Polycyclic polyprenylated acylphloroglucinol derivatives from Hypericum scabrum

Hu, Jiawen; Gao, Weiwei; Xu, Fang; Wei, Can-Jing; Shi, Mengjiao; Sun, Hua; Zhen, Bo; Wang, Jiajia; Ji, Tengfei; Jiang, Jian‐Dong

doi:10.1016/j.bmcl.2017.09.001

Cited by 19 publications

(11 citation statements)

References 20 publications

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“…There are 55 species and eight subspecies in China, and there are 27 species and four subspecies in Yunnan Province alone [1,2,3]. Hypericum plants have diverse pharmacological applications as folk medicines due to the diverse chemical constituents [4,5,6]. As a classical natural product from this family, polycyclic polyprenylated acylphloroglucinols (PPAPs) have intriguing chemical structures [7,8,9] and various biological activities, such as anti-neurodegenerative, anti-HIV, tumor inhibitory, antioxidative, antidepressant, and so on [10,11,12,13,14,15].…”

Section: Introductionmentioning

confidence: 99%

“…Currently, there are few studies on the chemical constituents of H. acmosepalum [18]. As a part of an ongoing research program aimed at the isolation, structural characterization, and pharmacological evaluation of bioactive PPAPs from the Hypericum genus [6,19,20], a preliminary study was carried out on the petroleum ether-soluble part of the 95% EtOH extract from the air-dried aerial parts of H. acmosepalum , and obtained five PPAP derivatives. The neuroprotective effect of those compounds was evaluated in human neuroblastoma SK-N-SH cells.…”

Section: Introductionmentioning

confidence: 99%

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Polycyclic Polyprenylated Acylphloroglucinol Derivatives from Hypericum acmosepalum

Wang

Shi

et al. 2018

Molecules

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Hypericum acmosepalum belongs to the Hypericum genus of the Guttiferae family. The characteristic components in Hypericum are mainly a series of polycyclic polyprenylated acylphloroglucinols (PPAPs), flavonoids, and xanthones. Among them, the PPAPs have received much attention due to their novel structures and diverse pharmacological activities and have become hot spots in organic chemistry and medicinal chemistry. However, there are few reports about the chemical constituents of Hypericum acmosepalum at present, especially the PPAPs. This research is dedicated to the study of the air-dried aerial parts of Hypericum acmosepalum, which were extracted with 95% EtOH under reflux, then suspended and successively partitioned with petroleum ether and ethyl acetate. Five PPAP derivatives were obtained using various chromatographic techniques, and their structures were determined by NMR spectroscopic data, including two new phloroglucinol derivatives, hyperacmosin A (1) and hyperacmosin B (2). Those compounds were evaluated for their neuroprotective effect using two models.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Polycyclic Polyprenylated Acylphloroglucinol Derivatives from Hypericum acmosepalum

Wang

Shi

et al. 2018

Molecules

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“…All isolates were evaluated for in vitro hepatoprotective effects against paracetamol-induced HepG2 cell damage with the MTT assay …”

Section: Experimental Sectionmentioning

confidence: 99%

Methylated Polycyclic Polyprenylated Acylphloroglucinol Derivatives from Hypericum ascyron

Shi

Wang

et al. 2018

J. Nat. Prod.

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Hyperascyrins A−H (1−11) and four known compounds (12−15) were acquired from the air-dried aerial parts of Hypericum ascyron and were all identified as methylated polycyclic polyprenylated acylphloroglucinol derivatives. Their structures were established by NMR spectroscopy, experimental and calculated electronic circular dichroism (ECD) data, and comparison with established compounds. Compounds 8 and 9 showed protection against paracetamol-induced HepG2 cell damage at 10 μM. The neuroprotective activities of all compounds (10 μM) were evaluated, and compounds 1 and 8 exhibited mild neuroprotection against glutamate-induced toxicity in SK-N-SH cells.

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“…The majority of plants from Hypericum genus are widely used in traditional and conventional medicines, and they are also used as herbal tea and food supplements because of their excellent bioactive properties. − The most famous ingredient in this genus is diverse polycyclic polyprenylated acylphloroglucinols (PPAPs), which features highly oxygenated acylphloroglucinol cores, decked with methyl, prenyl, or geranyl side chains. Owing to their fascinating chemical structures, PPAPs exhibit preferable anti-inflammatory, − anticancer, and antibacterial bioactivities, which have drawn extensive attention in the natural product and synthetic chemistry fields. In terms of biosynthetic pathways, the characteristic PPAPs belong to the postmodified products of acylphloroglucinol meroterpenoids, the hybrids of acylphloroglucinol and terpenoids.…”

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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Polycyclic polyprenylated acylphloroglucinol derivatives from Hypericum scabrum

Cited by 19 publications

References 20 publications

Polycyclic Polyprenylated Acylphloroglucinol Derivatives from Hypericum acmosepalum

Polycyclic Polyprenylated Acylphloroglucinol Derivatives from Hypericum acmosepalum

Methylated Polycyclic Polyprenylated Acylphloroglucinol Derivatives from Hypericum ascyron

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

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