Artemongolins A-K, undescribed germacrane-guaiane sesquiterpenoid dimers from Artemisia mongolica and their antihepatoma activities.
Antihepatoma activity
Artemisia mongolica
Artemongolins A–K
Sesquiterpenoid dimers
Journal
Archives of pharmacal research
ISSN: 1976-3786
Titre abrégé: Arch Pharm Res
Pays: Korea (South)
ID NLM: 8000036
Informations de publication
Date de publication:
Oct 2023
Oct 2023
Historique:
received:
24
04
2023
accepted:
19
09
2023
medline:
10
10
2023
pubmed:
29
9
2023
entrez:
28
9
2023
Statut:
ppublish
Résumé
Artemongolins A-K (1-11), which are undescribed sesquiterpenoid dimers, were obtained from Artemisia mongolica and characterized through comprehensive spectral data, including HRESIMS, IR, 1D and 2D NMR, and ECD calculations. The absolute configurations of compounds 1, 4, and 7 were undoubtedly determined by a single-crystal X-ray crystallography. Artemongolins A-K (1-11) featured a rare 5/7/5/5/5/10 hexacyclic system composed of a germacrene and a guaianolide by a fused 2-oxaspiro[4,4]nonane-1-one ring system. Antihepatoma evaluation against three human hepatoma cell lines demonstrated that the most active compounds 5 and 6 displayed inhibitory activity with IC
Identifiants
pubmed: 37770811
doi: 10.1007/s12272-023-01466-x
pii: 10.1007/s12272-023-01466-x
doi:
Substances chimiques
guaiane
0
Sesquiterpenes, Germacrane
0
Sesquiterpenes, Guaiane
0
Sesquiterpenes
0
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
782-794Subventions
Organisme : the Key Program of the National Natural Science Foundation of China
ID : 22137008
Organisme : the Xingdian Yingcai Project
ID : YNWR-KJLJ-2019-002
Organisme : the Youth Innovation Promotion Association of the Chinese Academy of Sciences
ID : 2020386
Organisme : the Reserve Talents of Young and Middle-aged Academic and Technical Leaders in Yunnan Province
ID : 202105AC160021
Informations de copyright
© 2023. The Pharmaceutical Society of Korea.
Références
Appendino G, Taglialatela-Scafati O, Romano A, Pollastro F, Avonto C, Rubiolo P (2009) Genepolide, a sesterpene γ-lactone with a novel carbon skeleton from Mountain wormwood (Artemisia umbelliformis). J Nat Prod 72(3):340–344. https://doi.org/10.1021/np800468m
doi: 10.1021/np800468m
pubmed: 19053512
Dai Q, Zhang C, Yuan Z, Sun Q, Jiang Y (2020) Current discovery strategies for hepatocellular carcinoma therapeutics. Expert Opin Drug Discov 15(2):243–258. https://doi.org/10.1080/17460441.2020.1696769
doi: 10.1080/17460441.2020.1696769
pubmed: 31809618
Dawkins J, Webster RM (2019) The hepatocellular carcinoma market. Nat Rev Drug Discov 18(1):13–14. https://doi.org/10.1038/nrd.2018.146
doi: 10.1038/nrd.2018.146
pubmed: 30168534
Dong W, Li TZ, Huang XY, He XF, Geng CA, Zhang XM, Chen JJ (2022) Artemzhongdianolides A1–A21, antihepatic fibrosis guaiane-type sesquiterpenoid dimers from Artemisia zhongdianensis. Bioorg Chem 128:106056. https://doi.org/10.1016/j.bioorg.2022.106056
doi: 10.1016/j.bioorg.2022.106056
pubmed: 35908354
Dong W, Ma WJ, Ma YB, Li FJ, Li TZ, Wang YC, He XF, Geng CA, Zhang XM, Chen JJ (2023a) Guaiane-type sesquiterpenoid dimers from Artemisia zhongdianensis and antihepatoma carcinoma activity via the p38MAPK pathway. Chin J Chem. https://doi.org/10.1002/cjoc.202300166
