Triterpenoids with a Five-Membered a-Ring: Distribution in Nature, Transformations, Synthesis, and Biological Activity

Гришко, В. В.; Толмачева, И. А.; Pereslavtseva, A. V.

doi:10.1007/s10600-015-1193-z

Cited by 26 publications

(17 citation statements)

References 101 publications

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“…The complex mechanism of regulation of triterpene variation underlying domestication requires further exploration. In addition, our results provide new evidence supporting the prediction that Ziziphus‐ specific ceanothane‐type triterpenes are derived from lupane‐type triterpenes (Grishko et al, 2015; Kang et al, 2016), sharing a common skeleton of lupeol. Identification of ZjOSCs and ZjP450 led to an entire pathway reconstruction that would signify the utility of enzymes to improve the production of ursolic acid through bioengineering approaches (Augustin et al, 2011; Moses et al, 2013; Sandeep et al, 2019; Shang and Huang, 2019).…”

Section: Discussionsupporting

confidence: 85%

Jujube metabolome selection determined the edible properties acquired during domestication

Zhong

Shi

Wang³

et al. 2021

The Plant Journal

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Plants supply both food and medicinal compounds, which are ascribed to diverse metabolites produced by plants. However, studies on domestication-driven changes in the metabolome and genetic basis of bioactive molecules in perennial fruit trees are generally lacking. Here, we conducted multidimensional analyses revealing a singular domestication event involving the genomic and metabolomic selection of jujube trees (Ziziphus jujuba Mill.). The genomic selection for domesticated genes was highly enriched in metabolic pathways, including carbohydrates and specialized metabolism. Domesticated metabolome profiling indicated that 187 metabolites exhibited significant divergence as a result of directional selection. Malic acid was directly selected during domestication, and the simultaneous selection of specialized metabolites, including triterpenes, consequently lead to edible properties. Cyclopeptide alkaloids (CPAs) were specifically targeted for the divergence between dry and fresh cultivars. We identified 1080 significantly associated loci for 986 metabolites. Among them, 15 triterpenes were directly selected at six major loci, allowing the identification of a homologous cluster containing seven 2,3-oxidosqualene cyclases (OSCs). An OSC gene was found to contribute to the reduction in the content of triterpenes during domestication. The complete pathway for synthesizing ursolic acid was dissected by integration of the metabolome and transcriptome. Additionally, an N-methyltransferase involved in the biosynthesis of CPA and responsible for inter-cultivar content variation was identified. The present study promotes our understanding of the selection process of the global metabolome subsequent to fruit tree domestication and facilitates the genetic manipulation of specialized metabolites to enhance their edible traits.

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Section: Discussionsupporting

confidence: 85%

Jujube metabolome selection determined the edible properties acquired during domestication

Zhong

Shi

Wang³

et al. 2021

The Plant Journal

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“…Native and semisynthetic derivatives of betulinic acid with a fragmented, expanded, or contracted A ring are of interest as either structurally original biological active compounds or as synthetic platforms for their preparation. [1][2][3] In nature, triterpenic biosynthetic pathways with a 5-membered A ring formation most often are based on cyclizations of the corresponding A-secotriterpenic precursors. 1 The same approach is successfully used in synthetic organic chemistry to obtain A-pentacyclic triterpenoids, including analogs of natural biologically active products.…”

mentioning

confidence: 99%

“…[1][2][3] In nature, triterpenic biosynthetic pathways with a 5-membered A ring formation most often are based on cyclizations of the corresponding A-secotriterpenic precursors. 1 The same approach is successfully used in synthetic organic chemistry to obtain A-pentacyclic triterpenoids, including analogs of natural biologically active products. Thus, the synthesis of natural epiceanotic acid with high anti-HIV-1 properties was carried out on the basis of the 2,3-dicarboxy-2,3-secolupane derivative.…”

mentioning

confidence: 99%

Synthesis, Cyclization, and Cytotoxic Activity of 2,3-Secolupane Triterpenoids With an Ethylketone Fragment

