Triterpenoid saponins from a cytotoxic root extract of Sideroxylonfoetidissimum subsp. gaumeri

Evaluation of the cytotoxicity of an ethanolic root extract of Sideroxylonfoetidissimum subsp. gaumeri (Sapotaceae) revealed activity against the murine macrophage-like cell line RAW 264.7. Systematic bioassay-guided fractionation of this extract gave an active saponin-containing fraction from which four saponins were isolated. Use of 1D (¹H, ¹³C, DEPT135) and 2D (COSY, TOCSY, HSQC, and HMBC) NMR, mass spectrometry and sugar analysis gave their structures as 3-O-(β-d-glucopyranosyl-(1 → 6)-β-d-glucopyranosyl)-28-O-(α-l-rhamnopyranosyl-(1 → 3)[β-d-xylopyranosyl-(1 → 4)]-β-d-xylopyranosyl-(1 → 4)-α-l-rhamnopyranosyl-(1 → 2)-α-l-arabinopyranosyl)-16α-hydroxyprotobassic acid, 3-O-β-d-glucopyranosyl-28-O-(α-l-rhamnopyranosyl-(1 → 3)[β-d-xylopyranosyl-(1 → 4)]-β-d-xylopyranosyl-(1 → 4)-α-l-rhamnopyranosyl-(1 → 2)-α-l-arabinopyranosyl)-16α-hydroxyprotobassic acid, 3-O-(β-d-glucopyranosyl-(1 → 6)-β-d-glucopyranosyl)-28-O-(α-l-rhamnopyranosyl-(1 → 3)-β-d-xylopyranosyl-(1 → 4)[β-d-apiofuranosyl-(1 → 3)]-α-l-rhamnopyranosyl-(1 → 2)-α-l-arabinopyranosyl)-16α-hydroxyprotobassic acid, and the known compound, 3-O-β-d-glucopyranosyl-28-O-(α-l-rhamnopyranosyl-(1 → 3)[β-d-xylopyranosyl-(1 → 4)]-β-d-xylopyranosyl-(1 → 4)-α-l-rhamnopyranosyl-(1 → 2)-α-l-arabinopyranosyl)-protobassic acid. Two further saponins were obtained from the same fraction, but as a 5:4 mixture comprising 3-O-(β-d-glucopyranosyl)-28-O-(α-l-rhamnopyranosyl-(1 → 3)-β-d-xylopyranosyl-(1 → 4)[β-d-apiofuranosyl-(1 → 3)]-α-l-rhamnopyranosyl-(1 → 2)-α-l-arabinopyranosyl)-16α-hydroxyprotobassic acid and 3-O-(β-d-apiofuranosyl-(1 → 3)-β-d-glucopyranosyl)-28-O-(α-l-rhamnopyranosyl-(1 → 3)[β-d-xylopyranosyl-(1 → 4)]-β-d-xylopyranosyl-(1 → 4)-α-l-rhamnopyranosyl-(1 → 2)-α-l-arabinopyranosyl)-16α-hydroxyprotobassic acid, respectively. This showed greater cytotoxicity (IC₅₀ = 11.9 ± 1.5 μg/ml) towards RAW 264.7 cells than the original extract (IC₅₀ = 39.5 ± 4.1 μg/ml), and the saponin-containing fraction derived from it (IC₅₀ = 33.7 ± 6.2 μg/ml).     

Two Antiproliferative Triterpene Saponins from Nematostylis anthophylla from the Highlands of Central Madagascar

Investigation of the endemic Madagascan plant Nematostylis anthophylla (Rubiaceae) for antiproliferative activity against the A2780 ovarian cancer cell line led to the isolation of the known triterpene saponin randianin ( 1 ), and the two new bioactive triterpene saponins 2″‐O‐acetylrandianin ( 2 ) and 6″‐O‐acetylrandianin ( 3 ). The structures of the two new compounds were elucidated based on analysis of their 1D‐ and 2D‐NMR spectra, and mass spectrometric data. The three isolated triterpene saponins displayed moderate but selective antiproliferative activities, with IC₅₀ values of 1.2, 1.7, and 2.2 μM , respectively, against the A2780 ovarian cancer, but only weak inhibitions of the proliferation of A2058 melanoma and the H522 lung cancer cell lines.     

