Euphorane C, an unusual C17-norabietane diterpenoid from Euphorbia dracunculoides induces cell cycle arrest and apoptosis in human leukemia K562 cells
Four new polycyclic diterpenoids euphoranes A − D (1–4), together with 12 known terpenoids (5–16) were isolated from the whole plants of Euphorbia dracunculoides. Compound 2 represents the first example of aromatic 15,16,17-trinorabietane diterpenoid in Euphorbia species, and euphorane C (3) is an u...
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| Format: | Article |
| Language: | English |
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Elsevier
2022-11-01
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| Series: | Arabian Journal of Chemistry |
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| Online Access: | http://www.sciencedirect.com/science/article/pii/S1878535222005196 |
| _version_ | 1797990450139758592 |
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| author | Xue-Long Yan Ming-Feng Zou Bei-Ling Chen Fang-Yu Yuan Qin-Feng Zhu Xu Zhang Yan Lin Qing-De Long Wu-Ling Liu Shang-Gao Liao |
| author_facet | Xue-Long Yan Ming-Feng Zou Bei-Ling Chen Fang-Yu Yuan Qin-Feng Zhu Xu Zhang Yan Lin Qing-De Long Wu-Ling Liu Shang-Gao Liao |
| author_sort | Xue-Long Yan |
| collection | DOAJ |
| description | Four new polycyclic diterpenoids euphoranes A − D (1–4), together with 12 known terpenoids (5–16) were isolated from the whole plants of Euphorbia dracunculoides. Compound 2 represents the first example of aromatic 15,16,17-trinorabietane diterpenoid in Euphorbia species, and euphorane C (3) is an unusual 17-norabietane diterpenoid. The absolute configurations of 1, 2, and 4 were determined by single crystal X-ray diffraction, while that of 3 was established with the aid of ECD and 1D NMR quantum chemical calculation. Moreover, the absolute stereochemistry of 11 was demonstrated for the first time by crystallographic data. Compounds 1–16 were screened for antiproliferative activities against five human cancer cell lines, and 3 showed significant cytotoxicity against the human leukemia K562 cells with IC50 value of 3.59 μM. Preliminary mechanistic investigation revealed that 3 could induce cell cycle arrest at G0/G1 phase and apoptosis in K562 cells. |
| first_indexed | 2024-04-11T08:36:39Z |
| format | Article |
| id | doaj.art-6f825be027fe42c68fb224e45627008e |
| institution | Directory Open Access Journal |
| issn | 1878-5352 |
| language | English |
| last_indexed | 2024-04-11T08:36:39Z |
| publishDate | 2022-11-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Arabian Journal of Chemistry |
| spelling | doaj.art-6f825be027fe42c68fb224e45627008e2022-12-22T04:34:19ZengElsevierArabian Journal of Chemistry1878-53522022-11-011511104203Euphorane C, an unusual C17-norabietane diterpenoid from Euphorbia dracunculoides induces cell cycle arrest and apoptosis in human leukemia K562 cellsXue-Long Yan0Ming-Feng Zou1Bei-Ling Chen2Fang-Yu Yuan3Qin-Feng Zhu4Xu Zhang5Yan Lin6Qing-De Long7Wu-Ling Liu8Shang-Gao Liao9State Key Laboratory of Functions and Applications of Medicinal Plants & School of Pharmacy, Guizhou Medical University, Guian New District 550025, Guizhou, China; School of Basic Medical Sciences, Guizhou Medical University, Guian New District 550025, Guizhou, ChinaSchool of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou, 510006, Guangdong, ChinaState Key Laboratory of Functions and Applications of Medicinal Plants & School of Pharmacy, Guizhou Medical University, Guian New District 550025, Guizhou, ChinaSchool of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou, 510006, Guangdong, ChinaState Key Laboratory of Functions and Applications of Medicinal Plants & School of Pharmacy, Guizhou Medical University, Guian New District 550025, Guizhou, ChinaState Key Laboratory of Functions and Applications of Medicinal Plants & School of Pharmacy, Guizhou Medical University, Guian New District 550025, Guizhou, ChinaState Key Laboratory of Functions and Applications of Medicinal Plants & School of Pharmacy, Guizhou Medical University, Guian New District 550025, Guizhou, ChinaState Key Laboratory of Functions and Applications of Medicinal Plants & School of Pharmacy, Guizhou Medical University, Guian New District 550025, Guizhou, ChinaState Key Laboratory of Functions and Applications of Medicinal Plants & School of Pharmacy, Guizhou Medical University, Guian New District 550025, Guizhou, China; Corresponding authors.State Key Laboratory of Functions and Applications of Medicinal Plants & School of Pharmacy, Guizhou Medical University, Guian New District 550025, Guizhou, China; Corresponding authors.Four new polycyclic diterpenoids euphoranes A − D (1–4), together with 12 known terpenoids (5–16) were isolated from the whole plants of Euphorbia dracunculoides. Compound 2 represents the first example of aromatic 15,16,17-trinorabietane diterpenoid in Euphorbia species, and euphorane C (3) is an unusual 17-norabietane diterpenoid. The absolute configurations of 1, 2, and 4 were determined by single crystal X-ray diffraction, while that of 3 was established with the aid of ECD and 1D NMR quantum chemical calculation. Moreover, the absolute stereochemistry of 11 was demonstrated for the first time by crystallographic data. Compounds 1–16 were screened for antiproliferative activities against five human cancer cell lines, and 3 showed significant cytotoxicity against the human leukemia K562 cells with IC50 value of 3.59 μM. Preliminary mechanistic investigation revealed that 3 could induce cell cycle arrest at G0/G1 phase and apoptosis in K562 cells.http://www.sciencedirect.com/science/article/pii/S1878535222005196Euphorbia dracunculoidesCytotoxicityApoptosisAbietane diterpenoidNorabietane |
| spellingShingle | Xue-Long Yan Ming-Feng Zou Bei-Ling Chen Fang-Yu Yuan Qin-Feng Zhu Xu Zhang Yan Lin Qing-De Long Wu-Ling Liu Shang-Gao Liao Euphorane C, an unusual C17-norabietane diterpenoid from Euphorbia dracunculoides induces cell cycle arrest and apoptosis in human leukemia K562 cells Arabian Journal of Chemistry Euphorbia dracunculoides Cytotoxicity Apoptosis Abietane diterpenoid Norabietane |
| title | Euphorane C, an unusual C17-norabietane diterpenoid from Euphorbia dracunculoides induces cell cycle arrest and apoptosis in human leukemia K562 cells |
| title_full | Euphorane C, an unusual C17-norabietane diterpenoid from Euphorbia dracunculoides induces cell cycle arrest and apoptosis in human leukemia K562 cells |
| title_fullStr | Euphorane C, an unusual C17-norabietane diterpenoid from Euphorbia dracunculoides induces cell cycle arrest and apoptosis in human leukemia K562 cells |
| title_full_unstemmed | Euphorane C, an unusual C17-norabietane diterpenoid from Euphorbia dracunculoides induces cell cycle arrest and apoptosis in human leukemia K562 cells |
| title_short | Euphorane C, an unusual C17-norabietane diterpenoid from Euphorbia dracunculoides induces cell cycle arrest and apoptosis in human leukemia K562 cells |
| title_sort | euphorane c an unusual c17 norabietane diterpenoid from euphorbia dracunculoides induces cell cycle arrest and apoptosis in human leukemia k562 cells |
| topic | Euphorbia dracunculoides Cytotoxicity Apoptosis Abietane diterpenoid Norabietane |
| url | http://www.sciencedirect.com/science/article/pii/S1878535222005196 |
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