Four New Picrotoxane-Type Sesquiterpenes From Dendrobium nobile Lindl
Four picrotoxane-type sesquiterpenes, dendroterpene A–D (1–4), together with four known compounds (5–8), were isolated from the stems of Dendrobium nobile Lindl. Their structures were elucidated by spectroscopic analysis, X-ray diffraction analysis, analysis of the ECD data according to the Klyne�...
| Main Authors: | , , , , , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
Frontiers Media S.A.
2019-11-01
|
| Series: | Frontiers in Chemistry |
| Subjects: | |
| Online Access: | https://www.frontiersin.org/article/10.3389/fchem.2019.00812/full |
| _version_ | 1818380277583446016 |
|---|---|
| author | Pei Wang Xin Chen Xin Chen Hao Wang Shengzhuo Huang Caihong Cai Jingzhe Yuan Guoliang Zhu Xinglian Xu Wenli Mei Haofu Dai |
| author_facet | Pei Wang Xin Chen Xin Chen Hao Wang Shengzhuo Huang Caihong Cai Jingzhe Yuan Guoliang Zhu Xinglian Xu Wenli Mei Haofu Dai |
| author_sort | Pei Wang |
| collection | DOAJ |
| description | Four picrotoxane-type sesquiterpenes, dendroterpene A–D (1–4), together with four known compounds (5–8), were isolated from the stems of Dendrobium nobile Lindl. Their structures were elucidated by spectroscopic analysis, X-ray diffraction analysis, analysis of the ECD data according to the Klyne's lactone sector rule, and quantum ECD calculation. Compounds 1 and 2 are two new picrotoxane-type sesquiterpenes with a new carbon skeleton containing a formamide group, which may be derived from the previously reported dendrobiumane B skeleton by the C(9)-C(11) carbon bond cleavage. Compounds 3, 5, 6, and 8 exhibited inhibitory activity against α-glycosidase. Compounds 5 and 6 were cytotoxic against SGC-7901, K562, A549, BEL-7402, and Hela cell lines. |
| first_indexed | 2024-12-14T02:16:08Z |
| format | Article |
| id | doaj.art-a0bf8da591da429786e977cfaa242456 |
| institution | Directory Open Access Journal |
| issn | 2296-2646 |
| language | English |
| last_indexed | 2024-12-14T02:16:08Z |
| publishDate | 2019-11-01 |
| publisher | Frontiers Media S.A. |
| record_format | Article |
| series | Frontiers in Chemistry |
| spelling | doaj.art-a0bf8da591da429786e977cfaa2424562022-12-21T23:20:37ZengFrontiers Media S.A.Frontiers in Chemistry2296-26462019-11-01710.3389/fchem.2019.00812496703Four New Picrotoxane-Type Sesquiterpenes From Dendrobium nobile LindlPei Wang0Xin Chen1Xin Chen2Hao Wang3Shengzhuo Huang4Caihong Cai5Jingzhe Yuan6Guoliang Zhu7Xinglian Xu8Wenli Mei9Haofu Dai10Hainan Key Laboratory of Research and Development of Natural Product From Li Folk Medicine, Institute of Tropical Bioscience and Biotechnology, Chinese Academy of Tropical Agricultural Sciences, Haikou, ChinaHainan Key Laboratory of Research and Development of Natural Product From Li Folk Medicine, Institute of Tropical Bioscience and Biotechnology, Chinese Academy of Tropical Agricultural Sciences, Haikou, ChinaNanjing Agricultural University, Nanjing, ChinaHainan Key Laboratory of Research and Development of Natural Product From Li Folk Medicine, Institute of Tropical Bioscience and Biotechnology, Chinese Academy of Tropical Agricultural Sciences, Haikou, ChinaHainan Key Laboratory of Research and Development of Natural Product From Li Folk Medicine, Institute of Tropical Bioscience and Biotechnology, Chinese Academy of Tropical Agricultural Sciences, Haikou, ChinaHainan Key Laboratory of Research and Development of Natural Product From Li Folk Medicine, Institute of Tropical Bioscience and Biotechnology, Chinese Academy of Tropical