New Benzophenone and Bioactive Constituents from Hypericum nagasawae

Wu, Fu-Sen; Wang, I-Chou; Liaw, Chia‐Ching; Huang, Hsueh-Yang; Chang, Tsung-Hsien; Chen, Chunlin; Sung, Ping‐Jyun; Cheng, Ming‐Jen; Kuo, Chu-Wen; Chen, Jih Jung

doi:10.1007/s10600-022-03810-x

Cited by 1 publication

(4 citation statements)

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“…ex Willd. [32] and H. nagasawae Hayata [33], respectively. In 1968, the isolation of a trioxygenated benzophenone cearoin 34 from extracts of Dalbergia cearensis Ducke and D. miscolobium Benth.…”

Section: Trioxygenated Bezophenonesmentioning

confidence: 98%

“…Some of the tested benzophenones showed moderate NO inhibitory activities on LSP-induced RAW 264.7 macrophage cells such as hydrocotoin 15 with an inhibition rate of 38.12% [256] and compounds 60, 78, 79, 88, 98, 120, 122, 162, at concentrations of 50 and 100 µM [81]. Additionally, low NO inhibitory activities on LSP induced RAW 264.7 macrophage cells displayed benzophenones aquilarinenside E 109 (200 µg/mL), 74 (10, 25 and 200 µg/mL) [243,251], 19 (IC50 = 23.41 µM), 33 (IC50 = 6.23 µM) [30], 30 (IC50 = 30.05 µM) [31], 32 (IC50 = 26.14 µM) [33], 192, 193 (IC50 > 20 µM) [125], 93 (IC50 > 100 µM), 59 (IC50 = 58.72 µM) [76], 95 (16.97%) [256], and 113 (IC50 = 95.4 µM) [87]. The anti-neuroinflammatory activity of 186 was evaluated by determining its ability to inhibit the production of NO in LPS-activated BV-2 microglial cells.…”

Section: Anti-inflammatory Activitymentioning

confidence: 99%

“…Cytotoxicity on Human Cancer Cell Lines Cytotoxicity assays performed on cell lines HD-MY-Z (Hodgkin's lymphoma), K-562 (chronic myeloid leukemia), KE-37 (T-cell leukemia), CCRF-CEM (acute lymphoblastic leukemia), HL-60 (myeloid leukemia), and Raji cells (non-Hodgkin's lymphoma) showed significant antiproliferative activity of elegaphenone 31 with IC 50 values of 15.9 µM (HD-MY-Z), 13.9 µM (K-562), 16.9 µM (KE-37) [32], and 108 with IC 50 = 8.9 µM (HL-60) [222]. Furthermore, hyperinagazone 32 exhibited IC 50 = 29.05 µM on CCRF-CEM [33], hyperinokone 30 showed IC 50 = 36.44, while 19 had IC 50 = 27.04 [31]. In addition, a short-term in vitro assay with 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced Epstein-Barr virus early antigen (EBV-EA) activation in Raji cells showed a significant inhibitory effect of maclurin 133, compared to a positive control of the strong antitumor promoter glycyrrhetic acid (enoxolone) [168].…”

Section: Estrogenic Activitymentioning

confidence: 99%

“…Additionally, 19 (IC 50 = 100.21 µM) and 71 (IC 50 = 63.67 µM) showed weak cytotoxic activity against A375 [210]. Cytotoxicity assays performed against cell lines SHSY-5Y (neuroblastoma), IMR-32 (neuroblastoma with rare areas of organoid differentiation) demonstrated IC 50 values of 16.83 µM (IMR-32) for compound 32 compared to doxorubicin (IC 50 = 0.037 µM) [33] and IC 50 values of 25.54 µM and 69.36 µM (SHSY-5Y) for 19 and 71, respectively, compared to cisplatin (IC 50 = 4.00 µM) [210]. In addition, 44 was found to possess high and selective cytotoxicity (IC 50 = 27.70 µM) against SHSY-5Y cells compared to cisplatin (IC 50 = 5.14 µM) [255].…”

Section: Estrogenic Activitymentioning

confidence: 99%

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Naturally Occurring Simple Oxygenated Benzophenones: Structural Diversity, Distribution, and Biological Properties

Marinov,

Kokanova-Nedialkova,

Nedialkov

2023

Diversity

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Naturally occurring benzophenones represent a relatively small group of plant metabolites with narrow distribution, mainly in members of Clusiaceae, Gentianaceae, Hypericaceae, Polygalaceae, Myrtaceae, etc.; however, there were reports of several compounds derived from microorganisms belonging to the Aspergillaceae and Valsaceae families and propolis. Benzophenones exhibit many biological activities, such as antioxidant, anti-inflammatory, cytotoxic, antimicrobial, etc. Few reviews on benzophenones that have appeared in the literature were focused on their prenylated derivatives. Summarized information on structural diversity, distribution, and biological activities of simple oxygenated naturally occurring benzophenones and their glycosides has not been found in the literature. Until 2000, only benzophenone C-glycosides were known to occur in nature. Since then, many O-glycosides have been isolated, structurally, and biologically characterized. This review covers the years from 1850 to 2023 and was compiled using databases such as Chemical Abstracts, Scopus, Google Scholar, PubMed, and ResearchGate. Based on their degree of oxidation, 210 chemical structures of benzophenone derivatives and glycosides were grouped into six categories. In addition, in one group of 40 miscellaneous benzophenones, where one or several protons are replaced by a methyl, alcohol, carboxyl, or acyl group, glycosidic forms with such an aglycone and dimeric compounds with xanthone was included. Simple oxygenated benzophenones and their glycosides were found in 77 plant genera belonging to 44 families. The allergy-associated bezophenone-1, benzophenone-2 and benzophenone-3 have limited distribution across natural sources. A wide range of biological activities (antioxidant, anti-inflammatory, cytotoxic, antitumor, cytoprotective, antimicrobial, MAO-A, antiarthritic, anticholinesterase, anti-atherosclerotic, laxative, etc.) of simple oxygenated benzophenones and their glycosides that appeared in the literature were discussed.

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Section: Trioxygenated Bezophenonesmentioning

confidence: 98%