Structural Elucidation and Cytotoxic Activity of New Monoterpenoid Indoles from <i>Gelsemium elegans</i>
Two new monoterpenoid indole alkaloids, gelselegandines F (<b>1</b>) and G (<b>2</b>), were isolated from the aerial parts of <i>Gelsemium elegans</i>. Their structures were elucidated by means of spectroscopic techniques and quantum chemical calculations. The ECD...
| Main Authors: | , , , , , , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2023-03-01
|
| Series: | Molecules |
| Subjects: | |
| Online Access: | https://www.mdpi.com/1420-3049/28/6/2531 |
| _version_ | 1797609930509778944 |
|---|---|
| author | Da Song Jia-Jun Liang Shi-Biao Pu Pan-Pan Zhang Yun-Lin Peng Xia Liu Ting-Ting Feng Xiang Pu Ying Zhou Xiong-Wei Liu Xin Wei |
| author_facet | Da Song Jia-Jun Liang Shi-Biao Pu Pan-Pan Zhang Yun-Lin Peng Xia Liu Ting-Ting Feng Xiang Pu Ying Zhou Xiong-Wei Liu Xin Wei |
| author_sort | Da Song |
| collection | DOAJ |
| description | Two new monoterpenoid indole alkaloids, gelselegandines F (<b>1</b>) and G (<b>2</b>), were isolated from the aerial parts of <i>Gelsemium elegans</i>. Their structures were elucidated by means of spectroscopic techniques and quantum chemical calculations. The ECD calculations were conducted at the B3LYP/6-311G(d,p) level and NMR calculations were carried out using the Gauge-Including Atomic Orbitals (GIAO) method. Structurally, the two new compounds possessed rare, cage-like, monoterpenoid indole skeletons. All isolated compounds and the total alkaloids extract were tested for cytotoxicity against four different tumor cell lines. The total alkaloids extract of <i>G. elegans</i> exhibited significant antitumor activity with IC<sub>50</sub> values ranging from 32.63 to 82.24 ug/mL. In order to discover anticancer leads from the active extraction, both new indole compounds (<b>1–2</b>) were then screened for cytotoxicity. Interestingly, compound <b>2</b> showed moderate cytotoxicity against K562 leukemia cells with an IC<sub>50</sub> value of 57.02 uM. |
| first_indexed | 2024-03-11T06:08:28Z |
| format | Article |
| id | doaj.art-92eca4969e564c3aa3786a268a52c668 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-11T06:08:28Z |
| publishDate | 2023-03-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-92eca4969e564c3aa3786a268a52c6682023-11-17T12:51:38ZengMDPI AGMolecules1420-30492023-03-01286253110.3390/molecules28062531Structural Elucidation and Cytotoxic Activity of New Monoterpenoid Indoles from <i>Gelsemium elegans</i>Da Song0Jia-Jun Liang1Shi-Biao Pu2Pan-Pan Zhang3Yun-Lin Peng4Xia Liu5Ting-Ting Feng6Xiang Pu7Ying Zhou8Xiong-Wei Liu9Xin Wei10School of Pharmacy, Guizhou University of Traditional Chinese Medicine, Guiyang 550025, ChinaSchool of Pharmacy, Guizhou University of Traditional Chinese Medicine, Guiyang 550025, ChinaCollege of Chinese Materia Medica, Yunnan University of Chinese Medicine, Kunming 650500, ChinaSchool of Pharmacy, Guizhou University of Traditional Chinese Medicine, Guiyang 550025, ChinaSchool of Pharmacy, Guizhou University of Traditional Chinese Medicine, Guiyang 550025, ChinaSchool of Pharmacy, Guizhou University of Traditional Chinese Medicine, Guiyang 550025, ChinaSchool of Pharmacy, Guizhou University of Traditional Chinese Medicine, Guiyang 550025, ChinaSchool of Pharmacy, Guizhou University of Traditional Chinese Medicine, Guiyang 550025, ChinaSchool of Pharmacy, Guizhou University of Traditional Chinese Medicine, Guiyang 550025, ChinaSchool of Pharmacy, Guizhou University of Traditional Chinese Medicine, Guiyang 550025, ChinaSchool of Pharmacy, Guizhou