Aquilanols A and B, Macrocyclic Humulene-Type Sesquiterpenoids from the Agarwood of Aquilaria malaccensis

被引：34

作者：

Chi Thanh Ma ^{[1
,5
]}

Eom, Taeyong ^{[4
]}

Cho, Eunji ^{[2
]}

Wu, Bo ^{[3
]}

Kim, Tae Ryong ^{[1
]}

Oh, Ki Bong ^{[2
]}

Han, Sang Beom ^{[4
]}

Kwon, Sung Won ^{[1
]}

Park, Jeong Hill ^{[1
]}

机构：

[1] Seoul Natl Univ, Coll Agr & Life Sci, Coll Pharm, Seoul 08826, South Korea

[2] Seoul Natl Univ, Coll Agr & Life Sci, Dept Agr Biotechnol, Seoul 08826, South Korea

[3] China Med Univ, Dept Chem, Shenyang 110122, Liaoning, Peoples R China

[4] Chung Ang Univ, Coll Pharm, Seoul 06974, South Korea

[5] Univ Med & Pharm, Fac Pharm, Ho Chi Minh City 700000, Vietnam

来源：

JOURNAL OF NATURAL PRODUCTS | 2017年 / 80卷 / 11期

基金：

新加坡国家研究基金会;

关键词：

2-(2-PHENYLETHYL)CHROMONE DERIVATIVES; =2-(2-PHENYLETHYL)-4H-1-BENZOPYRAN-4-ONE DERIVATIVES; CHINESE;

D O I：

10.1021/acs.jnatprod.7b00462

中图分类号：

Q94 [植物学];

学科分类号：

071001 ;

摘要：

Four new and five known sesquiterpenoids were isolated from the agarwood of Aquilaria malaccensis. Aquilanols A and B (1 and 2) have an unprecedented macrocyclic humulene structure with a bicyclic 7/10 ring system. Compound 2 was obtained as a scalemic mixture that was resolved by HPLC analysis using a chiral column. Their structures were deduced based on spectroscopic data analysis, and the absolute configurations were unambiguously determined by X-ray crystallographic data and ECD spectroscopic analysis. A putative biosynthetic pathway of these sesquiterpenoids is proposed.

引用

页码：3043 / 3048

页数：6

共 23 条

[1] HUMULANE DERIVATIVES FROM NAUPLIUS-INTERMEDIUS [J].

BOHLMANN, F ;

PAULS, A .

PHYTOCHEMISTRY, 1992, 31 (05) :1663-1665

[2] Chemical Constituents of Agarwood Originating from the Endemic Genus Aquilaria Plants [J].

Chen, Huai-Qiong ;

Wei, Jian-He ;

Yang, Jun-Shan ;

Zhang, Zheng ;

Yang, Yun ;

Gao, Zhi-Hui ;

Sui, Chun ;

Gong, Bao .

CHEMISTRY & BIODIVERSITY, 2012, 9 (02) :236-250

[3] hERG Channel Inhibitory Daphnane Diterpenoid Orthoesters and Polycephalones A and B with Unprecedented Skeletons from Gnidia polycephala [J].

De Mieri, Maria ;

Du, Kun ;

Neuburger, Markus ;

Saxena, Priyanka ;

Zietsman, Pieter C. ;

Hering, Steffen ;

van der Westhuizen, Jan H. ;

Hamburger, Matthias .

JOURNAL OF NATURAL PRODUCTS, 2015, 78 (07) :1697-1707

[4] OLEX2: a complete structure solution, refinement and analysis program [J].

Dolomanov, Oleg V. ;

Bourhis, Luc J. ;

Gildea, Richard J. ;

Howard, Judith A. K. ;

Puschmann, Horst .

JOURNAL OF APPLIED CRYSTALLOGRAPHY, 2009, 42 :339-341

[5] Theoretical studies on farnesyl cation cyclization: Pathways to pentalenene [J].

Gutta, Pradeep ;

Tantillo, Dean J. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (18) :6172-6179

[6] Anti-HIV terpenoids from Daphne aurantiaca Diels. stems [J].

Huang, Sheng-Zhuo ;

Zhang, Xuan ;

Ma, Qing-Yun ;

Zheng, Yong-Tang ;

Dai, Hao-Fu ;

Wang, Qi ;

Zhou, Jun ;

Zhao, You-Xing .

RSC ADVANCES, 2015, 5 (98) :80254-80263

[7] Daphnauranols A-C, new antifeedant sesquiterpenoids with a 5/6/7 ring system from Daphne aurantiaca [J].

Huang, Sheng-Zhuo ;

Li, Xiao-Nian ;

Ma, Qing-Yun ;

Dai, Hao-Fu ;

Li, Liang-Chun ;

Cai, Xiang-Hai ;

Liu, Yu-Qing ;

Zhou, Jun ;

Zhao, You-Xing .

TETRAHEDRON LETTERS, 2014, 55 (27) :3693-3696

[8] Anti-neuroinflammatory sesquiterpenes from Chinese eaglewood [J].

Huo, Hui-Xia ;

Zhu, Zhi-Xiang ;

Pang, Dao-Ran ;

Li, Yue-Ting ;

Huang, Zheng ;

Shi, She-Po ;

Zheng, Jiao ;

Zhang, Qian ;

Zhao, Yun-Fang ;

Tu, Peng-Fei ;

Li, Jun .

FITOTERAPIA, 2015, 106 :115-121

[9]

Lee SY, 2016, TROP FOREST, P1, DOI 10.1007/978-981-10-0833-7_1

[10] Five new eudesmane-type sesquiterpenoids from Chinese agarwood induced by artificial holing [J].

Li, Wei ;

Cai, Cai-Hong ;

Guo, Zhi-Kai ;

Wang, Hao ;

Zuo, Wen-Jian ;

Dong, Wen-Hua ;

Mei, Wen-Li ;

Dai, Hao-Fu .

FITOTERAPIA, 2015, 100 :44-49

← 1 2 3 →