Root Barks Of Periploca Sepium Research Articles

C21 steroidal glycosides from the root bark of Periploca sepium and their NO production inhibitory and cytotoxic activity

A series of C21 steroidal glycosides were isolated from the root bark of Periploca sepium, including a new compound, perisepiumoside A1 (1), and six known compounds (2-7). Their structures were elucidated by analysis of HR-ESI-MS, and 1D and 2D NMR spectroscopic data. All these compounds were tested for their NO production inhibitory activity in LPS-stimulated RAW 264.7 cells. Results showed that these C21 steroidal glycosides could remarkably inhibit NO production, particularly 1 and 2 with IC50 values of 30.81 ± 0.18 μM and 44.39 ± 0.21 μM, respectively. In addition, the cytotoxicity of these compounds was measured on A549, MCF-7, and HeLa cancer cell lines. Among them, compounds 1 and 7 displayed cytotoxicity against the A549 cell line with IC50 values of 28.41 ± 0.12 μM and 39.06 ± 0.05 μM, respectively.

A simple "turn-on" fluorescence sensor for salicylaldehyde skeleton based on switch of PET-AIE effect.

The selective detection of salicylaldehyde skeleton is of great significance in phytochemistry and biological research but rarely reported. In this research, a simple and highly selective "turn-on" fluorescence sensor (CDB-Am) for salicylaldehyde skeleton was developed based on switch of photoinduced electron transfer (PET) and aggregation-induced emission (AIE). CDB-Am bearing amino-cyanodistyrene structure responded to salicylaldehyde in the range of 3.1 to 40μM with a detection limit of 0.94μM. The sensing process of formation of Schiff-base adduct CDB-SA was confirmed by 1H NMR, MS, and FT-IR spectra, revealing that a recovered AIE property accounted for the turn-on fluorescence response of CDB-Am and the intramolecular hydrogen bonding played a crucial role in the disruption of PET process. This sensing ability was successfully applied for both fluorescence qualitative test of salicylaldehyde skeleton on TLC analysis and quantitative detection of salicylaldehyde skeleton with good accuracy in the root bark of Periploca sepium, suggesting the extensive applications in phytochemistry and traditional Chinese herbal medicine. Furthermore, CDB-Am exhibited the first excellent fluorescence imaging ability in detecting salicylaldehyde skeleton in a living system. This work supplied a new strategy of preparing a novel "turn-on" fluorescence probe for detecting salicylaldehyde skeleton in complex environments and living bodies.

Minor immunosuppressive spiroorthoester group-containing pregnane glycosides from the root barks of Periploca sepium

LC-MS guided chemical investigation of the periploside-rich extract of the root barks of Periploca sepium afforded six new minor pregnane glycosides, named periplosides A1−A6 (1–6). Their structures were characterized on the basis of extensive spectroscopic analysis. Compounds 1–6 were evaluated for their inhibitory activities against the proliferation of T and B lymphocytes in vitro, among them, compound 5 exhibited significant inhibitory activities and the most favorite selective index (SI) values against the proliferation of T lymphocyte (IC50 = 0.30 μM, SI = 176) and B lymphocyte (IC50 = 0.55 μM, SI = 97).

Five new polyphenolic derivatives with antimicrobial activities from the root barks of Periploca sepium

Five new polyphenolic derivatives, sepiumols A-E (1–5), were isolated from the root barks of Periploca sepium. Their structures were elucidated by interpretation of NMR spectroscopic and mass spectrometric data. Compounds 1, 3 and 5 were found to exhibit significant antifungal activity, particularly for 3 with the remarkable activity against Gibberella saubinetii and Alternaria longipes with MIC values of 1.56 and 3.13 μg/mL (ketoconazole: 0.78 μg/mL), respectively. In addition, compounds 1, 3 and 5 also displayed significant antibacterial activity against methicillin-resistant Staphylococcus aureu with MIC values of 12.50–25 μg/mL (ciprofloxacin: 0.78 μg/mL).

