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Phytochemistry
Elsevier Science Ltd.
Phytochemistry

Elsevier Science Ltd.

0031-9422

Phytochemistry/Journal PhytochemistrySCICCRIC
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    Lanostane triterpenoids from cultivated fruiting bodies of basidiomycete Ganoderma mbrekobenum

    Yangchum, ArunratFujii, RyomaChoowong, WilundaRachtawee, Pranee...
    9页
    查看更多>>摘要：In the quest for medicinally active compounds in mushrooms of the genus Ganoderma, eleven undescribed lanostane triterpenoids, including a novel chlorinated derivative, i.e., (20S,24E)-21-chloro-15 beta,20,29-trihydroxy3,7,11-trioxolanosta-8,24-dien-26-oic acid, were isolated from artificially cultivated fruiting bodies of the basidiomycete Ganoderma mbrekobenum. The structures were elucidated on the basis of NMR spectroscopic and mass spectrometry data. The configuration of the C-20 atom in the most abundant 20-hydroxy-lanostane, (20S,24E)-15 beta,20,29-trihydroxy-3,7,11-trioxolanosta-8,24-dien-26-oic acid, was established by chemical derivatization, and the absolute configuration of the lanostane skeleton was determined by ECD calculation. Two of the undescribed compounds exhibited moderate antimalarial activity.
      原文链接:
    • NSTL
    • Elsevier

    Alkaloids from the stem barks of Scutia buxifolia Reissek (Rhamnaceae): Structures and antimicrobial evaluation

    Dahmer, JaniceMarangon, PatriciaAdolpho, Luciana O.Reis, Frederico L....
    9页
    查看更多>>摘要：A reinvestigation of the chemical constituents of the stem barks of Scutia buxifolia, a member of the Rhamnaceae, resulted, along with the known alkaloids scutianine C and scutianene L, in the isolation of three undescribed diastereoisomeric alkaloids - scutianine N, 27-epi-scutianine N and 3, 4, 7-tri-epi-scutianine N -, one undescribed non macrocyclic alkaloid - scutianine Q - and a neutral compound -scutianene M. Their structures were determined using extensive NMR techniques and HRMS. The absolute configurations of the stereogenic centers of the three diastereoisomeric alkaloids have been assigned by gas chromatography employing modified cyclodextrins as chiral stationary phases. Scutianine Q had its structure and stereochemistry defined by single crystal X-ray crystallographic analysis. All tested compounds showed good to moderate antibacterial activity (MICs between 1.56 and 100 mu g mL-1) when evaluated in vitro against a panel of Gram-positive and Gram-negative bacteria. Some stereochemistry-activity relationships have been identified for the antibacterial activity of diastereoisomeric alkaloids against the Gram-negative bacteria Enterobacter aerogenes. The alkaloid 27-epi-scutianine N was as active as the standard antibiotic chloramphenicol (MIC = 1.56 mu g mL-1), while scutianine N and 3,4,27-tris-epi-Scutianine N were inactive (>100 mu g mL-1).
      原文链接:
    • NSTL
    • Elsevier

    Bioactive specialised metabolites from the endophytic fungus Xylaria sp. of Cudrania tricuspidata

    Song, JintongXu, KeLiu, ChunyuWang, Tian...
    9页
    查看更多>>摘要：Fourteen undescribed compounds, including five 2,5-diarylcyclopentenones xylariaones A1-B2, seven a-pyrone derivatives xylaripyones A G, one.-pyrone derivative xylaripyone H, one diketopiperazine cyclo-(L-Leu-N=ethyl-L-Glu), and two known diketopiperazines, were isolated from cultures of the endophytic fungus Xylaria sp., which was separated from Cudrania tricuspidata Bureau ex Lavall ' ee. Their structures were determined by analysing extensive spectroscopic data (HRESIMS and NMR) and electronic circular dichroism (ECD) calculations. Furthermore, these compounds were evaluated for potential antiproliferative activity against the human tumour cell lines PC3 and A549, and the results showed that xylaripyone D exhibited moderate inhibitory activity against the proliferation of PC3 cell lines with an IC50 value of 14.75 mu M. Meanwhile, xylariaone A3 and xylaripyone F displayed weak inhibitory effects on NO production in RAW 264.7 murine macrophages with IC50 values of 49.76 and 69.68 mu M, respectively.
      原文链接:
    • NSTL
    • Elsevier

    Iboga-type alkaloids with Indolizidino[8,7-b]Indole scaffold and bisindole alkaloids from Tabernaemontana bufalina Lour

