Hou-Li Zhang

Tannin extracts from immature fruits of Terminalia chebula Fructus Retz. promote cutaneous wound healing in rats

BackgroundTannins extracted from immature fruits of Terminalia chebula Fructus Retz. are considered as effective components promoting the process of wound healing. The objective of this study is to explore the optimal extraction and purification technology (OEPT) of tannins, while studying the use of this drug in the treatment of a cutaneous wound of rat as well as its antibacterial effects.MethodsThe content of tannin extracts was measured by the casein method, and antibacterial ability was studied by the micro-dilution method in vitro. In wound healing experiment, animals in group I, II and II were treated with vaseline ointment, tannin extracts (tannin content: 81%) and erythromycin ointment, respectively (5 mg of ointment were applied on each wound). To evaluate the process of wound healing, selected pharmacological and biochemical parameters were applied.ResultsAfter optimal extraction and purification, content of tannin extracts was increased to 81%. Tannin extracts showed the inhibition of Staphylococcus aureus and Klebsiella Pneumonia in vitro. After excision of wounds, on days 7 and 10, the percent of wound contraction of group was higher than that of group . After being hurt with wounds, on days 3, 7, and 10, the wound healing quality of group was found to be better than that of group in terms of granulation formation and collagen organization. After wound creation, on day 3, the vascular endothelial growth factor expression of group was higher than that of group .ConclusionThe results suggest that tannin extracts from dried immature fruits of Terminalia chebula Fructus Retz. can promote cutaneous wound healing in rats, probably resulting from a powerful anti-bacterial and angiogenic activity of the extracts.

Protostane Triterpenoids from the Rhizome of Alisma orientale Exhibit Inhibitory Effects on Human Carboxylesterase 2

Twelve new and 10 known protostane triterpenoids were isolated from the rhizome of Alisma orientale. Their structures were elucidated based on physical data analyses, including UV, HRESIMS, NMR experiments ((1)H, (13)C NMR, (1)H-(1)H COSY, HSQC, HMBC, and NOESY), and induced electronic circular dichroism. New compounds 1-12 were classified as protostanes (1-10), 29-norprotostane (11), and 24-norprotostane (12) by structure analyses. Furthermore, the inhibitory effects on human carboxylesterases (hCE-1, hCE-2) of compounds 1-22 were evaluated. Compounds 2, 6, 9, and 11 showed moderate inhibitory activities and were selective toward hCE-2 enzymes, with IC50 values of 8.68, 4.72, 4.58, and 2.02 μM, respectively. The inhibition kinetics of compound 11 toward hCE-2 were established, and the Ki value was determined as 1.76 μM using a mixed inhibition model. The interaction of bioactive compound 11 with hCE-2 was shown using molecular docking.

Biotransformation of 11-keto-β-boswellic acid by Cunninghamella blakesleana.

11-Keto-β-boswellic acid (KBA), as one of the active constituents in the gum resin of Boswellia serrata, possesses significant biological activities including anti-inflammatory activity. However, its extensive metabolism and low polarity has limited the systemic availability of KBA. The present research was aimed to obtain and explore the various possible derivatives of KBA through biotransformation by Cunninghamella blakesleana AS 3.970. A total of ten transformed compounds were isolated and purified, and their chemical structures were characterized as 7β-hydroxy-11-keto-β-boswellic acid; 7β, 15α-dihydroxy-11-keto-β-boswellic acid ; 7β, 16β-dihydroxy-11-keto-β-boswellic acid; 7β, 16α-dihydroxy-11-keto-β-boswellic acid; 7β, 22β-dihydroxy-11-keto-β-boswellic acid; 7β, 21β-dihydroxy-11-keto-β-boswellic acid; 7β, 20β-dihydroxy-11-keto-β-boswellic acid; 7β, 30-dihydroxy-11-keto-β-boswellic acid; 3α, 7β-dihydroxy-11-oxours-12-ene-24, 30-dioic acid and 3α, 7β-dihydroxy-30-(2-hydroxypropanoyloxy)-11-oxours-12-en-24-oic acid by various spectroscopic methods. The biotransformation processes include hydroxylation, oxidation and esterification. Primary structure-activity relationships (SAR) of inhibitory effects on NO production in RAW 264.7 macrophage cells are discussed.

Isolation and identification of metabolites of osthole in rats

Osthole (Ost), one of the major components of Cnidium monnieri (L.) Cusson, is had the structure of an isopentenoxy-coumarin with a range of pharmacological activities. In the present study, the metabolism of Ost in male Sprague-Dawley rats was investigated by identifying Ost metabolites excreted in rat urine. Following an oral dose of 40 mg/kg Ost, 10 phase I and 3 phase II metabolites were isolated from the urine of rats, and their structures identified on the basis of a range of spectroscopic data, including 2D-NMR techniques. These metabolites were fully characterized as 5′-hydroxyl-osthole (M-1), osthenol (M-2), 4′-hydroxyl-osthole (M-3), 3, 5′-dihydroxyl-osthole (M-4), 5′-hydroxyl-osthenol (M-5), 4′-hydroxyl-2′, 3′-dihydro-osthenol (M-6), 4′-hydroxyl-osthenol (M-7), 3, 4′-dihydroxyl-osthole (M-8), 2′, 3′-dihydroxyl-osthole (M-9), 5′-hydroxyl-2′, 3′-dihydroosthole (M-10), osthenol-7-O-β-D-glucuronide (M-11), osthole-4′-O-β-D-glucuronide (M-12) and osthole-5′-O-β-D-glycuronate (M-13). This is the first identification of M-1, M-3 to M-13 in vivo. On the basis of the metabolites profile, a possible metabolic pathway for Ost metabolism in rats has been proposed. This is the first systematic study on the phases I and II metabolites of 8-isopentenoxy-coumarin derivative.

