Minor secoiridoid aglycones from the low-polarity part of the traditional Chinese herb: Swertia mileensis

Abstract

Abstract:Eleven new secoiridoid aglycones involving unusual C 9 -skeleton: swerimilegenins A-F (1-6); bis-C 9 -skeleton: swerimilegenin G (7); and C 10 -skeleton: swerimilegenins H−K (8−11), as well as six known ones, were isolated from the low-polarity part of the traditional Chinese herb medicine Swertia mileensis. Their structures were determined by extensive spectroscopic data and X-ray diffraction. Biogenetically, swerimilegenin A (1) belonged to 10-nor-secoiridoid, and swerimilegenins B-F (2-6) were 1-nor-secoiridoids. Erythrocentaurin (12) and gentiogenal (15) showed moderate anti-HBV activity on HepG 2.2.15 cell line in vitro.

Biologically active secoiridoids: A comprehensive update

“…Compounds 138–143 are a group of simple secoiridoids with ring‐cracking characteristics, most of which were isolated from plants in the genus Swertia ( S. macrosperma 138 86 ; S. mileensis 139–140 85 ; S. patens 143 93 ). Rigenolides D‐E 141–142 were isolated from G. rigescens 83 and have a dienone moiety.…”

“…Depending to the position of the double bond and cleavage of the ring, aglycone can be divided into many subtypes (Figure 13). Compounds were isolated from Swertia (Swertia mileensis 110-111 85 ; Swertia macrosperma 112 86 ; Swertia cincta 115-116 87,88 ).…”

The Progress of Anti-HBV Constituents from Medicinal Plants in China

“…Two known compounds, erythrocentaurin ( 52 ) and gentiogenal ( 53 ) showed moderate anti-HBV activity on HepG2.2.15 cell line in vitro. Erythrocentaurin could inhibit the HBsAg secretion and HBV DNA replication with IC 50 values of 1.39 and 0.96 mM; gentiogenal showed activity inhibiting the secretions of HBsAg and HBeAg with IC 50 values of 3.92 and 2.99 mM, respectively [ 20 , 21 ] (Fig. 3 ).…”

Two New Linear Monoterpenoids fromSwertia mussotii

“…单萜类化合物是植物挥 发油的主要成分, 獐牙菜属植物也存在挥发油成分, 但 以不饱和脂肪酸形式存在于该属植物的链状单萜类化 合物还没有被报道, 该类型化合物在其它植物中也鲜有 报道. 化合物 3 和 4 是两个不常见的 C 9 骨架的环烯醚萜, 仅在青叶胆(Swertia mileensis)中报道过 [9] , 是首次从川 西獐牙菜中分离得到. 本课题组利用 HepG2.…”

“…本课题组利用 HepG2. 化合物 3 和 4 为已知的 C 9 骨架的环烯醚萜类化合 物, 经波谱分析并与文献中相应化合物波谱数据进行对 照, 经鉴定分别为 swerimilegenins B (3) 和 C (4) [9] . A, 300 g), 并将其用氯仿-甲醇溶解, 吸附于 550 g 硅胶, 经硅胶柱层析(18 cm×28 cm, 2500 g)用氯仿-甲 醇-水(V∶V∶V＝100∶0∶0, 95∶5∶0, 90∶10∶1, 80 ∶ 20 ∶ 2, 60 ∶ 40 ∶ 4) 依 次 洗 脱 , 得 到 6 个 组 分 (Fr.A1～Fr.A6).…”