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Phytochemistry
Elsevier Science Ltd.
Phytochemistry

Elsevier Science Ltd.

0031-9422

Phytochemistry/Journal PhytochemistrySCICCRIC
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    Phloroglucinol–meroterpenoids from the leaves of Eucalyptus camaldulensis Dehnh.

    Yangok K.Watanapokasin R.Daus M.Saithong S....
    10页
    查看更多>>摘要：? 2022 Elsevier LtdFourteen undescribed phloroglucinol-meroterpenoids, namely eucalypcamals A–N, were isolated from a CH2Cl2 extract of the leaves of Eucalyptus camaldulensis Dehnh. In addition, from the same extract, twelve known phloroglucinols, three known flavonoids, and four known phenolic compounds were also isolated. The structures of the undescribed compounds were analyzed by 1D and 2D nuclear magnetic resonance (NMR) spectroscopy, and high resolution electrospray ionization mass spectrometry (HRESIMS). The assignments of the absolute configurations were performed by comparing the experimental electronic circular dichroism (ECD) data with the calculated values. Eucalyprobusal E was found to be cytotoxic against HCT116, Jurkat, and MDA-MB-231 cell lines with IC50 values of 17.6, 9.44, and 17.9 μM, respectively. Eucalrobusone F exhibited antibacterial activity against methicillin-resistant S. aureus (MRSA) and S. aureus with minimum inhibitory concentration/minimum bactericidal concentration (MIC/MBC) values of 4/4 μg/mL while euglobal Ia1 showed antifungal activity with MIC/MFC values of 16/16 μg/mL.
      原文链接:
    • NSTL
    • Elsevier

    Bioactive pterocarpans from the root of Astragalus membranaceus var. mongholicus

    Xiao L.-M.Zhao Z.-X.Zhou Z.-Q.Zhi H....
    12页
    查看更多>>摘要：? 2022 Elsevier LtdEleven undescribed and three known pterocarpans were isolated and identified from the traditional Chinese medicine “Huang-qi”, Astragali Radix (the root of Astragalus membranaceus var. mongholicus (Bunge) P.K.Hsiao). The structures of these pterocarpans were determined using spectroscopic, X-ray crystallographic, quantum chemical calculation, and chemical methods. Pterocarpans, almost exclusively distributed in the family of Leguminosae, are the second largest subgroup of isoflavanoids. However, pterocarpan glycoside number is limited, most of which are glucosides, and only one pterocarpan apioside was isolated from nature. Notably, nine rare apiosyl-containing pterocarpan glycosides were isolated and identified. The hypoglycemic activities of all these compounds were evaluated using α-glucosidase and DPP-IV inhibitory assays respectively, and some isolates displayed the α-glucosidase inhibitory function. The antioxidant activities of all compounds were evaluated using the ORAC and DPPH radical scavenging assays, respectively. All compounds exhibited varying degrees of oxygen radical absorbance capacity, and some compounds displayed DPPH radical scavenging ability.
      原文链接:
    • NSTL
    • Elsevier

    Cipacinerasins A–K, structurally diverse limonoids from Cipadessa baccifera

    Liu H.-F.Ni zhangLi J.-Y.Pan W.-D....
    11页
    查看更多>>摘要：? 2022 Elsevier LtdEleven undescribed limonoids, cipacinerasins A–K, involving of four diverse carbon skeletal types, along with fifteen known analogues, were isolated from the branches and leaves of Cipadessa baccifera. Within them, cipacinerasins A and B feature a rearranged tetrahydropyranyl ring B formed between C-8 and C-30, are unusual miscellaneous-type limonoids. Cipacinerasins E and F are rare trijugin-type limonoids, of which the D-ring δ-lactone is cleaved. Their structures were elucidated on the basis of extensive spectroscopic data (HRESIMS, NMR, UV and IR), electronic circular dichroism (ECD) calculations, and single-crystal X-ray diffraction analysis. All compounds were evaluated in vitro cytotoxicity against five human tumor cell lines (K562, HeLa, PC3, LN-Cap and Hell), and cipacinerasin E showed moderate antitumor activity with IC50 values ranging from 8.0 to 24.8 μM.
      原文链接:
    • NSTL
    • Elsevier

    Marginaols G–M, anti-in?ammatory isopimarane diterpenoids, from the rhizomes of Kaempferia marginata

