Structurally Diverse Highly Oxygenated Triterpenoids from the Roots of Ailanthus altissima and Their Cytotoxicity

被引：20

作者：

Bai, Wei ^{[1
]}

Yang, Hong-Ying ^{[1
]}

Jiao, Xing-Zhi ^{[1
]}

Feng, Ke-Na ^{[2
,3
]}

Chen, Jian-Jun ^{[1
]}

Gao, Kun ^{[1
]}

机构：

[1] Lanzhou Univ, State Key Lab Appl Organ Chem, Coll Chem & Chem Engn, Lanzhou 730000, Gansu, Peoples R China

[2] Chinese Acad Sci, State Key Lab Phytochem & Plant Resources West Ch, Kunming 650201, Yunnan, Peoples R China

[3] Chinese Acad Sci, Yunnan Key Lab Nat Med Chem, Kunming Inst Bot, Kunming 650201, Yunnan, Peoples R China

来源：

JOURNAL OF NATURAL PRODUCTS | 2018年 / 81卷 / 08期

基金：

中国国家自然科学基金;

关键词：

BARRIGENOL-LIKE TRITERPENOIDS; XYLOCARPUS-GRANATUM; APOTIRUCALLANE; TIRUCALLANE; QUASSINOIDS; PROTOLIMONOIDS; SIMAROUBACEAE; CONSTITUENTS; NMR;

D O I：

10.1021/acs.jnatprod.8b00208

中图分类号：

Q94 [植物学];

学科分类号：

071001 ;

摘要：

Ten new triterpenoids, ailanaltiolides A-J (1-10), and three known analogues (11-13) were isolated from the roots of Ailanthus altissima. Compounds 1-7 are apotirucallane-type, compounds 8 and 9 are tirucallane-type, and compound 10 is a trinordammarane-type triterpenoid. This is the first study indicating the genus Ailanthus as a potential source for apotirucallane derivatives, which contain an alpha,beta-unsaturated-epsilon-lactone A-ring and diversely modified C-17 side chains. Spectroscopic data interpretation, electronic circular dichroism analysis, and X-ray crystallographic data defined the structures and absolute configurations of these triterpenoids. Compounds 2, 7, and 8 showed cytotoxicity against four tumor cell lines (HeLa, 786-O, HepG2, and A549). In particular, compound 2 exhibited the highest activity against 786-O cells with an IC50 value of 8.2 mu M in vitro.

引用

页码：1777 / 1785

页数：9

共 38 条

[11] Protolimonoids and Limonoids from the Chinese Mangrove Plant Xylocarpus granatum [J].

Cui, Jianxin ;

Deng, Zhiwei ;

Xu, Minjuan ;

Proksch, Peter ;

Li, Qingshan ;

Lin, Wenhan .

HELVETICA CHIMICA ACTA, 2009, 92 (01) :139-150

[12] ON ENANTIOMORPH-POLARITY ESTIMATION [J].

FLACK, HD .

ACTA CRYSTALLOGRAPHICA SECTION A, 1983, 39 (NOV) :876-881

[13] Tirucallane, apotirucallane, and octanorapotirucallane Triterpenes of Simarouba amara [J].

Grosvenor, Sumieya N. J. ;

Mascoll, Keisha ;

McLean, Stewart ;

Reynolds, William F. ;

Tinto, Winston F. .

JOURNAL OF NATURAL PRODUCTS, 2006, 69 (09) :1315-1318

[14] Ailanthone targets p23 to overcome MDV3100 resistance in castration-resistant prostate cancer [J].

He, Yundong ;

Peng, Shihong ;

Wang, Jinhua ;

Chen, Huang ;

Cong, Xiaonan ;

Chen, Ang ;

Hu, Meichun ;

Qin, Min ;

Wu, Haigang ;

Gao, Shuman ;

Wang, Liguo ;

Wang, Xin ;

Yi, Zhengfang ;

Liu, Mingyao .

NATURE COMMUNICATIONS, 2016, 7

[15] Tetracyclic triterpenoids and terpenylated coumarins from the bark of Ailanthus altissima ("Tree of Heaven") [J].

Hong, Zhi-Lai ;

Xiong, Juan ;

Wu, Shi-Biao ;

Zhu, Jing-Jing ;

Hong, Jun-Lin ;

Zhao, Yun ;

Xia, Gang ;

Hu, Jin-Feng .

PHYTOCHEMISTRY, 2013, 86 :159-167

[16] Anti-inflammatory Terpenoids from the Leaves and Twigs of Dysoxylum gotadhora [J].

Jiang, Kan ;

Chen, Lu-Lin ;

Wang, Shu-Fang ;

Wang, Yi ;

Li, Ya ;

Gao, Kun .

JOURNAL OF NATURAL PRODUCTS, 2015, 78 (05) :1037-1044

[17] A TWO-DIMENSIONAL NMR-STUDY OF ANGELIC AND TIGLIC ACID [J].

JOSEPHNATHAN, P ;

WESENER, JR ;

GUNTHER, H .

ORGANIC MAGNETIC RESONANCE, 1984, 22 (03) :190-191

[18]

Liu JiMei Liu JiMei, 2013, Chemistry and Industry of Forest Products, V33, P121

[19] Three new apo-tirucallols with six-membered hemiacetal from Meliaceae [J].

Luo, XD ;

Wu, SH ;

Wu, DG ;

Ma, YB ;

Qi, SH .

TETRAHEDRON, 2002, 58 (33) :6691-6695

[20] Tirucallane-type triterpenoids: nmr and X-ray diffraction analyses of 24-epi-piscidinol A and piscidinol A [J].

McChesney, JD ;

Dou, JH ;

Sindelar, RD ;

Goins, DK ;

Walker, LA ;

Rogers, RD .

JOURNAL OF CHEMICAL CRYSTALLOGRAPHY, 1997, 27 (05) :283-290

← 1 2 3 4 →