Complete 1H and 13C NMR data assignment of protolimonoids from the stem barks of Aphanamixis grandifolia

Wang, Junsong; Zhang, Yao; Luo, Jun; Kong, Ling–Yi

doi:10.1002/mrc.2768

Cited by 15 publications

(7 citation statements)

References 28 publications

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“…Its molecular formula C 30 H 48 O 3 (seven degrees of unsaturation) was established by the positive HR-ESIMS quasi molecular ion peak at m / z 457.3670 ([M + H] + , calculated for 457.3676) (Supplementary Material S33). The NMR spectroscopic data of 2 (Table 1 and Table 2) (Supplementary Materials S34‒S39) were closely related to those of aphagranin D [23], the difference being the absence of the 24-OH and 25-OH groups in 2 . This deduction were corroborated by the upshifted C-24 ( δ C 82.1 CH in aphagranin D; whereas δ C 46.8 CH 2 in 2 ) and C-25 ( δ C 79.0 qC in aphagranin D; whereas δ C 24.5 CH in 2 ), and the proton spin-spin system, i.e., H 2 -24‒H-25(H 3 -26)‒H 3 -27, observed in the 1 H‒ 1 H COSY spectrum of 2 (Supplementary Materials S42‒S44).…”

Section: Resultsmentioning

confidence: 99%

Mangrove Tirucallane- and Apotirucallane-Type Triterpenoids: Structure Diversity of the C-17 Side-Chain and Natural Agonists of Human Farnesoid/Pregnane–X–Receptor

et al. 2018

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Ten new triterpenoid compounds with structure diversity of the C-17 side-chain, including nine tirucallanes, named xylocarpols A–E (1–5) and agallochols A–D (6–9), and an apotirucallane, named 25-dehydroxy protoxylogranatin B (10), were isolated from the mangrove plants Xylocarpus granatum, Xylocarpus moluccensis, and Excoecaria agallocha. The structures of these compounds were established by HR-ESIMS and extensive one-dimensional (1D) and two-dimensional (2D) NMR investigations. The absolute configurations of 1 and 2 were unequivocally determined by single-crystal X-ray diffraction analyses, conducted with Cu Kα radiation; whereas those of 4, 6–8 were assigned by a modified Mosher’s method and the comparison of experimental electronic circular dichroism (ECD) spectra. Most notably, 5, 6, 7, and 9 displayed potent activation effects on farnesoid–X–receptor (FXR) at the concentration of 10.0 μM; 10 exhibited very significant agonistic effects on pregnane–X–receptor (PXR) at the concentration of 10.0 nM.

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Section: Resultsmentioning

confidence: 99%

Mangrove Tirucallane- and Apotirucallane-Type Triterpenoids: Structure Diversity of the C-17 Side-Chain and Natural Agonists of Human Farnesoid/Pregnane–X–Receptor

et al. 2018

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“…1) were isolated from the stem barks of Aphanamixis grandifolia and were elucidated by spectroscopic means as described in our previous reports. 48,[51][52][53][54] Reagents and Cells Dimethyl sulfoxide (DMSO), lipopolysaccharide (LPS) and 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) were purchased from Sigma-Aldrich (St Louis, MO, U.S.A.). Dulbecco's modified Eagle's medium (DMEM), penicillin and streptomycin were bought from Gibco BRL.…”

Section: Methodsmentioning

confidence: 99%

Relationship of Chemical Structure to in Vitro Anti-inflammatory Activity of Tirucallane Triterpenoids from the Stem Barks of Aphanamixis grandifolia

