Shao-Jiang Song

Five saponins from the root bark of Aralia elata

Five saponins, 3-O-[beta-D-glucopyranosyl (1-->2)-[beta-D-glucopyranosyl (1-->3)]-beta-D-glucopyranosyl]-oleanolic acid 28-O-beta-D-glucopyranosyl ester (aralia-saponin V), 3-O-[beta-D-glucopyranosyl (1-->2)-[beta-D-glucopyranosyl (1-->3)]-beta-D-glucopyranosyl]-echinocystic acid 28-O-beta-D-glucopyranosyl ester (aralia-saponin VI), 3-O-beta-D-glucopyranosyl (1-->2)-[beta-D-glucopyranosyl (1-->3)]-beta-D-glucopyranosyl]-hederagenin 28-O-beta-D-glucopyranosyl ester (aralia-saponin VII), 3-O-[beta-D-glucopyranosyl-(1-->3)-beta-D-glucopyranosyl-(1-->3)-[beta-D-glucopyranosyl-(1-->2)]-beta-D-glucopyranosyl]-caulophyllogenin 28-O-beta-D-glucopyranosyl ester (aralia-saponin VIII), 3-O-[beta-D-glucopyranosyl (1-->2)-[beta-D-glucopyranosyl(1-->3)]-alpha-L-arabinopyranosyl]-hederagenin 28-O-beta-D-glucopyranosyl ester (aralia-saponin IX), were isolated from the root bark of Aralia elata (Miq.) Seem., together with four known compounds. Their structures were determined on the basis of chemical and spectroscopic methods.

Triterpenoid saponins from Stauntonia chinensis

A new triterpenoid saponin, named stauntoside A (1) along with four known saponins (2,3,4,5) was isolated from Stauntonia chinensis DC., (Lardizabalaceae). Their structures were elucidated by spectroscopic analysis and chemical methods as 3-O-α-l-arabinopyranosyl-30-norhederagenin -28-O-β-d-glucopyranosyl-(1 → 6)-β-d-glucopyranosyl ester (1), 3-O-α-l-arabinopyranosyl-30- norhederagenin-28-O-α-l-rhamnopyranosyl-(1 → 4)-β-d-glucopyranosyl-(1 → 6)-β-d-glucopyranosyl ester (2), 3-O-α-l-rhamnopyranosyl-(1 → 2)-α-l-arabinopyranosyl-30-norhederagenin-28-O-α-l- rhamnopyranosyl-(1 → 4)-β-d-glucopyranosyl-(1 → 6)-β-d-glucopyranosyl ester (3), 3-O-α-l- arabinopyranosyl-hederagenin-28-O-α-l-rhamnopyranosyl-(1 → 4)-β-d-glucopyranosyl-(1 → 6)-β-d- glucopyranosyl ester (4), 3-O-α-l-rhamnopyranosyl-(1 → 2)-α-l-arabinopyranosyl-hederagenin -28-O-α-l-rhamnopyranosyl-(1 → 4)-β-d-glucopyranosyl-(1 → 6)-β-d-glucopyranosyl ester (5). The 1H and 13C NMR data for Glycoside L-G1 or Sinofoside A are paradox in the reported before. Thus, the structure elucidation of saponin 2, known as Glycoside L-G1 or Sinofoside A, was discussed and the unambiguous assignments were given.

Eclalbasaponin I from Aralia elata (Miq.) Seem. reduces oxidative stress-induced neural cell death by autophagy activation

Oxidative stress has been proposed to contribute to DNA damage and is involved in many neurodegenerative diseases. It has been reported that Aralia elata (Miq.) Seem. (A. elata) exhibits an anti-oxidative effect but the mechanisms underlying this protective effect are still unclear. In this study, six known triterpene saponins were isolated from the buds of A. elata, a well-known medicinal and edible plant in Northeast China. Subsequently, the anti-oxidative effects of all six triterpene saponins were screened by H2O2-induced damage in human neuronblastoma SH-SY5Y cells. Compound 6, also known as Eclalbasaponin I (EcI), was the most potent. Furthermore, the mechanism by which EcI combats H2O2-induced oxidative stress was investigated. The data suggested that EcI could down-regulate apoptosis induction and the generation of reactive oxygen species (ROS) induced by 200μM H2O2 in SH-SY5Y cells. Moreover, EcI increased the activities of antioxidant enzymes such as superoxide dismutase (SOD) and glutathione peroxides (GSH-Px), reduced the levels of malondialdehyde (MDA) to restore the antioxidant defense system, and activated the nuclear factor E2-related factor (Nrf2)/heme oxygenase 1 (HO-1) pathway to combat oxidative stress. In addition, EcI also promoted autophagy during this process. Interestingly, the protective effect was remarkably reversed by autophagy inhibitors, bafilomycin A1 (Baf) or 3-Methyladenine (3-MA). These results demonstrate that autophagy is contribute to the protective effect of EcI. Collectively, our findings provide a new insight into the potential protective effect of EcI by focusing on the role of autophagy.

