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Phytochemistry
Elsevier Science Ltd.
Phytochemistry

Elsevier Science Ltd.

0031-9422

Phytochemistry/Journal PhytochemistrySCICCRIC
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    Lanostane-type triterpenoids from the mycelial mat of Ganoderma lucidum and their hepatoprotective activities

    Zhang, XueqingGao, XiaoxuLong, GuoqingYang, Yongcheng...
    11页
    查看更多>>摘要：Ganoderma lucidum (G. lucidum), a well-known Polyporaceae family fungus, is valued for its edibility and medicinal properties. It is a rich source of active polysaccharides and triterpenoids. However, obtaining material for medicinal purposes relies on artificial cultivation in a greenhouse, which requires large amounts of tree trunk due to the low biomass transformation rate. Therefore, an effective and environment-friendly culture method should be developed and the chemical compounds in the cultured material should be studied. Here we report the isolation and structural elucidation of 10 undescribed lanostane triterpenoids and 21 known compounds from statically cultured mycelial mat of G. lucidum. The hepatoprotective activity of these compounds in H2O2- induced HepG2 cells was evaluated. The structure-activity relationship is discussed. Our results demonstrated that twelve ganoderic acid derivatives possess significant hepatoprotective activities, as judged by suppressed activities of ALT, AST and LDH and increased GSH levels in H2O2-injured HepG2 cells.
      原文链接:
    • NSTL
    • Elsevier

    Polyketides, diketopiperazines and an isochromanone from the marine-derived fungal strain Fusarium graminearum FM1010 from Hawaii

    Zaman, K. H. Ahammad UzSarotti, Ariel M.Wu, XiaohuaCao, Shugeng...
    8页
    查看更多>>摘要：The fungal strain Fusarium graminearum FM1010 was isolated from a shallow-water volcanic rock known as "live rock " at the Carl Smith Beach, Hilo, Hawaii. Eleven specialised metabolites, including two undescribed diketopiperazines, three undescribed polyketides, and one undescribed isochromanone, along with five known fusarielin derivatives were obtained from F. graminearum FM1010. The structures of the six undescribed compounds were elucidated by extensive analysis of NMR spectroscopy, HRESIMS, chemical reactions, and electronic circular dichroism (ECD) data. Kaneoheoic acids G-I showed mild inhibitory activity against S. aureus with the MIC values in the range of 20-40 mu g/mL when assayed in combination with chloramphenicol (half of the MIC, 1 mu g/mL), an FDA approved antibiotic. Kaneoheoic acid I exhibited both anti-proliferative activity against ovarian cancer cell line A2780 and TNF-alpha induced NF-kappa B inhibitory activity with the IC50 values of 18.52 and 15.86 mu M, respectively.
      原文链接:
    • NSTL
    • Elsevier

    Oblongolides from endophytic fungus Phoma bellidis Neerg. harbored in Tricyrtis maculata (D. Don) JFMacbr

    Zhang, XianYang, Hui-XiangYe, KeWei, Pan-Pan...
    8页
    查看更多>>摘要：Five previously undescribed oblongolides, namely phomaones A-E, along with four known compounds, were isolated from the endophytic fungus Phoma bellidis Neerg.. Their structures and absolute configurations were determined by extensive experimental spectroscopic methods as well as single crystal X-ray diffractions, ECD calculations and GIAO C-13 NMR calculations. Phomaone A represent the first example of oblongolides with glycol directly linked by two C-C bonds, and its biosynthetic pathway were proposed. The cytotoxicity of obtained compounds was evaluated against human cancer cell lines MCF-7, DU145, and SW480. All compounds except phomaone A showed the cytotoxicity against MCF-7 with IC50 value ranging from 12.45 to 49.84 mu M.
      原文链接:
    • NSTL
    • Elsevier

    Phytochemical and biological studies on rare and endangered plants endemic to China. Part XXII. Structurally diverse diterpenoids from the leaves and twigs of the endangered conifer Torreya jackii and their bioactivities

