Triterpenoid Constituents of Huperzia miyoshiana

Thirteen triterpenoids, including three new ones, miyoshianois A (1), B (2) and C (3), were isolated from Huperzia miyoshiana. The structures of these new compounds were established as 3-O-dihydroferuloyltohogenol (1), 16-oxo-3β,21β-dihydrox-y-serrat-14-en-24-ferulate (2) and 16-oxo-3a, 21β-dihydroxy-serrat-14-en-24-ferulate (3), respectively, on the basis of their spectroscopic analysis.     

Synthesis of 3β,20S-dihydroxydammar-24-en-12-one 3,20-di-O-β-D-glucopyranoside (chikusetsusaponin-LT8), a glycoside from Panax japonicus

A method for preparative production of 3β,20S-dihydroxydammar-24-en-12-one 3,20-di-O-β-D-glucopyranoside (1), a glycoside from Panax japonicus, chikusetsusaponin-LT₈ was developed. Chemical transformation of betulafolientriol, a component of Betula leaves extract, produced the 12-keto-20S-protopanaxadiol (3β,20S-dihydroxydammar-24-en-12-one) (2), exhaustive glycosylation of which by 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosylbromide (3) under Koenigs—Knorr reaction conditions with subsequent removal of protecting groups formed 3β,20S-dihydroxydammar-24-en-12-one 3,20-di-O-β-D-glucopyranoside (1). The principal glycosylation product was 3β,20S-dihydroxydammar-24-en-12-one 3-O-β-D-glucopyranoside if equimolar amounts of (2) and (3) were used. __________ Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 44–48, January–February, 2006.     

Triterpene glucosides of <Emphasis Type="Italic">Astragalus</Emphasis> and their genins. LXXIV. Cyclotrisectoside,the first trisdesmoside of cyclocephalogenin

The two trisdesmoside cycloartane glycosides astragaloside VII and cyclotrisectoside were isolated from Astragalus dissectus (Leguminosae) and identified. The latter was 20R,25-epoxy-24S-cycloartan-3β,6α,16β,24-tetraol 3-O-β-D-xylopyranoside-6,24-di-O-β-D-glucopyranoside and was a new natural compound. Presented at the Sixth International Symposium on the Chemistry of Natural Compounds (SCNC, Turkey, Ankara, 28–29 June 2005). __________ Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 132–134, March–April, 2007.     

Antidepressant-like effect of triterpenoids extracts from Poria cocos on the CUMS rats by 16S rRNA gene sequencing and LC–MS metabolomics

Abstract

Poria cocos is an edible medicinal mushroom with the effects of inducing diuresis, excreting dampness, invigorating the spleen and tranquilizing the mind. The triterpenoids of Poria cocos as the main active ingredients have shown health benefits of the central nervous system of the human body. Accordingly, this study aimed at further understanding the antidepressant-like effect and a potential mechanism of the triterpenoids extracts from Poria cocos (TPC). As a result, the TPC significantly ameliorated depression-like behaviors on chronic unpredictable mild stress (CUMS) rats, and restored the levels of brain-derived neurotrophic factor and nerve growth factor in the hippocampus of rats. Gut microiota analysis revealed that TPC could increase the biodiversity and markedly regulate the relative abundance of [Prevotella], Allobaculum and Ochrobactrum of CUMS rats. The cecal contents metabolomics pointed to thirteen biomarkers associated with TPC antidepressant effect, which involved in primary bile acid biosynthesis, taurine and hypotaurine metabolism, arginine and proline metabolism. Correlation analysis further showed that there was a strong correlation relationship between the gut microbiota and the cecal contents metabolites, especially compounds involved in energy metabolism, inflammation and immunity. In conclusion, TPC showed a potential antidepressant effect, which was possibly mediated the gut microbiota and cecal contents metabolism.     

Natural products of the medicinal fungus Ganoderma lucidum: occurrence,biological activities,and pharmacological functions

Ganoderma lucidum, a fungus used in traditional Chinese medicine, produces polysaccharides and oxygenated triterpenoids with a very broad spectrum of biological activities and pharmacological functions. Among the Ganoderma triterpenoids, many pairs of C-3 alpha/beta stereoisomers and C-3/C-15 positional isomers have been identified. Biosynthetic study has indicated that the C-3alpha series of oxygenated triterpenoids is derived from the C-3beta series via an oxidation-reduction pathway. The interaction of Ganoderma triterpenoids with human platelets in the induction of aggregation and inhibition of agonist-induced aggregation and signal transduction has been elucidated. Reduction of cellular mevalonate content to a stage in which cholesterol synthesis is strongly inhibited and cell growth is marginally arrested sensitizes hepatoma cells to the oxygenated triterpenoids. A combination treatment of lovastatin and Ganoderma triterpenoids in animal studies has exhibited a potential anticancer effect.     

