西南远志中4个新的三萜皂苷

目的 对西南远志Polygala crotalarioides的化学成分进行研究.方法 运用硅胶、RP-18、Sephadex LH-20、HPLC半制备等柱色谱方法分离西南远志的化学成分,根据理化性质和波谱数据鉴定化合物的结构.结果 从西南远志根中分离得到4个齐墩果酸型皂苷类化合物,分别鉴定为3-O-β-D-葡萄糖基远志皂苷元28-O-β-D-木糖基-(1→4)-α-L-鼠李糖基-(1→2)- [β-D-葡萄糖基-(1→3)]-β-D-岩藻糖基酯(1)、3-O-β-D-葡萄糖基远志皂苷元28-O-β-D-木糖基-(1→4)-α-L-鼠李糖基-(1→2)-[6- O-乙酰基-β-D-葡萄糖基-(1→3)]-[4-O-(E/Z)-对甲氧基肉桂酰基]-β-D-岩藻糖基酯(2)、3-O-β-D-葡萄糖基远志皂苷元28-O- β-D-木糖基-(1→4)-α-L-鼠李糖基-(1→2)-[6-O-乙酰基-β-D-葡萄糖基-(1→3)]-[4-O-(E/Z)-3″,4″-二甲氧基肉桂酰基]-β-D-岩藻糖基酯(3)和3-O-β-D-葡萄糖基远志皂苷元28-O-β-D-木糖基-(1→4)-α-L-鼠李糖基-(1→2)-[6-O-乙酰基-β-D-葡萄糖基-(1→3)]- [4-O-(E/Z)-3″,4″,5″-三甲氧基肉桂酰基]-β-D-岩藻糖基酯(4).结论 化合物1～4均为新化合物,分别命名为西南远志苷C、(E/Z)-西南远志苷D、E、F.其中化合物2～4为顺反异构体,因其构型原因,未能将其有效分离.     

东北铁线莲中皂苷类化学成分研究

目的研究东北铁线莲Clematis manshurica的化学成分。方法采用硅胶柱色谱、凝胶色谱及高压制备色谱等方法对东北铁线莲的三萜皂苷类成分进行分离纯化,并通过其理化性质及波谱数据对分离得到的化合物进行结构表征。结果从东北铁线莲中共分离得到10个齐墩果烷型三萜皂苷类化合物,分别鉴定为威灵仙皂苷L(1)、clematichinenosideA(2)、clematochinenoside F(3)、clematernoside A(4)、clematichinenoside B(5)、clematichinenoside C(6)、clematomandshurica saponin B(7)、clematomandshurica saponin D(8)、clematomandshurica saponin C(9)、huzhangoside B(10)。结论化合物1为新的三萜皂苷类化合物,2～6为首次从该植物中分离得到。     

Cytotoxic triterpenoid saponins from the defatted seeds of Camellia oleifera Abel

Five new oleanane-type triterpenoid saponins, oleiferasaponins D₁–D₅ (1–5), were isolated from the defatted seeds of Camellia oleifera Abel. Their structures were elucidated by spectroscopic and chemical methods. The cytotoxic activities of compounds 1–5 were evaluated against five human tumor cell lines (HCT-116, HepG2, BGC-823, NCI-H1650, and A2780). Compounds 1–2 exhibited cytotoxic activity against five human cancer cell lines, with IC₅₀ values ranging from 3.31 to 10.23 μM. Compounds 3–5 showed moderate cytotoxic activities toward the tested cell lines.     

Oleanane derivatives for pharmaceutical use: a patent review (2000-2016)

Introduction: Oleanolic acid has been considered a good start molecule for synthetic exploitation. Thus hundreds of oleanane triterpenoids have been synthesized and patented.

Also many oleanane saponins have been patented for their biological activities and possible pharmaceutical use.

Areas covered: Patents reporting the biological activities of oleanane derivatives and saponins with oleanane-type aglycones were examined. Among the synthesized oleanane derivatives, the most promising seem to be 2-cyano-3,12-dioxoolean-1,9(11)-dien-28-oic acid derivatives which interfere with many pathways involved in inflammation, oxidative stress and cell proliferation. Regarding oleanane-type saponins, several patents claiming their antiproliferative activity or their possible use as adjuvants in vaccines, were reported.

Expert opinion: Despite the great number of synthesized oleanane triterpenoids, only CDDO-Me entered clinical development as a possible drug for the treatment of chronic kidney disease (CKD) but a phase 3 clinical trial was terminated due to heart-related adverse effects. Further phase 2 clinical trials of CDDO-Me are in progress for the treatment of CKD and PAH (pulmonary arterial hypertension) patients without heart-related risk factors. Additional investigations leading to compounds with an improved activity/toxicity profile along with well-designed preclinical and clinical trials are needed. Regarding oleanane-type saponins, the real perspective seems to be as adjuvants in vaccines.     

Triterpene saponins of Maesa lanceolata stem wood

Phytochemical analysis of aqueous MeOH extract of Maesa lanceolata stem wood has led to the isolation of four new triterpene saponins characterized as 16α,21β-diacetoxy-22α-angeloyl-28-hydroxyolean-12-ene 3-O-[α-rhamnopyranosyl-(1″″ → 6?)-β-glucopyranosyl-(1? → 3′)][β-glucopyranosyl-(1″ → 2′)]-β-glucuronopyranoside (1), 16α-acetoxy-21β-hydroxy-22α-angeloyl-13β,28-oxydoolean-28α-ol 3-O-[α-rhamnopyranosyl-(1″″ → 6?)-β-glucopyranosyl-(1? → 4′)][β-glucopyranosyl-(1″ → 2′)]-α-arabinopyranoside (2), 16α-acetoxy-21β,22α-diangeloyl-13β,28-epoxyoleanane 3-O-[α-rhamnopyranosyl-(1″″ → 6?)-β-glucopyranosyl-(1? → 4′)][β-glucopyranosyl-(1″ → 2′)]-β-xylopyranoside (3), and 16α,22α-diacetoxy-13β,28-oxydoolean-28α-ol 3-O-[β-glucopyranosyl-(1″ → 2′)][β-glucopyranosyl-(1? → 3′)]-β-glucuronopyranoside (4), together with the known compounds β-acetylamyrin, physcion, emodin, chrysophanol, ursolic acid, 16α-hydroxy-12-oleanene 3-O-glucoside, β-amyrin, sitosterol 3-O-β-glucoside, stigmasterol, and 3β,28-dihydroxyolean-12-ene. Their structural elucidation was accomplished by homo- and heteronuclear 2D NMR technique as well as comparison with data from known compounds. The in vitro antibacterial activity of the aqueous MeOH extract was also investigated and zones of inhibition ranging from 32 ± 1.1 to 14 ± 0.2 mm were observed. Among the isolates, compound 1 was the most active with an minimum inhibitory concentration value of 25 μg/ml against Staphylococcus aureus.