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    188宝金博页面版: Monoterpene and tetrahydronaphthene derivatives from Senecio argunensis

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    内容提示： Monoterpene and tetrahydronaphthene derivativesfrom Senecio argunensisChao Feng Zhang, Ning Li, Lin Li, Mian Zhang*Research Department ofPharmacognosy, China Pharmaceutical University, Nanjing 210038, ChinaReceived 26 September 2008AbstractTwo new compounds, senarguines A and B, were isolated from Senecio argunensis. They were respectively identified as (Z)-3-ethylidene-9-hydroxyl-9-methyl-6,7-dioxaspiro [4.4] nonane-5,8–dione (1) and 3,6,6-trimethyl 6,7,8-tetrahydronaphtha-[1,2b]furan (2) on the basis of...

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    Monoterpene and tetrahydronaphthene derivativesfrom Senecio argunensisChao Feng Zhang, Ning Li, Lin Li, Mian Zhang*Research Department ofPharmacognosy, China Pharmaceutical University, Nanjing 210038, ChinaReceived 26 September 2008AbstractTwo new compounds, senarguines A and B, were isolated from Senecio argunensis. They were respectively identified as (Z)-3-ethylidene-9-hydroxyl-9-methyl-6,7-dioxaspiro [4.4] nonane-5,8–dione (1) and 3,6,6-trimethyl 6,7,8-tetrahydronaphtha-[1,2b]furan (2) on the basis of spectral data.# 2009 Mian Zhang. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.Keywords: Compositae; Senecio argunensis; Senarguine A; Senarguine BSenecio argunensis Turcz. (Compositae) is a perennial herb and often used for the treatment of sore throat,dysentery, and other diseases [1]. Some flavonoids were obtained from S. argunensis [2]. In our further study on thisplant, two new compounds, senarguines A and B, were isolated and respectively identified as (Z)-3-ethylidene-9-hydroxyl-9-methyl-6,7-dioxaspiro [4.4] nonane-5,8-dione (1) and 3,6,6-trimethyl 6,7,8-tetrahydronaphtha-[1,2b]furan (2) (Fig. 1) on the basis of spectral data (Table 1).The materials of S. argunensis were collected in Tonghua County of Jilin province, China, in July 2005, andauthenticated by Professor Mian Zhang, Department of Pharmacognosy, China Pharmaceutical University, where avoucher specimen of this plant (No. SA-2005-07) has been deposited.The air-dried herbs of S. argunensis (4.8 kg) were extracted with hot 90% EtOH (three times, five volumes, each25 L), followed by solvent evaporation under reduced pressure to yield a dark residue (1600 g). The residue wassuspended in water and partitioned with petroleum ether, CHCl3, EtOAc and n-BuOH successively to give threefractions. An aliquot ofthe EtOAc-soluble fraction (200 g) was subjected to silica gel column chromatography elutedwith CHCl3–MeOH (100:1–50:50) to yield seven fractions. Compounds 1 (26.2 mg) and 2 (11 mg) were obtainedfrom the fr. II after repeated silica gel chromatography (petroleum ether–EtOAc, 25:1–15:1) and Sephadex LH-20chromatography with CHCl3–MeOH (1:1).Compound 1 was obtained as white needle crystal (petroleum ether–acetone). ½a?Dgave coloration with ammonia vapor but not with 10% H2SO4ethanol solution on thin-layer chromatography. Themolecular formulawas determined as C10H12O5from the quasi-molecular ion peak at m/z 235.0578 [M + Na]+(calcd.235.0577) in HR-ESIMS. UV spectrum showed maximal absorption at 222 nm. The IR spectrum indicated that20À 103 (c 1.45, MeOH). Itwww.elsevier.com/locate/ccletAvailable online at www.sciencedirect.comChinese Chemical Letters 20 (2009) 598–600* Corresponding author.E-mail address: mianzhang@hotmail.com (M. Zhang).1001-8417/$ –see front matter # 2009 Mian Zhang. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.doi:10.1016/j.cclet.2009.01.017万方数据

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