doi: 10.1002/cjoc.202300166
Dong W, Yang KX, He XF, Li TZ, Chen JJ (2023b) New eudesmanolides from Artemisia verlotorum and their potential targets of hepatocellular carcinoma by network pharmacology. Fitoterapia 167:105491. https://doi.org/10.1016/j.fitote.2023.105491
doi: 10.1016/j.fitote.2023.105491
pubmed: 37001826
Dusmatova DE, Bobakulov KM, Mukhamatkhanova RF, Turgunov KK, Terenteva EO, Tsay EA, Sham’yanov ID, Tashkhodzhaev B, Azimova SS, Abdullaev ND (2021) Isolation of cytotoxic sesquiterpene lactones from the Tanacetopsis karataviensis (Kovalevsk.) Kovalevsk. Nat Prod Res 35(12):1939–1948. https://doi.org/10.1080/14786419.2019.1647423
doi: 10.1080/14786419.2019.1647423
pubmed: 31359772
Gao Z, Ma WJ, Li TZ, Ma YB, Hu J, Huang XY, Geng CA, He XF, Zhang XM, Chen JJ (2022) Artemidubolides A–T, cytotoxic unreported guaiane-type sesquiterpenoid dimers against three hepatoma cell lines from Artemisia dubia. Phytochemistry 202:113299. https://doi.org/10.1016/j.phytochem.2022.113299
doi: 10.1016/j.phytochem.2022.113299
pubmed: 35809862
Geng CA, Huang XY, Ma YB, Hou B, Li TZ, Zhang XM, Chen JJ (2017) (+/-)-Uncarilins A and B, dimeric isoechinulin-type alkaloids from Uncaria rhynchophylla. J Nat Prod 80(4):959–964. https://doi.org/10.1021/acs.jnatprod.6b00938
doi: 10.1021/acs.jnatprod.6b00938
pubmed: 28225280
He XF, Li QH, Li TZ, Ma YB, Dong W, Yang KX, Geng CA, Zhang HW, Wang Y, Chen JJ (2023a) Artemeriopolides A–D, two types of sesquiterpenoid dimers with rare carbon skeletons from Artemisia eriopoda and their antihepatoma cytotoxicity. Org Chem Front 10:2635–2641. https://doi.org/10.1039/D3QO00223C
doi: 10.1039/D3QO00223C
He XF, Ma WJ, Hu J, Li TZ, Geng CA, Ma YB, Wang MF, Yang KX, Zhang XM, Chen JJ (2023b) Diverse structures and antihepatoma effect of sesquiterpenoid dimers from Artemisia eriopoda by AKT/STAT signaling pathway. Signal Transduct Tar 8:64. https://doi.org/10.1038/s41392-022-01267-6
doi: 10.1038/s41392-022-01267-6
Hu JF, Zhu QX, Bai SP, Jia ZJ (1996) New eudesmane sesquiterpene and other constituents from Artemisia mongolica. Planta Med 62(5):477–478. https://doi.org/10.1055/s-2006-957946
doi: 10.1055/s-2006-957946
pubmed: 17252484
Hu JF, He WY, Kong M, Jia ZJ, Feng XZ (2006) Mongolenin: a new triterpene from Artemisia mongolica. Nat Prod Lett 14(3):211–215. https://doi.org/10.1080/10575630008041233
doi: 10.1080/10575630008041233
Li S, Liu R, Pan Q, Wang G, Cheng D, Yang J, Chen H, Xu G (2020) De novo lipogenesis is elicited dramatically in human hepatocellular carcinoma especially in hepatitis C virus-induced hepatocellular carcinoma. Med Comm 1(2):178–187. https://doi.org/10.1002/mco2.15
doi: 10.1002/mco2.15
Li TZ, Yang XT, Wang JP, Geng CA, Ma YB, Su LH, Zhang XM, Chen JJ (2021) Biomimetic synthesis of lavandiolides H, I, and K and artematrolide F via Diels–Alder reaction. Org Lett 23(21):8380–8384. https://doi.org/10.1021/acs.orglett.1c03120
doi: 10.1021/acs.orglett.1c03120
pubmed: 34634203
Mata R, Delgado G, De Vivar AR (1985) Sesquiterpene lactones of Artemisia klotzchiana. Phytochemistry 24(7):1515–1519. https://doi.org/10.1016/S0031-9422(00)81057-2
doi: 10.1016/S0031-9422(00)81057-2
Oikawa H, Tokiwano T (2004) Enzymatic catalysis of the Diels–Alder reaction in the biosynthesis of natural products. Nat Prod Rep 21(3):321–352. https://doi.org/10.1039/b305068h
