Clerodane furanoditerpenoids from the stems of Tinospora sinensis.
Absolute configuration
Antiproliferation
Clerodane
Furanoditerpenoid
Tinospora sinensis
α-glucosidase
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:
May 2022
May 2022
Historique:
received:
14
10
2021
accepted:
21
04
2022
pubmed:
29
4
2022
medline:
9
6
2022
entrez:
28
4
2022
Statut:
ppublish
Résumé
One new clerodane-type furanoditerpenoid tinosinoid A (1) and nine new nor-clerodane analogs tinosinoids B-J (2-10) have been isolated from the stems of Tinospora sinensis. The structures of the new compounds with absolute configurations have been elucidated by spectroscopic means, including MS, NMR and ECD techniques, as well as chemical correlation. Compound 1 is a rare sulfur-containing clerodane diterpenoid incorporating a 2-mercaptoethanol unit via a thioether bond, while compounds 4/5 and 9 represent two pairs of unusual equilibrium regioisomers through an interesting intramolecular transesterification. Our bioassays established that 1 and 8 displayed moderate antiproliferative effects against two human tumor cell lines, and 9 and 10 showed significant α-glucosidase inhibitory activities. A kinetics study revealed that compound 10 was a noncompetitive α-glucosidase inhibitor, and its possible binding mode to the enzyme was further probed by molecular docking experiments.
Identifiants
pubmed: 35478401
doi: 10.1007/s12272-022-01383-5
pii: 10.1007/s12272-022-01383-5
doi:
Substances chimiques
Diterpenes, Clerodane
0
Glycoside Hydrolase Inhibitors
0
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
328-339Subventions
Organisme : Natural Science Foundation of Shandong Province
ID : ZR2020QB155
Organisme : the Young Taishan Scholars Program
ID : tsqn20161037
Organisme : Jinan Science and Technology Bureau
ID : 2018GXRC003
Informations de copyright
© 2022. The Pharmaceutical Society of Korea.
Références
Atta ur R, Ahmad S, Rycroft DS, Parkanyi L, Choudhary MI, Clardy J (1988) Malabarolide, a novel furanoid bisnorditerpenoid from Tinospora malabarica. Tetrahedron Lett 29:4241–4244. https://doi.org/10.1016/S0040-4039(00)80464-5
doi: 10.1016/S0040-4039(00)80464-5
Atta ur R, Ahmad S, Ali S, Shah Z, Choudhary MI, Clardy J (1994) New furanoid diterpenoidal constituents of Tinospora malabarica. Tetrahedron 50:12109–12112. https://doi.org/10.1016/S0040-4020(01)89563-6
doi: 10.1016/S0040-4020(01)89563-6
Bao H, Zhang QW, Ye Y, Lin LG (2017) Naturally occurring furanoditerpenoids: distribution, chemistry and their pharmacological activities. Phytochem Rev 16:235–270. https://doi.org/10.1007/s11101-016-9472-2
doi: 10.1007/s11101-016-9472-2
Chakraborty S, Majumdar S (2021) Natural products for the treatment of pain: chemistry and pharmacology of salvinorin A, mitragynine, and collybolide. Biochemistry 60:1381–1400. https://doi.org/10.1021/acs.biochem.0c00629
doi: 10.1021/acs.biochem.0c00629
pubmed: 32930582
Chi S, She G, Han D, Wang W, Liu Z, Liu B (2016) Genus Tinospora: ethnopharmacology, phytochemistry, and pharmacology. Evid Based Complement Altern Med. https://doi.org/10.1155/2016/9232593
doi: 10.1155/2016/9232593
Dhameja M, Gupta P (2019) Synthetic heterocyclic candidates as promising α-glucosidase inhibitors: an overview. Eur J Med Chem 176:343–377. https://doi.org/10.1016/j.ejmech.2019.04.025
doi: 10.1016/j.ejmech.2019.04.025
