Triterpenoids

Connolly, Joseph D.; Hill, Robert A.

doi:10.1007/978-1-4899-4513-6_6

Cited by 10 publications

(8 citation statements)

References 1,930 publications

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“…All the bidesmosidic saponins that had two glycosidic sugar chains attached to a triterpenoid aglycon (KI-4, KK-2, KK-4, KK-5, Macranthidin A, B, and Disacoside) failed to induce fruiting bodies ( Table 1), indicating that the presence of a single sugar chain conjugated to a triterpenoid aglycon was crucial for the fruiting body induction in P. ostreatus, and that the presence of an additional sugar chain diminished the fruiting activity of the saponin. Monodesmosidic saponins generally have stronger biological activities than bidesmosidic saponins [13], and our results provided additional evidence that monodesmosidic saponins are biologically more active in stimulating mushroom development than bidesmosidic saponins. The numbers of fruiting bodies per plate is designated as, + between 1 and 10; ++, between 10 and 100; +++ more than 100.…”

Section: Structure-activity Relationships Proven By Synthetic Saponinssupporting

confidence: 59%

“…(3)), was isolated from dichloromethane extracts of the outer bark of Shirakaba wood (Betula platyphylla Sukatchev var. japonica Hara) and was identified by analytical data from 13 C-NMR and specific rotations and references in the literature [11][12][13]. Other triterpenoids, betulinic acid, and oleanolic acid, were also isolated from the bark of Betula platyphylla [11].…”

Section: Structure-activity Relationships Proven By Synthetic Saponinsmentioning

confidence: 99%

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An Active Compound for Fruiting Body Induction

Magae¹,

Nishimura²,

Ohara³

2009

Current Chemical Biology

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Mushroom development is important for both basic scientific research and for practical mushroom production. In previous screening studies of natural compounds that are effective for fruiting body development of oyster mushrooms (Pleurotus ostreatus) on agar medium, we identified a triterpenoid saponin that exerted a hormone-like effect. Not only did the saponin stimulate mushroom development, but P. ostreatus also changed its morphology as the concentration of saponin in the medium increased. We have synthesized a betulin glycoside by linking a sugar moiety to a triterpenoid betulin derived from outer bark of Betulla platyphylla. The sugar chain was further lengthened by transglycosylation using cyclodextrin glycosyltransferase (CGTase) of Bacillus macerans. Neither betulin nor the triterpenoid itself stimulated fruiting body development, but the activity was generated as a sugar moiety was introduced onto betulin. Fruiting activity correlated with the sugar length, indicating that the presence of the sugar moiety was indispensable for fruiting activity. We proposed that an as yet unknown hydrophobic compound with an attached sugar chain triggers fruiting in P. ostreatus. We synthesized a 3-O-alkyl-D-glucose (AG) and determined that AG with an eight-carbon alkyl chain effectively induced fruiting bodies for P. ostreatus. Thus, a sugar-containing amphipathic compound can stimulate fruiting body development.

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Section: Structure-activity Relationships Proven By Synthetic Saponinssupporting

confidence: 59%

Section: Structure-activity Relationships Proven By Synthetic Saponinsmentioning

confidence: 99%

An Active Compound for Fruiting Body Induction

Magae¹,

Nishimura²,

Ohara³

2009

Current Chemical Biology

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“…Many comprehensive reviews of OA and UA have been published and have covered different areas of interest, such as their isolation, structural determination, and pharmacological activities [ 12 , 87 – 90 ].…”

Section: Ursolic Acid (Ua)mentioning

confidence: 99%

Antimicrobial Activity of Oleanolic and Ursolic Acids: An Update

Jesus

Lago

Laurenti

et al. 2015

Evidence-Based Complementary and Alternative Medicine

169

122

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Triterpenoids are the most representative group of phytochemicals, as they comprise more than 20,000 recognized molecules. These compounds are biosynthesized in plants via squalene cyclization, a C30 hydrocarbon that is considered to be the precursor of all steroids. Due to their low hydrophilicity, triterpenes were considered to be inactive for a long period of time; however, evidence regarding their wide range of pharmacological activities is emerging, and elegant studies have highlighted these activities. Several triterpenic skeletons have been described, including some that have presented with pentacyclic features, such as oleanolic and ursolic acids. These compounds have displayed incontestable biological activity, such as antibacterial, antiviral, and antiprotozoal effects, which were not included in a single review until now. Thus, the present review investigates the potential use of these triterpenes against human pathogens, including their mechanisms of action, via in vivo studies, and the future perspectives about the use of compounds for human or even animal health are also discussed.

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“…The presence of this bond influences the whole structure by the special changes of the B-ring, which acquires the conformation of half-chair, boat, or twisted boat conformation, depending on the double bond location. − Apart from the characteristic steroid rings, the molecules of sterols have aliphatic, typically eight-carbon-atom chains attached to the C17 carbon atom of the cyclopentane ring which can be fully hydrogenated, possess one or more double bounds, and even possess additional substituents. The C3 hydroxyl group, by contrast, provides the amphipathic character to sterol molecules enabling them to be significant components of biological lipid membranes. , The class of sterols as well as their distribution in the living organisms depends on the particular species and even on the specification and function of a tissue and the cell type. ,, In this work we are focused on the comparative characteristics of three selected sterols, differing as regards molecular structures: desmosterol, zymosterol, and lanosterol. These compounds are known to be important precursors in the biosynthesis of cholesterol .…”

Section: Introductionmentioning

confidence: 99%

Crucial Role of the Double Bond Isomerism in the Steroid B-Ring on the Membrane Properties of Sterols. Grazing Incidence X-Ray Diffraction and Brewster Angle Microscopy Studies

et al. 2015

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Three cholesterol precursors-desmosterol, zymosterol, and lanosterol-were comprehensively characterized in monolayers formed at the air/water interface. The studies were based on registration of the surface pressure (π)-area (A) isotherms complemented with in situ analysis performed with application of modern physicochemical techniques: grazing incidence X-ray diffraction (GIXD) and Brewster angle microscopy (BAM). In this approach we were interested in the correlation between molecular structures of the studied sterols found in the cholesterol biosynthetic pathway and their membrane properties. Our results revealed that only desmosterol behaves in Langmuir monolayers comparably to cholesterol, the molecules of which arrange in the monolayers into a hexagonal lattice, while the two remaining sterols possess extremely different properties. We found that molecules of both zymosterol and lanosterol are organized on the water surface in the two-dimensional oblique unit cells despite the fact that they are oriented perpendicular to the monolayer plane. The comparison of chemical structures of the investigated sterols leads to the conclusion that the only structural motive that can be responsible for such unusual behavior is the double bond in the B sterol ring, which is located in desmosterol in a different position from in the other two sterols. This issue, which was neglected in the scientific literature, seems to have crucial importance for sterol activity in biomembranes. We showed that this structural modification in sterol molecules is directly responsible for their adaptation to proper functioning in biomembranes.

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Triterpenoids

Cited by 10 publications

References 1,930 publications

An Active Compound for Fruiting Body Induction

An Active Compound for Fruiting Body Induction

Antimicrobial Activity of Oleanolic and Ursolic Acids: An Update

Crucial Role of the Double Bond Isomerism in the Steroid B-Ring on the Membrane Properties of Sterols. Grazing Incidence X-Ray Diffraction and Brewster Angle Microscopy Studies

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