A pair of new enantiomeric hybrid phthalide–adenines with a rare 5-oxa-1-azaspiro[3,4]octane moiety and two pairs of new enantiomeric hybrid paraethyl phenol–adenines from Ligusticum chuanxiong
Three pairs of new enantiomeric adenine alkaloids, (+)/(−)-liguadenines A–C [(+)/(−)-1–3], were isolated from the rhizome of Ligusticum chuanxiong Hort. The structures and absolute configurations of these compounds were determined using spectroscopic data, single-crystal X-ray diffraction, and elect...
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| Format: | Article |
| Language: | English |
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Elsevier
2023-05-01
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| Series: | Arabian Journal of Chemistry |
| Subjects: | |
| Online Access: | http://www.sciencedirect.com/science/article/pii/S1878535223001582 |
| _version_ | 1797857683321126912 |
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| author | Rui Feng Juan Liu Li Guo Hong-Zhen Shu Qin-Mei Zhou Li Liu Cheng Peng Liang Xiong |
| author_facet | Rui Feng Juan Liu Li Guo Hong-Zhen Shu Qin-Mei Zhou Li Liu Cheng Peng Liang Xiong |
| author_sort | Rui Feng |
| collection | DOAJ |
| description | Three pairs of new enantiomeric adenine alkaloids, (+)/(−)-liguadenines A–C [(+)/(−)-1–3], were isolated from the rhizome of Ligusticum chuanxiong Hort. The structures and absolute configurations of these compounds were determined using spectroscopic data, single-crystal X-ray diffraction, and electronic circular dichroism analyses. To the best of our knowledge, compounds (+)-1 and (−)-1 are the first hybrid phthalide–adenines to be ever reported. The linkage between the phthalide and adenine units in these compounds forms a rare 5-oxa-1-azaspiro[3,4]octane moiety. Analyses of the anti-inflammatory activities of the isolated compounds show that (+)/(−)-1 and (+)-3 exhibit significant inhibitory activity against LPS-induced TNF-α and IL-6 production in RAW264.7 cells. RT-qPCR analysis confirms that the most active compound, (+)-3, exerts anti-inflammatory activity by downregulating the mRNA expressions of TNF-α and IL-6 in the cells. |
| first_indexed | 2024-04-09T21:00:46Z |
| format | Article |
| id | doaj.art-5dc0122d7d74423aad16b9881c912087 |
| institution | Directory Open Access Journal |
| issn | 1878-5352 |
| language | English |
| last_indexed | 2024-04-09T21:00:46Z |
| publishDate | 2023-05-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Arabian Journal of Chemistry |
| spelling | doaj.art-5dc0122d7d74423aad16b9881c9120872023-03-29T09:25:52ZengElsevierArabian Journal of Chemistry1878-53522023-05-01165104696A pair of new enantiomeric hybrid phthalide–adenines with a rare 5-oxa-1-azaspiro[3,4]octane moiety and two pairs of new enantiomeric hybrid paraethyl phenol–adenines from Ligusticum chuanxiongRui Feng0Juan Liu1Li Guo2Hong-Zhen Shu3Qin-Mei Zhou4Li Liu5Cheng Peng6Liang Xiong7State Key Laboratory of Southwestern Chinese Medicine Resources, Chengdu University of Traditional Chinese Medicine, Chengdu 611137, China; School of Pharmacy, Chengdu University of Traditional Chinese Medicine, Chengdu 611137, China; Institute of Innovative Medicine Ingredients of Southwest Specialty Medicinal Materials, Chengdu University of Traditional Chinese Medicine, Chengdu 611137, ChinaState Key Laboratory of Southwestern Chinese Medicine Resources, Chengdu University of Traditional Chinese Medicine, Chengdu 611137, China; School of Pharmacy, Chengdu University of Traditional Chinese Medicine, Chengdu 611137, China; Institute of Innovative Medicine Ingredients of Southwest Specialty Medicinal Materials, Chengdu University of Traditional Chinese Medicine, Chengdu 611137, ChinaState Key Laboratory of Southwestern Chinese Medicine Resources, Chengdu University of Traditional Chinese Medicine, Chengdu 611137, China; School of Pharmacy, Chengdu University of Traditional Chinese Medicine, Chengdu 611137, China; Institute of Innovative Medicine Ingredients of Southwest Specialty Medicinal Materials, Chengdu University of Traditional Chinese Medicine, Chengdu 611137, China; Corresponding authors at: State Key Laboratory of Southwestern Chinese Medicine Resources, Chengdu University of Traditional Chinese Medicine, Chengdu 611137, China.State Key Laboratory of Southwestern Chinese Medicine Resources, Chengdu University of Traditional Chinese Medicine, Chengdu 611137, China; School of Pharmacy, Chengdu University of Traditional Chinese Medicine, Chengdu 611137, China; Institute of Innovative Medicine Ingredients of Southwest Specialty