A new bibenzyl and a new methylflavan from the tubers of Bletilla striata

Jin Woo Lee; Jun Gu Kim; Dongho Lee; Mi Kyeong Lee; Bang Yeon Hwang

doi:10.1016/j.phytol.2021.06.007

A new bibenzyl and a new methylflavan from the tubers of Bletilla striata

Jin Woo Lee, Jun Gu Kim, Dongho Lee, Mi Kyeong Lee, Bang Yeon Hwang

Research output: Contribution to journal › Article › peer-review

1 Citation (Scopus)

Abstract

A new bibenzyl, (+)-(1S)-4ʹ,5ʺ-dihydroxy-1,3ʹ,5ʹ,3ʺ-tetramethoxybibenzyl (1), and a new methylflavan, (2S)-7,4′-dihydroxy-5-methoxy-8-methylflavan (2), together with 10 known compounds were isolated from the methanolic extract of the tubers of Bletilla striata. Their chemical structures were elucidated based on spectrometric data interpretation, especially 1D and 2D NMR, HRESIMS, and electronic circular dichroism (ECD) data. All isolates (1 - 12) were evaluated for their inhibitory properties on nitric oxide production induced in RAW 264.7 cells, and dihydrophenantrenes 4 and 6 exhibited the best inhibitory effects with IC₅₀ values of 29.5, and 6.5 μM, respectively. Additionally, significant activity possessed phenantrene 5 and methylflavane 2 with IC₅₀ values of 38.9, and 44.9 μM, respectively.

Original language	English
Pages (from-to)	149-153
Number of pages	5
Journal	Phytochemistry Letters
Volume	44
DOIs	https://doi.org/10.1016/j.phytol.2021.06.007
Publication status	Published - 2021 Aug

Bibliographical note

Funding Information:
This work was supported by the National Research Foundation of Korea (NRF) grant funded by the Korea government (MIST) (No. 2020R1A2C1008406). The authors wish to thank the Korea Basic Science Institute for the NMR spectroscopic measurements.

Funding Information:
This work was supported by the National Research Foundation of Korea (NRF) grant funded by the Korea government (MIST) (No. 2020R1A2C1008406 ). The authors wish to thank the Korea Basic Science Institute for the NMR spectroscopic measurements.

Publisher Copyright:
© 2021 Phytochemical Society of Europe

Keywords

Bibenzyl
Bletilla striata
Dihydrophenantrene
Methylflavan
Nitric oxide
Orchidaceae

ASJC Scopus subject areas

Biotechnology
Biochemistry
Agronomy and Crop Science
Plant Science

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10.1016/j.phytol.2021.06.007

Cite this

@article{11efac2fb5724fc281e9a8c9930dd373,

title = "A new bibenzyl and a new methylflavan from the tubers of Bletilla striata",

abstract = "A new bibenzyl, (+)-(1S)-4ʹ,5ʺ-dihydroxy-1,3ʹ,5ʹ,3ʺ-tetramethoxybibenzyl (1), and a new methylflavan, (2S)-7,4′-dihydroxy-5-methoxy-8-methylflavan (2), together with 10 known compounds were isolated from the methanolic extract of the tubers of Bletilla striata. Their chemical structures were elucidated based on spectrometric data interpretation, especially 1D and 2D NMR, HRESIMS, and electronic circular dichroism (ECD) data. All isolates (1 - 12) were evaluated for their inhibitory properties on nitric oxide production induced in RAW 264.7 cells, and dihydrophenantrenes 4 and 6 exhibited the best inhibitory effects with IC50 values of 29.5, and 6.5 μM, respectively. Additionally, significant activity possessed phenantrene 5 and methylflavane 2 with IC50 values of 38.9, and 44.9 μM, respectively.",

keywords = "Bibenzyl, Bletilla striata, Dihydrophenantrene, Methylflavan, Nitric oxide, Orchidaceae",

