Chemical Constituents of Physalis alkekengi var. franchetii
Chemical Constituents of Physalis alkekengi var. franchetii
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DOI：
10.1007/s10600-015-1517-z
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发表时间：
2015-11-01
影响因子：
0.8
通讯作者：
Seo, Eun-Kyoung
中科院分区：
文献类型：
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作者：
Han, Ah-Reum;Shim, Insop;Seo, Eun-Kyoung
alkekengi L. var. franchetii （Mast.）的果实花萼牧野（茄科）在东南亚被用作治疗泌尿系统问题、哮喘、咳嗽和炎症的传统药物。在植物化学方面，已有报道报道了从franchetii中提取的多种化合物，包括physalins[2 - 5]、flavonoids[2]、megastigmane glycoids[6]和生物碱[7]。据报道，该植物的提取物和部分分离物具有多种生物活性，如抗肿瘤[3]、抗菌[4]、抗氧化[4]、细胞毒[5]和降糖活性[7]。作为我们正在进行的从传统草药中寻找生物活性化合物的研究的一部分，我们对P. alkekengi var. franchetii的果实花萼进行了植物化学研究，并分离出了五种已知的化合物。化合物1 ~ 5分别为3c， 7-二甲基槲皮素（鼠李糖苷；1）[8]、3c, 4c， 7-三甲基槲皮素(2)[9]、physalin B(3)[10]、isophysalin B(4)[11]和3e -甲氧基- 2,3 -二氢- 4,7 -二脱氢physalin B(5)[12]。已知的黄酮类化合物1和2均为首次从alkkekeni和alkekeni变种franchetii中分离得到。此外，以前从未从Physalis属中分离到1。已知的physalins 3-5先前已从alkekengi var. franchetii的果实花萼中报道。用95%的MeOH在室温下过夜提取8 kg的alkekengi var. franchetii干果花萼。将MeOH提取物（793 g）悬浮在水中，依次用己烷、乙酸乙酯和正丁醇进行分割。正己烷馏分（85 g）经硅胶柱层析（CC）用正己烷-乙酸乙酯（1:00:1）的梯度混合物洗脱，得到14个馏分（H01-H14）。馏分H08 （1.1 g）用正己烷-丙酮（4:10 0:1）硅胶CC洗脱，得到1 （40.69 mg）和10个亚馏分（H08-01 - H08-10）。馏分H08-07 （14.39 mg）在Sephadex LH-20色谱柱上用100%的MeOH得到2 （1.05 mg）。乙酸乙酯组分（17 g）用甲醇和CH的梯度混合物洗脱的硅胶CC分离
The fruit calyxes of Physalis alkekengi L. var. franchetii (Mast.) Makino (Solanaceae) have been used as a traditional medicine in South East Asia for treating urinary problems, asthma, cough, and inflammation [1]. There have been phytochemical reports on various types of compounds from P. alkekengi var. franchetii, including physalins [2–5], flavonoids [2], megastigmane glycosids [6], and alkaloids [7]. The extracts and some isolates of this plant were reported to have diverse biological activities such as antitumor [3], antibacterial [4], antioxidant [4], cytotoxic [5], and hypoglycemic activities [7]. As a part of our ongoing research to find bioactive compounds from traditional herbal medicines, a phytochemical investigation on the fruit calyxes of P. alkekengi var. franchetii has been performed and resulted in the isolation of five known compounds. Compounds 1–5 were identified as 3c, 7-dimethylquercetin (rhamnazin; 1)[8], 3c, 4c, 7-trimethylquercetin (2)[9], physalin B (3)[10], isophysalin B (4)[11], and 3E-methoxy-2, 3-dihydro-4, 7-didehydrophysalin B (5)[12] by analyses of their MS and 1D and 2D NMR data as well as by comparison of their spectroscopic data with the literature values. The known flavonoids 1 and 2 were isolated for the first time as constituents of P. alkekengi as well as P. alkekengi var. franchetii. Moreover, 1 has never been isolated previously from the genus Physalis. The known physalins 3–5 have been previously reported from the fruit calyxes of P. alkekengi var. franchetii. The dried fruit calyxes of P. alkekengi var. franchetii (8 kg) were extracted with 95% MeOH overnight at room temperature. The MeOH extract (793 g) was then suspended in water and partitioned with hexane, EtOAc, and n-BuOH, sequentially. The hexane fraction (85 g) was subjected to silica gel column chromatography (CC) eluted with gradient mixtures of hexane–EtOAc (1: 0o0: 1), affording 14 fractions (H01–H14). Fraction H08 (1.1 g) was subjected to silica gel CC eluted with hexane–acetone (4: 1o0: 1), yielding 1 (40.69 mg) and 10 subfractions (H08-01–H08-10). Fraction H08-07 (14.39 mg) was chromatographed on a Sephadex LH-20 column using 100% MeOH to afford 2 (1.05 mg). The EtOAc fraction (17 g) was separated by silica gel CC eluted with gradient mixtures of MeOH in CH