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Hyperbeanols F-Q, diverse monoterpenoid polyprenylated acylphloroglucinols from the flowers of Hypericum beanii.

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Title: Hyperbeanols F-Q, diverse monoterpenoid polyprenylated acylphloroglucinols from the flowers of Hypericum beanii.
Authors: Li, Yi-Ran1, Xu, Wen-Jun1, Wei, Shan-Shan1, Lu, Wei-Jia1, Luo, Jun1 luojun@cpu.edu.cn, Kong, Ling-Yi1 cpu_lykong@126.com
Source: Phytochemistry. Mar2019, Vol. 159, p56-64. 9p.
Subjects: Hypericum, Phloroglucinol, Nuclear magnetic resonance spectroscopy, Chirality, Nitric oxide, Plant enzymes
Abstract: Abstract Hyperbeanols F-Q, which are twelve undescribed monoterpenoid polyprenylated acylphloroglucinols, and four known analogues were isolated from the dried flowers of Hypericum beanii. Their structures were elucidated by detailed HRESIMS and 1D and 2D NMR data analyses. The absolute configurations of hyperbeanols F H were established by the circular dichroism (CD) exciton chirality method. The plausible biosynthetic pathway speculation of hyperbeanols F-Q indicated that diverse reactions, including prenylation, 1,6-ene reaction, rearrangement, epoxidation and dehydration, contributed to their diverse skeletons. Hyperbeanols F I, O and hypercalin B exhibited moderate nitric oxide (NO) inhibitory activities in LPS-induced RAW 264.7 macrophages, with IC 50 values in the range of 17.11–28.74 μ M. Graphical abstract Twelve undescribed monoterpenoid polyprenylated acylphloroglucinols with diverse structures were isolated from the flowers of Hypericum beanii. Image 1 Highlights • Twelve undescribed monoterpenoid PPAPs were isolated from Hypericum beanii. • Absolute configurations of 1 – 3 were assigned by CD exciton chirality method. • Selected compounds exhibited moderate anti-inflammatory activities. [ABSTRACT FROM AUTHOR]
Copyright of Phytochemistry is the property of Pergamon Press - An Imprint of Elsevier Science and its content may not be copied or emailed to multiple sites without the copyright holder's express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract. (Copyright applies to all Abstracts.)
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DbLabel: Engineering Source
An: 134299241
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  Data: Hyperbeanols F-Q, diverse monoterpenoid polyprenylated acylphloroglucinols from the flowers of Hypericum beanii.
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  Data: <searchLink fieldCode="AR" term="%22Li%2C+Yi-Ran%22">Li, Yi-Ran</searchLink><relatesTo>1</relatesTo><br /><searchLink fieldCode="AR" term="%22Xu%2C+Wen-Jun%22">Xu, Wen-Jun</searchLink><relatesTo>1</relatesTo><br /><searchLink fieldCode="AR" term="%22Wei%2C+Shan-Shan%22">Wei, Shan-Shan</searchLink><relatesTo>1</relatesTo><br /><searchLink fieldCode="AR" term="%22Lu%2C+Wei-Jia%22">Lu, Wei-Jia</searchLink><relatesTo>1</relatesTo><br /><searchLink fieldCode="AR" term="%22Luo%2C+Jun%22">Luo, Jun</searchLink><relatesTo>1</relatesTo><i> luojun@cpu.edu.cn</i><br /><searchLink fieldCode="AR" term="%22Kong%2C+Ling-Yi%22">Kong, Ling-Yi</searchLink><relatesTo>1</relatesTo><i> cpu_lykong@126.com</i>
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  Data: <searchLink fieldCode="JN" term="%22Phytochemistry%22">Phytochemistry</searchLink>. Mar2019, Vol. 159, p56-64. 9p.
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  Data: <searchLink fieldCode="DE" term="%22Hypericum%22">Hypericum</searchLink><br /><searchLink fieldCode="DE" term="%22Phloroglucinol%22">Phloroglucinol</searchLink><br /><searchLink fieldCode="DE" term="%22Nuclear+magnetic+resonance+spectroscopy%22">Nuclear magnetic resonance spectroscopy</searchLink><br /><searchLink fieldCode="DE" term="%22Chirality%22">Chirality</searchLink><br /><searchLink fieldCode="DE" term="%22Nitric+oxide%22">Nitric oxide</searchLink><br /><searchLink fieldCode="DE" term="%22Plant+enzymes%22">Plant enzymes</searchLink>
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  Label: Abstract
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  Data: Abstract Hyperbeanols F-Q, which are twelve undescribed monoterpenoid polyprenylated acylphloroglucinols, and four known analogues were isolated from the dried flowers of Hypericum beanii. Their structures were elucidated by detailed HRESIMS and 1D and 2D NMR data analyses. The absolute configurations of hyperbeanols F H were established by the circular dichroism (CD) exciton chirality method. The plausible biosynthetic pathway speculation of hyperbeanols F-Q indicated that diverse reactions, including prenylation, 1,6-ene reaction, rearrangement, epoxidation and dehydration, contributed to their diverse skeletons. Hyperbeanols F I, O and hypercalin B exhibited moderate nitric oxide (NO) inhibitory activities in LPS-induced RAW 264.7 macrophages, with IC 50 values in the range of 17.11–28.74 μ M. Graphical abstract Twelve undescribed monoterpenoid polyprenylated acylphloroglucinols with diverse structures were isolated from the flowers of Hypericum beanii. Image 1 Highlights • Twelve undescribed monoterpenoid PPAPs were isolated from Hypericum beanii. • Absolute configurations of 1 – 3 were assigned by CD exciton chirality method. • Selected compounds exhibited moderate anti-inflammatory activities. [ABSTRACT FROM AUTHOR]
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  Data: <i>Copyright of Phytochemistry is the property of Pergamon Press - An Imprint of Elsevier Science and its content may not be copied or emailed to multiple sites without the copyright holder's express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract.</i> (Copyright applies to all Abstracts.)
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        Value: 10.1016/j.phytochem.2018.12.005
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      – Code: eng
        Text: English
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      – SubjectFull: Nuclear magnetic resonance spectroscopy
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      – TitleFull: Hyperbeanols F-Q, diverse monoterpenoid polyprenylated acylphloroglucinols from the flowers of Hypericum beanii.
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              Text: Mar2019
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