Absolute Configuration of Periplosides C and F and Isolation of Minor Spiro-orthoester Group-Containing Pregnane-type Steroidal Glycosides from Periploca sepium and Their T-Lymphocyte Proliferation Inhibitory Activities.

Further phytochemical investigation of the root bark of Periploca sepium afforded nine new spiro-orthoester group-containing pregnane-type glycosides termed periplosides O-V and 3-O-formyl-periploside A. The structures of these glycosides along with the absolute configuration of the unique seven-membered formyl acetal-bridged spiro-orthoester function and the 4,6-dideoxy-3-O-methyl-Δ3-2-hexosulosyl moiety were elucidated on the basis of spectroscopic data interpretation and chemical transformation. The absolute configurations of the major compounds periplosides C and F were established by single-crystal X-ray diffraction analysis. The isolated compounds were evaluated for their inhibitory activities against the proliferation of T-lymphocytes. As a result, periploside C, the most abundant glycoside containing a spiro-orthoester moiety found in the plant, exhibited the most favorite selective index value (SI = 82.5). The length and constitution of the saccharide chain in the periplosides were found to influence the inhibitory activity and the SI value.

C21 steroidal glycosides and oligosaccharides from the root bark of Periploca sepium

Four new C21 steroidal glycosides (1–4), named perisepiumosides FI (1–4) together with six known steroidal glycosides (5–10) and four oligosaccharides (11–14), were isolated from the root bark of Periploca sepium. Their structures were characterized on the basis of 1D and 2D–NMR spectroscopic data as well as HR-ESI-MS analysis. The evaluation of inhibition activity against human A-549 and HepG2 cell lines indicated that compounds 2, 8, 10 and 13 showed different levels of cytotoxic activities with IC50 values ranging from 0.61 to 7.86μM.

Insecticidal Pregnane Glycosides from the Root Barks of Periploca sepium

To explore novel lead compounds for botanical pesticides from natural sources, a new pregnane glycoside (periplocoside) P2 as well as its isomer, a known pregnane glycoside P1, were isolated from the root barks of Periploca sepium using a bioactivity-guided method, and their structures were confirmed by ID NMR, 2D NMR, IR, ESI-MSn and HRMS. Their insecticidal activities were evaluated against 3rd instar larvae of M separata, and the results indicated that P2 exhibited excellent insecticidal activity with LC₅₀ values of 2.9 and 2.2 mg/mL after 24 and 48 h, respectively, much lower than those of the positive control celangulin-V (24.7 and 21.0 mg/mL after 24 and 48 h, respectively). This work demonstrated that pregnane glycosides from Periploca sepium could be promising lead compounds for developing botanical pesticides urgently needed in agriculture.

A new pregnane glycoside from the root barks of Periploca sepium

Three compounds were isolated from the root barks of Periploca sepium. Their structures have been identified from physicochemical evidence and by spectral methods (MS, 2D NMR, and 1D TOCSY). These compounds are a new pregnane glycoside (periplocoside P) and two known oligosaccharides. Insecticidal activity bioassay showed that periplocoside P has insecticidal activity against the 3rd-instar larvae of Pseudaletia separata and Plutella xylostella. The LD50 values after 48 h were 10.8 and 3.6 μg · larva–1, respectively.

Five new C 21 steroidal glycosides from Periploca sepium

Five new C 21 steroidal glycosides, named periseosides A–E ( 1– 5), along with six known analogues, were isolated from the root barks of Periploca sepium. Their structures were elucidated on the basis of spectroscopic analysis and chemical evidence. All compounds were evaluated for their immunosuppressive activities.

