nach oben

Erschienen in:

01.10.2014 | Note

Hypelodins A and B, polyprenylated benzophenones from Hypericum elodeoides

verfasst von: Chika Hashida, Naonobu Tanaka, Kazuyoshi Kawazoe, Kotaro Murakami, Han-Dong Sun, Yoshihisa Takaishi, Yoshiki Kashiwada

Erschienen in: Journal of Natural Medicines | Ausgabe 4/2014

Einloggen, um Zugang zu erhalten

Abstract

Two new polyprenylated benzophenones, hypelodins A (1) and B (2), were isolated from the aerial parts of the Chinese medicinal plant Hyperium elodeoides (Choisy). Their structures were elucidated on the basis of spectroscopic evidence. Hypelodin A (1) is a polyprenylated benzophenone having a tetrahydropyrane ring with three prenyl groups and one 4-methyl-1,3-pentadiene moiety, while hypelodin B (2) has a cage-like structure with a 6/6/5/7/6/5 hexacyclic ring system.

Cuesta-Rubio O, Piccinelli AL, 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

Avato P (2005) A survey on the Hypericum genus: secondary metabolites and bioactivity. In: Atta-ur-Rahman A (ed) Studies in natural products chemistry, vol 30. Elsevier Science BV, Amsterdam, pp 603–634

Tanaka N, Kobayashi J (2014) Prenylated acylphloroglucinols and meroterpenoids from Hypericum plants. Heterocycles. doi:10.3987/REV-14-SR(K)1

Tanaka N, Abe S, Kobayashi J (2012) Biyoulactones D and E, meroterpenoids from Hypericum chinense. Tetrahedron Lett 53:1507–1510CrossRef

Tanaka N, Abe S, Hasegawa K, Shiro M, Kobayashi J (2011) Biyoulactones A-C, new pentacyclic meroterpenoids from Hypericum chinense. Org Lett 13:5488–5491PubMedCrossRef

Mamemura T, Tanaka N, Shibazaki A, Gonoi T, Kobayashi J (2011) Yojironins A-D, meroterpenoids and prenylated acylphloroglucinols from Hypericum yojiroanum. Tetrahedron Lett 52:3575–3578CrossRef

Tanaka N, Kakuguchi Y, Ishiyama H, Kubota T, Kobayashi J (2009) Yezo’otogirins A-C, new tricyclic terpenoids from Hypericum yezoense. Tetrahedron Lett 50:4747–4750CrossRef

Tanaka N, Mamemura T, Abe S, Imabayashi K, Kashiwada Y, Takaishi Y, Suzuki T, Takebe Y, Kubota T, Kobayashi J (2010) Biyouxanthones A-D, prenylated xanthones from roots of Hypericum chinense. Heterocycles 80:613–621CrossRef

Tanaka N, Kashiwada Y, Kim SY, Sekiya M, Ikeshiro Y, Takaishi Y (2009) Xanthones from Hypericum chinense and their cytotoxicity evaluation. Phytochemistry 70:1456–1461PubMedCrossRef

10.

Tanaka N, Kubota T, Kashiwada Y, Takaishi Y, Kobayashi J (2009) Petiolins F-I, benzophenone rhamnosides from Hypericum pseudopetiolatum var. kiusianum. Chem Pharm Bull 57:1171–1173PubMedCrossRef

11.

Tanaka N, Kashiwada Y, Nakano T, Shibata H, Higuchi T, Sekiya M, Ikeshiro Y, Takaishi Y (2009) Chromone and chromanone glucosides from Hypericum sikokumontanum and their anti-Helicobacter pylori activities. Phytochemistry 70:141–146PubMedCrossRef

12.

Abe S, Tanaka N, Kobayashi J (2012) Prenylated acylohloroglucinols, chipericumins A-D, from Hypericum chinense. J Nat Prod 75:484–488PubMedCrossRef

13.

Tanaka N, Mamemura T, Shibazaki A, Kobayashi J (2011) Yojironins E-I, prenylated acylphloroglucinols from Hypericum yojiroanum. Bioorg Med Chem Lett 21:5393–5397PubMedCrossRef

14.

Shanghai Science and Technology Press (2009) In: Nanjing University of Chinese Medicine (eds) Chinese Materia Medica, Shanghai, pp 3394

15.

Liu X, Yang XW, Chen CQ, Wu CY, Zhang JJ, Ma JZ, Wang H, Yang LX, Xu G (2013) Bioactive polyprenylated acylphloroglucinol derivatives from Hypericum cohaerens. J Nat Prod 76:1612–1618PubMedCrossRef

16.

Shan MD, Hu LH, Chen ZL (2001) Three new hyperforin analogues from Hypericum perforatum. J Nat Prod 64:127–130PubMedCrossRef

17.

Thoison O, Cuong DD, Gramain A, Chiaroni A, Hung NV, Sévenet T (2005) Further rearranged prenylxanthones and benzophenones from Garcinia bracteata. Tetrahedron 61:8529–8535CrossRef

18.

Ciochina R, Grossman RB (2006) Polycyclic polyprenylated acylphloroglucinols. Chem Rev 106:3963–3986PubMedCrossRef

19.

Cerrini S, Lamba D, Delle Monache F, Pinherio RM (1993) Nemorosonol, a derivative of tricyclo-[4.3.1.0^3,7]-decane-7-hydroxy-2,9-dione from Clusia nemorosa. Phytochemistry 32:1023–1028CrossRef

20.

Delle Monache F, Delle Monache G, Pinheiro RM, Radics L (1988) Nemorosonol, a derivative of tricyclo-[4.3.1.0^3,7]-decane-7-hydroxy-2,9-dione from Clusia nemorosa. Phytochemistry 27:2305–2308CrossRef

Titel: Hypelodins A and B, polyprenylated benzophenones from Hypericum elodeoides
verfasst von: Chika Hashida
Naonobu Tanaka
Kazuyoshi Kawazoe
Kotaro Murakami
Han-Dong Sun
Yoshihisa Takaishi
Yoshiki Kashiwada
Publikationsdatum: 01.10.2014
Verlag: Springer Japan
Erschienen in: Journal of Natural Medicines / Ausgabe 4/2014
Print ISSN: 1340-3443
Elektronische ISSN: 1861-0293
DOI: https://doi.org/10.1007/s11418-014-0853-9

Springer Medizin

Abstract

Bitte loggen Sie sich ein, um Zugang zu diesem Inhalt zu erhalten

Weitere Artikel der Ausgabe 4/2014

Salacia reticulata has therapeutic effects on obesity

Cytotoxicity of compounds from the fruits of Derris indica against cholangiocarcinoma and HepG2 cell lines

Sucutinirane-diterpene derivatives induce apoptosis via oxidative stress in HL-60 cells

Application of anatomy and HPTLC in characterizing species of Dioscorea (Dioscoreaceae)

Structure of constituents isolated from the flower buds of Cananga odorata and their inhibitory effects on aldose reductase

Transcriptional activation of a geranylgeranyl diphosphate synthase gene, GGPPS2, isolated from Scoparia dulcis by treatment with methyl jasmonate and yeast extract