Synthesis and Anti-tumor Evaluation of B-ring Modified Caged Xanthone Analogues of Gambogic Acid
Gambogic acid （GA, 1）, the most prominent member of Garcinia natural products, has been reported to be a promising anti-tumor agent. Previous studies have suggested that the planar B ring and the unique 4-oxa-tricyclo- [4.3.1.03.7]dec-2-one caged motif were essential for anti-tumor activity. To furt...
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| Published in | Chinese journal of chemistry Vol. 30; no. 1; pp. 35 - 42 |
|---|---|
| Main Author | |
| Format | Journal Article |
| Language | English |
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Weinheim
WILEY-VCH Verlag
2012
WILEY‐VCH Verlag Wiley Wiley Subscription Services, Inc |
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| Abstract | Gambogic acid （GA, 1）, the most prominent member of Garcinia natural products, has been reported to be a promising anti-tumor agent. Previous studies have suggested that the planar B ring and the unique 4-oxa-tricyclo- [4.3.1.03.7]dec-2-one caged motif were essential for anti-tumor activity. To further explore the structure-activity relationship （SAR） of caged Garcinia xanthones, two new series of B-ring modified caged GA analogues 13a-13e and 15a-lge were synthesized utilizing a Claisen/Diel-Alder cascade reaction. Subsequently, these compounds were evaluated for their in vitro antitumor activities against A549, MCF-7, SMMC-7721 and BGC-823 cancer cell lines by MTT assay. Among them, 13b-13e exhibited micromolar inhibition against several cancer cell lines, being approximately 2-4 fold less potent in comparison to GA. SAR analysis revealed that the peripheral gem-dimethyl groups are essential for maintaining antitumor activity and substituent group on C1 position of B-ring has a significant effect on potency, while modifications at C-2, C-3 and C-4 positions are relatively tolerated. These findings will enhance our understanding of the SAR of Garcinia xanthones and lead to the development of simplified analogues as potential anti-tumor agents. |
|---|---|
| AbstractList | Gambogic acid (GA,
1
), the most prominent member of
Garcinia
natural products, has been reported to be a promising anti‐tumor agent. Previous studies have suggested that the planar B ring and the unique 4‐oxa‐tricyclo[4.3.1.0
3,7
]dec‐2‐one caged motif were essential for anti‐tumor activity. To further explore the structure‐activity relationship (SAR) of caged
Garcinia
xanthones, two new series of B‐ring modified caged GA analogues
13a
–
13e
and
15a
–
15e
were synthesized utilizing a Claisen/Diel‐Alder cascade reaction. Subsequently, these compounds were evaluated for their
in vitro
anti‐tumor activities against A549, MCF‐7, SMMC‐7721 and BGC‐823 cancer cell lines by MTT assay. Among them,
13b
–
13e
exhibited micromolar inhibition against several cancer cell lines, being approximately 2–4 fold less potent in comparison to GA. SAR analysis revealed that the peripheral gem‐dimethyl groups are essential for maintaining anti‐tumor activity and substituent group on C1 position of B‐ring has a significant effect on potency, while modifications at C‐2, C‐3 and C‐4 positions are relatively tolerated. These findings will enhance our understanding of the SAR of
Garcinia
xanthones and lead to the development of simplified analogues as potential anti‐tumor agents. Gambogic acid (GA, 1), the most prominent member of Garcinia natural products, has been reported to be a promising anti-tumor agent. Previous studies have suggested that the planar B ring and the unique 4-oxa-tricyclo[4.3.1.03,7]dec-2-one caged motif were essential for anti-tumor activity. To further explore the structure-activity relationship (SAR) of caged Garcinia xanthones, two new series of B-ring modified caged GA analogues 13a13e and 15a15e were synthesized utilizing a Claisen/Diel-Alder cascade reaction. Subsequently, these compounds were evaluated for their in vitro anti-tumor activities against A549, MCF-7, SMMC-7721 and BGC-823 cancer cell lines by MTT assay. Among them, 13b13e exhibited micromolar inhibition against several cancer cell lines, being approximately 24 fold less potent in comparison to GA. SAR analysis revealed that the peripheral gem-dimethyl groups are essential for maintaining anti-tumor activity and substituent group on C1 position of B-ring has a significant effect on potency, while modifications at C-2, C-3 and C-4 positions are relatively tolerated. These findings will enhance our understanding of the SAR of Garcinia xanthones and lead to the development of simplified analogues as potential anti-tumor agents. Gambogic acid （GA, 1）, the most prominent member of Garcinia natural products, has been reported to be