Five Pairs of Meroterpenoid Enantiomers from Rhododendron capitatum

被引：45

作者：

Liao, Hai-Bing ^{[1
]}

Huang, Guang-Hui ^{[1
]}

Yu, Mei-Hua ^{[1
]}

Lei, Chun ^{[1
]}

Hou, Ai-Jun ^{[1
,2
]}

机构：

[1] Fudan Univ, Dept Pharmacognosy, Sch Pharm, 826 Zhang Heng Rd, Shanghai 201203, Peoples R China

[2] Fudan Univ, State Key Lab Med Neurobiol, 826 Zhang Heng Rd, Shanghai 201203, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 82卷 / 03期

基金：

中国国家自然科学基金;

关键词：

FAMILY; ACID;

D O I：

10.1021/acs.joc.6b02800

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Chemical investigation on the aerial parts of Rhododendron capitatum resulted in the discovery of five enantiomeric pairs of new meroterpenoids, (+)-/(-)-rhodonoids C (1a and 1b), E (3a and 3b), F (4a and 4b), and (-)-/(+)-rhodonoids D (2a and 2b) and G (5a and 5b). These enantiomeric pairs existed as partial racemates in a plant and were obtained by chiral HPLC separation. Their structures with absolute configurations were assigned by spectroscopic data, single-crystal X-ray diffraction, and ECD analysis. Compounds 1a and 1b are the first pair of meromonoterpenes incorporating an unprecedented 6/6/6/5 ring system, and la showed antiviral activity against herpes simplex virus type 1 (HSV-1) in vitro. Compounds 2a and 2b are the first examples of meromonoterpenes featuring a unique 6/6/5/5 ring system.

引用

页码：1632 / 1637

页数：6

共 18 条

[1] Meroterpenoids produced by fungi [J].

Geris, Regina ;

Simpson, Thomas J. .

NATURAL PRODUCT REPORTS, 2009, 26 (08) :1063-1094

[2]

Itoh T, 2010, NAT CHEM, V2, P858, DOI [10.1038/NCHEM.764, 10.1038/nchem.764]

[3] Tetracyclic Chromane Derivatives from Rhododendron anthopogonoides [J].

Iwata, Naoki ;

Kitanaka, Susumu .

JOURNAL OF NATURAL PRODUCTS, 2010, 73 (07) :1203-1206

[4]

Jia M. R, 2005, ZHONGGUO MINZU YAOZH, P516

[5] C-13 NUCLEAR MAGNETIC-RESONANCE SPECTRA OF CANNABICHROMENE, CANNABICITRAN, AND CANNABICYCLOL AND THEIR ANALOGS [J].

KANE, VV ;

MARTIN, AR ;

PETERS, JA ;

CREWS, P .

JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (10) :1793-1796

[6] Isolation of rhododaurichromanic acid B and the anti-HIV principles rhododaurichromanic acid A and rhododaurichromenic acid from Rhododendron dauricum [J].

Kashiwada, Y ;

Yamazaki, K ;

Ikeshiro, Y ;

Yamagishi, T ;

Fujioka, T ;

Mihashi, K ;

Mizuki, K ;

Cosentino, LM ;

Fowke, K ;

Morris-Natschke, SL ;

Lee, KH .

TETRAHEDRON, 2001, 57 (08) :1559-1563

[7] Formal [3+3] cycloaddition approach to chromenes and chromanes.: Concise total syntheses of (±)-rhododaurichromanic acids A and B and methyl (±)-daurichromenic ester [J].

Kurdyumov, AV ;

Hsung, RP ;

Ihlen, K ;

Wang, JS .

ORGANIC LETTERS, 2003, 5 (21) :3935-3938

[8] Mollanol A, a Diterpenoid with a New C-Nor-D-homograyanane Skeleton from the Fruits of Rhododendron molle [J].

Li, Yong ;

Liu, Yun-Bao ;

Liu, Yang-Lan ;

Wang, Chen ;

Wu, Lian-Qiu ;

Li, Li ;

Ma, Shuang-Gang ;

Qu, Jing ;

Yu, Shi-Shan .

ORGANIC LETTERS, 2014, 16 (16) :4320-4323

[9] Grayanoids from the Ericaceae family: structures, biological activities and mechanism of action [J].

Li, Yong ;

Liu, Yun-Bao ;

Yu, Shi-Shan .

PHYTOCHEMISTRY REVIEWS, 2013, 12 (02) :305-325

[10] Two Enantiomeric Pairs of Meroterpenoids from Rhododendron capitatum [J].

Liao, Hai-Bing ;

Lei, Chun ;

Gao, Li-Xin ;

Li, Jing-Ya ;

Li, Jia ;

Hou, Ai-Jun .

ORGANIC LETTERS, 2015, 17 (20) :5040-5043

← 1 2 →