    Chunglok W.Yotnoi B.Chulrik W.Chokchaisiri S....
    8页
    查看更多>>摘要：? 2022 Elsevier LtdMarginaols G–M, a series of undescribed isopimarane diterpenoids, together with four known analogs were isolated from the rhizomes of Kaempferia marginata. The structures of these isolated compounds were characterized using high-resolution mass spectrometry and extensive 1D- and 2D-nuclear magnetic resonance (NMR) analyses. In addition, the absolute con?gurations of marginaol G and H were determined by X-ray crystallographic analysis and comparison with the literature values. When compared to the standard drug dexamethasone (IC50 4.7 μM), marginaol G, H, and 6β-acetoxysandaracopimaradien-1α,9α-diol had an intriguing anti-inflammatory effect on NO inhibition in lipopolysaccharide (LPS)-stimulated RAW264.7 macrophages, with IC50 values ranging from 4.5 to 7.3 μM and being less cytotoxic to the cells. The anti-inflammatory action of these isopimarane diterpenoids from K. marginata supports the use of Thai traditional medicine for inflammation treatment.
      原文链接:
    • NSTL
    • Elsevier

    Plant genetic diversity by DNA barcoding to investigate propolis origin

    Sartori A.G.D.O.Cesar A.S.M.Coutinho L.L.Alencar S.M.D....
    11页
    查看更多>>摘要：? 2022 Elsevier LtdIdentify the botanical origins of a certain type of propolis may be challenging and time demanding, since it involves bee's behavior observation, plant resins collection and chemical analysis. Thus, this study aimed to determine the plant genetic materials in propolis from southern Brazil using the DNA barcoding to investigate their botanical origins, as well as to compare it with the phytochemical composition determined by ultra-high-performance liquid chromatography coupled with high-resolution mass spectrometry (UHPLC-HRMS) and with the pollinic profile. As principal results, non-native Populus carolinensis Moench (Salicaceae) was almost the only DNA source in some propolis samples, which coincided with the presence of flavonoids typical from poplar exudates. Conversely, other propolis samples had DNA material coming mainly from native plant species, most of them characterized to the species level, although no specific chemical markers from those plants could be identified by UHPLC-HRMS. However, pollen from several plants identified by the DNA barcoding were extracted from some propolis samples. Despite the identification of typical diterpenes, DNA material from Araucaria angustifolia (Bertol.) Kuntze (Araucariaceae), which have been indicated as a major resin source for propolis from preservation areas in southern Brazil, was found in very small abundancies, likely because bees do not drag tissue material containing DNA when collecting resin from this native species. In conclusion, DNA barcoding analysis successfully provided information about the provenance of propolis, although, depending on the plant resin sources, this information is likely to come from pollen.
      原文链接:
    • NSTL
    • Elsevier

    Unravelling the key aroma compounds in the characteristic fragrance of Dendrobium officinale flowers for potential industrial application

    Yang Y.-H.Zhao J.Du Z.-Z.
    8页
    查看更多>>摘要：? 2022 Elsevier LtdDendrobium officinale Kimura et Migo, one of the most important orchids because of its medicinal and edible value, has a typical Dendrobium Sw. flora scent, which has great application potential and commercial value to be characterized. The aroma-active compounds originating from D. officinale fresh flowers (DFF) were investigated using a sensomics approach. A combined solid phase microextraction and solvent-assisted flavor evaporation method were used to accurately capture the overall aromatic profile. Exactly 34 odorants were detected and identified by aroma extract dilution analysis (AEDA) coupled with gas chromatography/olfactometry?mass spectrometry (GC/O?MS) in DFF, of which nine odorants had a flavor dilution (FD) factor ≥27. All 34 odorants were further quantified. The odor activity values (OAVs) were calculated with the highest value of 7444, in which 18 compounds were confirmed to be key odorants, including 1-octen-3-ol, hexanal, nonanal, phenylacetaldehyde, linalool, 4-oxoisophorone, theaspirane, methyl salicylate, etc. Among the studies above, 42 out of 78 volatiles and 14 out of 34 odorants were identified in DFF for the first time. Then, the aroma profile of the DFF was simulated successfully by aroma recombination experiments based on the quantitation results, and the omission test suggested that alcohols are the decisive type of compounds in the DFF key odorants. In addition, a progressive addition test showed that the aroma recombinate prepared with 18 reference key odorants was able to reconstruct the characteristic aroma of DFF. In comparison, the recombinate constituted by mixing all 34 reference odorants in the same concentrations as determined in the DDF sample could mimic the flower scent and closely match the sensory attributes of the original D. officinale fresh flower.
      原文链接:
    • NSTL
    • Elsevier

    Structure elucidation of linear triquinane sesquiterpenoids, hirsutuminoids A-Q, from the fungus Stereum hirsutum and their activities