a promising anti-tumor agent. Previous studies have suggested that the planar B ring and the unique 4-oxa-tricyclo- [4.3.1.03.7]dec-2-one caged motif were essential for anti-tumor activity. To further explore the structure-activity relationship （SAR） of caged Garcinia xanthones, two new series of B-ring modified caged GA analogues 13a-13e and 15a-lge were synthesized utilizing a Claisen/Diel-Alder cascade reaction. Subsequently, these compounds were evaluated for their in vitro antitumor activities against A549, MCF-7, SMMC-7721 and BGC-823 cancer cell lines by MTT assay. Among them, 13b-13e exhibited micromolar inhibition against several cancer cell lines, being approximately 2-4 fold less potent in comparison to GA. SAR analysis revealed that the peripheral gem-dimethyl groups are essential for maintaining antitumor activity and substituent group on C1 position of B-ring has a significant effect on potency, while modifications at C-2, C-3 and C-4 positions are relatively tolerated. These findings will enhance our understanding of the SAR of Garcinia xanthones and lead to the development of simplified analogues as potential anti-tumor agents. Gambogic acid (GA,1), the most prominent member of Garcinia natural products, has been reported to be a promising anti-tumor agent. Previous studies have suggested that the planar B ring and the unique 4-oxa-tricyclo[4.3.1.03,7]dec-2-one caged motif were essential for anti-tumor activity. To further explore the structure-activity relationship (SAR) of caged Garcinia xanthones, two new series of B-ring modified caged GA analogues 13a-13e and 15a-15e were synthesized utilizing a Claisen/Diel-Alder cascade reaction. Subsequently, these compounds were evaluated for their in vitro anti-tumor activities against A549, MCF-7, SMMC-7721 and BGC-823 cancer cell lines by MTT assay. Among them, 13b-13e exhibited micromolar inhibition against several cancer cell lines, being approximately 2-4 fold less potent in comparison to GA. SAR analysis revealed that the peripheral gem-dimethyl groups are essential for maintaining anti-tumor activity and substituent group on C1 position of B-ring has a significant effect on potency, while modifications at C-2, C-3 and C-4 positions are relatively tolerated. These findings will enhance our understanding of the SAR of Garcinia xanthones and lead to the development of simplified analogues as potential anti-tumor agents. Gambogic acid (GA, 1), the most prominent member of Garcinia natural products, has been reported to be a promising anti‐tumor agent. Previous studies have suggested that the planar B ring and the unique 4‐oxa‐tricyclo[4.3.1.03,7]dec‐2‐one caged motif were essential for anti‐tumor activity. To further explore the structure‐activity relationship (SAR) of caged Garcinia xanthones, two new series of B‐ring modified caged GA analogues 13a–13e and 15a–15e were synthesized utilizing a Claisen/Diel‐Alder cascade reaction. Subsequently, these compounds were evaluated for their in vitro anti‐tumor activities against A549, MCF‐7, SMMC‐7721 and BGC‐823 cancer cell lines by MTT assay. Among them, 13b–13e exhibited micromolar inhibition against several cancer cell lines, being approximately 2–4 fold less potent in comparison to GA. SAR analysis revealed that the peripheral gem‐dimethyl groups are essential for maintaining anti‐tumor activity and substituent group on C1 position of B‐ring has a significant effect on potency, while modifications at C‐2, C‐3 and C‐4 positions are relatively tolerated. These findings will enhance our understanding of the SAR of Garcinia xanthones and lead to the development of simplified analogues as potential anti‐tumor agents. Two new series of B‐ring modified caged xanhone analogues of Gambogic acid analogues were designed and synthesized utilizing a Claisen/Diel‐Alder cascade reaction. These compounds were evaluated for their in vitro anti‐tumor activities against A549, MCF‐7, SMMC‐7721 and BGC‐823 cancer cell lines by MTT assay. The structure‐activity relationship (SAR) was also discussed. |
| Author | Gao, Yuan Lin, Changjun You, Qidong Wang, Xiaojian Yu, Zhuoqin Zhang, Xiaojin Li, Xiang Li, Nianguang Guo, Qinglong |
| AuthorAffiliation | State Key Laboratory of Natural Medicines （China Pharmaceutical University）, Nanjing, Jiangsu 210009, China Department of Medicinal Chemistry, School of Pharmacy, China Pharmaceutical University, Nanjing, Jiangsu 21009, China Jiangsu Key Laboratory of Carcinogenesis and Intervention, China Pharmaceutical University, Nanjing, Jiangsu 210009, China |
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| CitedBy_id | crossref_primary_10_1016_j_bmcl_2015_04_031 crossref_primary_10_1002_chin_201222188 crossref_primary_10_15212_AMM_2022_0001 crossref_primary_10_1016_j_bmc_2024_117655 crossref_primary_10_1016_j_phytochem_2022_113484 crossref_primary_10_1039_D0QO00659A crossref_primary_10_3390_molecules24040791 |
