On the origins of triterpenoid skeletal diversity

Xu, Ran; Fazio, Gia C.; Matsuda, Seiichi P. T.

doi:10.1016/j.phytochem.2003.11.014

Cited by 514 publications

(393 citation statements)

References 238 publications

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“…These results for 578 miliacin can be directly extrapolated to any compound with an oleanane, and potentially an ursane or 579 lupane structure. For compounds that originate from oleanane after successive migrations of methyl 580 groups (friedo rearrangements leading to structures such as taraxerane, glutinane, multiflorane and 581 friedelane; i.e Xu et al, 2004), additional fractionations of hydrogen can be expected. 582…”

Section: Implications For Biosynthesis 553mentioning

confidence: 99%

“…Even with low natural abundance of deuterons (around 1. Like other pentacyclic triterpenes, miliacin is formed from mevalonic acid via the mevalonate 181 pathway through the cyclisation of squalene epoxide by an oxidosqualene cyclase (Xu et al, 2004; 182 see Section 6). This scheme leads to the formation of germanicol, a triterpene alcohol constituted of 183 five six-membered rings (Fig.…”

Section: Introduction 50 51mentioning

confidence: 99%

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Contribution of NAD 2D-NMR in liquid crystals to the determination of hydrogen isotope profile of methyl groups in miliacin

Berdagué

Lesot

Jacob

et al. 2016

Geochimica et Cosmochimica Acta

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. Contribution of NAD 2D-NMR in liquid crystals to the determination of hydrogen isotope profile of methyl groups in miliacin. Geochimica et Cosmochimica Acta, Elsevier, 2016Elsevier, , 173, pp.337-351. 10.1016Elsevier, /j.gca.2015 Accepted Manuscript This is a PDF file of an unedited manuscript that has been accepted for publication. As a service to our customers we are providing this early version of the manuscript. The manuscript will undergo copyediting, typesetting, and review of the resulting proof before it is published in its final form. Please note that during the production process errors may be discovered which could affect the content, and all legal disclaimers that apply to the journal pertain. 14 15 Contribution of NAD 2D-NMR in liquid crystals to the determination of Abstract 16The hydrogen isotopic composition (δD or (D/H) value) of molecular biomarkers preserved in 17 sedimentary archives is increasingly used to provide clues about the evolution of past climatic 18conditions. The rationale is that intact biomarkers retain isotopic information related to the climatic 19 conditions that prevailed at the time of their synthesis. Some of these biomarkers may be degraded 20 during diagenesis, however. The extent to which these degradations alter the original δD value of the 21 source biomarker is presently debated and the capacity to resolve the debate by determinations of 22 compound-specific δD values alone is limited. The "bulk" or "global" δD value of any molecule is in 23 fact a composite of δD values at each site within this molecule ((δD i or (D/H) i with i= number of 24 hydrogen/deuterium atoms in the considered molecule). Determination of this site-specific δD i value 25 in biomarkers could not only yield outstanding paleoenvironmental information but also help forecast 26 the impacts of diagenesis and define essential steps in biosynthetic pathways.

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Section: Implications For Biosynthesis 553mentioning

confidence: 99%

Section: Introduction 50 51mentioning

confidence: 99%

Contribution of NAD 2D-NMR in liquid crystals to the determination of hydrogen isotope profile of methyl groups in miliacin

Berdagué

Lesot

Jacob

et al. 2016

Geochimica et Cosmochimica Acta

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“…31) It has been reported that many terpene cyclases have broad substrate specificities, and that other classes of terpenes have been created in vitro. [2][3][4][5][6][7][8][9][10][11][12][13][14][15] A combination of studies identifying enzymatic products biosynthesized from unusual substrates and the analysis of genome sequences should lead not only to the discovery of additional functions of these enzymes in the organism, but also to the identification of novel natural terpenoids that have functions in their producers.…”

Section: Identification Of Bifunctional Sesquarterpene/ Triterpene Cymentioning

confidence: 99%

“…[1][2][3][4][5][6][7][8][9][10][11][12][13][14][15] These compounds including hormones, vitamins, drugs, flavorings, and pigments, are categorized by number of C 5 isoprene units, as follows: hemi-(C 5 ), 1 unit; mono-(C 10 ), 2 units; sesqui-(C 15 ), 3 units; di-(C 20 ), 4 units; sester-(C 25 ), 5 units; tri-(C 30 ), 6 units; and tetraterpenes (C 40 ), 8 units. [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15] In contrast, little is known about C 35 terpenes. To the best of my knowledge, only 19 cyclic and eight linear C 35 terpenes have been identified to date, [16][17][18][19][20][21][22][23][24][25][26][27][28][29][30][31][32][33]…”

