Juncusol

Juncusol
Names
Chemical structure of juncusol
IUPAC name 5-ethenyl-1,6-dimethyl-9,10-dihydrophenanthrene-2,7-diol
Other names 1,6-Dimethyl-5-vinyl-9,10-dihydro-2,7-phenanthrenediol
Identifiers
CAS Number	62023-90-9
ChemSpider	65579
Jmol interactive 3D	Image
PubChem	72740
SMILES CC1=C(C=CC2=C1CCC3=CC(=C(C(=C32)C=C)C)O)O
Properties
Chemical formula	C₁₈H₁₈O₂
Molar mass	266.33 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Juncusol is a 9,10-dihydrophrenathrene found in Juncus species such as J. acutus,^[1] J. effusus^[2]^[3] or J. roemerianus.^[4]^[5]

It can also be synthetized.^[6]^[7]^[8]

This compound shows antimicrobial activity against Bacillus subtilis and Staphylococcus aureus.^[4] It also has a toxic effect on estuarine fish and shrimp.^[9]

References

↑ Phenanthrenoids from Juncus acutus L., New Natural Lipopolysaccharide-Inducible Nitric Oxide Synthase Inhibitors. Fathi Abdelmohsen Abdelhalim Behery, Zain Elabdin Metwally Naeem, Galal Taha Maatooq, Mohamed Mahmoud Abdelfattah Amer, Zhi-Hong Wen, Jyh-Horng Sheu, Atallah Fouad Ahmed, Chemical and Pharmaceutical Bulletin, 2007, Vol. 55, No. 8, pages 1264-1266, doi:10.1248/cpb.55.1264
↑ Bhattacharyya,Experientia,36,(1980),27
↑ Shima,Phytochem.,30,(1991),3149
1 2 Antimicrobial activity of juncusol, a novel 9-10-dihydrophenanthrene from the marsh plant Juncus roemerianus. Kirit D. Chapatwala, Armando A. de la Cruz and D.Howard Miles, Life Sciences, 9 November 1981, Volume 29, Issue 19, Pages 1997–2001, doi:10.1016/0024-3205(81)90609-3
↑ The structure of juncusol. A novel cytotoxic dihydrophenanthrene from the Estuarine marsh plant Juncus roemerianus. D H Miles, J Bhattacharyya, N V Mody, J L Atwood, S Black and P A Hedin, Journal of the American Chemical Society, February 1977, volume 99, issue 2, pages 618-620, PubMed
↑ Total synthesis of juncusol. Edward McDonald and Roger T. Martin, Tetrahedron Letters, 1978, Volume 19, Issue 47, Pages 4723–4726, doi:10.1016/S0040-4039(01)85715-4
↑ Regiospecific total synthesis of juncusol. Dale L. Boger and Michael D. Mullican, J. Org. Chem., 1984, volume 49, issue 21, pages 4045–4050, doi:10.1021/jo00195a034
↑ A novel synthesis of juncusol. Peter A. Jacobi and Wanjun Zheng, Tetrahedron Letters, 4 March 1991, Volume 32, Issue 10, Pages 1279–1282, doi:10.1016/S0040-4039(00)79645-6
↑ Toxic effects of juncusol a marsh plant phenolic extract on estuarine fish and shrimp. Chapatwala K.D, Life Sciences, 1982, volume 30, issue 21, pages 1805-1810, PubMed

External links

Juncusol at kanaya.naist.jp/knapsack_jsp

Phenanthrenoids and their glycosides (molecules with a C6-C2-C6 backbone)