New Steroidal Glycosides from Rhizomes of Clintonia udensis

A total of 10 steroidal glycosides, together with three new spirostanol glycosides (6–8), a new furostanol glycoside (9), and a new cholestane glycoside (10), were isolated from the rhizomes of Clintonia udensis (Liliaceae). The structures of the new compounds were determined on the basis of extensive spectroscopic analyses, including 2-D nuclear magnetic resonance (NMR) data, and of hydrolytic cleavage followed by chromatographic or spectroscopic analyses. The isolated glycosides were evaluated for their cytotoxic activity against HL-60 leukemia cells. Spirostanol glycosides 1 and 2, and furostanol glycoside 4 showed cytotoxic activity with IC₅₀ values of 3.2±0.02, 2.2±0.12, and 2.2±0.06 μg/ml, respectively. Neither the spirostanol and furostanol saponins with a hydroxy group at C-1 (6 and 9) and C-12 (7 and 8) nor cholestane glycosides (5 and 10) exhibited apparent cytotoxic activity at a sample concentration of 10 μg/ml.     

Haemolytic acylated triterpenoid saponins from Harpullia austro-caledonica

Eight new acylated triterpenoid saponins were isolated from the stem bark of Harpullia austro-caledonica along with the known harpuloside (9). Their structures were established using 1D and 2D NMR and mass spectrometry as 3-O-beta-D-galactopyranosyl-(1-->2)-beta-D-glucuronopyranosyl-21 beta, 22 alpha-di-O-angeloylbarringtogenol C (1), 3-O-alpha-L-rhamnopyranosyl-(1-->3)-[beta-D-galactopyranosyl-(1-->2)]-beta-D-glucuronopyranosyl-21 beta, 22 alpha-di-O-angeloyl barringtogenol C (2), 3-O-alpha-L-arabinofuranosyl-(1-->3)-[beta-D-galactopyranosyl-(1-->2)]-beta-D-glucuronopyranosyl-21 beta, 22 alpha-di-O-angeloylbarringtogenol C (3), 3-O-alpha-L-arabinofuranosyl-(1-->2)-beta-D-glucuronopyranosyl-21 beta, 22 alpha-di-O-angeloylprotoaescigenin (4), 3-O-alpha-L-arabinofuranosyl-(1-->3)-[alpha-L-arabinofuranosyl-(1-->2)]-beta-D-glucuronopyranosyl-21 beta, 22 alpha-di-O-angeloyl protoaescigenin (5), 3-O-alpha-L-arabinofuranosyl-(1-->3)-[beta-D-xylopyranosyl-(1-->2)]-beta-D-glucuronopyranosyl-21 beta, 22 alpha-di-O-angeloylprotoaescigenin (6), 3-O-alpha-L-arabinofuranosyl-(1-->3)-[beta-D-glucopyranosyl-(1-->2)]-beta-D-glucuronopyranosyl-21 beta, 22 alpha-di-O-angeloylprotoaescigenin (7), 3-O-beta-D-xylopyranosyl-(1-->2)-beta-D-glucuronopyranosyl-21 beta, 22 alpha-di-O-angeloylprotoaescigenin (8). The EtOH extract of the stem bark showed in vitro cytotoxic activity against KB cells (90% at 10 microg/ml). At a concentration of 5 microg/ml, the saponin mixture showed haemolytic activity and caused 100% haemolysis of a 10% suspension of sheep erythrocytes.     

Athenolide A,a New Steroidal Lactone from the Leaves of Athenaea martiana (Solanaceae) Determined by Means of HPLC‐HR‐MS‐SPE‐NMR Analysis

Athenaea (Solanaceae) is an endemic genus belonging to the Brazilian Atlantic Rainforest. Recently, botanical investigations suggested the re‐evaluation of the generic status of the genus Athenaea as a synonym of Aureliana. In this study, the first investigation of the Athenaea genus performed on Athenaea martiana by means of HPLC‐HR‐MS‐SPE‐NMR combined with high‐resolution radical scavenging profile led to identification of several phenolic acids as radical scavengers: protocatechuic acid ( 1 ), 4‐hydroxybenzoic acid ( 2 ), caffeic acid ( 3 ), vanillic acid ( 4 ), and ferulic acid ( 6 ). Additional analysis revealed a new steroidal lactone, named athenolide A ( 9 ). Their structures were elucidated by extensive use of NMR spectroscopy as well as HR‐MS. Chemotaxonomic considerations based on these results supported the chemical relationships between the Athenaea and Aureliana genera, in agreement with the recent botanical findings.     