Medicinal Materials, Chengdu University of Traditional Chinese Medicine, Chengdu 611137, ChinaState Key Laboratory of Southwestern Chinese Medicine Resources, Chengdu University of Traditional Chinese Medicine, Chengdu 611137, China; Institute of Innovative Medicine Ingredients of Southwest Specialty Medicinal Materials, Chengdu University of Traditional Chinese Medicine, Chengdu 611137, ChinaChiataj Qingchunbao Pharmaceutical Co., Ltd, Hangzhou 310023, ChinaState Key Laboratory of Southwestern Chinese Medicine Resources, Chengdu University of Traditional Chinese Medicine, Chengdu 611137, China; School of Pharmacy, Chengdu University of Traditional Chinese Medicine, Chengdu 611137, China; Corresponding authors at: State Key Laboratory of Southwestern Chinese Medicine Resources, Chengdu University of Traditional Chinese Medicine, Chengdu 611137, China.State Key Laboratory of Southwestern Chinese Medicine Resources, Chengdu University of Traditional Chinese Medicine, Chengdu 611137, China; School of Pharmacy, Chengdu University of Traditional Chinese Medicine, Chengdu 611137, China; Institute of Innovative Medicine Ingredients of Southwest Specialty Medicinal Materials, Chengdu University of Traditional Chinese Medicine, Chengdu 611137, China; Corresponding authors at: State Key Laboratory of Southwestern Chinese Medicine Resources, Chengdu University of Traditional Chinese Medicine, Chengdu 611137, China.Three pairs of new enantiomeric adenine alkaloids, (+)/(−)-liguadenines A–C [(+)/(−)-1–3], were isolated from the rhizome of Ligusticum chuanxiong Hort. The structures and absolute configurations of these compounds were determined using spectroscopic data, single-crystal X-ray diffraction, and electronic circular dichroism analyses. To the best of our knowledge, compounds (+)-1 and (−)-1 are the first hybrid phthalide–adenines to be ever reported. The linkage between the phthalide and adenine units in these compounds forms a rare 5-oxa-1-azaspiro[3,4]octane moiety. Analyses of the anti-inflammatory activities of the isolated compounds show that (+)/(−)-1 and (+)-3 exhibit significant inhibitory activity against LPS-induced TNF-α and IL-6 production in RAW264.7 cells. RT-qPCR analysis confirms that the most active compound, (+)-3, exerts anti-inflammatory activity by downregulating the mRNA expressions of TNF-α and IL-6 in the cells.http://www.sciencedirect.com/science/article/pii/S1878535223001582Ligusticum chuanxiongEnantiomersAdenine alkaloidsHybrid phthalide–adeninesHybrid paraethyl phenol–adeninesAnti-inflammatory activity |
| spellingShingle | Rui Feng Juan Liu Li Guo Hong-Zhen Shu Qin-Mei Zhou Li Liu Cheng Peng Liang Xiong A pair of new enantiomeric hybrid phthalide–adenines with a rare 5-oxa-1-azaspiro[3,4]octane moiety and two pairs of new enantiomeric hybrid paraethyl phenol–adenines from Ligusticum chuanxiong Arabian Journal of Chemistry Ligusticum chuanxiong Enantiomers Adenine alkaloids Hybrid phthalide–adenines Hybrid paraethyl phenol–adenines Anti-inflammatory activity |
| title | A pair of new enantiomeric hybrid phthalide–adenines with a rare 5-oxa-1-azaspiro[3,4]octane moiety and two pairs of new enantiomeric hybrid paraethyl phenol–adenines from Ligusticum chuanxiong |
| title_full | A pair of new enantiomeric hybrid phthalide–adenines with a rare 5-oxa-1-azaspiro[3,4]octane moiety and two pairs of new enantiomeric hybrid paraethyl phenol–adenines from Ligusticum chuanxiong |
| title_fullStr | A pair of new enantiomeric hybrid phthalide–adenines with a rare 5-oxa-1-azaspiro[3,4]octane moiety and two pairs of new enantiomeric hybrid paraethyl phenol–adenines from Ligusticum chuanxiong |
| title_full_unstemmed | A pair of new enantiomeric hybrid phthalide–adenines with a rare 5-oxa-1-azaspiro[3,4]octane moiety and two pairs of new enantiomeric hybrid paraethyl phenol–adenines from Ligusticum chuanxiong |
| title_short | A pair of new enantiomeric hybrid phthalide–adenines with a rare 5-oxa-1-azaspiro[3,4]octane moiety and two pairs of new enantiomeric hybrid paraethyl phenol–adenines from Ligusticum chuanxiong |
| title_sort | pair of new enantiomeric hybrid phthalide adenines with a rare 5 oxa 1 azaspiro 3 4 octane moiety and two pairs of new enantiomeric hybrid paraethyl phenol adenines from ligusticum chuanxiong |
| topic | Ligusticum chuanxiong Enantiomers Adenine alkaloids Hybrid phthalide–adenines Hybrid paraethyl phenol–adenines Anti-inflammatory activity |
| url | http://www.sciencedirect.com/science/article/pii/S1878535223001582 |
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