Inhibitory Effects of Highly Oxygenated Lanostane Derivatives from the Fungus Ganoderma lucidum on P-Glycoprotein and α-Glucosidase

Twelve new highly oxygenated lanostane triterpenoids and nine known ganoderic acids were isolated from the fruiting body of Ganoderma lucidum. The new compounds were lanostane nortriterpenoids with 27 carbons (1-5 and 8), lanostane nor-triterpenoids with 25 carbons (6 and 7), and lanostane triterpenoids (9-12) based on multiple spectroscopic data analysis, including HRESIMS, 1D-NMR, 2D-NMR, and CD. Compounds 1-5 were identified as rare nor-lanostanoids that contain a 17β-pentatomic lactone ring. Compound 13, possessing a lactone ring, had been isolated previously. The P-glycoprotein (P-gp) inhibitory effects of compounds 1-21 were evaluated at a concentration of 20 μM using an adriamycin (ADM)-resistant human breast adenocarcinoma cell line (MCF-7/ADR). Compounds 1, 5, 18, and 20 and verapamil increased the accumulation of ADM in MCF-7/ADR cells approximately 3-fold when compared with the negative control. These data support the significant P-glycoprotein inhibitory activities of compounds 1, 5, 18, and 20. In silico docking analysis suggested these compounds had similar P-gp recognition mechanisms compared with those of verapamil (a classical inhibitor). Furthermore, in an in vitro bioassay, compounds 2, 4, 5, 6, and 18 showed moderate inhibitory effects against α-glucosidase compared with those of the positive control acarbose.

Novel protostane-type triterpenoids with inhibitory human carboxylesterase 2 activities

The rhizomes of Alisma orientalis have been used for centuries in China and other Asian countries as an effective herbal remedy. The phytochemical investigation of A. orientalis and biotransformation of two major triterpenoids alisols A (11) and B 23-acetate (13) by Cunninghamella elagans AS 3.2028 and Penicillium janthinellum AS 3.510 have led to the isolation of ten new protostane-type triterpenoids (1–5 and 18–22), including one novel 26-nor-protostane (1) and one unusual 17-nor-protostane (2), together with twelve known analogues. Their structures were determined by 1D and 2D NMR, and HRESIMS spectroscopic analyses. All the isolated compounds were assayed for their inhibitory activities against human carboxylesterase 2 (HCE-2). Compounds 1, 3–9, 12, 14–16, 19, and 20 showed significant inhibitory activities on HCE-2 with IC50 values from 0.51 ± 0.09 μM to 9.45 ± 0.73 μM. The inhibition kinetics of compound 5 toward HCE-2 were established, and its Ki value was determined as 0.57 μM. The interaction of compound 5 with HCE-2 was investigated using molecular docking.

Two new protostane-type triterpenoids from Alisma orientalis

Abstract Two new protostane-type triterpenoids, 17-epi alisolide (1) and 24-epi alismanol D (2), were isolated from Alisma orientalis together with one known compound. Their structural elucidations were conducted by NMR, UV and HRESIMS spectroscopic analyses, and comparison with the literature data. All the isolated compounds were evaluated for inhibitory effects on HCE-2. Compound 2 displayed moderate inhibitory activity against HCE-2 with IC50 value of 23.1 μM.

2,4-Dihydr-oxy-N'-(3,4,5-trimethoxy-benzyl-idene)benzohydrazide.

In the title compound, C17H18N2O6, the molecule is slightly twisted, with a dihedral angle of 18.1 (2)° between the two benzene rings. In the crystal structure, molecules are linked into a network by intermolecular N—H⋯O, O—H⋯N and O—H⋯O hydrogen bonds. An intramolecular O—H⋯O hydrogen bond is also present.

Two new ent-kaurane diterpenoids from Pteris semipinnata

In this study, two new compounds and six known compounds were isolated from the aerial parts of Pteris semipinnata. The chemical structures of these two new compounds were elucidated as 6β,11α-dihydroxy-15-oxo-ent-kaur-16-en-19-oic acid (1) and 7α,11α-dihydroxy-15-oxo-ent-kaur-16-en-19-oic acid (2) by the extensive spectral methods including 2D NMR and HR-MS techniques.

(E)-N'-(5-Chloro-2-hydroxy-benzyl-idene)-3,5-dihydroxy-benzohydrazide mono-hydrate.

In the title compound, C14H11ClN2O4·H2O, the dihedral angle between the two benzene rings is 8.5 (2)° and an intramolecular O—H⋯N hydrogen bond is observed in the Schiff base molecule. In the crystal structure, the water molecule accepts an N—H⋯O hydrogen bond and makes O—H⋯O hydrogen bonds to two further Schiff base molecules. Further intermolecular O—H⋯O hydrogen bonds lead to the formation of layers parallel to the bc plane.