doi: 10.1039/b305068h
pubmed: 15162222
Shang C, Huang XY, Wang Y, Dong W, He XF, Li TZ, Chen JJ (2023) Artemongolides A–F, undescribed sesquiterpenoid dimers from Artemisia mongolica and their antihepatic fibrosis activities. Org Biomol Chem 21:823–831. https://doi.org/10.1039/d2ob02182j
doi: 10.1039/d2ob02182j
pubmed: 36601986
Shao ZG, Li LZ, Zheng YZ, Gong Q, Ke CQ, Yao S, Zhang HY, Tang CP, Ye Y (2022) Anti-inflammatory sesquiterpenoid dimers from Artemisia atrovirens. Fitoterapia 159:105199. https://doi.org/10.1016/j.fitote.2022.105199
doi: 10.1016/j.fitote.2022.105199
pubmed: 35452745
Shen C, Huang XY, Geng CA, Li TZ, Wang JP, Tang S, Su LH, Gao Z, Zhang XM, Chen JJ (2020) Cytotoxic sesquiterpenoids against hepatic stellate cell line LX2 from Artemisia lavandulaefolia. Bioorg Chem 103:104107. https://doi.org/10.1016/j.bioorg.2020.104107
doi: 10.1016/j.bioorg.2020.104107
pubmed: 32745752
Su LH, Geng CA, Li TZ, Ma YB, Huang XY, Zhang XM, Chen JJ (2020) Artatrovirenols A and B: two cagelike sesquiterpenoids from Artemisia atrovirens. J Org Chem 85:13466–13471. https://doi.org/10.1021/acs.joc.0c01491
doi: 10.1021/acs.joc.0c01491
pubmed: 33089682
Su LH, Li TZ, Ma YB, Geng CA, Huang XY, Zhang X, Gao Z, Chen JJ (2021) Artematrovirenolides A–D and artematrolides S–Z, sesquiterpenoid dimers with cytotoxicity against three hepatoma cell lines from Artemisia atrovirens. Chin J Chem 40(1):104–114. https://doi.org/10.1002/cjoc.202100528
doi: 10.1002/cjoc.202100528
Su LH, Zhang XT, Ma YB, Geng CA, Huang XY, Hu J, Li TZ, Tang S, Shen C, Gao Z, Zhang XM, Chen JJ (2021) New guaiane-type sesquiterpenoid dimers from Artemisia atrovirens and their antihepatoma activity. Acta Pharm Sin B 11(6):1648–1666. https://doi.org/10.1016/j.apsb.2020.12.006
doi: 10.1016/j.apsb.2020.12.006
pubmed: 34221874
Su LH, Li TZ, Geng CA, Ma YB, Huang XY, Wang JP, Zhang XM, Chen JJ (2021) Trimeric and dimeric sesquiterpenoids from Artemisia atrovirens and their cytotoxicities. Org Chem Front 8(6):1249–1256. https://doi.org/10.1039/d0qo01615b
doi: 10.1039/d0qo01615b
Su LH, Ma WJ, Ma YB, Li TZ, Geng CA, Dong W, He XF, Chen JJ (2023a) Artemiprinolides A–M, thirteen undescribed sesquiterpenoid dimers from Artemisia princeps and their antihepatoma activity. Phytochemistry 211:113714. https://doi.org/10.1016/j.phytochem.2023.113714
doi: 10.1016/j.phytochem.2023.113714
pubmed: 37156434
Su LH, Ma WJ, Ma YB, Li TZ, Geng CA, Dong W, He XF, Zhang XM, Chen JJ (2023b) Artemiprincepsolides A–F, novel germacrane-guaiane and eudesmane-guaiane sesquiterpenoid dimers from Artemisia princeps and their antihepatoma activity. Chin J Chem. https://doi.org/10.1002/cjoc.202300242
doi: 10.1002/cjoc.202300242
Sung H, Ferlay J, Siegel RL, Laversanne M, Soerjomataram I, Jemal A, Bray F (2021) Global cancer statistics 2020: GLOBOCAN estimates of incidence and mortality worldwide for 36 cancers in 185 countries. CA Cancer J Clin 71(3):209–249. https://doi.org/10.3322/caac.21660
doi: 10.3322/caac.21660
pubmed: 33538338
Tang S, Ma YB, Geng CA, Shen C, Li TZ, Zhang XM, Su LH, Gao Z, Hu J, Chen JJ (2020a) Artemyrianins A–G from Artemisia myriantha and their cytotoxicity against HepG2 cells. Nat Prod Bioprospect 10:251–260. https://doi.org/10.1007/s13659-020-00255-z
