Hyperpatulols A–I, spirocyclic acylphloroglucinol derivatives with anti-migration activities from the flowers of Hypericum patulum

Liu, Yangyang; Ao, Zhen; Xu, Qi-Qi; Zhu, Di; Chen, Chen; Wang, Xiaobing; Luo, Jian‐Guang; Kong, Ling–Yi

doi:10.1016/j.bioorg.2019.03.025

Cited by 15 publications

(5 citation statements)

References 35 publications

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“…In the HMBC spectrum, 1 H– 13 C{ 1 H} long-range correlation signals from Me-15 to C-4, C-5, C-6, and C-8, and from H 2 -7 to C-1, C-2, C-6, C-9, and C-19 could readily establish a six-membered carbon ring B. Furthermore, the typical α,β-unsaturated carbonyl signals [δ C 192.5 (C-4), 127.4 (C-3), and 179.0 (C-2)] along with the above established fragments generated a seven-membered ring A. Moreover, the 1 H– 13 C{ 1 H} long-range correlation signals of Me-25 to C-20, C-23 and C-24 as well as the above established fragment could assign a pentacyclic ring D. Rings B and D were connected through a key methylene (C-19) from the HMBC correlations of H 2 -7 to C-19 and C-1.…”

Section: Resultsmentioning

confidence: 99%

Hypermoins A–D: Rearranged Nor-Polyprenylated Acylphloroglucinols from the Flowers of Hypericum monogynum

Zeng

Zhang

et al. 2021

J. Org. Chem.

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Hypermonins A–D (1–4), four rearranged nor-polycyclic polyprenylated acylphloroglucinols (PPAPs) with unprecedented skeletons, together with two new biosynthesis related PPAPs (5 and 6) were isolated and identified from the flowers of Hypericum monogynum. Hypermoins A–D represented the first examples of highly modified norPPAPs characterized by a rare 7/6/6/5-tetracyclic system. From the biogenic synthesis pathway analysis, all isolates shared the same biosynthetic intermediate, and the addition of two methyls or one methyl to this intermediate through methyltranferase could generate different types of PPAPs (1–7). Their planner structures as well as absolute configuration were confirmed via spectroscopic analysis, ECD calculation, and X-ray crystallography. All isolates potentially reversed multidrug resistance (MDR) activity in both two cancer cells, HepG2/ADR and MCF-7/ADR. Specifically, hypermoin E (5) and hyperielliptone HA (7) were found to be the best MDR modulators with the reversal fold ranging from 41 to 236, which is higher than the positive control verapamil.

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Section: Resultsmentioning

confidence: 99%

Hypermoins A–D: Rearranged Nor-Polyprenylated Acylphloroglucinols from the Flowers of Hypericum monogynum

Zeng

Zhang

et al. 2021

J. Org. Chem.

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“…Hypericum patulum, also called “Jinsimei”, is a perennial shrub widely distributed in China, which was extensively used to treat gonorrhea, hepatitis, and bruises. − As a part of our systematic search for PPAPs with complicated structures from Hypericum plants, the chemical constituents of H. patulum were investigated, and an unprecedented nor -PPAP with a novel 8/6 bicyclic skeleton, hypaluton A ( 1 ), along with a new congener, hypaluton B ( 2 ), and hypercohin A ( 3 ), a known analog, was obtained (Figure ).…”

Section: Introductionmentioning

confidence: 99%

Hypaluton A, an Immunosuppressive 3,4-nor-Polycyclic Polyprenylated Acylphloroglucinol from Hypericum patulum

Duan

Xie

et al. 2021

J. Org. Chem.

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Hypaluton A (1), an unprecedented nor-polycyclic polyprenylated acylphloroglucinol (PPAP) bearing a new 8/6 bicyclic architecture, along with a new congener, hypaluton B (2), was obtained from Hypericum patulum. Their structures were confirmed by spectroscopic analyses, quantum-chemical 13C NMR calculations, electronic circular dichroism comparisons, and calculations. Hypaluton A is the first PPAP possessing an unparalleled 3,4-nor-bicyclic polyprenylated acylphloroglucinol (BPAP) scaffold, which might be derived from the common [5.3.1]-type-BPAP by losing seven carbons (C-3/4 of the acylphloroglucinol core and the isoprenyl at C-3) via the breakage at C-4–C-5 and C-2–C-3 bonds in the acylphloroglucinol core, together with the benzoyl migration through the hemiketalization/retro-Claisen cascade. More significantly, compound 1 is also the first discovered [6.3.0]-PPAP, which displayed pronounced inhibitory activity against lipopolysaccharide-induced B lymphocyte proliferation.

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“…It is used as herbal tea and folk medicines for anti-inflammation, detoxification, cooling blood, and hemostasis. It is also used as landscaping for people to enjoy due to its bright and beautiful flowers. , As a continuation for clarifying the main bioactive acylphloroglucinols in many Hypericum species, ,− H. bellum was systematically investigated in our current study.…”

Section: Introductionmentioning

confidence: 99%

Anti-Inflammatory, Antioxidant, and Anti-Nonalcoholic Steatohepatitis Acylphloroglucinol Meroterpenoids from Hypericum bellum Flowers

Zhou

et al. 2021

J. Agric. Food Chem.

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In this work, 26 methylated acylphloroglucinol meroterpenoids with diverse skeletons, including 18 new ones (bellumones A-R, 1−18), were identified from the flowers of Hypericum bellum. Their structures including absolute configurations were elucidated by detailed spectroscopic data, calculated electronic circular dichroism (ECD), and X-ray diffraction (XRD). Through methylation at C-5, prenylation with different chain lengths of the acylphloroglucinol-derived core, along with different types of secondary cyclization, type A bicyclic polyprenylated acylphloroglucinols (BPAPs) (1−5 and 19−24) and dearomatized isoprenylated acylphloroglucinols (DIAPs) (6−18 and 25−26) were obtained. The significant results of anti-inflammatory, antioxidant, and anti-nonalcoholic steatohepatitis (anti-NASH) activities suggest its usefulness in daily health care.

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Hyperpatulols A–I, spirocyclic acylphloroglucinol derivatives with anti-migration activities from the flowers of Hypericum patulum

Cited by 15 publications

References 35 publications

Hypermoins A–D: Rearranged Nor-Polyprenylated Acylphloroglucinols from the Flowers of Hypericum monogynum

Hypermoins A–D: Rearranged Nor-Polyprenylated Acylphloroglucinols from the Flowers of Hypericum monogynum

Hypaluton A, an Immunosuppressive 3,4-nor-Polycyclic Polyprenylated Acylphloroglucinol from Hypericum patulum

Anti-Inflammatory, Antioxidant, and Anti-Nonalcoholic Steatohepatitis Acylphloroglucinol Meroterpenoids from Hypericum bellum Flowers

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