    Chen, Shun-QingJia, JiaHu, Jing-YaoWu, Jun...
    11页
    查看更多>>摘要：Phytochemical investigation on the aerial parts of Tabernaemontana bufalina Lour. (Apocynaceae) led to the identification of four undescribed monoterpenoid indole alkaloids named taberbufamines A-D, an undescribed natural product, and fourteen known indole alkaloids. The structures of the undescribed alkaloids were established by spectroscopic and computational methods, and their absolute configurations were further determined by quantum chemical TDDFT calculations and the experimental ECD spectra. Taberbufamines A and B possessed an uncommon skeleton incorporating an indolizidino [8,7-b]indole motif with a 2-hydroxymethyl-butyl group attached at the pyrrolidine ring. Biosynthetically, Taberbufamines A and B might be derived from iboga-type alkaloid through rearrangement. Vobatensine C showed significant bioactivity against A-549, Bel-7402, and HCT-116 cells with IC50 values of 2.61, 1.19, and 1.74 mu M, respectively. Ervahanine A showed antimicrobial activity against Bacillus subtilis, Mycobacterium smegmatis, and Helicobacter pylori with MIC values of 4, 8, and 16 mu g/mL, respectively. 19(S)-hydroxyibogamine was shown as butyrylcholinesterase inhibitor (IC50 of 20.06 mu M) and alpha-glycosidase inhibitor (IC50 of 17.18 mu M), while tabernamine, ervahanine B, and ervadivaricatine B only showed alpha-glycosidase inhibitory activities with IC50 values in the range of 0.95-4.61 mu M.
      原文链接:
    • NSTL
    • Elsevier

    Structural characterization of phenolic constituents from the rhizome of Imperata cylindrica var. major and their anti-inflammatory activity

    Han, YuZhang, YiWang, TaoRuan, Jing-Ya...
    13页
    查看更多>>摘要：As one of raw materials, the rhizome of Imperata cylindrica var. major (Nees) C.E. Hubb. is used in kinds of preparations curing inflammation related diseases, while its effective substances are not yet clear. In this paper, its chemical constituents and their anti-inflammatory activities were investigated. As results, ten compounds, named as imperphenoside A (1), imperphenols B (2) and C (3), imperphenosides D-F (4-6), and imperlignanosides A-D (7-10), along with previously reported thirty-seven known ones (11-47) were obtained from it. Their structures were ascertained basing on the extensive spectroscopic methods and electronic circular dichroism data analysis. Meanwhile, compounds 4, 11, 12, 24, 27, 31, 32, 37, 43, 45, and 47 exhibited nitric oxide inhibitory effects in concentration dependent at 3, 10, and 30 mu M on lipopolysaccharides induced RAW 264.7 cells. Moreover, the western blot analysis indicated that compounds 4, 11, 43, and 47 could restrain the phosphorylation of nuclear factor kappa-B kinase to down-regulate the protein expression of inflammatory cytokines such as inducible nitric oxide synthase, interleukin-6 and tumor necrosis factor-alpha. In conclusion, they might play the anti-inflammatory effects through regulating NF-kappa B signaling pathway.
      原文链接:
    • NSTL
    • Elsevier

    Diverse diterpenoids with alpha-glucosidase and beta-glucuronidase inhibitory activities from Euphorbia milii

    Yu, Hang-FeiCheng, Yu-ChenWu, Cai-MengRan, Kun...
    11页
    查看更多>>摘要：Four undescribed regular rosane-type diterpenoids euphominoids M-P and three undescribed rearranged rosane-type diterpenoids euphomilones C-E were isolated from the whole plants of Euphorbia milii Des Moul., along with nine known compounds. Their structures were elucidated by detailed interpretation of the NMR and mass spectroscopy. The absolute configurations were established by single-crystal X-ray diffraction experiments, as well as comparative analyses of calculated and experimental ECD spectra. Euphominoid M featured a highly oxygenated ring A and a rare four-membered oxygen ring while euphomilones C-E possessed 7/5/6 or 5/7/6 fused ring systems, which were rarely occurring in rosane-type diterpenoids. In the in-vitro bioassays, 19-norrosa1,3,5(10),15-tetraene-2,3-diol and antiquorin showed more potent alpha-glucosidase inhibitory activity than the positive control acarbose while euphominoid C exhibited significant inhibitory activity against both alpha-glucosi-dase and beta-glucuronidase. To the best of our knowledge, it was the first time that rosane-type diterpenoids were reported as beta-glucuronidase inhibitors.
      原文链接:
    • NSTL
    • Elsevier

    Marginols A-H, unprecedented pimarane diterpenoids from Kaempferia marginata and their NO inhibitory activities

    Do, Kiep MinhKodama, TakeshiShin, Min-KyoungLien Huong Ton Nu...
    10页
    查看更多>>摘要：Kaempferia marginata rhizomes are used as an herb in food and as traditional medicine for the treatment of inflammatory-related diseases in Asian countries. In contrast to the previously reported phytochemical investigation of Thai and Chinese K. marginata rhizomes, which demonstrated the presence of sandaracopimaradiene and ent-sandaracopimaradiene, our first investigation of Vietnamese K. marginata rhizomes led to the isolation of eight undescribed pimarane diterpenoids, marginols A-H, along with 18 known pimarane diterpenoids. The structures of these compounds were elucidated by spectroscopic techniques, including 1D and 2D NMR, HRESIMS, and CD spectroscopy and/or by comparisons of their NMR data with previously reported data. Furthermore, evaluations of the NO production inhibitory activity against LPS-stimulated RAW264.7 cells revealed that the undescribed compounds, marginols B and D-G, and the known compounds, sandaracopimaradien-6 beta,9 alpha-diol-1-one and 6-acetoxysandaracopimardien-9-ol-1-one, showed potent activities. These results provide insights into the chemodiversity of Vietnamese K. marginata rhizomes as well as their traditional usage from the viewpoint of their chemical constituents.
      原文链接:
    • NSTL
    • Elsevier

