULAR-DICHROISM; LAMBERTELLOL-B; CONSTITUENTS; BUTANOLIDES; GLYCOSIDES; ALCOHOLS; ACID; ROOT;

D O I：

10.1021/ol300130s

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Two novel tricyclic spirolactones bearing long linear alkyl chains, yaoshanenolides A (1) and B (2), formed by Diels-Alder[4 + 2] cycloaddition of a molecule of each butenolide with beta-phellandrene, were isolated from the bark of Machilus yaoshansis. Their structures and absolute configurations were determined by extensive spectroscopic methods, especially 2D NMR and ECD data analysis. The proposed biosynthetic pathway is discussed. Both compounds exhibited nonselective cytotoxic activities against several human cancer cell lines.

引用

页码：1004 / 1007

页数：4

共 31 条

[1] GENERAL-SYNTHESIS OF 1-OXASPIRO[4.5]DECAN-2-ONES AND 1-OXASPIRO[4.5]DECANES FROM 5-METHYLENE-2(5H)-FURANONE [J].

ALONSO, D ;

FONT, J ;

ORTUNO, RM .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (19) :5567-5572

[2] BIOLOGICALLY-ACTIVE GAMMA-LACTONES AND METHYLKETOALKENES FROM LINDERA-BENZOIN [J].

ANDERSON, JE ;

MA, W ;

SMITH, DL ;

CHANG, CJ ;

MCLAUGHLIN, JL .

JOURNAL OF NATURAL PRODUCTS, 1992, 55 (01) :71-83

[3]

[Anonymous], GAUSS 03 REV E 01

[4]

[Anonymous], 2009, 200910 MOE CHEM COMP

[5]

[Anonymous], DICT TRAD CHIN MED

[6] Application of electronic circular dichroism in configurational and conformational analysis of organic compounds [J].

Berova, Nina ;

Di Bari, Lorenzo ;

Pescitelli, Gennaro .

CHEMICAL SOCIETY REVIEWS, 2007, 36 (06) :914-931

[7] Abyssomicin C -: A polycyclic antibiotic from a marine Verrucosispora strain as an inhibitor of the p-aminobenzoic acid/tetrahydrofolate biosynthesis pathway [J].

Bister, B ;

Bischoff, D ;

Ströbele, M ;

Riedlinger, J ;

Reicke, A ;

Wolter, F ;

Bull, AT ;

Zähner, H ;

Fiedler, HP ;

Süssmuth, RD .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (19) :2574-2576

[8] Chemical and cytotoxic constituents from the leaves of Cinnamomum kotoense [J].

Chen, Ching-Hsein ;

Lo, Wen-Li ;

Liu, Ya-Chen ;

Chen, Chung-Yi .

JOURNAL OF NATURAL PRODUCTS, 2006, 69 (06) :927-933

[9] New cytotoxic butanolides from Litsea acutivena [J].

Cheng, HI ;

Lin, WY ;

Duh, CY ;

Lee, KH ;

Tsai, IL ;

Chen, IS .

JOURNAL OF NATURAL PRODUCTS, 2001, 64 (12) :1502-1505

[10] Steryl epoxide, secobutanolide and butanolides from the stem wood of Machilus zuihoensis [J].

Cheng, MJ ;

Tsai, IL ;

Lee, SJ ;

Jayaprakasam, B ;

Chen, IS .

PHYTOCHEMISTRY, 2005, 66 (10) :1180-1185

← 1 2 3 4 →