Abietane diterpenoids and taraxerane-type triterpenes from .

Two abietane diterpenoids, named teuvismine A () and B (), along with two new taraxerane-type triterpenes, named teuvisoic acid A () and B () were isolated from whole plants of . The structures were elucidated by the analysis of HRESIMS spectroscopy and NMR spectroscopy, as well as the comparison with published data. All isolates were evaluated for their cytotoxic activities against five human cancer cell lines (HCT116, H460, HepG2, BGC823, and HeLa cells).

A review on medical plants based on diterpenoids and sesquiterpenoids: phytochemistry, pharmacology and clinical applications.

Natural products, owing to their chemical diversity, biological activity, and historical success, continue to be a precious source of lead compounds and potential candidates for drug discovery. , in particular, presents a promising avenue for drug discovery due to its long history of usage in traditional Chinese medicine and its well-established clinical applications. Diterpenoids and sesquiterpenoids, the characteristic metabolites of , have consistently attracted considerable attention in related scientific research because of their diverse structures and extensive range of bioactivities, including anti-inflammatory and anti-cancer properties.

Bmk9 and Uricase Nanoparticle Complex for the Treatment of Gouty Arthritis and Uric Acid Nephropathy.

Uric acid is the final product of purine metabolism, and excessive serum uric acid can cause gouty arthritis and uric acid nephropathy. Therefore, lowering the uric acid level and alleviating inflammation in the body are the key points to treating these diseases. A stable nanosuspension of peptide BmK9 was prepared by the precipitation-ultrasonication method.

Identification of poly(ADP-ribose)polymerase 1 and 2 (PARP1/2) as targets of andrographolide using an integrated chemical biology approach.

Here, we describe the identification of PARP1/2 as direct binding proteins of andrographolide (Andro) using protein microarray, surface plasmon resonance (SPR), and enzyme activity assays. We then evaluated the proliferation inhibition, apoptosis, and cell migration effects of Andro on the MDA-MB-436 cell line in vitro. The final biological evaluation confirmed that Andro was a highly effective single agent in the MDA-MB-436 xenograft model and had a low hERG-mediated cardiac toxicity.

Synthesis and biological evaluation of Isosteviol derivatives as FXa inhibitors.

Firstly, a series of Isosteviol derivatives were synthesized and evaluated for FXa inhibitory activity. Among these compounds, the inhibitory activity of compounds 22, 35 and 38 on FXa was better than that of Isosteviol. Secondly, surface plasmon resonance (SPR) assays were performed for selected compounds.

Synthesis and biological evaluation of Vinpocetine derivatives.

A new series of Vinpocetine derivatives were synthesized and evaluated for their inhibitory activity on PDE1A in vitro. Seven compounds with higher inhibitory activity were selected for surface plasmon resonance (SPR) binding experiments. Compared with Vinpocetine, these high potency compounds presented a higher binding affinity with PDE1A, which was consistent with inhibitory activity.

Synthesis and biological evaluation of panaxatriol derivatives against myocardial ischemia/reperfusion injury in the rat.

Panaxatriol (PT) is a natural product derived from ginseng that possesses cardioprotective effects in isolated rat hearts. To develop more potent therapeutic agents against myocardial ischemia/reperfusion (MI/R) injury from natural products, a novel series of heterocycle ring-fused panaxatriol derivatives were designed and synthesized. In vitro results showed that approximately half of them exhibited increased cytoprotective activity compared with PT in a cardiomyocyte model of oxygen-glucose deprivation and reperfusion (OGD/R) injury.

Discovery of novel, potent, isosteviol-based antithrombotic agents.

Thrombosis is a pathological coagulation process and can lead to many serious thrombotic diseases. Here, we report a novel potent antithrombotic compound (6k) based on isosteviol with anticoagulant and antiplatelet activities. 6k selectively inhibited FXa (K = 0.

Isolation and characterization of -pimarane diterpenoids from .