doi: 10.1007/s13659-020-00255-z
pubmed: 32596763
pmcid: 7367949
Tang S, Zhang XT, Ma YB, Huang XY, Geng CA, Li TZ, Zhang XM, Shen C, Su LH, Gao Z, Chen JJ (2020b) Artemyrianolides A–S, cytotoxic sesquiterpenoids from Artemisia myriantha. J Nat Prod 83(9):2618–2630. https://doi.org/10.1021/acs.jnatprod.0c00396
doi: 10.1021/acs.jnatprod.0c00396
pubmed: 32842729
Wang JP, Li TZ, Huang XY, Geng CA, Shen C, Sun JJ, Xue D, Chen JJ (2021) Synthesis and anti-fibrotic effects of santamarin derivatives as cytotoxic agents against hepatic stellate cell line LX2. Bioorg Med Chem Lett 41:127994. https://doi.org/10.1016/j.bmcl.2021.127994
doi: 10.1016/j.bmcl.2021.127994
pubmed: 33775837
Wang S, Sun J, Zeng KW, Chen X, Zhou W, Zhang C, Jin H, Jiang Y, Tu PF (2014) Sesquiterpenes from Artemisia argyi: absolute configurations and biological activitie. Eur J Org Chem 2014(5):973–983. https://doi.org/10.1002/ejoc.201301445
doi: 10.1002/ejoc.201301445
Wang Q, Zhang T, Ke CQ, Tang C, Yao S, Lin L, Ye Y (2020) Sesquiterpene lactone dimers from Artemisia lavandulifolia inhibit interleukin-1β production in macrophages through activating autophagy. Bioorg Chem 105:104451. https://doi.org/10.1016/j.bioorg.2020.104451
doi: 10.1016/j.bioorg.2020.104451
pubmed: 33197851
Xue GM, Han C, Chen C, Li LN, Wang XB, Yang MH, Gu YC, Luo JG, Kong LY (2017) Artemisians A–D, diseco-guaianolide involved heterodimeric [4 + 2] adducts from Artemisia argyi. Org Lett 19(19):5410–5413. https://doi.org/10.1021/acs.orglett.7b02681
doi: 10.1021/acs.orglett.7b02681
pubmed: 28956447
Xue GM, Zhu DR, Zhu TY, Wang XB, Luo JG, Kong LY (2019a) Lactone ring-opening seco-guaianolide involved heterodimers linked via an ester bond from Artemisia argyi with NO inhibitory activity. Fitoterapia 132:94–100. https://doi.org/10.1016/j.fitote.2018.12.004
doi: 10.1016/j.fitote.2018.12.004
pubmed: 30529065
Xue GM, Zhu DR, Han C, Wang XB, Luo JG, Kong LY (2019b) Artemisianins A–D, new stereoisomers of seco-guaianolide involved heterodimeric [4 + 2] adducts from Artemisia argyi induce apoptosis via enhancement of endoplasmic reticulum stress. Bioorg Chem 84:295–301. https://doi.org/10.1016/j.bioorg.2018.11.013
doi: 10.1016/j.bioorg.2018.11.013
pubmed: 30529847
Yang JD, Roberts LR (2010) Hepatocellular carcinoma: a global view. Nat Rev Gastroenterol Hepatol 7(8):448–458. https://doi.org/10.1038/nrgastro.2010.100
doi: 10.1038/nrgastro.2010.100
pubmed: 20628345
pmcid: 3926946
Zhang XT, Hu J, Su LH, Geng CA, Chen JJ (2021) Artematrolide a inhibited cervical cancer cell proliferation via ROS/ERK/mTOR pathway and metabolic shift. Phytomedicine 91:153707. https://doi.org/10.1016/j.phymed.2021.153707
doi: 10.1016/j.phymed.2021.153707
pubmed: 34450376
Zhou XD, Chai XY, Zeng KW, Zhao MB, Jiang Y, Tu PF (2015) Artesin A, a new cage-shaped dimeric guaianolide from Artemisia sieversiana. Tetrahedron Lett 56(9):1141–1143. https://doi.org/10.1016/j.tetlet.2015.01.081
doi: 10.1016/j.tetlet.2015.01.081
Zhu Z, Turak A, Aisa HA (2022) Sesquiterpene lactones from Artemisia mongolica. Phytochemistry 199:113158. https://doi.org/10.1016/j.phytochem.2022.113158
doi: 10.1016/j.phytochem.2022.113158
pubmed: 35301035