    Zhao Z.-Z.Zhao X.Si Y.-Y.Wang Z.-Z....
    12页
    查看更多>>摘要：? 2022 Elsevier LtdEighteen linear triquinane sesquiterpenoids (LTSs), including seventeen previously undescribed ones (hirsutuminoids A-Q), were isolated from the fermentation of the fungus Stereum hirsutum (Willd.) Pers. The structures and absolute configurations of the isolates were characterized by extensive spectroscopic analysis (1D, 2D NMR, and HRMS data), together with comparing the experimental and calculated data of both electronic circular dichroism and NMR data, as well as X-ray crystallography. Based on the literature survey and efforts on constructing the absolute configurations of these LTSs in this study, one empirical rule about the orientations of substitutions at C-2/C-3/C-7/C-9 was summarized. Anti-inflammatory and cytotoxic bioassays showed that only hirsutuminoid B inhibited the nitric oxide (NO) production in RAW 264.7 macrophages with an IC50 value, 18.9 μM.
      原文链接:
    • NSTL
    • Elsevier

    Cytotoxic cardiac glycosides from the root of Streblus asper

    Osman Mohammed R.M.Huang Y.Huang X.Deng S....
    11页
    查看更多>>摘要：? 2022 Elsevier LtdBioassay-guided separation of the root of Streblus asper led to the identification of six undescribed cardiac glycosides, including a rare cardiac glycoside dimer, along with twelve previously reported analogues. Their structures were determined on the basis of analyses of spectroscopic methods (1D and 2D-NMR spectroscopy), high-resolution electrospray ionization mass spectrometry (HRESIMS), circular dichroism (CD), and comparison of their spectroscopic data with previously reported data. Regarding their cytotoxic activities, microculture tetrazolium assays showed that all isolated cardiac glycosides strongly inhibited MCC-803, T24, SKOV-3, HepG2, Wi-38, and A549 cancer cell lines, with IC50 values ranging from 0.075 μM to 0.752 μM. One cardiac glycoside, a rare cardiac glycoside dimer, exhibited the strongest activity against the six cancer cell lines, with IC50 values ranging from 0.075 μM to 0.214 μM. In addition, the structure-activity relationships (SARs) of cardiac glycosides were investigated. In summary, S. asper showed marked cytotoxicity to several cancer cell lines, which could be meaningful for discovering new anticancer agents.
      原文链接:
    • NSTL
    • Elsevier

    Sesquiterpene lactone and its unique proaporphine hybrids from Magnolia grandiflora L. and their anti-inflammatory activity

    Cho H.M.Park E.J.Park Y.J.Ponce-Zea J....
    10页
    查看更多>>摘要：? 2022 Elsevier LtdTwo undescribed sesquiterpene lactone-proaporphine hybrid skeletons, two undescribed sesquiterpenes, and four known compounds were isolated from the aerial part of Magnolia grandiflora L. The structures of isolated compounds were unambiguously determined based on the interpretation of a combination of NMR spectroscopy, HRESIMS, DP4+ probability calculation of carbon data, X-ray crystallographic analyses, and ECD calculation. The isolated compounds were investigated for their anti-inflammatory activity against nitric oxide production and the protein expression of COX-2 in LPS-stimulated RAW 264.7 cells.
      原文链接:
    • NSTL
    • Elsevier

    Naming of new natural products: Standard, pitfalls and tips-and-tricks

    Bailly C.
    13页
    查看更多>>摘要：? 2022 Elsevier LtdNaming a newly discovered natural product (NP) is a pleasant but difficult exercise. In most cases, the NP name will be given with reference to the species of origin, be it a plant, a marine organism, a mammalian or microbial species. For a long time, the use of biologically-based trivial names has been recommended to identify the parental linkage between the product and the originating genus or species. But the recommendation is not always followed and a multiplicity of trivial names have been attributed to NP, based on locations (country, region, city), foods, music, animals, forenames, etc. Tips-and-tricks associated with the naming of NP are underlined here. Usually, NP are differentiated across a homogeneous chemical series with a letter (from the Latin or Greek alphabet), followed or not with a number. In other cases, the change of a single letter distinguishes a series of NP. Common pitfalls associated with the naming of NP are enumerated, including the complexity of names, use of synonyms, duplicated names, confusing names and inappropriate terminology. The difficulties regularly encountered with the naming of NP are discussed. Four essential recommendations are recalled: (i) a thorough analysis of the existing products to avoid duplicated names and confusion, (ii) the use of a biologically-based trivial name to retrace the origin of the product, (iii) the strict adherence to the codes of chemical nomenclature, and (iv) the preference for simple names to facilitate transmission. Naming a new NP is a rewarding task, which shall be performed with all due skill, care and diligence.
      原文链接:
    • NSTL
    • Elsevier