Five new -pimarane diterpenoids 16-nor-2-oxopimar-8(14)-ene-15,19-dial (), 16-nor-2α,19-dihydroxypimar-8-en-15-al (), 3--acetyldarutigenol (), 19-acetylkirenol (), -16-nor-3,15-dihydroxypimar-8(14)-ene () were isolated and characterized from the ethanol extract of . Their structures were elucidated on the basis of spectroscopic analysis. The absolute configuration of C-15 in compounds and was assigned using Snatzke's method.

Semisynthesis of epoxy-pimarane diterpenoids from kirenol and their FXa inhibition activities.

Kirenol is one of the biologically active diterpenoids from Siegesbeckia pubescens. In terms of the high content and typical structure, many ent-diterpenoids separated from S. pubescens were presumed to be biologically related to kirenol.

Semisynthesis of ent-norstrobane diterpenoids as potential inhibitor for factor Xa.

A semisynthesis of two ent-strobane diterpenoids strobols C (7) and D (14) was accomplished via a Wagnar-Meerwein rearrangement. Compounds 7, 14, and the intermediate products were evaluated for their inhibition on factor Xa (FXa). Among all the compounds screened for FXa inhibitory activity, three compounds 6, 7, and 9 showed significant inhibitory activities with IC values of 1067 ± 164, 81 ± 11, 1023 ± 89 nM, respectively.

Synthesis and evaluation of panaxatriol derivatives as Na, K-ATPase inhibitors.

Panaxatriol, a triterpene bearing a steroid-like structure similar to cardiac glycosides, was presumed to share the same bioactivity with cardiac glycosides, and may be a potential Na, K-ATPase inhibitor. In this paper, a series of panaxatriol derivatives were synthesized and evaluated for Na, K-ATPase inhibitory activities. The results of biological tests showed that more than half of the synthesized derivatives presented increased inhibitory activities compared with panaxatriol.

The synthesis and anti-metastatic effects of optical isomers of ionone alkaloid 9-(N,N-dimethyl)-4,7-megastigmedien-3-one.

Ionone alkaloid 9-(N,N-dimethyl)-4,7-megastigmedien-3-one (compound 1) is a new anti-metastatic natural product. However, it was previously reported as optical isomers mixture. Herein, the optical isomers (6a-6d) of compound 1 were synthesized.

Isolation and characterization of diterpene glycosides from Siegesbeckia pubescens.

Five new diterpenoid glycosides, siegesides A-E (1-5), along with the known compound darutoside (6) were isolated and characterized from the ethanol extract of Siegesbeckia pubescens. The structural elucidation of the isolates was accomplished by extensive HRESIMS and NMR analysis. Compounds 1 and 2 are epimers of 6.

ent-Strobane and ent-Pimarane Diterpenoids from Siegesbeckia pubescens.

Two strobane diterpenoids, strobols A (1) and B (2), 15 new pimarane diterpenoids (3-6 and 8-18), and the known compounds kirenol (19), darutigenol (20), and ent-2β,15,16,19-tetrahydroxypimar-8(14)-ene (7) were isolated from the aerial parts of Siegesbeckia pubescens Makino. The structures of the new compounds were established based on the interpretation of HRESIMS and NMR analysis. The configurations of 1, 6, and 17 were confirmed by X-ray crystallographic data.

Dimeric Abietane Diterpenoids and Sesquiterpenoid Lactones from Teucrium viscidum.

A new abietane diterpenoid, teuvisone (2), a pair of new dimeric abietane diterpenoid stereoisomers, biteuvisones A (3) and B (4), and three new sesquiterpenoid lactones, teuvislactones A-C (6, 7, and 10), were isolated from the whole plants of Teucrium viscidum, along with four known terpenoids (1, 5, 8, and 9). The structures of the new compounds were elucidated by spectroscopic analysis, and the absolute configurations of 5-10 were determined by electronic circular dichroism analysis. The isolated compounds were evaluated for their cytotoxic effects against five human cancer cell lines and for their α-glucosidase inhibitory effects.