University of Traditional Chinese Medicine, Guiyang 550025, ChinaTwo new monoterpenoid indole alkaloids, gelselegandines F (<b>1</b>) and G (<b>2</b>), were isolated from the aerial parts of <i>Gelsemium elegans</i>. Their structures were elucidated by means of spectroscopic techniques and quantum chemical calculations. The ECD calculations were conducted at the B3LYP/6-311G(d,p) level and NMR calculations were carried out using the Gauge-Including Atomic Orbitals (GIAO) method. Structurally, the two new compounds possessed rare, cage-like, monoterpenoid indole skeletons. All isolated compounds and the total alkaloids extract were tested for cytotoxicity against four different tumor cell lines. The total alkaloids extract of <i>G. elegans</i> exhibited significant antitumor activity with IC<sub>50</sub> values ranging from 32.63 to 82.24 ug/mL. In order to discover anticancer leads from the active extraction, both new indole compounds (<b>1–2</b>) were then screened for cytotoxicity. Interestingly, compound <b>2</b> showed moderate cytotoxicity against K562 leukemia cells with an IC<sub>50</sub> value of 57.02 uM.https://www.mdpi.com/1420-3049/28/6/2531gelselegandines F and Gcytotoxicityleukemic cells<i>Gelsemium elegans</i> |
| spellingShingle | Da Song Jia-Jun Liang Shi-Biao Pu Pan-Pan Zhang Yun-Lin Peng Xia Liu Ting-Ting Feng Xiang Pu Ying Zhou Xiong-Wei Liu Xin Wei Structural Elucidation and Cytotoxic Activity of New Monoterpenoid Indoles from <i>Gelsemium elegans</i> Molecules gelselegandines F and G cytotoxicity leukemic cells <i>Gelsemium elegans</i> |
| title | Structural Elucidation and Cytotoxic Activity of New Monoterpenoid Indoles from <i>Gelsemium elegans</i> |
| title_full | Structural Elucidation and Cytotoxic Activity of New Monoterpenoid Indoles from <i>Gelsemium elegans</i> |
| title_fullStr | Structural Elucidation and Cytotoxic Activity of New Monoterpenoid Indoles from <i>Gelsemium elegans</i> |
| title_full_unstemmed | Structural Elucidation and Cytotoxic Activity of New Monoterpenoid Indoles from <i>Gelsemium elegans</i> |
| title_short | Structural Elucidation and Cytotoxic Activity of New Monoterpenoid Indoles from <i>Gelsemium elegans</i> |
| title_sort | structural elucidation and cytotoxic activity of new monoterpenoid indoles from i gelsemium elegans i |
| topic | gelselegandines F and G cytotoxicity leukemic cells <i>Gelsemium elegans</i> |
| url | https://www.mdpi.com/1420-3049/28/6/2531 |
| work_keys_str_mv | AT dasong structuralelucidationandcytotoxicactivityofnewmonoterpenoidindolesfromigelsemiumelegansi AT jiajunliang structuralelucidationandcytotoxicactivityofnewmonoterpenoidindolesfromigelsemiumelegansi AT shibiaopu structuralelucidationandcytotoxicactivityofnewmonoterpenoidindolesfromigelsemiumelegansi AT panpanzhang structuralelucidationandcytotoxicactivityofnewmonoterpenoidindolesfromigelsemiumelegansi AT yunlinpeng structuralelucidationandcytotoxicactivityofnewmonoterpenoidindolesfromigelsemiumelegansi AT xialiu structuralelucidationandcytotoxicactivityofnewmonoterpenoidindolesfromigelsemiumelegansi AT tingtingfeng structuralelucidationandcytotoxicactivityofnewmonoterpenoidindolesfromigelsemiumelegansi AT xiangpu structuralelucidationandcytotoxicactivityofnewmonoterpenoidindolesfromigelsemiumelegansi AT yingzhou structuralelucidationandcytotoxicactivityofnewmonoterpenoidindolesfromigelsemiumelegansi AT xiongweiliu structuralelucidationandcytotoxicactivityofnewmonoterpenoidindolesfromigelsemiumelegansi AT xinwei structuralelucidationandcytotoxicactivityofnewmonoterpenoidindolesfromigelsemiumelegansi |