Polyprenylated Benzoylphloroglucinol-Type Derivatives Including Novel Cage Compounds from &lt;i&gt;Hypericum erectum&lt;/i&gt;

Ishida, Yohei; Shirota, Osamu; Sekita, Setsuko; Someya, Keita; Tokita, Fumihiko; Nakane, Takahisa; Kuroyanagi, Masanori

doi:10.1248/cpb.58.336

Cited by 45 publications

(16 citation statements)

References 20 publications

(25 reference statements)

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“…1 ). The structures of the known compounds were elucidated by comparing their NMR data with those reported in the literature, and they were identified as attenuatumione C ( 7 ) 24 , sampsonione K ( 8 ) 10 , otogirinin D ( 9 ) 25 , and sampsoniones M ( 10 ) 10 and N ( 11 ) 11 .…”

Section: Resultsmentioning

confidence: 99%

Hyperisampsins H–M, Cytotoxic Polycyclic Polyprenylated Acylphloroglucinols from Hypericum sampsonii

Zhu

Chen

Tong

et al. 2015

Sci Rep

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Six new polycyclic polyprenylated acylphloroglucinols (PPAPs), named hyperisampsins H–M (1–6), were isolated from the aerial parts of Hypericum sampsonii, together with five known analogs (7–11). The structures of 1–6 were established by extensive spectroscopic analyses, including HRESIMS and NMR. In addition, the absolute configurations of these new compounds were determined by electronic circular dichroism (ECD) calculations. Compounds 1 and 2 represent the first examples of PPAPs possessing a unique γ-lactone ring at C-23, while 3–6 differed from normal PPAPs with an unprecedented 1,2-dioxane ring. Compounds 1–7 were evaluated for their cytotoxic activities against a panel of human cancer cell lines in vitro, of which 3, 4, and 6 exhibited significant cytotoxic activities with IC50 values ranging from 0.56 to 3.00 μM. Moreover, compound 3 induces leukemia cell apoptotic death, evidenced by activation of caspase-3, degradation of PARP, up-regulation of Bax, and down-regulation of Bcl-2 and Bcl-xl.

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Section: Resultsmentioning

confidence: 99%

Hyperisampsins H–M, Cytotoxic Polycyclic Polyprenylated Acylphloroglucinols from Hypericum sampsonii

Zhu

Chen

Tong

et al. 2015

Sci Rep

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“…Both types of substituents are susceptible to cyclization and oxidation processes resulting in bi-1,2 or tricyclic 3,4 molecules, as well as complex caged compounds. 5,6 The structural diversity among acylphloroglucinols leads to various pharmacological activities in vitro and in vivo. As reported by the Gibbons group, several representative members of this class of compounds display significant antibacterial activity especially against Gram-positive bacteria.…”

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confidence: 99%

Bi-, Tri-, and Polycyclic Acylphloroglucinols from Hypericum empetrifolium

Schmidt

Jürgenliemk

Schmidt³

et al. 2012

J. Nat. Prod.

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The ¹H NMR-guided fractionation of a petroleum ether extract of Hypericum empetrifolium led to the isolation of four new bicyclic (1-4), four known bicyclic (5-8), three new tricyclic (9-11), and three new polycyclic acylphloroglucinols (12/13 and 14) possessing a monoterpenoid citran moiety. Compounds 12/13 were isolated as a mixture of two inseparable structural isomers. The compounds showed in vitro antiproliferative activity against human microvascular endothelial cells (HMEC-1) with IC₅₀ values in the range 9.2 ± 2.0 to 29.6 ± 3.5 μM.

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“…The 1 H-NMR spectrum ( Table 1) Comparison of the 1 H-and 13 C-NMR data ( Table 1) of 1 with those of otogirinin B [11] indicated that their structures were closely related, except that the 14-lavandulyl group of 1 replaced a 14-geranyl group of otogirinin B [11]. This was supported by both HMBCs (Fig.…”

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confidence: 76%

“…Compound 1 showed similar CD Cotton effects (221 ([q] ¼ þ 1410) and 252 ([q] ¼ þ1049) nm) compared with those of the analogous benzoylphloroglucinol derivative otogirinin B[11]. Compound 1 showed similar CD Cotton effects (221 ([q] ¼ þ 1410) and 252 ([q] ¼ þ1049) nm) compared with those of the analogous benzoylphloroglucinol derivative otogirinin B[11].…”

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confidence: 99%

ChemInform Abstract: Garcimultiflorone G (I), a Novel Benzoylphloroglucinol Derivative from Garcinia multiflora with Inhibitory Activity on Neutrophil Pro‐Inflammatory Responses.

et al. 2014

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A novel benzoylphloroglucinol derivative, garcimultiflorone G (1), was isolated from the fruits of Garcinia multiflora. The structure of 1 was determined through extensive 1D-and 2D-NMR, and MS analyses. Garcimultiflorone G (1) showed inhibitory effects against superoxide anion (O .À 2 ) generation and elastase release by human neutrophils in response to formyl-l-methionyl-l-leucyl-l-phenylalanine/ cytochalasin B (fMLP/CB), with IC 50 values of 6.97 AE 1.56 and 11.70 AE 1.58 mm, respectively.

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Polyprenylated Benzoylphloroglucinol-Type Derivatives Including Novel Cage Compounds from <i>Hypericum erectum</i>

Abstract: ]undecane skeletons arising from a polyprenylated phloroglucinol precursor by a transannular cyclization reaction. The isolated compounds were tested for suppressive activity, but they showed only weak activity.

Cited by 45 publications

References 20 publications

Hyperisampsins H–M, Cytotoxic Polycyclic Polyprenylated Acylphloroglucinols from Hypericum sampsonii

Hyperisampsins H–M, Cytotoxic Polycyclic Polyprenylated Acylphloroglucinols from Hypericum sampsonii

Bi-, Tri-, and Polycyclic Acylphloroglucinols from Hypericum empetrifolium

ChemInform Abstract: Garcimultiflorone G (I), a Novel Benzoylphloroglucinol Derivative from Garcinia multiflora with Inhibitory Activity on Neutrophil Pro‐Inflammatory Responses.

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