    Li, HaoTang, YuLiang, Kai-YuanZang, Yi...
    9页
    查看更多>>摘要：A phytochemical investigation on the MeOH extract of the leaves and twigs of the endangered conifer Torreya jackii Chun led to the isolation and characterization of 21 structurally diverse diterpenoids. Among them, six are previously undescribed, including four abietane-type (torreyins A-D, resp.) and two labdane-type diterpenoids (torreyins E and F). Their structures and absolute configurations were determined by a combination of spectroscopic methods, calculated/experimental electronic circular dichroism (ECD) data, and single-crystal X-ray diffraction analyses. In particular, torreyins A-C are rare 11,12-seco-abietane type diterpenoids possessing a dilactone moiety, and their biosynthetic pathway starting from a co-occurring abietane derivative (i.e., cyrtophyllone B) was briefly proposed. Among the isolates, 7-oxo-dehydroabietic acid and 15-methoxy-7,13-abietadien-18-oic acid showed considerable inhibitory effects against acetyl-coenzyme A carboxylase 1 (ACC1) and protein tyrosine phosphatase 1 B (PTP1B), with IC50 values of 3.1 and 6.8 mu M, respectively.
      原文链接:
    • NSTL
    • Elsevier

    Discovery of Undescribed Monoterpenoid Polyprenylated Acylphloroglucinols with Immunosuppressive Activities from Hypericum longistylum

    Shi, ZhengyiTan, XiaoshengHu, HongZhang, Na...
    8页
    查看更多>>摘要：Acylphlorostylums A-G (1-7), seven undescribed monoterpenoid polyprenylated acylphloroglucinols, were isolated and identified from Hypericum longistylum. Significantly, acylphlorostylums A and B were the first monoterpenoid polyprenylated acylphloroglucinols possessing a dodecahydro-1H-benzo [b]cyclopenta [e]oxepine moiety bearing a 6/7/5 fused tricyclic ring system that assembled by the attack from 4-OH to C-13. In addition, acylphlorostylums A-G exhibited moderate in vitro immunosuppressive activity in anti-CD3/anti-CD28 monoclonal antibodies, lipopolysaccharide and concanavalin A-induced murine splenocyte proliferation, with IC50 values ranging from 1.51 +/- 0.12 to 18.49 +/- 1.67 mu M, underscoring those isolates as novel chemical templates in the development of novel immunosuppressors.
      原文链接:
    • NSTL
    • Elsevier

    Dimeric Erythrina alkaloids as well as their key units from Erythrina variegata

    Tang, Yu-TingWu, JingBao, Mei-FenTan, Qin-Gang...
    8页
    查看更多>>摘要：Ten dimeric and two monomeric Erythrina alkaloids, all of them are undescribed, were isolated from the bark of Erythrina variegata L. and named as erythrivarines O-Z. Their structures were determined on the basis of NMR and UV-spectroscopy and mass spectrometry. Dimeric Erythrina alkaloids with a C-10/11'& nbsp;linkage in erythrivarine O and a C-7/10'& nbsp;connectivity in erythrivarines P-U are not yet reported. The two identified monomeric alkaloids may be the precursors of the described dimeric derivatives. These co-occurring dimeric and monomeric alkaloids enabled us to propose a possible biosynthetic pathway leading to these dimers. Their effects of preventing hearing loss were additionally evaluated and erythrivarine T showed as a potential protector of the House Ear Institute-Organ of Corti 1 (HEI-OC-1) cells against neomycin.
      原文链接:
    • NSTL
    • Elsevier

    Induction of volatile organic compounds in Triticum aestivum (wheat) plants following infection by different Rhizoctonia pathogens is species specific