苦瓜总皂甙对金黄色葡萄球菌抑制作用的研究

研究苦瓜总皂甙的抑菌作用及抑菌条件。以苦瓜正丁醇浸提物为原料,研究其对金黄色葡萄球菌的抑菌作用。试验结果表明,苦瓜总皂甙对金黄色葡萄球菌的抑制作用明显,最低抑菌浓度为30 mg/mL;抑菌最适pH值范围5~8;苦瓜总皂甙的热稳定性好,在121℃处理10 min仍具有较好的抑菌活性。金黄色葡萄球菌生长曲线表明,对数生长期的金黄色葡萄球菌对苦瓜总皂甙较敏感,而对接近稳定期的菌体抑制作用较弱。     

空心莲子草营养器官结构与三萜皂苷动态积累的关系

采用组织化学定位、显微制片技术和三萜皂苷定量分析方法对空心莲子草营养器官结构与三萜皂苷类物质积累关系进行了研究。结果表明：空心莲子草宿根、根状茎、茎和叶中均有三萜皂苷物质的积累,叶和根状茎内含量十分丰富。在相同采收期内含量依次为：叶＞根状茎＞根＞茎,叶中主要积累于栅栏组织细胞内。空心莲子草的根和根状茎横切面均属于异常结构,具有成同心环状排列的三生维管束。在宿根和根状茎的次生韧皮部、栓内层、三生韧皮部和结合组织内均有三萜皂苷的分布,三生结构在宿根和根状茎中占有主要地位,是三萜皂苷积累的主要场所。在不同采收期内叶、根状茎和根中三萜皂苷的积累趋势基本一致,均随生长期的增加而递增。空心莲子草茎的横切面由表皮、皮层、维管束和髓腔组成,仅部分皮层细胞和初生韧皮部内有三萜皂苷分布。     

胡芦巴水溶性甾体皂苷的提取分离工艺研究

以薯蓣皂苷元的提取率为指标,应用L9(3^4)正交试验设计优化了从脱多糖、脱脂胡芦巴豆粉中提取甾体皂苷的工艺条件,并且筛选了ZTC澄清剂对胡芦巴甾体皂苷水提取液的澄清条件。实验结果表明,影响水提取的主次因素为：提取次数＞提取温度＞固液比＞提取时间;最佳水提取条件为：固液比为1：10,在70℃下提取3次,每次120min得出胡芦巴种子水提取液的澄清条件如下：ZTCl 1澄清剂的加入次序是先加B组分再加入A组分;澄清剂B和A的最佳用量分别为1．0g/L和O．5g／L;加入组分A或B后在80℃下作用30min即可达到澄清目的。     

复合酶解法提取三七皂苷的实验研究

以三七提取液中总皂苷的含量和提取物得率为指标,考察了乙醇回流法、渗漉法、纤维素酶解法、果胶酶解法、复合酶解法的优劣,并采用单因素法和四因素（纤维素酶用量、果胶酶用量、酶解温度、乙醇浓度）三水平正交设计法对复合酶解法提取工艺条件进行优选,得到如下较理想的提取工艺条件：纤维素酶用量为15U／g（生药）、果胶酶用量为140U／g（生药）,酶解pH值为4．5,酶解温度为50℃,乙醇浓度为80％,提取时间为2．5h。所得三七提取液中总皂苷的含量为12．01％,提取物得率为35．82％。     

秦岭产珠子参叶的达玛烷型皂甙研究(1)

从陕西省秦岭产珠子参(Panax japonicus C.A.Meyer var.major(Burk.)Wu etFeng)的叶中分离到十个新的达玛烷型四环三萜皂甙,经光谱测定和化学降解,其中四个的化学结构分别为珠子参甙(majoroside)F_1(1)、F_2(2)、F_3(3)和F_4(4)。同时,还分离到已知的人参甙(ginsenoside)Rd(5)、Re(6)、Rg_1(7)、Rg_2(8)和F_2(9)。