Kirenol, a compound from Herba Siegesbeckiae, induces apoptosis in human chronic myeloid leukemia K562 cells.

Kirenol is a biologically active substance isolated from Herba Siegesbeckiae. In the experiments, we explored a novel antitumor activity of kirenol. The data demonstrated that kirenol had strong cytotoxic effects to human chronic myeloid leukemia K562 cells, the 50% inhibitory concentration (IC50) for kirenol was 53.

Kirenol exerts a potent anti-arthritic effect in collagen-induced arthritis by modifying the T cells balance.

Rheumatoid arthritis is characterized by the imbalance of T cells, which leads to increased pro-inflammatory and reduced anti-inflammatory cytokines. Modulating the balance among T cells is crucial for the treatment of RA. Kirenol is a major diterpenoid components of Herba Siegesbeckiae, which has been applied for arthritic therapy for centuries.

Angiogenesis inhibition and cell cycle arrest induced by treatment with Pseudolarix acid B alone or combined with 5-fluorouracil.

Angiogenesis inhibitors combined with chemotherapeutic drugs have significant efficacy in the treatment of a variety of cancers. Pseudolarix acid B (PAB) is a traditional pregnancy-terminating agent, which has previously been shown to reduce tumor growth and angiogenesis. In this study, we used the high content screening assay to examine the effects of PAB on human umbilical vein endothelial cells (HUVECs).

Effects of kirenol on bovine type II collagen-induced rat lymphocytes in vivo and in vitro.

Objective: To investigate the effect of kirenol on bovine type II collagen (CII)-specific lymphocytes in vivo and in vitro, and explore the mechanism of kirenol-induced immunosuppression in antigen-specific lymphocytes.

Methods: Twenty-four Wistar rats were randomized into control group, collagen-induced arthritis (CIA) model group, kirenol group (2 mg/kg), and prednisolone group (2 mg/kg). After CII injection, the rats in the latter two groups received intragastric administration of kirenol and prednisolone for 30 days, and the spleens and draining lymph nodes of the rats were harvested to prepare single cell suspensions for measurement of the cytokine levels using ELISA.

Pseudolaric acid B inhibits inducible cyclooxygenase-2 expression via downregulation of the NF-κB pathway in HT-29 cells.

Purpose: Pseudolaric acid B (PAB) is a diterpene acid isolated from the root and trunk bark of Pseudolaric kaempferi Gordon. Previous work has found that PAB has anti-inflammatory and anti-tumor effects in xenograft models of human hepatocellular carcinoma. The aim of this study is to evaluate the correlation between anti-cancer and anti-inflammatory effects of PAB and its molecular mechanisms on HT-29 cells.

[Studies on chemical constituents of Rabdosia serra].

Objective: To study the chemical constituents of aerial part of Rabdosia serra.

Method: The compounds were isolated by extraction, coloum chromatography over silica gel and ODS, and preparative HPLC. Their structures were identified by various spectroscopic methods including MS, IR, 1D and 2D NMR data.

Three triterpenoid saponins acylated with monoterpenic acid from Gymnocladus chinensis.

A new triterpenoid saponin acylated with monoterpenic acid, together with two known triterpenoid saponins, has been isolated from the fruit of Gymnocladus chinensis Baill. Their structures were elucidated as 2β,23-dihydroxy-3-O-α-L-rhamnopyranosyl-21-O-{(6S)-2-trans-2,6-dimethyl-6-O-[3-O-(β-D-glucopyranosyl)-4-O-((6S)-2-trans-2,6-dimethyl-6-hydroxy-2,7-octadienoyl)-β-L-arabinopyranosyl]-2,7-octadienoyl}-acacic acid 28-O-β-D-xylopyranosyl-(1 → 3)-β-D-xylopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 2)-[α-L-rhamnopyranosyl-(1 → 6)]-β-D-glucopyranosyl ester (1), gymnocladus saponin E (2), and gymnocladus saponin F(2) (3).