Bioactive polycyclic polyprenylated acylphloroglucinols from Hypericum scabrum

Zhou, Zhong-Bo; Mou, Peng-Yun; Huang, You-Yi; Zeng, Hong; Huang, Zu-Liang; Wei, Xian Fu

doi:10.1016/j.fitote.2022.105249

Cited by 4 publications

(5 citation statements)

References 25 publications

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“…In 2014, 2016, 2017, and 2022, four papers reported the isolation and structural determination of 10 PPAPs: uraliones F, G, K, and O (abbreviated herein as UF, UG, UK, and UO, respectively) from Hypericum uralum , attenuatumiones E and F (AE and AF) from H. attenuatum , and scabrumiones A–D (SA–SD) from H. scabrum . − These compounds were determined to be type B PPAPs with a characteristic bicyclo[3.3.1]nonane-2,4,9-trione core decorated by an acyl group at C-3 and the additional feature of being fused to a partly reduced furan ring at C-1–C-2–O-2 ( 1b – 10b , Figure ). However, the 1 H and 13 C NMR spectroscopic data of UG and AE were almost identical to those of ascyronone F ( 2a ) and furohyperforin isomer 2 ( 3a ) (Tables and and Tables S1–S4 in the Supporting Information), respectively, previously reported type A PPAPs with a characteristic bicyclo[3.3.1]nonane-2,4,9-trione core decorated by an acyl group at C-1 and the additional feature of being fused to a partly reduced furan ring at C-3–C-2–O-2 ( 1a – 10a , Figure ).…”

Section: Resultsmentioning

confidence: 99%

“…Accordingly, we also use this rule to revise the proposed configuration of hypericumoxide B (12), hypericumoxide C ( 13), and hyperscabin G ( 14) at C-18 (Figure 4). 190.8 0.12 hyperhimatin P 29 191.1 0.13 hyperibrin C 30 190.7 0.12 hyperibrin F 31 190.3 0.00 propolone C 32 188.1 0.00 hyperacmosin O 33 190.8 0.15 UF 10 190.9 0.04 UG 10 190.6 0.18 AE 9 190.8 0.00 AF 9 191.0 0.16 UK 10 191.1 0.17 UO 11 190.6 0.00 SA 12 190.7 0.00 SB 12 189.6 0.18 SC 12 189.5 0.00 SD 12 190.6 0.00 The patterns change for PPAPs that are almost identical with the compounds in Table 4 but that have a benzoyl group on C-1 instead of an isobutyryl group (Table 5). In PPAPs in which H-18 is trans to the C-9 carbonyl group, the values of δ The very shielded shifts of δ (H-18) in UF, hyperascyrin F, 23 hyperibrin C, 30 and sampsonione M 24 compared to other PPAPs are striking.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

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Structure Revision of Type B Polycyclic Polyprenylated Acylphloroglucinols Fused to a Partly Reduced Furan Ring

Qiu,

Grossman,

Yang

2023

J. Nat. Prod.

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Four previous papers reported the isolation and structural determination of 10 polycyclic polyprenylated acylphloroglucinols (PPAPs), uraliones F, G, K, and O, attenuatumiones E and F, and scabrumiones A−D, from Hypericum species. Their structures were identified as type B PPAPs that featured not only the characteristic acyl group at C-3 of the bicyclo[3.3.1]nonane core but also a partly reduced furan ring fused to the C-1−C-2−O-2 atoms of the core. However, the 1D and 2D NMR data of these compounds were more consistent with type A PPAPs that featured not only the acyl group at C-1 but also a partially reduced furan ring fused to the C-3−C-2−O-2 atoms of the core. Now we revise these 10 previously proposed structures to the corresponding type A PPAPs via NMR analysis. Additionally, we propose a rule that uses NMR data to determine whether a particular PPAP that is fused to a partly reduced furan ring at C-3−C-2−O-2 or C-1−C-2−O-2 is type A or type B, respectively. We also propose a rule to assign the relative configurations of corresponding type A PPAPs at C-18 and revise the configurations of sampsonione N, hypericumoxides A−C, and hyperscabin G.

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Section: Resultsmentioning

confidence: 99%

Section: ■ Results and Discussionmentioning

confidence: 99%

Structure Revision of Type B Polycyclic Polyprenylated Acylphloroglucinols Fused to a Partly Reduced Furan Ring

Qiu,

Grossman,

Yang

2023

J. Nat. Prod.

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“…Also, our present observations are in agreement with another previous study by Keser et al, [ 29 ] who reported the potent antimicrobial activity of H. scabrum against E. coli, Proteus vulgaris, P. aeruginosa, Listeria monocytogenes, Klebsielle pneumonia and Bacillus subtilis . It was reported that H. scabrum contains a variety of secondary metabolites such as flavonoids [ 30 ], xanthones [ 31 ], and especially phloroglucinols [ 32 , 33 ]. It was found that lipophilic fractions of Hypericum species contain phloroglucinol derivatives, which have been demonstrated to have antifungal and antibacterial properties against pathogens like S. aureus, B. cereus, B. subtilis, and Nocardia gardenen [ 34 ] .…”

Section: Discussionmentioning

confidence: 99%

In vitro antimicrobial and antibiofilm screening of eighteen Iranian medicinal plants