Lignans from the seeds of Chinese hawthorn (Crataegus pinnatifida var. major N.E.Br.) against β-amyloid aggregation

Abstract Phytochemical investigation on the seeds of hawthorn (Crataegus spp.) led to the isolation of a new compound, (7′R, 8′R, 8S)-isolariciresinol (1), along with six known compounds (2–7). The structures of all compounds were determined based on spectroscopic data interpretation. The Aβ1–42 inhibition activity of all isolated compounds was evaluated in vitro. As a result, compounds 5 and 6 showed stronger inhibition of Aβ1–42 aggregation than curcumin, with inhibition rates of 70.59 and 68.14% at 20 μM. The possible mechanism of interaction between Aβ1–42 and the active compounds 5 and 6 was also investigated by molecular docking.

Alkaloids with neuroprotective effects from the leaves of Isatis indigotica collected in the Anhui Province, China

Six undescribed alkaloids, indiforine A-F, together with four known ones, were isolated from the leaves of Isatis indigotica Fortune. Their structures were elucidated on the basis of extensive spectroscopic analyses. The absolute configurations of indiforine A and B were determined by comparison of the experimental and calculated electronic circular dichroism spectra, as well as experimental and calculated optical rotations. The isolated alkaloids were evaluated for their neuroprotective activities against H2O2-induced cell injury in human neuroblastoma SH-SY5Y cells. The results showed that in H2O2-induced SH-SY5Y cell injury models, indiforine A and B exhibited potent neuroprotective activities. Further investigation of the most potent indiforine A by Hoechst 33258 staining and Annexin V/PI analysis demonstrated that it could protect SH-SY5Y cells from oxidative damage through inhibiting cell apoptosis.

Enantiomeric neolignans from Picrasma quassioides exhibit distinctive cytotoxicity on hepatic carcinoma cells through ROS generation and apoptosis induction

Three pairs of enantiomeric neolignans 1a/1b-3a/3b were isolated from the stems of Picrasma quassioides, and separated successfully by chiral-phase HPLC. Their structures were established by comprehensive spectroscopic analyses as well as ECD spectroscopy. The in vitro cytotoxicity of the isolates was evaluated against human hepatocellular carcinoma HepG2 and Hep3B cells. Among them, 1 and its enantiomers 1a/1b, 3 and 3a/3b displayed similar cytotoxicity in pair-wise comparison against HepG2 and Hep3B cells, and the similar effects of 2 and 2a/2b were found in Hep3B cells. Interestingly, 2a and 2b had different cytotoxic activities on HepG2 cells with IC50 values of 35.6u202fμM and 104.4u202fμM, respectively. In addition, 2 exerted middle cytotoxicity against HepG2 cells with an IC50 value of 78.6u202fμM. The different cytotoxicity between enantiomers 2a and 2b attracted our interest. To investigate the underlying mechanisms responsible for the distinct cytotoxicity, we further assessed the effects of 2a and 2b on cell cycle distribution, cell apoptosis and reactive oxygen species (ROS) generation. The results indicated that 2a had more significant effect than 2b on apoptosis induction and ROS generation, but both had no obvious effect on cell cycle of HepG2 cells. It is concluded that the different configurations of 2a/2b determined the enantioselective cytotoxicity on HepG2 cells through apoptosis induction and ROS generation.

