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Phytochemistry
Elsevier Science Ltd.
Phytochemistry

Elsevier Science Ltd.

0031-9422

Phytochemistry/Journal PhytochemistrySCICCRIC
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    Two pairs of undescribed enantiomers isolated from the fungus Penicillium griseofulvum

    Zang, YiYu, MuyuanShi, ZhengyiChen, Chunmei...
    7页
    查看更多>>摘要:Two pairs of undescribed enantiomers including a 2,5-diketopiperazine namely (+/-)-janthinolide G and a related analogue (+/-)-janthinolide H, were isolated from the crude extract of the fungus Penicillium griseofulvum together with five known compounds. Both two structures were determined by spectroscopic method and HRESIMS, whereas absolute stereochemistry was elucidated by using theoretical NMR calculation and ECD calculation. Janthinolide G is the first example of 2,5-diketopiperazine enantiomers with a cleavage diketopiperazine ring and comprises a terminal oxime group rarely seen in natural products. Biological screening of selected compounds found that 4 and 7 both exhibited weak alpha-glucosidase inhibitory effects, and a potential correlation was afforded by docking studies of alpha-glucosidase protein (PDB: 3TOP) and bioactive molecules. The plausible biosynthetic pathways of two unreported isolates are proposed here.

    Balance of Delta(5)-and Delta(7)-sterols and stanols in halophytes in connection with salinity tolerance

    Rozentsvet, Olga A.Kotlova, Ekaterina R.Bogdanova, Elena S.Nesterov, Viktor N....
    10页
    查看更多>>摘要:Sterols (STs) have a key role in regulating the fluidity and permeability of membranes in plants (phytosterols) that have wide structural diversity. We studied the effect of structural STs diversity on salt tolerance in halophytes. Specifically, we used gas chromatography-mass spectrometry (GC-MS), including two-dimensional gas chromatography-mass spectrometry (GCxGC-MS), to assess the STs composition in leaves of 21 species of wild-growing halophytes from four families (Asteraceae, Chenopodiaceae, Plumbaginaceae, Tamaricaceae) and three ecological groups (Euhalophytes (Eu), recretophytes (Re), salt excluders (Ex)). Fifteen molecular species of STs from three main groups, & UDelta;(5)-, & UDelta;(7)-and & UDelta;(0)- STs (stanols), were detected. Plants of the genus Artemisia were characterized by a high content of stigmasterol (30-49% of the total STs), while beta-sitosterol was the major compound in two Limonium spp., where it comprised 84-92% of the total STs. Species of Chenopodiaceae were able to accumulate both & UDelta;(5)-and & UDelta;(7)-STs and stanols. The content of the predominant & UDelta;(5)-STs decreased in the order Ex & RARR; Re & RARR; Eu. Molecular species with a saturated steroid nucleus were identified in Eu and Re, suggesting their special salt-accumulating and salt-releasing functions. The structural analogues of stigmasterol, having a double bond C-22, were stigmasta-7,22-dien-3 beta-ol (spinasterol) and stigmast-22-en-3 beta-ol (& UDelta;(7-)-sitosterol). The ratio of & UDelta;(5)-stig-masterol/& UDelta;(5)-beta-sitosterol increased in Ex plants, and spinasterol/& UDelta;(7-)-sitosterol and 22-stigmastenol/sitostanol increased in Eu plants. These data support the well-known role of stigmasterol and its isomers in plant responses to abiotic and biotic factors. The variability in STs types and their ratios suggested some involvement of the sterol membrane components in plant adaptation to growth conditions. The balance of & UDelta;(5)-, & UDelta;(7)-and stanols, as well as the accumulation of molecular analogues of stigmasterol, was suggested to be associated with salt tolerance of the plant species in this investigation.

    Proposal for structural revision of several monosubstituted tricycloalternarenes

    Fraga, Braulio M.Diaz, Carmen E.
    10页
    查看更多>>摘要:Cycloalternarenes are a group of meroterpenes isolated from epiphytic fungi with a mono-, bi, trior tetracyclic skeleton. We have detected in the bibliography a series of monosubstituted tricycloalternarenes with erroneous structures. Thus, in this work we make several proposals to correct the structures of nineteen 4-hydroxy-tricycloalternarenes, TCA 6a, TCA 11a(2), (2E)-and (2Z)-TCA 12a, 2H-(2E)-TCA 12a, TCAs 9a and F-2, methyl nortricycloalternarate, TCAs K, L, S-W, X-2 and tricycloalterfurenes A-C, and four 6-hydroxy-tricycloalternarenes, TCA 12b, TCA 13b, tricycloalterfurene D and TCA F-3. Moreover, the graphic representation of TCA 14b and TCAs 15b-18b had been corrected. In addition, we have suggested that mono-hydroxylated tricycloalternarenes can only exist in nature substituted at the 4 alpha-or 6 beta-position (4R- or 6R-configuration), which could also be explained considering biogenetic reasons. We have also determined the C-4 and C-6 configuration of several monosubstituted tricycloalternarenes, whose planar structure had been previously determined. Thus, compounds of the "series a " such as TCAs 1a-8a, 11a and ACTG-toxin H have a 4R-configuration, whilst in the "series b " TCAs 3b-7b and TCAs 9b-11b possess a 6R-configuration.

    Derrisrobustones A-D, isoflavones from the twig extract of Derris robusta (DC.) Benth. and their alpha-glucosidase inhibitory activity

    Suthiphasilp, VirayuPayaka, ApirakChaiyosang, BoonyanootHarding, David J....
    7页
    查看更多>>摘要:Three previously undescribed isoflavones, derrisrobustones A-C, and a previously undescribed natural isoflavone, derrisrobustone D, along with eight known isoflavones, were isolated from the twig extract of Derris robusta (DC.) Benth. All structures were identified by extensive spectroscopic analysis. Derrisrobustones A-C were obtained as scalemic mixtures and were resolved by chiral HPLC. The (1 & DPRIME;R, 2 & DPRIME;R) absolute configuration of (+)-derrisrobustone B was established by single-crystal X-ray crystallography using Cu K alpha radiation. The absolute configurations of derrisrobustones A and C were determined by analysis of experimental and calculated ECD data. All compounds were evaluated for their alpha-glucosidase inhibitory activity. Of these, derrubone displayed the best alpha-glucosidase inhibitory activity with an IC50 value of 64.2 mu M.