    Piesik, DariuszLemanczyk, GrzegorzBocianowski, JanBuszewski, Boguslaw...
    9页
    查看更多>>摘要：The most popular means of plant protection is the chemical method, but this control is often connected with the need for repeating chemical treatments. Thus, eco-friendly strategies should be developed where, under the European Green Deal, aromatic plants and their repellent properties seem to constitute a good alternative. In earlier studies, we have shown that insect injury, bacteria infestation and pathogen infection induce plant volatile organic compounds (VOCs) emission, which can provide defensive functions to plants.& nbsp;In this study, Triticum aestivum L. (Poaceae) cv. 'Jenga' wheat plants were intentionally infected with one of four Rhizoctonia species (R. cerealis, R. solani, R. zeae, and R. oryzae). The soil was inoculated by the pathogens during sowing, whereas shoots were inoculated at stage BBCH 33. In greenhouse experiments, we measured VOCs from wheat 3, 7 and 11 days following stem infestation, or 42 days following soil inoculation of Rhizoctonia spp. VOC emissions were found to be largest on days 7 or 11 post-stem inoculation (> 3 days post-stem inoculation > 42 days post-soil inoculation). T. aestivum infected by pathogens induced five common green leaf volatiles (GLVs), namely (Z)-3-hexenal = (Z)-3-HAL, (E)-2-hexenal = (E)-2-HAL, (Z)-3-hexen-1-ol= (Z)-3HOL, (E)2-hexenol = (E)-2-HOL, (Z)-3-hexen-1-yl acetate = (Z)-3-HAC], six common terpenes (beta-pinene = beta-PIN, beta-myrcene = beta-MYR, Z-ocimene = Z-OCI, linalool = LIN, benzyl acetate = BAC, beta-caryophyllene =beta-CAR), and indole = IND. We found that R. cerealis infested T. aestivum emitted the largest amounts of (Z)-3-HAL and (Z)-3HAC, while T. aestivum infested by R. solani released the largest amount of LIN (7 or 11 days following stem infestation). VOCs released by the T. aestivum after R. cerealis (AGD I) and R. solani (AG 5) infestations were significantly larger in comparison to R. zeae (WAG-Z) and R. oryzae (WAG-O) for the volatiles (Z)-3-HAL, (E)-2HAL, (Z)-3-HOL, (E)-2-HOL, (Z)-3-HAC, beta-PIN, beta-MYR, and LIN. With the exception of (E)-2-HOL, beta-MYR, LIN, BAC, beta-CAR, the other VOCs were emitted in similar amounts by infected T. aestivum 3 days following stem and soil inoculation. The quantities of induced VOCs were higher at days 7 and 11 than at 3 days post-infection, and greater when T. aestivum was infected with Rhizoctonia on the stem base than through the soil.
      原文链接:
    • NSTL
    • Elsevier

    Isoindolines and phthalides from the rhizomes of Ligusticum chuanxiong and their relaxant effects on the uterine smooth muscle

    Liu, JuanFeng, RuiDai, OuNi, Hong...
    8页
    查看更多>>摘要：Three undescribed isoindoline alkaloids, (+)-(R)-3-butyl-3-ethoxyisoindolin-1-one, (+)-(3S,6S,7R)-3-butyl-6,7-dihydroxy-3-methoxy-4,5,6,7-tetrahydroisoindolin-1-one, and (- )-(3R,6S,7R)-3-butyl-6,7-dihydroxy-3-methoxy-4,5,6,7-tetrahydroisoindolin-1-one, along with nine known phthalides were isolated from a water decoction of the rhizomes of Ligusticum chuanxiong using chromatographic methods. Their structures and absolute configurations were determined by extensive spectroscopic analyses and ECD data calculations. The relaxant effects of the isolated compounds on uterine contractions induced by oxytocin were investigated using a rat uterine smooth muscle contraction model. Furthermore, the effects of riligustilide on extracellular Ca2+ influx and intracellular Ca2+ release were assessed using high-KCl solution-induced and oxytocin-induced uterine smooth muscle contraction in a Ca2+-free balanced salt solution. The results showed that all the tested phthalides had inhibitory effects on oxytocin-induced uterine smooth muscle contraction. Riligustilide, a phthalide dimer, was the most active. Further examinations indicated that riligustilide reduced uterine smooth muscle contraction by inhibiting extracellular Ca2+ influx and intracellular Ca2+ release.
      原文链接:
    • NSTL
    • Elsevier

    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.
      原文链接:
    • NSTL
    • Elsevier

    Structures and neuroprotective activities of triterpenoids from Cynomorium coccineum subsp. songaricum (Rupr.) J. Leonard

    Zhang, BoYang, Sheng-LiLi, XinZhang, Qian-Ru...
    7页
    查看更多>>摘要：Cynomorium coccineum subsp. songaricum (Rupr.) J. Leonard has been widely used as a Chinese herbal remedy or a functional food for treating symptoms of aging or neurodegenerative diseases. A further investigation on the finding of active constituents led to the isolation and identification of four previously undescribed triterpenoids, together with 20 known compounds. Their structures were elucidated by extensive spectroscopic analysis (IR, NMR, HRMS, and CD). Sixteen compounds showed significant neuroprotective effects against glutamate-induced or oxygen-glucose deprivation-induced SK-N-SH cell death. Our findings revealed the active constituents of C. coccineum subsp. songaricum and indicated that both oleanane-type and ursane-type triterpenes could be valuable platforms for neurodegenerative agents based on primary structure-activity relationship analysis.
      原文链接:
    • NSTL
    • Elsevier