Gymnopusin

Gymnopusin
Names
Chemical structure of gymnopusin
Other names 7,9-Dihydroxy-2,3,4-trimethoxyphenanthrene
Identifiers
CAS Registry Number	113476-61-2
ChemSpider	28648972
InChI InChI=1S/C17H16O5/c1-20-14-7-9-6-13(19)16(21-2)17(22-3)15(9)11-5-4-10(18)8-12(11)14/h4-8,18-19H,1-3H3 Key: GIVSZLKTIBWYRM-UHFFFAOYSA-N InChI=1/C17H16O5/c1-20-14-7-9-6-13(19)16(21-2)17(22-3)15(9)11-5-4-10(18)8-12(11)14/h4-8,18-19H,1-3H3 Key: GIVSZLKTIBWYRM-UHFFFAOYAJ
Jmol-3D images	Image
SMILES COC1=CC2=CC(=C(C(=C2C3=C1C=C(C=C3)O)OC)OC)O
Properties
Molecular formula	C₁₇H₁₆O₅
Molar mass	300.31 g·mol⁻¹
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Gymnopusin is a phenanthrenediol produced by the orchid Bulbophyllum gymnopus.^[1] It is also found in Bulbophyllum reptans^[2] and Maxillaria densa.^[3]

References

↑ Structure and synthesis of gymnopusin, a novel phenanthrenediol from the orchid Bulbophyllum gymnopus. Andrew B. Hughes and Melvyn V. Sargent, J. Chem. Soc., 1989, Perkin Trans. 1, pages 1787-1791, doi:10.1039/P19890001787
↑ Kovacs,Phytochem.,69,(2008),1084
↑ Phytotoxicity and ultrastructural effects of gymnopusin from the orchid Maxillaria densa on duckweed (Lemna pausicostata) frond and root tissues. Valencia-Islas NA, Paul RN, Shier WT, Mata R and Abbas HK, Phytochemistry, 2002, volume 61, issue 2, pages 141-148, PubMed, doi:10.1016/S0031-9422(02)00220-0

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

Phenanthrols

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)

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