A new cyclolignan glycoside from the tubers of Pinellia ternata

A new 2,7′-type cyclolignan glycoside, cyclolignanyingoside A (1), together with six known compounds (2–7) were isolated from the tubers of Pinellia ternata (Thunb.) Breit. The structure of 1 was elucidated on the basis of chemical and spectral analysis, including 1D, 2D NMR analyses, HR-ESI-MS, and CD spectrometry. The cytotoxic, antioxidant and tyrosinase-inhibiting activities of all the isolates were determined. However, all the isolates exhibited no activity on the selected cell lines (Hep-3B, Bcap-37, and MCF-7). In addition, compounds 1–3 and 7 exhibited strong 2,2′-azino-bis (3-ethylbenzothiazoline-6-sulphonic acid) free radical scavenging activity, and compounds 2 and 4 showed a moderate mushroom tyrsinase inhibitory activity.

Timosaponin AIII: A novel potential anti-tumor compound from Anemarrhena asphodeloides

HIGHLIGHTSTimosaponin AIII inhibits tumor cell proliferation by suppressing invasion and migration.Timosaponin AIII induces apoptosis and triggers autophagy in cancer cells.Timosaponin AIII reverses multi‐drug resistance in tumor cells through PI3K/Akt signaling pathway. ABSTRACT Timosaponin AIII, a major steroidal saponin found in Anemarrhena asphodeloides Bge., which has been widely used as anti‐pyretic, anti‐diabetic, anti‐inflammatory, anti‐platelet aggregator and anti‐depressant agents in traditional Chinese medicine. Recent pharmacological study showed that timosaponin AIII had potent cytotoxicity, which was potential to be developed as an anticancer agent, however the molecular mechanism underlying the anticancer activity has not been fully elucidated. This review aims to give a systematic summary of the study of timosaponin AIII to reveal its anti‐tumor activities by investigating invasion and migration, apoptosis, autophagy and reversing multi‐drug resistance. Furthermore, we also make an overview of the mechanisms identified till now. These meaningful findings may provide novel insights on exploiting timosaponin AIII as a new anti‐tumor agent.

Synthesis of new sarsasapogenin derivatives with antiproliferative and apoptotic effects in MCF-7 cells

Graphical abstract Figure. No caption available. HighlightsNew sarsasapogenin derivatives were synthesized and evaluated for their cytotoxicity.The structure‐activity relationship was investigated.Compound 4c exhibited the greatest cytotoxic activity against MCF‐7 cell line.Compound 4c inhibited the colony formation and induced the apoptosis of MCF‐7 cells.The mitochondrial pathway was involved in the compound 4c‐mediated apoptosis. ABSTRACT Sarsasapogenin, a kind of mainly effective component of Anemarrhena asphodeloides Bunge, possesses good antitumor properties. Two series of new sarsasapogenin derivatives were synthesized and evaluated for their cytotoxicities against three human cancer cell lines (HepG2, A549, MCF‐7) using the MTT assay. The structure‐activity relationship revealed that the N, N‐dimethylamino, pyrrolidinyl, and imidazolyl substituted at the C26 position could increase the antitumor efficacy of the 3‐oxo sarsasapogenin series of compounds. Compound 4c with pyrrolidinyl substituted at the C26 position exhibited the greatest cytotoxic activity against MCF‐7 cell line (IC50 = 10.66 &mgr;M), which was 4.3‐fold more potent than sarsasapogenin. Action mechanism investigations showed that 4c could inhibit the colony formation and induce the apoptosis of MCF‐7 cells. Further researches showed that a decrease in mitochondrial membrane potential and increases in the expression level of cleaved‐PARP and the ratio of Bax/Bcl‐2 were observed in MCF‐7 cells after treatment with 4c, suggesting that the mitochondrial pathway was involved in the 4c‐mediated apoptosis. These results show that compound 4c may serve as a lead for further optimization.

Two new sesquineolignans from the seeds of Crataegus pinnatifida and their β-amyloid aggregation inhibitory activitiy

Abstract Two new sesquineolignans, hawthornsesquinins K and L (1 and 2), were isolated from the seeds of Crataegus pinnatifida. Their structures were determined by spectroscopic analyses, including 1D, 2D NMR and HRESIMS data. All isolated compounds were tested for their β-amyloid aggregation inhibitory activity and neuroprotective effects against H2O2-induced damage in SH-SY5Y cells. The results indicated that compound 1 showed prominent inhibition of Aβ1–42 aggregation and significant neuroprotective effect on H2O2-induced cellular damage in SH-SY5Y cells.