pubmed: 31112894
Fukuda N, Yonemitsu M, Kimura T, Hachiyama S, Miyahara K, Kawasaki T (1985) Studies on the constituents of the stems of Tinospora tuberculata Beumee. II. New diterpenoids, borapetoside A and borapetol A. Chem Pharm Bull 33:4438–4444. https://doi.org/10.1248/cpb.33.4438
doi: 10.1248/cpb.33.4438
Hou WL, Li YF, Zhang Q, Wei X, Peng A, Chen LJ, Wei XQ (2009) Triterpene acids isolated from Lagerstroemia speciosa leaves as alpha-glucosidase inhibitors. Phytother Res 23:614–618. https://doi.org/10.1002/ptr.2661
doi: 10.1002/ptr.2661
pubmed: 19107840
Ibrahim SRM, Abdallah HM, El-Halawany AM, Mohamed GA (2016) Naturally occurring thiophenes: isolation, purification, structural elucidation, and evaluation of bioactivities. Phytochem Rev 15:197–220. https://doi.org/10.1007/s11101-015-9403-7
doi: 10.1007/s11101-015-9403-7
Jiang H, Zhang J, Liu YF, Wang HS, Liang D (2017) Clerodane diterpenoid glucosides from the stems of Tinospora sinensis. J Nat Prod 80:975–982. https://doi.org/10.1021/acs.jnatprod.6b00976
doi: 10.1021/acs.jnatprod.6b00976
pubmed: 28358196
Jiang H, Zhang GJ, Liao HB, Liang D (2018) New terpenoid and phenylpropanoid glycosides from Tinospora sinensis. Fitoterapia 131:127–133. https://doi.org/10.1016/j.fitote.2018.10.018
doi: 10.1016/j.fitote.2018.10.018
pubmed: 30339924
John TF, French LG, Erlichman JS (2006) The antinociceptive effect of salvinorin A in mice. Eur J Pharmaco 545:129–133. https://doi.org/10.1016/j.ejphar.2006.06.077
doi: 10.1016/j.ejphar.2006.06.077
Kutrzeba LM, Li XC, Ding Y, Ferreira D, Zjawiony JK (2010) Intramolecular transacetylation in salvinorins D and E. J Nat Prod 73:707–708. https://doi.org/10.1021/np900447w
doi: 10.1021/np900447w
pubmed: 20337449
Lam SH, Ruan CT, Hsieh PH, Su MJ, Lee SS (2012) Hypoglycemic diterpenoids from Tinospora crispa. J Nat Prod 75:153–159. https://doi.org/10.1021/np200692v
doi: 10.1021/np200692v
pubmed: 22283497
Lam SH, Chen PH, Hung HY, Hwang TL, Chiang CC, Thang TD, Kuo PC, Wu TS (2018) Chemical constituents from the stems of Tinospora sinensis and their bioactivity. Molecules 23:1–12. https://doi.org/10.3390/molecules23102541
doi: 10.3390/molecules23102541
Lee DYW, Karnati VVR, He M, Liu-Chen LY, Kondaveti L, Ma Z, Wang Y, Chen Y, Beguin C, Carlezon WA, Cohen B (2005) Synthesis and in vitro pharmacological studies of new C(2) modified salvinorin A analogues. Bioorg Med Chem Lett 15:3744–3747. https://doi.org/10.1016/j.bmcl.2005.05.048
doi: 10.1016/j.bmcl.2005.05.048
pubmed: 15993589
Li W, Wei K, Fu H, Koike K (2007) Structure and absolute configuration of clerodane diterpene glycosides and a rearranged cadinane sesquiterpene glycoside from the stems of tinospora sinensis. J Nat Prod 70:1971–1976. https://doi.org/10.1021/np070367i
doi: 10.1021/np070367i
pubmed: 18020421
Li GH, Ding WB, Wan FH, Li YZ (2016a) Two new clerodane diterpenes from Tinospora sagittata. Molecules. https://doi.org/10.3390/molecules21091250
doi: 10.3390/molecules21091250
pubmed: 28042836
pmcid: 6155868
Li RT, Morris-Natschke SL, Lee KH (2016b) Clerodane diterpenes: sources, structures, and biological activities. Nat Prod Rep 33:1166–1226. https://doi.org/10.1039/c5np00137d
doi: 10.1039/c5np00137d
pubmed: 27433555
pmcid: 5154363
Pan L, Terrazas C, Lezama-Davila CM, Rege N, Gallucci JC, Satoskar AR, Kinghorn AD (2012) Cordifolide A, a sulfur-containing clerodane diterpene glycoside from Tinospora cordifolia. Org Lett 14:2118–2121. https://doi.org/10.1021/ol300657h