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confidence: 99%

Unique Biosynthesis of Sesquarterpenes (C₃₅Terpenes)

Sato

2013

Bioscience, Biotechnology, and Biochemistry

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“…The triterpenoids, a large and structurally diverse group of natural products derived from squalene or related acyclic 30-carbon precursors, are uniquely abundant in Ac, especially in its fruiting bodies. This large group of natural products displays well over 100 distinct skeletons and has well-characterized biological activities [25,26]. Studies have shown that triterpenoids can modulate the function of immune cells [27][28][29].…”

mentioning

confidence: 99%

A triterpenoid methyl antcinate K isolated from Antrodia cinnamomea promotes dendritic cell activation and Th2 differentiation

Chen

Shen

et al. 2009

Eur J Immunol

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Dendritic cells (DC) play a central role in the initiation and regulation of immune responses.Increasing evidence has indicated that manipulation of DC can serve as a therapeutic mechanism for immunomodulation. In this study we tested some unique compounds isolated from Antrodia cinnamomea, a medicinal fungus in Taiwan, on mouse bone marrowderived DC activation. A triterpenoid methyl antcinate K (me-AntK) promoted DC maturation by enhancing the expression of MHC class II, CD86, and reducing the endocytosis. TNF-a, MCP-1, and MIP-1b were secreted by DC after me-AntK treatment, indicating augmentation of innate immunity by me-AntK. Interestingly, the me-AntK-activated DC induced Ag-specific T-cell proliferation and facilitated Th2 differentiation. Examining signaling responses, we found that me-AntK treatment uniquely activated JNK and ERK in DC. Our results demonstrate that me-AntK is the first natural triterpenoid to promote the ability of DC to prime Th2 responses. This suggests that me-AntK can potentially be applied to enhance immune responses and modulate DC function in immunotherapy.Key words: DC . Immunomodulation . Th2 . Triterpenoid Supporting Information available online Introduction DC are specialized leukocytes which take up and process Ag in peripheral tissues and then transport and present Ag to activate T cells in secondary lymphoid organs [1,2]. DC are heterogeneous but all subsets have intrinsic and cooperative Ag-presenting function [3,4]. Exposure of DC to pathogen products or pro-inflammatory stimuli induces DC maturation, which dramatically enhances the ability of DC to activate Ag-specific T cells [5]. TLR are important receptors involved in detection of PAMP in DC. TLR ligation induces the activation of NF-kB and MAP kinase pathways, resulting in DC maturation, which is characterized by upregulation of MHC class II and costimulatory molecule expression as well as cytokine and chemokine production [6]. Befitting the key regulatory role of DC in 2482immune responses, DC are being developed for the treatment of cancers, allergies, and viral infections, and as adjuvants for potent new vaccines to prevent or treat cancers and infectious diseases [7,8]. Thus, DC are manipulated as pharmacological targets for discovering novel biological modifiers of immune responses [9][10][11].Natural products and their derivatives have historically been a rich source of therapeutic agents and lead molecules in drug discovery [12]. A number of biologically active natural products have been isolated from Aphyllophorales, many of which are known as polypores. Polypores are a large group of terrestrial fungi of the phylum Basidiomycota (basidiomycetes), and they are a major source of pharmacologically active substances [13]. For example, Ganoderma lucidum (Ling Zhi or Reishi), a wellknown fungus that has been used for medicinal purposes for centuries, has been studied extensively [14,15]. A precious basidiomycete Antrodia cinnamomea [syn. A. camphorata] (Ac) restrictively grows in a unique host, the endemic and en...

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On the origins of triterpenoid skeletal diversity

Cited by 514 publications

References 238 publications

Contribution of NAD 2D-NMR in liquid crystals to the determination of hydrogen isotope profile of methyl groups in miliacin

Contribution of NAD 2D-NMR in liquid crystals to the determination of hydrogen isotope profile of methyl groups in miliacin

Unique Biosynthesis of Sesquarterpenes (C₃₅Terpenes)

A triterpenoid methyl antcinate K isolated from Antrodia cinnamomea promotes dendritic cell activation and Th2 differentiation

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On the origins of triterpenoid skeletal diversity

Cited by 514 publications

References 238 publications

Contribution of NAD 2D-NMR in liquid crystals to the determination of hydrogen isotope profile of methyl groups in miliacin

Contribution of NAD 2D-NMR in liquid crystals to the determination of hydrogen isotope profile of methyl groups in miliacin

Unique Biosynthesis of Sesquarterpenes (C35Terpenes)

A triterpenoid methyl antcinate K isolated from Antrodia cinnamomea promotes dendritic cell activation and Th2 differentiation

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Unique Biosynthesis of Sesquarterpenes (C₃₅Terpenes)