Three New Serratane Triterpenoids from Phlegmariurus squarrosus

Three new serratane triterpenoids, (3α,14α,15α,21α)‐3,14,15,21,29‐pentahydroxyserratan‐24‐oic acid ( 1 ), (3α,21β)‐serrat‐14‐ene‐3,21,24,30‐tetraol ( 2 ), and (3α,21α)‐serrat‐14‐ene‐3,21,24,29‐tetraol ( 3 ), were isolated from Phlegmariurus squarrosus, together with eight known compounds. Their chemical structures were elucidated on the basis of in‐depth spectroscopic analyses.     

Three New Lanostane Triterpenoids from Inonotus obliquus

Three new lanostane‐type triterpenoids, inonotsulides A, B, and C ( 1 – 3 , resp.) were isolated from the sclerotia of Inonotus obliquus (Pers .: Fr.) (Japanese name: Kabanoanatake; Russian name: Chaga). Their structures were determined to be (20R,24S)‐3β,25‐dihydroxylanost‐8‐en‐20,24‐olide ( 1 ), (20R,24R)‐3β,25‐dihydroxylanost‐8‐en‐20,24‐olide ( 2 ), and (20R,24S)‐3β,25‐dihydroxylanosta‐7,9(11)‐dien‐20,24‐olide ( 3 ) on the basis of chemical transformation, NMR spectroscopy including 1D and 2D (¹H,¹H‐COSY, NOESY, HMQC, HMBC), EI‐MS, and single‐crystal X‐ray analysis.     

Acid-Catalyzed E-Ring Expansion and Isomerization of 3-Acetylbetulin: Synthesis of Cytotoxic Anhydrobetulin Saponins

22(17 → 28)abeo-Lupene derivatives 5a and 6a were obtained after the acid-catalyzed E-ring expansion of 3-acetylbetulin (1a). Glycosylation of these dehydrated triterpenoids using Schmidt's trichloroacetimidate sugar donors in the presence of trimethylsilyl trifluoromethanesulfonate (TMSOTf) provided the new anhydrobetulin saponins 7b–7e in which the terminal olefin C-20(29) isomerizes to form a C-19 tetrasubstituted alkene. The preliminary cytotoxic evaluation revealed that saponins 7b–7d exhibited a moderate cytotoxic activity against A549, DLD-1, and WS1 human cell lines with IC₅₀ ranging from 22 to 49 μM.     

Synthesis of a furano abietane cyano enone—A new scaffold for biological exploration

A six step synthesis of furano abietane cyano enone 12 is described, in which the key step is a palladium-catalyzed intramolecular Heck reaction of bromo 3-phenoxyacrylate 17, prepared from enone phenol 13 in high yield.     

Optimization,Validation and Application of HPLC-PDA Methods for Quantification of Triterpenoids in Vaccinium vitis-idaea L.

Triterpenoids have regained much attention as promising multi-targeting bioactive agents of natural origin in the treatment of numerous disorders. Due to the high potential for phytopharmaceutical development, accurate qualitative and quantitative analysis of triterpenoids for screening and quality control is required. Vaccinium vitis-idaea L. (lingonberry) raw materials have aroused interest as a rich source of triterpenoids. However, currently, no validated, rapid, and easy-to-perform quantification method is available for the routine control of these compounds in lingonberries. This research aimed at developing and validating HPLC-PDA methods for the determination and screening of triterpenoids in extracts of lingonberry leaves, fruits, and flowers. The developed methods were deemed satisfactory by validation, which revealed acceptable analytical specificity, linearity (r² > 0.9999), precision (RSD < 2%), trueness (94.70–105.81%), and sensitivity (LOD: 0.08–0.65 µg/mL). The real sample analysis demonstrated established methods applicability for quantification of 13 triterpenoids in lingonberries and emphasized differences between raw materials. Lingonberry fruits were distinguished by the richness of ursolic acid; lingonberry flowers by similar profile to fruits, but low content of neutral triterpenoids; whereas lingonberry leaves by the particularly high level of α-amyrin. Thus, the proposed methods proved to be reliable and applicable for quantification and routine analysis of triterpenoids in lingonberry samples.