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| Copyright | Copyright © 2012 SIOC, CAS, Shanghai & WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim Copyright © 2012 SIOC, CAS, Shanghai & WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim |
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| DocumentTitleAlternate | Synthesis and Anti-tumor Evaluation of B-ring Modified Caged Xanthone Analogues of Gambogic Acid |
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| Keywords | synthesis 4-oxa-tricyclo APOPTOSIS 03 gambogic acid ANGIOGENESIS PHOSPHORYLATION CELL-CYCLE ARREST KAPPA-B SAR studies 1 BIOMIMETIC TOTAL-SYNTHESIS 3 anti-tumor activity 7]dec-2-one CONSTRUCTION GROWTH INHIBITS PROLIFERATION |
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| Notes | 31-1547/O6 Li, Xiang Zhang, Xiaojin Wang, XiaojianLi, Nianguang Lin, Changjun Gao, Yuana＇CYu, ZhuoqinGuo, Qinglong You, Qidonga State Key Laboratory of Natural Medicines （China Pharmaceutical University）, Nanjing, Jiangsu 210009, China b Department of Medicinal Chemistry, School of Pharmacy, China Pharmaceutical University, Nanjing, Jiangsu 21009, China C Jiangsu Key Laboratory of Carcinogenesis and Intervention, China Pharmaceutical University, Nanjing, Jiangsu 210009, China Gambogic acid （GA, 1）, the most prominent member of Garcinia natural products, has been reported to be a promising anti-tumor agent. Previous studies have suggested that the planar B ring and the unique 4-oxa-tricyclo- [4.3.1.03.7]dec-2-one caged motif were essential for anti-tumor activity. To further explore the structure-activity relationship （SAR） of caged Garcinia xanthones, two new series of B-ring modified caged GA analogues 13a-13e and 15a-lge were synthesized utilizing a Claisen/Diel-Alder cascade reaction. Subsequently, these compounds were evaluated for their in vitro antitumor activities against A549, MCF-7, SMMC-7721 and BGC-823 cancer cell lines by MTT assay. Among them, 13b-13e exhibited micromolar inhibition against several cancer cell lines, being approximately 2-4 fold less potent in comparison to GA. SAR analysis revealed that the peripheral gem-dimethyl groups are essential for maintaining antitumor activity and substituent group on C1 position of B-ring has a significant effect on potency, while modifications at C-2, C-3 and C-4 positions are relatively tolerated. These findings will enhance our understanding of the SAR of Garcinia xanthones and lead to the development of simplified analogues as potential anti-tumor agents. 4-oxa-tricyclo[4.3.1.03.7]dec-2-0ne, gambogic acid, synthesis, anti-tumor activity, SAR studies National Natural Science Foundation of China (Key Program) - No. 90713038 and 21072231 istex:EEB1226A947ED2BFB2187B0E657429F72C9D97BB National Major Science and Technology Project of China (Innovation and Development of New Drugs) - No. 2008ZX09401-001, 2009ZX09501-003 and 2010ZX09401-401 ArticleID:CJOC201100045 ark:/67375/WNG-2FXSJXS6-J ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 14 |
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| SSID | ssj0027726 |
| Score | 1.9081008 |
| Snippet | Gambogic acid （GA, 1）, the most prominent member of Garcinia natural products, has been reported to be a promising anti-tumor agent. Previous studies have... Gambogic acid (GA, 1), the most prominent member of Garcinia natural products, has been reported to be a promising anti‐tumor agent. Previous studies have... Gambogic acid (GA, 1 ), the most prominent member of Garcinia natural products, has been reported to be a promising anti‐tumor agent. Previous studies have... Gambogic acid (GA, 1), the most prominent member of Garcinia natural products, has been reported to be a promising anti-tumor agent. Previous studies have... Gambogic acid (GA,1), the most prominent member of Garcinia natural products, has been reported to be a promising anti-tumor agent. Previous studies have... |
| Source | Web of Science |
| SourceID | proquest webofscience crossref wiley istex chongqing |
| SourceType | Aggregation Database Enrichment Source Index Database Publisher |
| StartPage | 35 |
| SubjectTerms | 4-oxa-tricyclo[4.3.1.03 4‐oxa‐tricyclo[4.3.1.03,7]dec‐2‐one 7]dec-2-one anti-tumor activity Chemistry Chemistry, Multidisciplinary gambogic acid MCF-7细胞 Physical Sciences SAR studies Science & Technology synthesis Tumors 体外抗肿瘤活性 修改 反应合成 抗肿瘤剂 活性评价 酮衍生物 黄酸 |
| Title | Synthesis and Anti-tumor Evaluation of B-ring Modified Caged Xanthone Analogues of Gambogic Acid |
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