Phenanthrols

1-Phenanthrol
2-Phenanthrol
3-Phenanthrol
4-Phenanthrol
9-Phenanthrol

polyhydroxylated phenanthrenes

coeloginanthrin (3,5,7-trihydroxy-1,2-dimethoxyphenanthrene)
confusaridin (2,6-dihydroxy-3,4,7,8-tetramethoxyphenanthrene)
confusarin (2,7-dihydroxy-3,4,8-trimethoxyphenanthrene)
dehydroeffusol
dehydrojuncusol (1,6-dimethyl-5-vinyl-8-phenanthrene-2,7-diol)
flavanthrinin (2,7-dihydroxy-4-methoxyphenanthrene)
gymnopusin (2,7-dihydroxy-3,4,9-trimethoxyphenanthrene)
Nudol (2,7-dihydroxy-3,4-dimethoxyphenanthrene)
Perakensol (7-hydroxy-2,3,6-trimethoxyphenanthrene)
plicatol A (2,5-dihydroxy-4,9,10-trimethoxyphenanthrene)
Plicatol B (2,5-dihydroxy-4-methoxyphenanthrene)

2,3,4-trimethoxy-7,8-methylenedioxyphenanthrene
2,5-dihydroxy-3,4-dimethoxyphenanthrene
2,5-dihydroxy-3,4,9-trimethoxyphenanthrene
2,7-dihydroxy-3,4,6-trimethoxyphenanthrene
2,7-dihydroxy-3,4,9-trimethoxyphenanthrene
2,7-Dihydroxy-3,6-dimethoxyphenanthrene
3-hydroxy-2,4,-dimethoxy-7,8-methylenedioxyphenanthrene
2-hydroxy-3,5,7-trimethoxyphenanthrene
2-hydroxy-3,5,7-trimethoxy-9,10-dihydrophenanthrene
3,4,8-Trimethoxyphenanthrene-2,5-diol
4,6-dimethoxyphenanthrene-2,3,7-triol
4,9-dimethoxyphenanthrene-2,5-diol
7-Hydroxy-2,3,4,8-tetramethoxyphenanthrene

9,10-dihydrophenanthrene derivatives

coelogin (2,6-Dihydroxy-7,8-dimethoxy-9,10-dihydro-5H-phenanthro[4,5-bcd]pyran)
coeloginin (2,6-Dihydroxy-7,8-dimethoxy-9,1O-dihydro-5H-phenanthro[4,5-bcd]pyran-5-one)
coeloginanthridin (3,5,7-trihydroxy-1,2-dimethoxy-9,10-dihydrophenanthrene)
coelonin (9,10-dihydro-2,7-dihydroxy-4-methoxyphenanthrene)
effusol (5-ethenyl-1-methyl-9,10-dihydrophenanthrene-2,7-diol)
hircinol (9,10-dihydro-4-methoxyphenanthrene-2,5-diol)
juncusol (1,6-Dimethyl-5-vinyl-9,10-dihydro-2,7-phenanthrenediol)
loroglossol (5-hydroxy-2,4-dimethyoxy-9,10-dihydrophenanthrene)
orchinol (9,10-Dihydro-5,7-dimethoxyphenanthren-2-ol)
Plicatol C (2,5,9-trihydroxy-4-methoxy-9,10-dihydrophenanthrene)
4-methoxy-9,10-dihydrophenanthrene-2,3,7-triol
4,6-dimethoxy-9,10-dihydrophenanthrene-2,3,7-triol
9,10-dihydro-2,7-dihydroxy-3,4-dimethoxyphenanthrene
9,10-dihydro-2,7-dihydroxy-3,4,6-trimethoxyphenanthrene
9,10-Dihydro-2,5-dimethoxyphenanthrene-1,7-diol
9,10-dihydro-2,5-dihydroxy-3,4-dimethoxyphenanthrene

glycosides

Phenanthrene glycosides	denneanoside A, B, C, D and E

9,10-dihydrophenanthrene glycoside	denneanoside F

dimeric phenanthrenes

cirrhopetalanthrin (2,2′,7,7′-tetrahydroxy-4,4′-dimethoxy-1,1′-biphenanthryl)
flavanthrin (9,9′,10,10′-tetrahydro-2,2′,7,7′-tetrahydroxy-4,4′-dimethoxy-1,1′-biphenanthryl)
reptanthrin
isoreptanthrin
8,8'-bidehydrojuncusol (1,1',6,6'-tetramethyl-5,5'-divinyl-8,8'-biphenanthrene-2,2',7,7'-tetraol)

Cyclic bibenzyl-dihydrophenanthrene derivative

Cavicularin

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