Two new adamantyl-like polyprenylated acylphloroglucinols from Hypericum attenuatum choisy

Li, Dongyan; Zhu, Hucheng; Qi, Changxing; Xue, Yongbo; Yao, Guangmin; Luo, Zengwei; Wang, Jianping; Zhang, Jinwen; Du, Guang; Zhang, Yonghui

doi:10.1016/j.tetlet.2015.02.056

Cited by 26 publications

(7 citation statements)

References 17 publications

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“…As part of our continuing efforts to discover bioactive PPAPs in the genus Hypericum , a series of PPAPs and other components were previously identified 19 20 21 22 23 . In our current study, further chemical investigation of H. sampsonii has led to the isolation of six new PPAPs, termed hyperisampsins H–M ( 1 – 6 ), together with five known analogs ( 7 – 11 ).…”

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

Zhu

Chen

Tong

et al. 2015

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

Zhu

Chen

Tong

et al. 2015

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“…1 ) were isolated from the aerial parts of H. scabrum . Although there are many examples of homo-adamantane PPAPs with a tricyclo[4.3.1.1 5,7 ]-undecane skeleton 12 , 23 , 24 , compound 1 illustrates the first example of an esterified PPAP that features an unrivaled tricyclo-[4.3.1.1 1,4 ]-undecane skeleton. Compound 2 is a reasonably simple monocyclic polyprenylated acylphloroglucinol (MPAP) with a unique cycloheptane ring decorated with prenyl substituents, and compound 3 has an unusual 5,5-spiroketal lactone core.…”

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confidence: 99%

Unusual derivatives from Hypericum scabrum

Soroury

Alilou

Gelbrich

et al. 2021

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Three new compounds (1–3) with unusual skeletons were isolated from the n-hexane extract of the air-dried aerial parts of Hypericum scabrum. Compound 1 represents the first example of an esterified polycyclic polyprenylated acylphloroglucinol that features a unique tricyclo-[4.3.1.11,4]-undecane skeleton. Compound 2 is a fairly simple MPAP, but with an unexpected cycloheptane ring decorated with prenyl substituents, and compound 3 has an unusual 5,5-spiroketal lactone core. Their structures were determined by extensive spectroscopic and spectrometric techniques (1D and 2D NMR, HRESI-TOFMS). Absolute configurations were established by ECD calculations, and the absolute structure of 2 was confirmed by a single crystal determination. Plausible biogenetic pathways of compounds 1–3 were also proposed. The in vitro antiprotozoal activity of the compounds against Trypanosoma brucei rhodesiense and Plasmodium falciparum and cytotoxicity against rat myoblast (L6) cells were determined. Compound 1 showed a moderate activity against T. brucei and P. falciparum, with IC50 values of 3.07 and 2.25 μM, respectively.

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“…) generation and elastase release 7.2 μM 6.0 μM garcimultiflorone G (317) 156 superoxide anion (•O 2 − ) generation 7.0 μM hyperattenin C (61) 71 HIV on C8166 cells 8.1 μM (EC 50 ) anti-HIV 1.65 (SI) hyperattenin B (88) 71 HIV on C8166 cells 9.9 μM, 0.97 hyperisampsin D (279) 149 HIV-1 in MT-4 cells 0.97 μM, 7.7 hyperisampsin A (281) 149 HIV-1 in MT-4 cells 3.0 μM, 4.8 hyperattenin K (331) 147 HIV-1 in MT-4 cells 3.4 μM, 3.5 hyperascyrone E (349) 161 HIV-1 in MT-4 cells 3.6 μM, 2.1 hyperascyrone B (360) 161 HIV-1 in MT-4 cells 4.2 μM, 0.36 hyperascyrone C (361) 161 HIV-1 in MT-4 cells 2.4 μM, 0.23 hyperascyrone F (373) 161 HIV-1 in MT-4 cells 2.4 μM, 5.6 coccinone C (174) 97 FcB1 (P. falciparum) 9.0 μM (IC 50 ) antiplasmodial coccinone D (175) 97 FcB1 (P. falciparum) 7.0 μM coccinone E (176) 97 FcB1 (P. falciparum) 4.9 μM 7-epi-isogarcinol (178) 97 FcB1 (P. falciparum) 5.1 μM 14-deoxy-7-epi-isogarcinol (179) 97 FcB1 (P. falciparum) 2.5 μM symphonone B (180) 123 FcB1 (P. falciparum) In addition, a formal synthesis of (±)-nemorosone (426) from 476 in 6 steps was also suggested. 341 This modular approach serves as a platform to quickly assemble PPAPs for further synthetic studies.…”

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Research Progress of Polycyclic Polyprenylated Acylphloroglucinols

2018

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Polycyclic polyprenylated acylphloroglucinols (PPAPs) are a class of hybrid natural products sharing the mevalonate/methylerythritol phosphate and polyketide biosynthetic pathways and showing considerable structure and bioactivity diversity. This review discusses the progress of research into the chemistry and biological activity of 421 natural PPAPs in the past 11 years as well as in-depth studies of biological activities and total synthesis of some PPAPs isolated before 2006. We created an online database of all PPAPs known to date at http://www.chem.uky.edu/research/grossman/PPAPs . Two subclasses of biosynthetically related metabolites, spirocyclic PPAPs with octahydrospiro[cyclohexan-1,5'-indene]-2,4,6-trione core and complicated PPAPs produced by intramolecular [4 + 2] cycloadditions of MPAPs, are brought into the PPAP family. Some PPAPs' relative or absolute configurations are reassigned or critically discussed, and the confusing trivial names in PPAPs investigations are clarified. Pharmacologic studies have revealed a new molecular mechanism whereby hyperforin and its derivatives regulate neurotransmitter levels by activating TRPC6 as well as the antitumor mechanism of garcinol and its analogues. The antineoplastic potential of some type B PPAPs such as oblongifolin C and guttiferone K has increased significantly. As a result of the recent appearances of innovative synthetic methods and strategies, the total syntheses of 22 natural PPAPs including hyperforin, garcinol, and plukenetione A have been accomplished.

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Two new adamantyl-like polyprenylated acylphloroglucinols from Hypericum attenuatum choisy

Cited by 26 publications

References 17 publications

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

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

Unusual derivatives from Hypericum scabrum

Research Progress of Polycyclic Polyprenylated Acylphloroglucinols

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