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Molecules 2012, 17(12), 13910-13916; doi:10.3390/molecules171213910
Article

A New Prenylated Naphthoquinoid from the Aerial Parts of Clinopodium chinense (Benth.) O. Kuntze

1,†
, 1,†
, 1
, 1,2
, 1,*  and 3
1 Key Laboratory of Bioactive Substances and Resources Utilization of Chinese Herbal Medicine, Ministry of Education, Institute of Medicinal Plant Development, Chinese Academy of Medical Sciences & Peking Union Medical College, Beijing 100193, China 2 Department of Pharmacy, School of Pharmacy, Hebei United University, Tangshan 063000, China 3 Beijing Hong Tai Chi Chung Medical Technology Co., Ltd., Beijing 102600, China These authors contributed equally to this work.
* Author to whom correspondence should be addressed.
Received: 19 October 2012 / Revised: 16 November 2012 / Accepted: 19 November 2012 / Published: 23 November 2012
(This article belongs to the Section Metabolites)
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Abstract

A new prenylated naphthoquinoid, named (3R,4aR,10bR)-3,10-dihydroxy-2,2-dimethyl-3,4,4a,10b-tetrahydro-2H-naphtho[1,2-b]-pyran-5H-6-one (1), was isolated from the aerial parts of Clinopodium chinense (Benth.) O. Kuntze, together with six known compounds: apigenin (2), luteolin (3), neoeriocitrin (4), naringenin (5), narirutin (6), and didymin (7). Neoeriocitrin was isolated for the first time from the species C. chinense. Their structures were elucidated by spectroscopic methods, including 1D, 2D (1H-1H-COSY, HSQC, HMBC and NOESY) NMR, HR-ESI-MS. The absolute configuration of 1 was determinated using the CD method. We highlight that the structure of 1 is characterized by a rarely seen prenylated naphthoquinoid framework.
Keywords: Clinopodium chinense (Benth.) O. Kuntze; prenylated naphthoquinoid; (3R,4aR,10bR)-3,10-dihydroxy-2,2-dimethyl-3,4,4a,10b-tetrahydro-2H-naphtho[1,2-b]-pyran- 5H-6-one; CD Clinopodium chinense (Benth.) O. Kuntze; prenylated naphthoquinoid; (3R,4aR,10bR)-3,10-dihydroxy-2,2-dimethyl-3,4,4a,10b-tetrahydro-2H-naphtho[1,2-b]-pyran- 5H-6-one; CD
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

Zhong, M.; Sun, G.; Zhang, X.; Sun, G.; Xu, X.; Yu, S. A New Prenylated Naphthoquinoid from the Aerial Parts of Clinopodium chinense (Benth.) O. Kuntze. Molecules 2012, 17, 13910-13916.

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