Phenolic Glycosides from Orostachys malacophylla
Phenolic Glycosides from Orostachys malacophylla
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DOI：
10.1007/s10600-022-03784-w
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发表时间：
2022-07
影响因子：
0.8
通讯作者：
Jingdong Zhang;Xiaoyong Zhang;Sihong Wang
中科院分区：
文献类型：
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作者：
Jingdong Zhang;Xiaoyong Zhang;Sihong Wang
Orostachys属通常用于观赏目的[1，2]。然而，已经开发了各种商业化的瓦松属原料、粉末、小袋和片剂形式，并在超市中销售[3]。此外，干燥的瓦松属物种很难通过肉眼区分。因此，有必要分离化学成分以区分物种，以评估瓦松属物种食用的安全性[4]。目前，对瓦松的化学成分、抗氧化活性、脂肪肝状况、脂质积累和活性氧的产生等方面进行了研究。菲施。已被分离和分析[5-9]。在我们对O. [10-12]，采用α-葡萄糖苷酶活性指导的方法，对淡竹叶中的酚苷类成分进行了研究。首次从野牡丹的乙酸乙酯提取物中分离得到6个化合物：6-O-乙酰熊果苷（1，17.5 mg）、对羧基苯基-β-D-吡喃葡萄糖苷（2，8.0 mg）、对羟基苯基-α-L-吡喃鼠李糖苷（3，4.0 mg）、水仙酸（4，8.2 mg）、熊果苷（5，17.5 mg）和对羧基苯基-6 ′-O-乙酸酯-β-D-吡喃葡萄糖苷（6，8.4 mg）。经RP-18柱层析纯化。化合物6的NMR特征信号与化合物2的骨架一致。因此，推断化合物6基于化合物2的数据。在化合物2骨架的基础上只多了一个乙酰基。化合物6经鉴定为对羧基苯基-6 ′-O-乙酸酯-β-D-吡喃葡萄糖苷。化合物1-6被测定为对α-葡萄糖苷酶的抑制活性[13]。化合物的抑制活性（IC_（50））分别为465.4、42.0、482.8、64.6、831.1和18.0 μmol/L。化合物2、4和6具有中等的α-糖苷酶抑制活性，是植物中不常见的化合物。有趣的是，这类化学特征是在瓦松属植物中首次发现的，可以被认为是瓦松属植物的特征成分。一般评论与我们以前发表的论文一致[10-12]。乙酸乙酯萃取物经硅胶柱层析（120× 10 cm，硅胶75 μm），二氯甲烷-甲醇（100：11：1）洗脱，得到11个亚组分（Frs.第1-11段）。将级分10（0.5g）进一步施加到具有甲醇-水梯度的YMC* GEL ODS-A柱上以获得六种化合物。根据先前报告的程序测定α-葡糖苷酶抑制活性[13]。
The genus Orostachys is commonly used for ornamental purposes [1, 2]. However, various commercial Orostachys ingredients in raw, powder, pouch and tablet forms have been developed and sold in supermarkets [3]. In addition, dried Orostachys species are difficult to distinguish by the naked eye. Therefore, it is necessary to isolate chemical components to discriminate the species in order to assess the safety of Orostachys species for eating [4]. So far, some chemical constituents, antioxidant activity, fatty-liver conditions, lipid accumulation and reactive oxygen species production of Orostachys malacophylla (Pall.) Fisch. have been isolated and analyzed [5–9]. In our continued phytochemical studies of O. malacophylla [10–12], through an α-glucosidase activity-guided method, phenolic glycoside constituents were investigated. The six compounds, 6-O-acetylarbutin (1, 17.5 mg), p-carboxyphenyl-β-D-glycopyranoside (2, 8.0 mg), p-hydroxyphenyl-α-L-rhamnopyranoside (3, 4.0 mg), cissusic acid (4, 8.2 mg), arbutin (5, 17.5 mg), and p-carboxyphenyl-6′-O-acetate-β-D-glycopyranoside (6, 8.4 mg) were first isolated from the ethyl acetate extract of O. malacophylla, purifying by RP-18 column chromatography. The NMR featured signals of compound 6 that were consistent with the compound 2 skeleton. Consequently, compound 6 is inferred to be based on the data of compound 2. There is merely an extra acetyl on the basis of the skeleton of compound 2. Thus, compound 6 was identified as p-carboxyphenyl-6′-O-acetate-β-D-glycopyranoside. Compounds 1–6 were assayed as inhibitory activities for α-glucosidase [13]. Among the compounds in the series, inhibitory activities with IC50 values are 465.4, 42.0, 482.8, 64.6, 831.1, and 18.0 μmol/L, respectively. Compounds 2, 4, and 6 with moderate α-glycosidase inhibitory activity were uncommon chemical compositions in plant species. Interestingly, this type of chemical feature was the first to be discovered in the genus Orostachys, and could be considered a characteristic component of O. malacophylla.General comments are consistent with our previously published papers [10–12]. The ethyl acetate extract was subjected to column chromatography using silica gel (120× 10 cm, silica gel 75 μm), and eluted with dichloromethane–methanol (100: 1–1: 1) to obtain 11 subfractions (Frs. 1–11). Fraction 10 (0.5 g) was further applied to YMC* GEL ODS-A column with a gradient of methanol–water to obtain six compounds. The α-glucosidase inhibitory activity was determined according to the procedures previously reported [13].