A New Cardenolide and Two New Pregnane Glycosides from the Root Barks of Periploca sepium

AbstractA new cardenolide and two new pregnane glycosides, periplogenin 3‐[O‐β‐glucopyranosyl‐(1→4)‐β‐sarmentopyranoside] (1), (3β,20S)‐pregn‐5‐ene‐3,17,20‐triol 20‐[O‐β‐glucopyranosyl‐(1→6)‐O‐glucopyranosyl‐(1→4)‐β‐canaropyranoside] (2), and (3β,14β,17α)‐3,14,17‐trihydroxy‐21‐methoxypregn‐5‐en‐20‐one 3‐[O‐β‐oleandropyranosyl‐(1→4)‐O‐β‐cymaropyranosyl‐(1→4)‐β‐cymaropyranoside] (3), were isolated from the root barks of Periploca sepium Bge, together with seven related known compounds, periplogenin, xysmalogenin, (3β,20S)‐pregn‐5‐ene‐3,17,20‐triol, (3β,14β,17α)‐3,14,17‐trihydroxy‐21‐methoxypregn‐5‐en‐20‐one, (3β,20S)‐pregn‐5‐ene‐3,20‐diol 3‐β‐glucopyranoside 20‐β‐glucopyranoside, (3β,20S)‐pregn‐5‐ene‐3,20‐diol 3‐[O‐2‐O‐acetyl‐β‐digitalopyranosyl‐(1→4)‐β‐cymaropyranoside] 20‐[O‐β‐glucopyranosyl‐(1→6)‐O‐β‐glucopyranosyl‐(1→2)‐β‐digitalopyranoside], and (3β,20S)‐ pregn‐5‐ene‐3,20‐diol 20‐[O‐β‐glucopyranosyl‐(1→6)‐β‐glucopyranoside]. Their structures were elucidated on the basis of spectroscopic analyses.

Perisesaccharides A–E, New Oligosaccharides from the Root Barks ofPeriploca sepium

Five new oligosaccharides, named perisesaccharides A-E (1- 5), were isolated from the root barks of Periploca sepium. Their structures were elucidated by NMR and HRESIMS data. The absolute configurations of these compounds were determined by a combination of X-ray diffraction analysis, modified Mosher's method, circular dichroism spectroscopy, and acid hydrolysis. The boat conformation of oleandronic acid delta-lactone was reported for the first time.

Repellent from Traditional Chinese Medicine, Periploca sepium Bunge

By using a new bioassay-guided method, 2-hydroxy-4-methoxybenzaldehyde isolated from the root bark of Periploca sepium, a traditional Chinese medicine, showed repellent activity against the olive weevil (Dyscerus perforatus) at 62.5, 125, 250 and 500 microg/disc, respectively. In addition, it also exhibited antinematodal activity against Bursaphelenchus xylophilus at a minimum effective dose of 200 microg/ball. The three related compounds obtained were also evaluated for the above-mentioned bioactivities.

A New Pregnane and a New Diphenylmethane from the Root Barks of Periploca sepium

AbstractA new polyoxygenated pregnane genin and a new diphenylmethane, along with five known pregnane derivatives, were isolated from the root barks of Periploca sepium. The structures of the new compounds were elucidated as (3β,14β)‐3,14‐dihydroxy‐21‐methoxypregn‐5‐en‐20‐one (1) and 2‐hydroxy‐5‐(2‐hydroxy‐4‐methoxybenzyl)‐4‐methoxybenzaldehyde (2) on the basis of spectroscopic methods, especially 2D‐NMR and MS analyses. The known compounds were identified by comparing their physical and spectroscopic data with those reported in the literature.

Pregnane glycosides from an antitumour fraction of Periploca sepium

Three new pregnane glycosides (S-4a, S-5 and S-10) and two known pregnane glycosides (S-4b and S-6) were isolated from an antitumour fraction of the root barks of Periploca sepium. Their structures were determined by 1H and 13C NMR, FABMS and SIMS spectroscopy and some chemical transformations. One of the glycosides (S-4a) contained the new aglycone Δ5-pregnene-3β,16β,20(R)-triol.