Structurally diverse cucurbitane-type triterpenoids from the tubers of Hemsleya chinensis with cytotoxic activity
Copyright © 2024 Elsevier Ltd. All rights reserved..
Ten previously undescribed cucurbitane-type triterpenoids, namely hemslyencins A-F (1-6) and hemslyencosides A-D (7-10), together with twenty previously reported compounds (11-30), were isolated from the tubers of Hemsleya chinensis. Their structures were elucidated by unambiguous spectroscopic data (UV, IR, HR-ESI-MS, 1D and 2D NMR data). Hemslyencins A and B (1 and 2) possessing unique 9, 11-seco-ring system with a six-membered lactone moiety, were the first examples among of the cucurbitane-type triterpenoids, and hemslyencins C and D (3 and 4) and hemslyencoside D (10) are the infrequent pentacyclic cucurbitane triterpenes featuring a 6/6/6/5/6 fused system. The cytotoxic activities of all isolated compounds were evaluated against MCF-7, HCT-116, HeLa, and HepG2 cancer cells, and their structure-activity relationships (SARs) was discussed as well. Compounds 17, 25, and 26 showed significant cytotoxic effects with IC50 values ranging from 1.31 to 9.89 μM, among which compound 25 induced both apoptosis and cell cycle arrest at G2/M phase in a dose dependent manner against MCF-7 cells.
| Medienart: |
E-Artikel |
|---|
| Erscheinungsjahr: |
2024 |
|---|---|
| Erschienen: |
2024 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:220 |
|---|---|
| Enthalten in: |
Phytochemistry - 220(2024) vom: 15. März, Seite 114033 |
| Sprache: |
Englisch |
|---|
| Beteiligte Personen: |
Li, Xiao-San [VerfasserIn] |
|---|
| Links: |
|---|
| Themen: |
Antineoplastic Agents |
|---|
| Anmerkungen: |
Date Completed 18.03.2024 Date Revised 18.03.2024 published: Print-Electronic Citation Status MEDLINE |
|---|
| doi: |
10.1016/j.phytochem.2024.114033 |
|---|
| funding: |
|
|---|---|
| Förderinstitution / Projekttitel: |
|
| PPN (Katalog-ID): |
NLM368636313 |
|---|
| LEADER | 01000caa a22002652 4500 | ||
|---|---|---|---|
| 001 | NLM368636313 | ||
| 003 | DE-627 | ||
| 005 | 20240318234359.0 | ||
| 007 | cr uuu---uuuuu | ||
| 008 | 240220s2024 xx |||||o 00| ||eng c | ||
| 024 | 7 | |a 10.1016/j.phytochem.2024.114033 |2 doi | |
| 028 | 5 | 2 | |a pubmed24n1334.xml |
| 035 | |a (DE-627)NLM368636313 | ||
| 035 | |a (NLM)38373572 | ||
| 035 | |a (PII)S0031-9422(24)00070-0 | ||
| 040 | |a DE-627 |b ger |c DE-627 |e rakwb | ||
| 041 | |a eng | ||
| 100 | 1 | |a Li, Xiao-San |e verfasserin |4 aut | |
| 245 | 1 | 0 | |a Structurally diverse cucurbitane-type triterpenoids from the tubers of Hemsleya chinensis with cytotoxic activity |
| 264 | 1 | |c 2024 | |
| 336 | |a Text |b txt |2 rdacontent | ||
| 337 | |a ƒaComputermedien |b c |2 rdamedia | ||
| 338 | |a ƒa Online-Ressource |b cr |2 rdacarrier | ||
| 500 | |a Date Completed 18.03.2024 | ||
| 500 | |a Date Revised 18.03.2024 | ||
| 500 | |a published: Print-Electronic | ||
| 500 | |a Citation Status MEDLINE | ||
| 520 | |a Copyright © 2024 Elsevier Ltd. All rights reserved. | ||
| 520 | |a Ten previously undescribed cucurbitane-type triterpenoids, namely hemslyencins A-F (1-6) and hemslyencosides A-D (7-10), together with twenty previously reported compounds (11-30), were isolated from the tubers of Hemsleya chinensis. Their structures were elucidated by unambiguous spectroscopic data (UV, IR, HR-ESI-MS, 1D and 2D NMR data). Hemslyencins A and B (1 and 2) possessing unique 9, 11-seco-ring system with a six-membered lactone moiety, were the first examples among of the cucurbitane-type triterpenoids, and hemslyencins C and D (3 and 4) and hemslyencoside D (10) are the infrequent pentacyclic cucurbitane triterpenes featuring a 6/6/6/5/6 fused system. The cytotoxic activities of all isolated compounds were evaluated against MCF-7, HCT-116, HeLa, and HepG2 cancer cells, and their structure-activity relationships (SARs) was discussed as well. Compounds 17, 25, and 26 showed significant cytotoxic effects with IC50 values ranging from 1.31 to 9.89 μM, among which compound 25 induced both apoptosis and cell cycle arrest at G2/M phase in a dose dependent manner against MCF-7 cells | ||
| 650 | 4 | |a Journal Article | |
| 650 | 4 | |a Chemical constituents | |
| 650 | 4 | |a Cucurbitaceae | |
| 650 | 4 | |a Cucurbitane-type triterpenoids | |
| 650 | 4 | |a Cytotoxic activity | |
| 650 | 4 | |a Hemsleya chinensis | |
| 650 | 7 | |a cucurbitane |2 NLM | |
| 650 | 7 | |a Triterpenes |2 NLM | |
| 650 | 7 | |a Glycosides |2 NLM | |
| 650 | 7 | |a Antineoplastic Agents |2 NLM | |
| 700 | 1 | |a Wang, Qi-Lin |e verfasserin |4 aut | |
| 700 | 1 | |a Xu, Zhi-Peng |e verfasserin |4 aut | |
| 700 | 1 | |a Liu, Ming-Shang |e verfasserin |4 aut | |
| 700 | 1 | |a Liang, Xiao-Yan |e verfasserin |4 aut | |
| 700 | 1 | |a Zheng, Jia-Chon |e verfasserin |4 aut | |
| 700 | 1 | |a Deng, Hong-Yao |e verfasserin |4 aut | |
| 700 | 1 | |a Liu, Li |e verfasserin |4 aut | |
| 700 | 1 | |a Huang, Yong-Mei |e verfasserin |4 aut | |
| 700 | 1 | |a Yang, Mao-Xun |e verfasserin |4 aut | |
| 700 | 1 | |a Yang, Xue-Mei |e verfasserin |4 aut | |
| 773 | 0 | 8 | |i Enthalten in |t Phytochemistry |d 1986 |g 220(2024) vom: 15. März, Seite 114033 |w (DE-627)NLM013477943 |x 1873-3700 |7 nnns |
| 773 | 1 | 8 | |g volume:220 |g year:2024 |g day:15 |g month:03 |g pages:114033 |
| 856 | 4 | 0 | |u http://dx.doi.org/10.1016/j.phytochem.2024.114033 |3 Volltext |
| 912 | |a GBV_USEFLAG_A | ||
| 912 | |a GBV_NLM | ||
| 951 | |a AR | ||
| 952 | |d 220 |j 2024 |b 15 |c 03 |h 114033 | ||