Guo

Wang

Zhang

et al. 2012

CHEMICAL & PHARMACEUTICAL BULLETIN

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A series of tirucallane triterpenoids isolated from the stem barks of Aphanamixis grandifolia were assessed for their anti-inflammatory activity, exhibiting from weak to strong anti-inflammatory activity, by testing their inhibitory effects on nitric oxide (NO) production and tumor necrosis factor-α (TNF-α) level in lipopolysaccharide (LPS) induced RAW264.7 murine macrophages. To explore the relationship between the structures and anti-inflammatory activity, a vast pool of molecular descriptors for each isolate were calculated. Genetic algorithms (GA) or simulated annealing (SA) based partial least squares (GA-PLS and SA-PLS) algorithms identified some important descriptor combinations, which were correlated with both sets of the anti-inflammatory data by partial least squares 2 (PLS2) method. S-Plot was used to visualize the descriptor influence in the PLS2 model, disclosed five most important molecular descriptors, nOHt, RDF150m, lip_vio-lation, Mor32m and JhetZ.Key words Aphanamixis grandifolia; tirucallane triterpenoid; anti-inflammatory activity; nitric oxide; tumor necrosis factor-α; structure-activity relationship Inflammation is a normal and crucial response of the organism to various stimuli including physical damage, ultra violet irradiation, microbial invasion and immune reactions, playing a pivotal role in host defense.1,2) While inflammatory cascades may cause pain, tissue damage, and a wide range of human acute and chronic inflammatory diseases, such as chronic asthma, rheumatoid arthritis and multiple sclerosis, and psoriasis.3) Many of these diseases with increasing incidence rate are particularly debilitating to the patient's functional capacity and quality of life.Macrophages have vital functions in maintaining body homeostasis, as well as in inflammatory processes, which are endowed with the ability to release a variety of mediators including the free radical nitric oxide (NO), 4) one of the most versatile regulator in the immune system. 5) Overproduction of NO can exacerbate inflammation, playing an important role in the pathogenesis of several chronic and systemic inflammation diseases, such as rheumatoid arthritis. 6,7)Tumor necrosis factor-α (TNF-α), one of the most important pro-inflammatory cytokines, is also massively produced by the activated macrophages and monocytes at local sites of inflammation.8) Its excessive production further triggers the secretion of other inflammatory cytokines such as interleukin-1β (IL-1β), interleukin-6 (IL-6) and granulocyte-macrophage colony-stimulating factor (GM-CSF) and thereby aggravates the inflammation in many autoimmune/inflammatory diseases. 9-11)Exposure to major anti-inflammatory agents, such as corticosteroids, non-steroidal anti-inflammatory drugs (NSAIDs), is known to increase substantially the risk of serious side effects.3,12) Therefore, there is an unmet medical need for new treatment strategies, which could be possibly filled by rational phytopharmaceuticals with a favorable benefit/risk ratio. Recent investigations into the anti-inflamm...

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“…For biological applications of triterpenoid compounds, see: Faizi et al (2002); Wang et al (2011); Dong et al (2012). For isolation of the title compound from the barks of Melia azedarach, see: Chang & Chiang (1969 Symmetry code: (i) Àx; y À 1 2 ; Àz þ 1 2 .…”

Section: Related Literaturementioning

confidence: 99%

Crystal structure of 16-hydroxy-4,4,10,13,14-pentamethyl-17-(6-methylhept-5-en-2-yl)-4,5,6,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3(2H)-one

Chen

Xiao-xia

2015

Acta Cryst E

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The title compound, C30H48O2, contains a fused four-ring triterpenoid system. In the molecule, the two cyclohexane rings adopt a chair conformation and a twist boat conformation, respectively, the central cyclohexene ring adopts a half-chair conformation whereas the five membered ring adopts an envelope conformation. In the crystal, O—H⋯O hydrogen bonds between the hydroxy and carbonyl groups of adjacent molecules link the molecules into supramolecular chains propagating along the b-axis direction.

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Complete ¹H and ¹³C NMR data assignment of protolimonoids from the stem barks of Aphanamixis grandifolia

Abstract: Seven new protolimonoids, named aphagranins A-G (1-7), along with four known compounds, were isolated from the ethanol extract of the stem barks of Aphanamixis grandifolia. Structure elucidation and signal assignments were achieved on the basis of spectral and chemical evidences.

Cited by 15 publications

References 28 publications

Mangrove Tirucallane- and Apotirucallane-Type Triterpenoids: Structure Diversity of the C-17 Side-Chain and Natural Agonists of Human Farnesoid/Pregnane–X–Receptor

Mangrove Tirucallane- and Apotirucallane-Type Triterpenoids: Structure Diversity of the C-17 Side-Chain and Natural Agonists of Human Farnesoid/Pregnane–X–Receptor

Relationship of Chemical Structure to <i>in Vitro</i> Anti-inflammatory Activity of Tirucallane Triterpenoids from the Stem Barks of <i>Aphanamixis grandifolia</i>

Crystal structure of 16-hydroxy-4,4,10,13,14-pentamethyl-17-(6-methylhept-5-en-2-yl)-4,5,6,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3(2H)-one

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