Phenanthrenes have been reported from flowering plants, mainly in the family
Orchidaceae, and a few in the families
Dioscoreaceae,
Combretaceae and
Betulaceae, as well as in the lower plant class
Marchantiophyta (liverworts). The rhizome of
Dioscorea communis contains phenanthrenes (
7-hydroxy-2,3,4,8-tetramethoxyphenanthrene,
2,3,4-trimethoxy-7,8-methylenedioxyphenanthrene,
3-hydroxy-2,4,-dimethoxy-7,8-methylenedioxyphenanthrene,
2-hydroxy-3,5,7-trimethoxyphenanthrene and
2-hydroxy-3,5,7-trimethoxy-9,10-dihydrophenanthrene). The dimeric phenanthrenoid
8,8'-bidehydrojuncusol and the monomeric
dehydrojuncusol can be isolated from
Juncus acutus.
Perakensol is a phenanthrenoid that can be isolated from
Alseodaphne perakensis.
In orchids Phenanthrenes have been reported in species of
Dendrobium,
Bulbophyllum,
Eria,
Maxillaria,
Bletilla,
Coelogyne,
Cymbidium,
Ephemerantha and
Epidendrum. Three phenanthrenes can be isolated from the stems of the orchid
Flickingeria fimbriata. The structures are 2,5-dihydroxy-4,9,10-trimethoxyphenanthrene, 2,5-dihydroxy-4-methoxyphenanthrene and 2,5,9-trihydroxy-4-methoxy-9,10-dihydrophenanthrene. These molecules are named
plicatol A,
B and
C.
Nudol is a phenanthrene from the orchids
Eulophia nuda,
Eria carinata and
Eria stricta.
9,10-Dihydro-2,5-dimethoxyphenanthrene-1,7-diol is a phenanthrene from
Eulophia nuda. This compound shows cytotoxic activity against human cancer cells.
2,7-Dihydroxy-3,6-dimethoxyphenanthrene is a phenanthrene from
Dehaasia longipedicellata.
Bulbophyllum gymnopus produces the phenanthrenediol
gymnopusin.
Bulbophyllum reptans contains
gymnopusin,
confusarin (2,7-dihydroxy-3,4,8-trimethoxyphenanthrene),
2,7-dihydroxy-3,4,6-trimethoxyphenanthrene and its
9,10-dihydro derivative,
flavanthrinin (2,7-dihydroxy-4-methoxyphenanthrene) and its 9,10-dihydro derivative (
coelonin),
cirrhopetalanthrin (2,2′,7,7′-tetrahydroxy-4,4′-dimethoxy-1,1′-biphenanthryl), its 9,9′,10,10′-tetrahydro derivative (
flavanthrin) and the dimeric phenanthrenes
reptanthrin and
isoreptanthrin.
Bulbophyllum vaginatum contains the two phenanthrenes
4,9-dimethoxyphenanthrene-2,5-diol and
4,6-dimethoxyphenanthrene-2,3,7-triol, and the two dihydrophenanthrenes
4-methoxy-9,10-dihydrophenanthrene-2,3,7-triol and
4,6-dimethoxy-9,10-dihydrophenanthrene-2,3,7-triol.
Coelogyne cristata contains
coeloginanthridin (3,5,7-trihydroxy-1,2-dimethoxy-9,10-dihydrophenanthrene), a 9,10-dihydrophenanthrene derivative, and
coeloginanthrin (3,5,7-trihydroxy-1,2-dimethoxyphenanthrene), the corresponding phenanthrene analogue,
coelogin and
coeloginin.
Orchinol and
loroglossol have a phytoalexin effect and reduce the growth of
Cattleya aurantiaca seedlings. The phenanthrenes
2,5-dihydroxy-3,4-dimethoxyphenanthrene,
9,10-dihydro-2,5-dihydroxy-3,4-dimethoxyphenanthrene, 2,7-dihydroxy-3,4-dimethoxyphenanthrene (
nudol),
9,10-dihydro-2,7-dihydroxy-3,4-dimethoxyphenanthrene,
2,5-dihydroxy-3,4,9-trimethoxyphenanthrene and
2,7-dihydroxy-3,4,9-trimethoxyphenanthrene can be isolated from
Maxillaria densa.
Cirrhopetalanthrin is a dimeric phenanthrene derivative from
Cirrhopetalum maculosum.
Glycosides Five phenanthrene glycosides,
denneanoside A,
B,
C,
D and
E and one 9,10-dihydrophenanthrene glycoside,
denneanoside F, can be isolated from the stem of
Dendrobium denneanum. == Metabolism ==