Prenylated benzophenone derivatives from Hypericum patulum.
Hypatulin C
Hypericaceae
Hypericum patulum
Prenylated benzophenone
Journal
Journal of natural medicines
ISSN: 1861-0293
Titre abrégé: J Nat Med
Pays: Japan
ID NLM: 101518405
Informations de publication
Date de publication:
Jan 2020
Jan 2020
Historique:
received:
21
06
2019
accepted:
24
07
2019
pubmed:
5
8
2019
medline:
24
3
2020
entrez:
5
8
2019
Statut:
ppublish
Résumé
A new prenylated benzophenone, hypatulin C (1), was isolated from the leaves of Hypericum patulum together with a biogenetically related analog, hypelodin B (2). Hypatulin C (1) had a tricyclic [4.3.1.0
Identifiants
pubmed: 31377922
doi: 10.1007/s11418-019-01350-3
pii: 10.1007/s11418-019-01350-3
doi:
Substances chimiques
Benzophenones
0
hypelodin B
0
Phloroglucinol
DHD7FFG6YS
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
264-268Références
Yang XW, Grossman RB, Xu G (2018) Research progress of polycyclic polyprenylated acylphloroglucinols. Chem Rev 118:3508–3558
doi: 10.1021/acs.chemrev.7b00551
Zhao J, Li W, Wang JC (2015) Recent advances regarding constituents and bioactivities of plants from the genus Hypericum. Chem Biodivers 12:309–349
doi: 10.1002/cbdv.201300304
Wu SB, Long C, Kennelly EJ (2014) Structural diversity and bioactivities of natural benzophenones. Nat Prod Rep 31:1158–1174
doi: 10.1039/C4NP00027G
Cuesta-Rubio O, Piccinelli A, Rastrelli L (2005) Chemistry and biological activity of polyisoprenylated benzophenone derivatives. In: Atta-ur-Rahman A (ed) Studies in natural products chemistry, vol 32. Elsevier Science BV, Amsterdam, pp 671–720
Niwa K, Tanaka N, Kim SY, Kojoma M, Kashiwada Y (2018) Hyperdioxane A, a conjugate of dibenzo-1,4-dioxane and sesquiterpene from Hypericum ascyron. Org Lett 20:5977–5980
doi: 10.1021/acs.orglett.8b02739
Niwa K, Tanaka N, Kashiwada Y (2017) Frondhyperins A−D, shor ketide−phenylketide conjugates from Hypericum frondosum cv. Sunburst. Tetraheron Lett 58:1495–1498
doi: 10.1016/j.tetlet.2017.02.089
Lu S, Tanaka N, Tatano Y, Kashiwada Y (2016) Erecricins A−E, prenylated acylphloroglucinols from the roots of Hypericum erectum. Fitoterapia 114:188–193
doi: 10.1016/j.fitote.2016.08.014
Tanaka N, Niwa K, Kashiwada Y (2016) Merohyperins A−C, meroterpenes from the leaves of Hypericum chinense. Tetrahedron Lett 57:3175–3178
doi: 10.1016/j.tetlet.2016.06.028
Tanaka N, Kobayashi J (2015) Prenylated acylphloroglucinols and meroterpenoids from Hypericum plants. Heterocycles 90:23–40
doi: 10.3987/REV-14-SR(K)1
Tanaka N, Takaishi Y, Shikishima Y, Nakanishi Y, Bastow K, Lee KH, Honda G, Ito M, Takeda Y, Kodzhimatov OK, Ashurmetov O (2004) Prenylated benzophenones and xanthones from Hyepricum scabrum. J Nat Prod 67:1870–1875
doi: 10.1021/np040024+
Hashida C, Tanaka N, Kawazoe K, Murakami K, Sun HD, Takaishi Y, Kashiwada Y (2014) Hypelodins A and B, polyprenylated benzophenones from Hypericum elodeoides. J Nat Med 68:737–742
doi: 10.1007/s11418-014-0853-9
Oya A, Tanaka N, Kusama T, Kim SY, Hayashi S, Kojoma M, Hishida A, Kawahara N, Sakai K, Gonoi T, Kobayashi J (2015) Prenylated benzophenones from Triadenum japonicum. J Nat Prod 78:258–264
doi: 10.1021/np500827h
Tanaka N, Yano Y, Tatano Y, Kashiwada Y (2016) Hypatulins A and B, meroterpenes from Hypericum patulum. Org Lett 18:5360–5363
doi: 10.1021/acs.orglett.6b02725
Yang XW, Li MM, Liu X, Ferreira D, Ding Y, Zhang JJ, Liao Y, Qin HB, Xu G (2015) Polycyclic polyprenylated acylphloroglucinol congeners possessing diverse structures from Hypericum henryi. J Nat Prod 78:885–895
doi: 10.1021/acs.jnatprod.5b00057
Yang XW, Yang J, Liao Y, Ye Y, Li YP, Yang SY, Xia F, Xu G (2015) Hypercohin K, a polycyclic polyprenylated acylphloroglucinol with an unusual spiro-fused cyclopropane ring from Hypericum cohaerens. Tetrahedron Lett 56:5537–5540
doi: 10.1016/j.tetlet.2015.08.033
Frisch MJ, Trucks GW, Schlegel HB, et al. Gaussian 09, Revision C. 01. Wallingford, CT: Gaussian, 2010
Schaumlöffel T, Hemberger A, Bringmann Y, SpecDis G Version 1.61. Germany: University of Wuerzburg, 2013