doi: 10.1021/ol300657h
pubmed: 22497272
pmcid: 3348544
Raab A, Feldmann J (2019) Biological sulphur-containing compounds—analytical challenges. Anal Chim Acta 1079:20–29. https://doi.org/10.1016/j.aca.2019.05.064
doi: 10.1016/j.aca.2019.05.064
pubmed: 31387711
Roach JJ, Shenvi RA (2018) A review of salvinorin analogs and their kappa-opioid receptor activity. Bioorg Med Chem Lett 28:1436–1445. https://doi.org/10.1016/j.bmcl.2018.03.029
doi: 10.1016/j.bmcl.2018.03.029
pubmed: 29615341
pmcid: 5912166
Rosak C, Mertes G (2012) Critical evaluation of the role of acarbose in the treatment of diabetes: patient considerations. Diabetes Metab Syndr Obes Targets Ther 5:357–367. https://doi.org/10.2147/dmso.S28340
doi: 10.2147/dmso.S28340
Roth BL, Baner K, Westkaemper R, Siebert D, Rice KC, Steinberg S, Ernsberger P, Rothman RB (2002) Salvinorin A: a potent naturally occurring nonnitrogenous kappa opioid selective agonist. Proc Natl Acad Sci USA 99:11934–11939. https://doi.org/10.1073/pnas.182234399
doi: 10.1073/pnas.182234399
pubmed: 12192085
pmcid: 129372
Shul’ts EE, Mironov ME, Kharitonov YV (2014) Furanoditerpenoids of the labdane series: occurrence in plants, total synthesis, several transformations, and biological activity. Chem Nat Compd 50:2–21. https://doi.org/10.1007/s10600-014-0861-8
doi: 10.1007/s10600-014-0861-8
Singh B, Nathawat S, Sharma RA (2021) Ethnopharmacological and phytochemical attributes of Indian Tinospora species: a comprehensive review. Arab J Chem 14:103381. https://doi.org/10.1016/j.arabjc.2021.103381
doi: 10.1016/j.arabjc.2021.103381
Song XQ, Yu JH, Sun J, Liu KL, Zhang JS, Zhang H (2021) Bioactive sesquiterpenoids from the flower buds of Tussilago farfara. Bioorg Chem 107:104632. https://doi.org/10.1016/j.bioorg.2021.104632
doi: 10.1016/j.bioorg.2021.104632
pubmed: 33450544
Sun J, Yu JH, Zhang JS, Song XQ, Bao J, Zhang H (2019) Chromane enantiomers from the flower buds of Tussilago farfara L. and assignments of their absolute configurations. Chem Biodivers 16:e1800581. https://doi.org/10.1002/cbdv.201800581
doi: 10.1002/cbdv.201800581
pubmed: 30600902
Wu ZY, Chen XQ (1996) Flora of China, vol 30. Science Press, Beijing, pp 19–20
Yin S, Sykes ML, Davis RA, Shelper T, Avery VM, Camp D, Quinn RJ (2010) New galloylated flavanonols from the Australian plant Glochidion sumatranum. Planta Med 76:1877–1881. https://doi.org/10.1055/s-0030-1250071
doi: 10.1055/s-0030-1250071
pubmed: 20597044
Yu ZP, Yu JH, Zhang JS, Yu SJ, Zhang H (2019) Inunicosides A-K, rare polyacylated ent-kaurane diterpenoid glycosides from the flowers of Inula japonica. Tetrahedron 75. https://doi.org/10.1016/j.tet.2019.130732
doi: 10.1016/j.tet.2019.130732
Zhang JS, Hu Y, Song KS, Wu F, Zhu K, Xu DF, Zhang H (2021) Diterpenoid glucosides with cystathionine γ-lyase inhibitory activity from Tinospora sinensis. Bioorg Chem 116:105400. https://doi.org/10.1016/j.bioorg.2021.105400
doi: 10.1016/j.bioorg.2021.105400
pubmed: 34627118
Zheng YX, Tian JH, Yang WH, Chen SG, Liu DH, Fang HT, Zhang HL, Ye XQ (2020) Inhibition mechanism of ferulic acid against α-amylase and α-glucosidase. Food Chem 317:126346. https://doi.org/10.1016/j.foodchem.2020.126346
doi: 10.1016/j.foodchem.2020.126346
pubmed: 32070843