author = "Lee, {Jin Woo} and Kim, {Jun Gu} and Dongho Lee and Lee, {Mi Kyeong} and Hwang, {Bang Yeon}",

note = "Funding Information: This work was supported by the National Research Foundation of Korea (NRF) grant funded by the Korea government (MIST) (No. 2020R1A2C1008406). The authors wish to thank the Korea Basic Science Institute for the NMR spectroscopic measurements. Funding Information: This work was supported by the National Research Foundation of Korea (NRF) grant funded by the Korea government (MIST) (No. 2020R1A2C1008406 ). The authors wish to thank the Korea Basic Science Institute for the NMR spectroscopic measurements. Publisher Copyright: {\textcopyright} 2021 Phytochemical Society of Europe",

year = "2021",

month = aug,

doi = "10.1016/j.phytol.2021.06.007",

language = "English",

volume = "44",

pages = "149--153",

journal = "Phytochemistry Letters",

issn = "1874-3900",

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AU - Lee, Jin Woo

AU - Kim, Jun Gu

AU - Lee, Dongho

AU - Lee, Mi Kyeong

AU - Hwang, Bang Yeon

N1 - Funding Information: This work was supported by the National Research Foundation of Korea (NRF) grant funded by the Korea government (MIST) (No. 2020R1A2C1008406). The authors wish to thank the Korea Basic Science Institute for the NMR spectroscopic measurements. Funding Information: This work was supported by the National Research Foundation of Korea (NRF) grant funded by the Korea government (MIST) (No. 2020R1A2C1008406 ). The authors wish to thank the Korea Basic Science Institute for the NMR spectroscopic measurements. Publisher Copyright: © 2021 Phytochemical Society of Europe

PY - 2021/8

Y1 - 2021/8

N2 - A new bibenzyl, (+)-(1S)-4ʹ,5ʺ-dihydroxy-1,3ʹ,5ʹ,3ʺ-tetramethoxybibenzyl (1), and a new methylflavan, (2S)-7,4′-dihydroxy-5-methoxy-8-methylflavan (2), together with 10 known compounds were isolated from the methanolic extract of the tubers of Bletilla striata. Their chemical structures were elucidated based on spectrometric data interpretation, especially 1D and 2D NMR, HRESIMS, and electronic circular dichroism (ECD) data. All isolates (1 - 12) were evaluated for their inhibitory properties on nitric oxide production induced in RAW 264.7 cells, and dihydrophenantrenes 4 and 6 exhibited the best inhibitory effects with IC50 values of 29.5, and 6.5 μM, respectively. Additionally, significant activity possessed phenantrene 5 and methylflavane 2 with IC50 values of 38.9, and 44.9 μM, respectively.

AB - A new bibenzyl, (+)-(1S)-4ʹ,5ʺ-dihydroxy-1,3ʹ,5ʹ,3ʺ-tetramethoxybibenzyl (1), and a new methylflavan, (2S)-7,4′-dihydroxy-5-methoxy-8-methylflavan (2), together with 10 known compounds were isolated from the methanolic extract of the tubers of Bletilla striata. Their chemical structures were elucidated based on spectrometric data interpretation, especially 1D and 2D NMR, HRESIMS, and electronic circular dichroism (ECD) data. All isolates (1 - 12) were evaluated for their inhibitory properties on nitric oxide production induced in RAW 264.7 cells, and dihydrophenantrenes 4 and 6 exhibited the best inhibitory effects with IC50 values of 29.5, and 6.5 μM, respectively. Additionally, significant activity possessed phenantrene 5 and methylflavane 2 with IC50 values of 38.9, and 44.9 μM, respectively.

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KW - Dihydrophenantrene

KW - Methylflavan

KW - Nitric oxide

KW - Orchidaceae

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DO - 10.1016/j.phytol.2021.06.007

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VL - 44

SP - 149

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JO - Phytochemistry Letters

JF - Phytochemistry Letters

ER -

A new bibenzyl and a new methylflavan from the tubers of Bletilla striata

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

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