Determination of the absolute configurations and anti-angiogenic activities of new diarylheptanoid glucosides from Curcuma phaeocaulis
Diarylheptanoids, potential therapeutic agents and dietary supplements, are the main active compounds in the genus Curcuma, however, determination of the absolute configurations of the flexible polyhydric main chains in linear diarylheptanoids is still a challenge. In this study, an exploration of t...
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| Format: | Article |
| Language: | English |
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Elsevier
2024-02-01
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| Series: | Arabian Journal of Chemistry |
| Subjects: | |
| Online Access: | http://www.sciencedirect.com/science/article/pii/S1878535223010341 |
| _version_ | 1797356128132136960 |
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| author | Cheng-Zhe Li Cheng Peng Xiao-Cui Li Guang-Xu Wu Hong-Zhen Shu Fang Wang Fei Liu Liang Xiong |
| author_facet | Cheng-Zhe Li Cheng Peng Xiao-Cui Li Guang-Xu Wu Hong-Zhen Shu Fang Wang Fei Liu Liang Xiong |
| author_sort | Cheng-Zhe Li |
| collection | DOAJ |
| description | Diarylheptanoids, potential therapeutic agents and dietary supplements, are the main active compounds in the genus Curcuma, however, determination of the absolute configurations of the flexible polyhydric main chains in linear diarylheptanoids is still a challenge. In this study, an exploration of the phytochemical constituents of Curcuma phaeocaulis led to the isolation of eight novel linear diarylheptanoids (1–8). Enzymatic hydrolysis, preparation of acetonide derivatives, preparation of MTPA esters, and electronic circular dichroism calculations were comprehensively performed in order to determine their absolute configurations. In in vitro assays, compounds 2, 3, and 6 exhibited anti-angiogenic activities, and compounds 2, 3, and their aglycones inhibited the proliferation of HepG2 cells. These findings suggest that diarylheptanoid glucosides of C. phaeocaulis may be useful for suppression of hepatoma growth and metastasis. |
| first_indexed | 2024-03-08T14:21:09Z |
| format | Article |
| id | doaj.art-733da547fe49437393992312352b437f |
| institution | Directory Open Access Journal |
| issn | 1878-5352 |
| language | English |
| last_indexed | 2024-03-08T14:21:09Z |
| publishDate | 2024-02-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Arabian Journal of Chemistry |
| spelling | doaj.art-733da547fe49437393992312352b437f2024-01-14T05:37:59ZengElsevierArabian Journal of Chemistry1878-53522024-02-01172105572Determination of the absolute configurations and anti-angiogenic activities of new diarylheptanoid glucosides from Curcuma phaeocaulisCheng-Zhe Li0Cheng Peng1Xiao-Cui Li2Guang-Xu Wu3Hong-Zhen Shu4Fang Wang5Fei Liu6Liang 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, 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, 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, ChinaShandong Academy of Pharmaceutical Sciences, 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, China; Corresponding authors at: State Key Laboratory of Southwestern Chinese Medicine Resources, Chengdu University of Traditional Chinese Medicine, Chengdu 611137, China.Diarylheptanoids, potential therapeutic agents and dietary supplements, are the main active compounds in the genus Curcuma, however, determination of the absolute configurations of the flexible polyhydric main chains in linear diarylheptanoids is still a challenge. In this study, an exploration of the phytochemical constituents of Curcuma phaeocaulis led to the isolation of eight novel linear diarylheptanoids (1–8). Enzymatic hydrolysis, preparation of acetonide derivatives, preparation of MTPA esters, and electronic circular dichroism calculations were comprehensively performed in order to determine their absolute configurations. In in vitro assays, compounds 2, 3, and 6 exhibited anti-angiogenic activities, and compounds 2, 3, and their aglycones inhibited the proliferation of HepG2 cells. These findings suggest that diarylheptanoid glucosides of C. phaeocaulis may be useful for suppression of hepatoma growth and metastasis.http://www.sciencedirect.com/science/article/pii/S1878535223010341Curcuma phaeocaulisDiarylheptanoidsAbsolute configurationsAnti-angiogenic activities |
| spellingShingle | Cheng-Zhe Li Cheng Peng Xiao-Cui Li Guang-Xu Wu Hong-Zhen Shu Fang Wang Fei Liu Liang Xiong Determination of the absolute configurations and anti-angiogenic activities of new diarylheptanoid glucosides from Curcuma phaeocaulis Arabian Journal of Chemistry Curcuma phaeocaulis Diarylheptanoids Absolute configurations Anti-angiogenic activities |
| title | Determination of the absolute configurations and anti-angiogenic activities of new diarylheptanoid glucosides from Curcuma phaeocaulis |
| title_full | Determination of the absolute configurations and anti-angiogenic activities of new diarylheptanoid glucosides from Curcuma phaeocaulis |
| title_fullStr | Determination of the absolute configurations and anti-angiogenic activities of new diarylheptanoid glucosides from Curcuma phaeocaulis |
| title_full_unstemmed | Determination of the absolute configurations and anti-angiogenic activities of new diarylheptanoid glucosides from Curcuma phaeocaulis |
| title_short | Determination of the absolute configurations and anti-angiogenic activities of new diarylheptanoid glucosides from Curcuma phaeocaulis |
| title_sort | determination of the absolute configurations and anti angiogenic activities of new diarylheptanoid glucosides from curcuma phaeocaulis |
| topic | Curcuma phaeocaulis Diarylheptanoids Absolute configurations Anti-angiogenic activities |
| url | http://www.sciencedirect.com/science/article/pii/S1878535223010341 |
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