Hamidi,

Toosi,

Javadi

et al. 2024

BMC Complement Med Ther

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Background Natural products are one of the best candidates for controlling drug-resistant pathogens, the advantages of which include low production costs and low side effects. In this study, as potential antimicrobials, the anti-bacterial and antibiofilm activities of several Iranian native medicinal plants were screened. Methods The antibacterial/antifungal and anti-biofilm activities of 18 medicinal plants including Reseda lutea L., Nepeta sintenisii Bunge., Stachys turcomanica Trautv., Stachys lavandulifolia Vahl, Diarthron antoninae (Pobed.) Kit Tan., Ziziphora clinopodioides Lam., Euphorbia kopetdaghi Prokh, Euphorbia serpens Kunth., Hymenocrater calycinus Benth., Scutellaria pinnatifida A.Ham., Viola tricolor L., Hypericum helianthemoides (Spach) Boiss., Hypericum scabrum L., Convolvulus lineatus L., Scabiosa rotata M.Bieb Greuter & Burdet, Delphinium semibarbatum Bien. Ex Boiss., Glycyrrhiza triphylla Fisch. & C.A.Mey., and Ziziphus jujuba Mill., against two Gram-positive bacteria, Staphylococcus aureus, Bacillus cereus, as well as two Gram-negative bacteria, Pseudomonas aeruginosa, Escherichia coli; and Candida albicans as a fungal strain, were evaluated. The minimum inhibitory concentration (MIC) and minimum bactericidal/fungicidal concentration (MBC/MFC) values of the extracts against tested microorganisms were reported and we investigated their effect on the biofilm inhibition of Pseudomonas aeruginosa PAO1, Staphylococcus epidermis, Staphylococcus aureus and Streptococcus mutans. In addition, the effect of the extracts on the eradication of the biofilms of these bacteria was evaluated. Results In this study, H. scabrum was found to exhibit potentially significant activity against Gram-positive bacteria with the MIC range of 6.25–25 µg/mL. This extract also showed a significant effect on inhibiting the biofilm of S. aureus, S. mutans, and S. epidermidis and eradicating the biofilm of S. epidermidis DSMZ 3270. In addition, Hymenocrater calycinus root extract had moderate antibacterial activity against B. cereus with the MIC and MBC 62.5 µg/mL, respectively. Conclusions The results of this study showed that the root extracts of two plants, Hypericum scabrum and Hymenocrater calycinus, had antimicrobial and anti-biofilm effects. Based on the observed anti-biofilm effects, these two plants may be considered in future studies to find responsible antimicrobial compounds.

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“…and H. petiolulatum Hook.f. ex Thomson ex Dyer against HL-60, SW-480 or other human tumor cell lines, such as SMMC-7721 (hepatic), A-549 (lung), MCF-7 (breast), PANC-1 (pancreatic) and NB4 (leukemia) [ 11 , 12 , 13 , 14 , 16 , 17 , 68 ]. Again, in some cases the IC 50 values were equal to that of the control (e.g., cisplatin) and there was selectivity, i.e., weaker cytotoxicity on a normal cell line, e.g., Beas-2B (bronchial epithelium) [ 11 ].…”

Section: Discussionmentioning

confidence: 99%

“…aureus was 11.2 μM [ 17 ]. Some BPAPs from H. scabrum had a weak effect on MRSA and B. subtilis with MIC values of 320 μM but no effect on MDR Pseudomonas aeruginosa [ 68 ]. The lowest MIC of dimethylated acylphloroglucinol meroterpenoids from H. elodeoides Choisy against oral bacteria, including Streptococcus spp., was 6.25 μg/mL [ 20 ].…”

Section: Discussionmentioning

confidence: 99%

Cytotoxic and Antibacterial Prenylated Acylphloroglucinols from Hypericum olympicum L.

Ilieva

Momekov

Zaharieva

et al. 2023

Plants

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Two new bicyclo[3.3.1]nonane type bicyclic polyprenylated acylphloroglucinol derivatives (BPAPs), olympiforin A and B as well as three known prenylated phloroglucinols, were isolated from the aerial parts of Hypericum olympicum L. The structures of the isolated compounds were established by means of spectral techniques (HRESIMS and 1D and 2D NMR). All compounds were tested on a panel of human tumor (MDA-MB-231, EJ, K-562, HL-60 and HL-60/DOX) and non- tumorigenic (HEK-293 and EA.hy926) cell lines using the MTT assay. All tested compounds exerted significant in vitro cytotoxicity with IC50 values ranging from 1.2 to 24.9 μM and from 0.9 to 34 μM on tumor and non-cancerous cell lines, respectively. Most of the compounds had good selectivity and were more cytotoxic to the tumor cell lines than to the normal ones. A degradation of the precursor caspase 9 for some of the compounds was observed; therefore, the intrinsic pathway of apoptosis is the most likely mechanism of cytotoxic activity. The BPAPs were examined for antibacterial and antibiofilm activity through the broth microdilution method and the protocol of Stepanović. They showed a moderate effect against Enterococcus faecalis and Streptococcus pyogenes but a very profound activity against Staphylococcus aureus with minimum inhibitory concentrations (MIC) in the range of 0.78–2 mg/L. Olympiforin B also had a great effect against methicillin-resistant S. aureus (MRSA) with an MIC value of 1 mg/L and a very significant antibiofilm activity on that strain with a minimum biofilm inhibition concentration (MBIC) value of 0.5 mg/L. The structures of the isolated compounds were in silico evaluated using ADME and drug likeness tests.

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Bioactive polycyclic polyprenylated acylphloroglucinols from Hypericum scabrum

Cited by 4 publications

References 25 publications

Structure Revision of Type B Polycyclic Polyprenylated Acylphloroglucinols Fused to a Partly Reduced Furan Ring

Structure Revision of Type B Polycyclic Polyprenylated Acylphloroglucinols Fused to a Partly Reduced Furan Ring

In vitro antimicrobial and antibiofilm screening of eighteen Iranian medicinal plants

Cytotoxic and Antibacterial Prenylated Acylphloroglucinols from Hypericum olympicum L.

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