    Chemical diversity of kanuka: Inter- and intraspecific variation of foliage terpenes and flavanones of Kunzea (Myrtaceae) in Aotearoa/New Zealand

    Fuller, Ioan D.de Lange, Peter J.Burgess, Elaine J.Sansom, Catherine E....
    8页
    查看更多>>摘要：Kunzea (Myrtaceae) trees and shrubs, generally called kanuka, grow across most of Aotearoa/New Zealand (NZ). With the exception of K. sinclairii, an offshore island endemic, kanuka had been treated as an Australasian species K. ericoides. However, a 2014 taxonomic revision recognized ten species, all endemic to NZ. Kanuka chemistry is less studied than that of its closest relative in NZ, manuka (Leptospermum scoparium), which shows very distinct regional foliage chemotypes. We have used a miniaturized method with GC and H-1 NMR to analyze foliage chemistry of voucher specimens from across the geographic ranges of the ten NZ Kunzea species. We found common mono- and sesquiterpenes, with alpha-pinene dominant in all samples, but only traces of antimicrobial triketones. Two unusual flavanones, with unsubstituted B-rings and known bioactivity against Phytophthora, did distinguish some of the samples. 5,7-Dihydroxy-6,8-dimethyl flavanone was only found at high concentrations in the three K. sinclairii samples in this study's sample set, but this compound has separately been reported in K. robusta samples from a nearby region. Therefore none of the NZ Kunzea species was distinguished by the chemistry analyzed in this study, but there is a possibility of regional flavonoid chemotypes cutting across the species boundaries.
      原文链接:
    • NSTL
    • Elsevier

    Cadinane sesquiterpenoids from the fungus Antrodiella albocinnamomea and their inhibitory activity against nitric oxide production

    Yu, Wei-WeiMa, Jin-TaoHe, JuanLi, Zheng-Hui...
    6页
    查看更多>>摘要：Seven previously undescribed cadinane sesquiterpenoids, albocinnamins A.G, were isolated from the fungus Antrodiella albocinnamomea. Their structures with absolute configurations were elucidated on the basis of extensive spectroscopic methods, as well as single crystal X-ray diffraction. Cadinane sesquiterpenoids were reported from A. albocinnamomea for the first time. All of these sesquiterpenoids possess an unusual ether ring with minor modifications. Albocinnamins D and G showed certain inhibitory activities against nitric oxide production in LPS-activated RAW264.7 macrophages with IC50 values of 26.1 and 19.2 mu M, respectively.
      原文链接:
    • NSTL
    • Elsevier

    Highly oxygenated isoryanodane diterpenoids from the leaves of Cinnamomum cassia and their immunomodulatory activities

    Zhou, LeiZheng, GuijuanLi, HengGao, Biao...
    10页
    查看更多>>摘要：A total of twelve highly oxygenated isoryanodane (also known as cinncassiol D-type) diterpenoids including nine undescribed ones, named cinnacassins A I, were isolated from the leaves of Cinnamomum cassia. Their chemical structures were elucidated by extensive spectrometric and spectroscopic techniques including HRESIMS, 1D and 2D NMR, single-crystal X-ray diffraction analysis, calculated C-13-NMR DP4+ analysis, and chemical methods. The absolute configuration of cinnacassin A was unambiguously delineated by single-crystal X-ray diffraction analysis. Cinnacassin H represents the first example of 16-O-glucosylated isoryanodane diterpenoid, and cinnacassin I is the first isoryanod-13(18)-ene diterpenoid. The relationship of the configuration C-18 and the chemical shifts of H2-19 and C-20 in the 19-hydroxy-isoryanodane diterpenoids was discussed, and the 18S-configuration of three known 19-hydroxy-isoryanodane diterpenoids, cinncassiol D1, 19-O-beta-D-glucopyranosylcinncassiol D1, and cinncassiol D3 was assigned. All the isolated isoryanodane diterpenoids were evaluated for their immunomodulatory effects in vitro, and cinnacassin A and cinncassiol D1 enhanced the proliferation of Con A-induced murine T cells with enhancement rates ranging from 17.9% to 45.4%, which were more potent than the positive control, thymosin alpha(1). In addition, cinncassiol D-1 significantly promoted the proliferation of LPSinduced murine B cells with an enhancement rate up to 116.1%, two-fold more potent than thymosin a1 at a concentration of 1.5625 mu M.
      原文链接:
    • NSTL
    • Elsevier