Inhibitory Effects of Cucurbitane-Type Triterpenoids from Momordica charantia Fruit on Lipopolysaccharide-Stimulated Pro-Inflammatory Cytokine Production in Bone Marrow-Derived Dendritic Cells

The bitter melon, Momordica charantia L., was once an important food and medicinal herb. Various studies have focused on the potential treatment of stomach disease with M. charantia and on its anti-diabetic properties. However, very little is known about the specific compounds responsible for its anti-inflammatory activities. In addition, the in vitro inhibitory effect of M. charantia on pro-inflammatory cytokine production by lipopolysaccharide (LPS)-stimulated bone marrow-derived dendritic cells (BMDCs) has not been reported. Phytochemical investigation of M. charantia fruit led to the isolation of 15 compounds (1−15). Their chemical structures were elucidated spectroscopically (one- and two-dimensional nuclear magnetic resonance) and with electrospray ionization mass spectrometry. The anti-inflammatory effects of the isolated compounds were evaluated by measuring the production of the pro-inflammatory cytokines interleukin IL-6, IL-12 p40, and tumor necrosis factor α (TNF-α) in LPS-stimulated BMDCs. The cucurbitanes were potent inhibitors of the cytokines TNF-α, IL-6, and IL-12 p40, indicating promising anti-inflammatory effects. Based on these studies and in silico simulations, we determined that the ligand likely docked in the receptors. These results suggest that cucurbitanes from M. charantia are potential candidates for treating inflammatory diseases.     

A New Triterpenoid Saponin and a New Glycoside from Epigynum aurilum

A new triterpenoid saponin with novel sugar moiety (1), a new trisaccharide derivative (2), as well as a known monosaccharide derivative (3), were isolated from the dried stem of Epigyhum aurilum. The structures of compounds 1 and 2 were determined by MS and NMR spectram analyses.     

A New Triterpenoid from "Gualou-xiebai-baijiu-tang" Consisting of Fructus trichosanthis and Bulbus allii mtacrostemi

A new triterpenoid saponin was isolated by bioactivity-guided isolation from "Gualou-xiebai-baijiu-tang" consisting ofFructus trichosanthisi and Bulbus allii macrostemi. Its structure was determined as 3-O-β-D-galactopyranosyl-hederagenin 28-O-β-D-xylopyranosyl (1→6)- β-D-galactopyranosyl ester by means of chemical evidences and spectral analysis.     

New tri- and tetracyclic diterpenes from Euphorbia villosa

Three new tetracyclic diterpenes were isolated from the chloroform-soluble extract of Euphorbia villosa, together with one new and one known lathyrane diterpene. The structures were elucidated by means of various spectroscopic methods, including HREI-MS, HRFAB-MS, UV, and 1D and 2D NMR techniques. Spectral analyses revealed that two of the tetracyclic compounds contain the rare 5-6-6-4 fused ring system, while the third has a 5-6-7-3 fused diterpene core. Such diterpene skeletons have previously been found only in euphoractines A-E isolated from Euphorbia micractina. As a new structural feature, the diterpene framework described here has a C-2 epimer configuration. The new lathyrane diterpene is a diester of a hitherto unknown polyfunctional parent alcohol.     

Chemical constituents from Piper wallichii

Fifteen known compounds including four triterpenoids (1–4), one sterol (5), one diketopiperazine alkaloid (6) and nine phenolics (7–15) were isolated from the stems of Piper wallichii. Their structures were elucidated by means of spectroscopic analysis, and acidic hydrolysis in case of the 2-oxo-3β,19α,23-trihydroxyurs-12-en-28-oic acid β-D-glucopyranosyl ester (1). The structure of compound 1 was fully assigned by 1D and 2D NMR experiments for the first time. All isolates were tested for their antibacterial, antifungal, anti-inflammatory and antiplatelet aggregation bioactivities.     

Polymorphic forms of lupane triterpenoid betulonic aldehyde (betulonal)

The lupane triterpenoid betulonic aldehyde [also known as betulonal; systematic name: lup‐20(29)‐en‐28‐al‐3‐one, C₃₀H₄₆O₂] is a product of betulin oxidation. Crystals were obtained from hexane [form (I)] and dimethyl sulfoxide [form (II)] solutions. Forms (I) and (II) are both orthorhombic. The molecular geometric parameters in the two forms are similar, but the structures are different with respect to the crystal packing. Polymorph (I) contains two independent molecules in the asymmetric unit, while polymorph (II) contains only one molecule, which has a disordered aldehyde group [the disorder ratio is 0.769 (4):0.231 (4)]. In each molecule, the six‐membered rings have chair conformations, whereas the cyclopentane ring in each molecule adopts an envelope conformation. All the rings in the lupane nucleus are trans‐fused. The extended structures of both polymorphs are stabilized by weak intermolecular C—H...O and van der Waals interactions. Weak intramolecular C—H...O interactions are also observed.     

A new triterpene from the leaves of Craibiodendron yunnanense

A new triterpene, taraxast-20(30)-en-3β,12β-diol (1), and eight known compounds were isolated from the leaves of Craibiodendron yunnanense. Their structures were established on the basis of spectral evidence. Published in Khimiya Prirodnykh Soedinenii, No. 1, pp. 35–37, January–February, 2008.     

三萜骨架功能分子

具有独特立体结构的三萜化合物是一类重要的生物活性天然产物,在消炎、降血脂、保肝护肾、抗菌、抗肿瘤、抗真菌等方面有着重要药用价值。利用其独特手性结构、亲脂性、生物活性以及生物相容性等特性,设计合成新型功能分子,可作为药物载体,发挥其识别功能以及用于医用材料等方面具有重要的作用。本文介绍了近年来以三萜为骨架设计合成的新型功能分子在离子、分子识别和自组装性能方面研究现状及其潜在的应用前景。     

Fast analysis of triterpenoids in Ganoderma lucidum spores by ultra‐performance liquid chromatography coupled with triple quadrupole mass spectrometry

A rapid and reliable method was established for simultaneous determination of main triterpenoids in Ganoderma lucidum spores using ultra‐high‐performance liquid chromatography coupled with triple quadrupole mass spectrometry (UPLC‐TQ‐MS). The established method was validated in terms of linearity, sensitivity, precision, accuracy and stability, and was successfully applied to determine the contents of 10 main triterpenoids in different batches of G. lucidum spores. The analysis results showed that moderate levels of triterpenoids were found in G. lucidum spores. In addition, a MS full scan with a daughter ion scan experiment was performed to identify the potential derivatives of triterpenoids present in G. lucidum spores. As a result, a total of 22 triterpenoids from different G. lucidum spores were unequivocally or tentatively identified via comparisons with authentic standards and literatures. This method provides both qualitative and quantitative results without the need for repetitive UPLC‐MS analyses, thereby increasing efficiency and productivity, making it suitable for high‐throughput applications. Copyright © 2013 John Wiley & Sons, Ltd.     

A immunosuppressive triterpenoid saponin from the stems of Epigynum griffithianum

Abstract

Chemical investigation of the stems of Epigunum griffithianum led to the isolation and identification of a new triterpenoid saponin (1) and two known compounds (epigynosides A (2) and B (3)). These structures were elucidated by means of spectroscopic analysis (1D and 2D NMR, MS, UV, IR) as well as comparison with the reported data. Compound 1 was evaluated in vitro for the immunosuppressive activities on proliferation of mice splenocyte and displayed significant immunosuppressive activities compared to the positive control (dexamethasone) with the concentration at 25?μM.