Agricultural Sciences, Haikou, ChinaHainan Key Laboratory of Research and Development of Natural Product From Li Folk Medicine, Institute of Tropical Bioscience and Biotechnology, Chinese Academy of Tropical Agricultural Sciences, Haikou, ChinaEast China University of Science and Technology, Shanghai, ChinaNanjing Agricultural University, Nanjing, ChinaHainan Key Laboratory of Research and Development of Natural Product From Li Folk Medicine, Institute of Tropical Bioscience and Biotechnology, Chinese Academy of Tropical Agricultural Sciences, Haikou, ChinaHainan Key Laboratory of Research and Development of Natural Product From Li Folk Medicine, Institute of Tropical Bioscience and Biotechnology, Chinese Academy of Tropical Agricultural Sciences, Haikou, ChinaFour picrotoxane-type sesquiterpenes, dendroterpene A–D (1–4), together with four known compounds (5–8), were isolated from the stems of Dendrobium nobile Lindl. Their structures were elucidated by spectroscopic analysis, X-ray diffraction analysis, analysis of the ECD data according to the Klyne's lactone sector rule, and quantum ECD calculation. Compounds 1 and 2 are two new picrotoxane-type sesquiterpenes with a new carbon skeleton containing a formamide group, which may be derived from the previously reported dendrobiumane B skeleton by the C(9)-C(11) carbon bond cleavage. Compounds 3, 5, 6, and 8 exhibited inhibitory activity against α-glycosidase. Compounds 5 and 6 were cytotoxic against SGC-7901, K562, A549, BEL-7402, and Hela cell lines.https://www.frontiersin.org/article/10.3389/fchem.2019.00812/fullDendrobium nobile Lindlpicrotoxanesesquiterpenesα-glycosidase inhibitorcytotoxicity |
| spellingShingle | Pei Wang Xin Chen Xin Chen Hao Wang Shengzhuo Huang Caihong Cai Jingzhe Yuan Guoliang Zhu Xinglian Xu Wenli Mei Haofu Dai Four New Picrotoxane-Type Sesquiterpenes From Dendrobium nobile Lindl Frontiers in Chemistry Dendrobium nobile Lindl picrotoxane sesquiterpenes α-glycosidase inhibitor cytotoxicity |
| title | Four New Picrotoxane-Type Sesquiterpenes From Dendrobium nobile Lindl |
| title_full | Four New Picrotoxane-Type Sesquiterpenes From Dendrobium nobile Lindl |
| title_fullStr | Four New Picrotoxane-Type Sesquiterpenes From Dendrobium nobile Lindl |
| title_full_unstemmed | Four New Picrotoxane-Type Sesquiterpenes From Dendrobium nobile Lindl |
| title_short | Four New Picrotoxane-Type Sesquiterpenes From Dendrobium nobile Lindl |
| title_sort | four new picrotoxane type sesquiterpenes from dendrobium nobile lindl |
| topic | Dendrobium nobile Lindl picrotoxane sesquiterpenes α-glycosidase inhibitor cytotoxicity |
| url | https://www.frontiersin.org/article/10.3389/fchem.2019.00812/full |
| work_keys_str_mv | AT peiwang fournewpicrotoxanetypesesquiterpenesfromdendrobiumnobilelindl AT xinchen fournewpicrotoxanetypesesquiterpenesfromdendrobiumnobilelindl AT xinchen fournewpicrotoxanetypesesquiterpenesfromdendrobiumnobilelindl AT haowang fournewpicrotoxanetypesesquiterpenesfromdendrobiumnobilelindl AT shengzhuohuang fournewpicrotoxanetypesesquiterpenesfromdendrobiumnobilelindl AT caihongcai fournewpicrotoxanetypesesquiterpenesfromdendrobiumnobilelindl AT jingzheyuan fournewpicrotoxanetypesesquiterpenesfromdendrobiumnobilelindl AT guoliangzhu fournewpicrotoxanetypesesquiterpenesfromdendrobiumnobilelindl AT xinglianxu fournewpicrotoxanetypesesquiterpenesfromdendrobiumnobilelindl AT wenlimei fournewpicrotoxanetypesesquiterpenesfromdendrobiumnobilelindl AT haofudai fournewpicrotoxanetypesesquiterpenesfromdendrobiumnobilelindl |