Riccardin C

Riccardin C
	; Riccardin C, flat molecule representation
Names
	IUPAC name 14-oxapentacyclo[20.2.2.210,13.115,19.02,7]nonacosa-1(24),2(7),3,5,10(29),11,13(28),15,17,19(27),22,25-dodecaene-5,16,24-triol
Identifiers
CAS Number	84575-08-6 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL411317;
ChemSpider	8246532;
PubChem CID	10070992;
CompTox Dashboard (EPA)	DTXSID101030291 ;
	InChI InChI=1S/C28H24O4/c29-22-9-13-24-21(17-22)8-3-18-4-10-23(11-5-18)32-28-16-20(7-14-26(28)30)2-1-19-6-12-25(24)27(31)15-19/h4-7,9-17,29-31H,1-3,8H2 Key: JMKSVONWZFVEAI-UHFFFAOYSA-N;
	SMILES C1CC2=C(C=CC(=C2)O)C3=C(C=C(CCC4=CC(=C(C=C4)O)OC5=CC=C1C=C5)C=C3)O;
Properties
Chemical formula	C28H24O4
Molar mass	424.49 g/mol
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Riccardin C is a macrocyclic bis(bibenzyl). It is a secondary metabolite isolated from the Siberian cowslip subspecies Primula veris subsp. macrocalyx,^[2]^[3] in Reboulia hemisphaerica^[4] and in the Chinese liverwort Plagiochasma intermedium.^[5]

In 2005, the compound was prepared by total synthesis together with the strained compound cavicularin.^[6]^[7]

References

^ Fugmann, Burkhard; Lang-Fugmann, Susanne; Steglich, Wolfgang (14 May 2014). RÖMPP Encyclopedia Natural Products, 1st Edition, 2000. Georg Thieme Verlag. p. 553. ISBN 978-3-13-179311-9.
^ Riccardin C, a bisbibenzyl compound from Primula macrocalyx. Yu. S. Kosenkova, M. P. Polovinka, N. I. Komarova, D. V. Korchagina, N. Yu. Kurochkina, V. A. Cheremushkina and N. F. Salakhutdinov, Chemistry Of Natural Compounds, Volume 43, Number 6, pages 712-713, doi:10.1007/s10600-007-0241-8
^ Seasonal Dynamics of Riccardin C Accumulation in Primula macrocalyx Bge. Yu. S. Kosenkova, M.P. Polovinka, N.I. Komarova, D.V. Korchagina, N. Yu. Kurochkina, V.A. Cheremushkina and N.F. Salakhutdinov, Chemistry for Sustainable Development, 2009, 17, pages 507-511 (article^{[permanent dead link]})
^ RiccardinC, a novel cyclic bibenzyl derivative from Reboulia hemisphaerica. Yoshinori Asakawa, Reiko Matsuda, Phytochemistry, Volume 21, Issue 8, 1982, Pages 2143–2144, doi:10.1016/0031-9422(82)83073-2
^ Antifungal macrocyclic bis(bibenzyls) from the Chinese liverwort Ptagiochasm intermedlum L. Chun-Feng Xie, Jian-Bo Qu, Xiu-Zhen Wu, Na Liu, Mei Ji and Hong-Xiang Lou, Natural Product Research: Formerly Natural Product Letters, 2010, Volume 24, Issue 6, pages 515-520, doi:10.1080/14786410802271587
^ David C. Harrowven; Timothy Woodcock; Peter D. Howes (2005). "Total Synthesis of Cavicularin and Riccardin C: Addressing the Synthesis of an Arene That Adopts a Boat Configuration". Angewandte Chemie. 44 (25): 3899–3901. doi:10.1002/anie.200500466. PMID 15900530. Archived from the original on 2012-12-10.
^ Kostiuk, S. L., Woodcock, T., Dudin, L. F., Howes, P. D. and Harrowven, D. C. (2011), Unified Syntheses of Cavicularin and Riccardin C: Addressing the Synthesis of an Arene Adopting a Boat Configuration. Chemistry - A European Journal, 17: 10906–10915. doi:10.1002/chem.201101550

[1] Fugmann, Burkhard; Lang-Fugmann, Susanne; Steglich, Wolfgang (14 May 2014). RÖMPP Encyclopedia Natural Products, 1st Edition, 2000. Georg Thieme Verlag. p. 553. ISBN 978-3-13-179311-9.

[2] Riccardin C, a bisbibenzyl compound from Primula macrocalyx. Yu. S. Kosenkova, M. P. Polovinka, N. I. Komarova, D. V. Korchagina, N. Yu. Kurochkina, V. A. Cheremushkina and N. F. Salakhutdinov, Chemistry Of Natural Compounds, Volume 43, Number 6, pages 712-713, doi:10.1007/s10600-007-0241-8

[3] Seasonal Dynamics of Riccardin C Accumulation in Primula macrocalyx Bge. Yu. S. Kosenkova, M.P. Polovinka, N.I. Komarova, D.V. Korchagina, N. Yu. Kurochkina, V.A. Cheremushkina and N.F. Salakhutdinov, Chemistry for Sustainable Development, 2009, 17, pages 507-511 (article^{[permanent dead link]})

[4] RiccardinC, a novel cyclic bibenzyl derivative from Reboulia hemisphaerica. Yoshinori Asakawa, Reiko Matsuda, Phytochemistry, Volume 21, Issue 8, 1982, Pages 2143–2144, doi:10.1016/0031-9422(82)83073-2

[5] Antifungal macrocyclic bis(bibenzyls) from the Chinese liverwort Ptagiochasm intermedlum L. Chun-Feng Xie, Jian-Bo Qu, Xiu-Zhen Wu, Na Liu, Mei Ji and Hong-Xiang Lou, Natural Product Research: Formerly Natural Product Letters, 2010, Volume 24, Issue 6, pages 515-520, doi:10.1080/14786410802271587

[6] David C. Harrowven; Timothy Woodcock; Peter D. Howes (2005). "Total Synthesis of Cavicularin and Riccardin C: Addressing the Synthesis of an Arene That Adopts a Boat Configuration". Angewandte Chemie. 44 (25): 3899–3901. doi:10.1002/anie.200500466. PMID 15900530. Archived from the original on 2012-12-10.

[7] Kostiuk, S. L., Woodcock, T., Dudin, L. F., Howes, P. D. and Harrowven, D. C. (2011), Unified Syntheses of Cavicularin and Riccardin C: Addressing the Synthesis of an Arene Adopting a Boat Configuration. Chemistry - A European Journal, 17: 10906–10915. doi:10.1002/chem.201101550

[1]

[2]

[3]

[4]

[5]

[6]

[7]

v t e Dihydrostilbenoids and their glycosides
Dihydrostilbenoids	Batatasin-III (3,3′-dihydroxy-5-methoxybibenzyl) Combretastatin and combretastatin B-1 Dihydro-resveratrol Isonotholaenic acid Lunularic acid Lunularin Notholaenic acid Tyrolobibenzyl A, B and C
Oligomeric forms	Bis(bibenzyls): 13,13'-O-Isoproylidenericcardin D Marchantin B and E Neomarchantin A Plagiochin E Riccardin H Macrocyclic bis(benzyls): Marchantin A and C Riccardin B and C Cyclic bibenzyl-dihydrophenanthrene derivative: Cavicularin