Konysheva

Ерошенко

Гришко

2019

Natural Product Communications

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3-Ethyl substituted triterpenoids with a fragmented and 5-membered A ring were synthesized from the lupane ketoxime via the Beckmann reaction and intramolecular oxonitrile cyclization, respectively. Transformations of the triterpenic isopropylidene fragment with the formation of C(30) and C(20) modified derivatives were performed by either allylic C(30) oxidation or ozonolytic cleavage of the C(20)-C(29) double bond. Antitumor activity of the synthesized compounds was evaluated by the 3-(4,5-dimethylthiazol-2-yl)-2,3-diphenyl-tetrazolium bromide test against 7 human cancer cell lines. Methyl 1-cyano-3-ethyl-3-oxo-2,3-seco-2-norlup-20(29)-en-30-al-28-oate (4), methyl 3-[1-bromoethyl]-1-cyano-3-oxo-2,3-seco-2-norlup-20(29)-en-30-al-28-oate (6), and methyl 1-cyano-3-ethyl-2-norlup-1(3),20(29)-dien-30-al-28-oate (9) were selected as compounds with highest cytotoxicity (IC50 1.38-15.91 μM).

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“…myrrhanol C and myrrhanone A), tricyclic triterpenoids (e.g. arabidiol and achilleol B), pentacyclic triterpenoids (ceanothanolic and rosamultic acid), as well as the two most common categories in the study of chaga terpenoids, namely tetracyclic triterpenoids and steroids (Daniel and Mammen, 2016;Grishko et al, 2015;Kimura et al, 2001;Perveen, 2018;Xiang et al, 2006;Xu et al, 2018). The steroids and tetracyclic triterpenoids both contain four cycloalkane rings joined mutually, therefore it is sometimes difficult to conceptually separate them from each other.…”

Section: Terpenoidsmentioning

confidence: 99%

Bioactive Compounds and Bioactive Properties of Chaga (Inonotus obliquus) Mushroom: A Review

Peng¹,

Shahidi²

2020

JFB

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Chaga (Inonotus obliquus) is an edible herbal mushroom extensively distributed in the temperate to frigid regions of the Northern hemisphere, especially the Baltic and Siberian areas. Chaga parasites itself on the trunk of various angiosperms, especially birch tree, for decades and grows to be a shapeless black mass. The medicinal/nutraceutical use of chaga mushroom has been recorded in different ancient cultures of Ainu, Khanty, First Nations, and other Indigenous populations. To date, due to its prevalent use as folk medicine/functional food, a plethora of studies on bioactive compounds and corresponding compositional analysis has been conducted in the past 20 years. In this contribution, various nutraceutical and pharmaceutical potential, including antioxidant, anti-inflammatory, anti-tumor, immunomodulatory, antimutagenic activity, anti-virus, analgesic, antibacterial, antifungal, anti-hyperglycemic, and anti-hyperuricemia activities/effects, as well as main bioactive compounds including phenolics, terpenoids, polysaccharides, fatty acids, and alkaloids of chaga mushroom have been thoroughly reviewed, and tabulated using a total 171 original articles. However, only key bioactivities and bioactives are selectively discussed. Besides, the up-to-date toxicity concerns and risk assessment about the misuse of chaga, which limit its acceptance and use as medicinal/nutraceutical products, have also been clarified.

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Triterpenoids with a Five-Membered a-Ring: Distribution in Nature, Transformations, Synthesis, and Biological Activity

Cited by 26 publications

References 101 publications

Jujube metabolome selection determined the edible properties acquired during domestication

Jujube metabolome selection determined the edible properties acquired during domestication

Synthesis, Cyclization, and Cytotoxic Activity of 2,3-Secolupane Triterpenoids With an Ethylketone Fragment

Bioactive Compounds and Bioactive Properties of Chaga (Inonotus obliquus) Mushroom: A Review

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