Bioactive Diarylheptanoids from Alpinia coriandriodora

doi:10.1007/s13659-020-00264-y

Natural Products and Bioprospecting ›› 2021, Vol. 11 ›› Issue (1): 63-72.DOI: 10.1007/s13659-020-00264-y

• ORIGINAL ARTICLES • Previous Articles Next Articles

Bioactive Diarylheptanoids from Alpinia coriandriodora

Xiao-Li Cheng^1,3, Han-Xiang Li^1,2, Juan Chen^1,2, Ping Wu^1,2,3, Jing-Hua Xue^1,2, Zhong-Yu Zhou^1,2,3, Nia-He Xia^1,2,3, Xiao-Yi Wei^1,2,3

1 Key Laboratory of Plant Resources Conservation and Sustainable Utilization, South China Botanical Garden, Chinese Academy of Sciences, Tianhe District, Xingke Road 723, Guangzhou 510650, People's Republic of China;
2 Guangdong Provincial Key Laboratory of Digital Botanical Garden, South China Botanical Garden, Chinese Academy of Sciences, Xingke Road 723, Tianhe District, Guangzhou 510650, People's Republic of China;
3 School of Life Sciences, University of Chinese Academy of Sciences, Yuquanlu 19 A, Beijing 100049, People's Republic of China

Received:2020-08-14 Revised:2020-08-30 Online:2021-03-11 Published:2021-02-24
Contact: Xiao-Yi Wei
Supported by:
We are grateful to Mr. Yunfei Yuan, South China Botanical Garden, Chinese Academy of Sciences (CAS), for NMR spectroscopic measurements and Ms. Aijun Sun, South China Sea Institute of Oceanology, CAS, for HRESIMS measurements. We also gratefully acknowledge support from the Guangzhou Branch of the Supercomputing Center of CAS. This work was financially supported by NSFC Grants (Nos. 81172942 and 81872773).

Bioactive Diarylheptanoids from Alpinia coriandriodora

Xiao-Li Cheng^1,3, Han-Xiang Li^1,2, Juan Chen^1,2, Ping Wu^1,2,3, Jing-Hua Xue^1,2, Zhong-Yu Zhou^1,2,3, Nia-He Xia^1,2,3, Xiao-Yi Wei^1,2,3

1 Key Laboratory of Plant Resources Conservation and Sustainable Utilization, South China Botanical Garden, Chinese Academy of Sciences, Tianhe District, Xingke Road 723, Guangzhou 510650, People's Republic of China;
2 Guangdong Provincial Key Laboratory of Digital Botanical Garden, South China Botanical Garden, Chinese Academy of Sciences, Xingke Road 723, Tianhe District, Guangzhou 510650, People's Republic of China;
3 School of Life Sciences, University of Chinese Academy of Sciences, Yuquanlu 19 A, Beijing 100049, People's Republic of China

通讯作者: Xiao-Yi Wei
基金资助:
We are grateful to Mr. Yunfei Yuan, South China Botanical Garden, Chinese Academy of Sciences (CAS), for NMR spectroscopic measurements and Ms. Aijun Sun, South China Sea Institute of Oceanology, CAS, for HRESIMS measurements. We also gratefully acknowledge support from the Guangzhou Branch of the Supercomputing Center of CAS. This work was financially supported by NSFC Grants (Nos. 81172942 and 81872773).

Abstract

Abstract: Eight new diarylheptanoids, coriandralpinins A-H (1-8), were isolated from the rhizomes of Alpinia coriandriodora, an edible plant of the ginger family. Their structures, including the absolute configurations, were established by extensive spectroscopic analysis and ECD calculations. Compounds 1-8 have a 1,5-O-bridged diarylheptanoid structure featuring polyoxygenated aryl units. When evaluated for intracellular antioxidant activity using t-BHP stressed RAW264.7 macrophages, all these compounds scavenged reactive oxygen species (ROS) in a concentration-dependent manner. Compounds 3 and 5 also showed inhibitory activity against NO release in LPS-induced RAW 264.7 cells. Six known flavonols, 7,4'-diO-methylkaempferol, 7-O-methylquercetin, 7,4'-di-O-methylquercetin, 7,3',4'-tri-O-methylquercetin, kaempferol 3-O-β-D-(6-O-α-L-rhamnopyranosyl)glucopyranoside, and 3-O-β-D-glucopyranuronosylquercetin were also isolated and characterized from the rhizomes.

Key words: Alpinia coriandriodora, Diarylheptanoid, Antioxidant, Anti-inflammatory

摘要： Eight new diarylheptanoids, coriandralpinins A-H (1-8), were isolated from the rhizomes of Alpinia coriandriodora, an edible plant of the ginger family. Their structures, including the absolute configurations, were established by extensive spectroscopic analysis and ECD calculations. Compounds 1-8 have a 1,5-O-bridged diarylheptanoid structure featuring polyoxygenated aryl units. When evaluated for intracellular antioxidant activity using t-BHP stressed RAW264.7 macrophages, all these compounds scavenged reactive oxygen species (ROS) in a concentration-dependent manner. Compounds 3 and 5 also showed inhibitory activity against NO release in LPS-induced RAW 264.7 cells. Six known flavonols, 7,4'-diO-methylkaempferol, 7-O-methylquercetin, 7,4'-di-O-methylquercetin, 7,3',4'-tri-O-methylquercetin, kaempferol 3-O-β-D-(6-O-α-L-rhamnopyranosyl)glucopyranoside, and 3-O-β-D-glucopyranuronosylquercetin were also isolated and characterized from the rhizomes.

关键词: Alpinia coriandriodora, Diarylheptanoid, Antioxidant, Anti-inflammatory

Xiao-Li Cheng, Han-Xiang Li, Juan Chen, Ping Wu, Jing-Hua Xue, Zhong-Yu Zhou, Nia-He Xia, Xiao-Yi Wei. Bioactive Diarylheptanoids from Alpinia coriandriodora[J]. Natural Products and Bioprospecting, 2021, 11(1): 63-72.

Xiao-Li Cheng, Han-Xiang Li, Juan Chen, Ping Wu, Jing-Hua Xue, Zhong-Yu Zhou, Nia-He Xia, Xiao-Yi Wei. Bioactive Diarylheptanoids from Alpinia coriandriodora[J]. 应用天然产物, 2021, 11(1): 63-72.

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Bioactive Diarylheptanoids from Alpinia coriandriodora

Bioactive Diarylheptanoids from Alpinia coriandriodora

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