Phenanthrenoids are chemical compounds formed with a

phenanthrene Phenanthrene is a polycyclic aromatic hydrocarbon (PAH) with formula C14H10, consisting of three fused benzene rings. It is a colorless, crystal-like solid, but can also appear yellow. Phenanthrene is used to make dyes, plastics and pesticides, e ...

backbone. These compounds occur naturally in plants, although they can also be synthesized.

Phenanthrols

Phenanthrols are any of five isomeric phenols derived from phenanthrene ( 1-phenanthrol, 2-phenanthrol, 3-phenanthrol, 4-phenanthrol, 9-phenanthrol). These molecules can be biomarkers of smoking and/or PAH worker exposure.

Chemistry

Under UV irradiation, stilbene and its derivatives undergo intramolecular cyclization to form dihydrophenanthrenes.

Natural occurrences

Phenanthrenes have been reported from flowering plants, mainly in the family

Orchidaceae Orchids are plants that belong to the family Orchidaceae (), a diverse and widespread group of flowering plants with blooms that are often colourful and fragrant. Along with the Asteraceae, they are one of the two largest families of flowering ...

, and a few in the families

Dioscoreaceae Dioscoreaceae () is a family of monocotyledonous flowering plants, with about 715 known species in nine genera. The best-known member of the family is the yam (some species of '' Dioscorea''). The APG system (1998) and APG II system (2003) both ...

Combretaceae The Combretaceae, often called the white mangrove family, are a family of flowering plants in the order Myrtales. The family includes about 530 species of trees, shrubs, and lianas in ca 10 genera. The family includes the leadwood tree, ''Combre ...

and

Betulaceae Betulaceae, the birch family, includes six genera of deciduous nut-bearing trees and shrubs, including the birches, alders, hazels, hornbeams, hazel-hornbeam, and hop-hornbeams numbering a total of 167 species. They are mostly natives of the t ...

, as well as in the lower plant class

Marchantiophyta The Marchantiophyta () are a division of non-vascular land plants commonly referred to as hepatics or liverworts. Like mosses and hornworts, they have a gametophyte-dominant life cycle, in which cells of the plant carry only a single set of g ...

(liverworts). The rhizome of ''

Dioscorea communis ''Dioscorea communis'' or ''Tamus communis'' is a species of flowering plant in the yam family Dioscoreaceae and is commonly known as black bryony, lady's-seal or black bindweed. Description It is a climbing herbaceous plant growing to 2–4 m t ...

'' 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 ''Juncus acutus'', the spiny rush, sharp rush or sharp-pointed rush, is a flowering plant in the monocot family Juncaceae found throughout the Americas, Northern and Southern Africa, Western and Southern Europe and West Asia. It grows in salt m ...

''. Perakensol is a phenanthrenoid that can be isolated from ''

Alseodaphne perakensis ''Alseodaphne'' is a genus of plants in the family Lauraceae, endemic to China and Southeast Asia. The genus has 96 species of evergreen trees to shrubs. They have bisexual flowers, a fruit stalk that is red, green, or yellow, and black fruit.

''.

In orchids

Phenanthrenes have been reported in species of ''

Dendrobium ''Dendrobium'' is a genus of mostly epiphytic and lithophytic orchids in the family Orchidaceae. It is a very large genus, containing more than 1,800 species that are found in diverse habitats throughout much of south, east and southeast Asia, i ...

'', ''

Bulbophyllum ''Bulbophyllum'' is a genus of mostly epiphytic and lithophytic orchids in the family Orchidaceae. It is the largest genus in the orchid family and one of the largest genera of flowering plants with more than 2,000 species, exceeded in number onl ...

'', ''

Eria ''Eria'' is a genus of orchids with more than 50 species distributed in China, the Himalayas, the Indian Subcontinent, Southeast Asia, New Guinea, Polynesia, Melanesia and Micronesia. Species ''Eria'' species accepted by the Plants of the Worl ...

'', ''

Maxillaria ''Maxillaria'', abbreviated as Max in the horticultural trade, is a large genus of orchids (family Orchidaceae). This is a diverse genus, with very different morphological forms. Their characteristics can vary widely. They are commonly called sp ...

'', ''

Bletilla ''Bletilla'', common name urn orchid, is a temperate, terrestrial plant, terrestrial genus of orchids containing five currently recognized species distributed through China, Japan, Taiwan, south to Vietnam, Thailand and Myanmar. The name is actu ...

'', ''

Coelogyne ''Coelogyne'' is a genus of over 200 sympodial epiphytes from the family Orchidaceae, distributed across India, China, Indonesia and the Fiji islands, with the main centers in Borneo, Sumatra and the Himalayas. They can be found from tropical ...

'', ''

Cymbidium ''Cymbidium'' , commonly known as boat orchids, is a genus of evergreen flowering plants in the orchid family Orchidaceae. Orchids in this genus are epiphytic, lithophytic, terrestrial or rarely leafless saprophytic herbs usually with pseudobulbs ...

'', '' Ephemerantha'' and ''

Epidendrum ''Epidendrum'' , abbreviated Epi in the horticultural trade, is a large neotropical genus of the orchid family. With more than 1,500 species, some authors describe it as a mega-genus. The genus name (from Greek ''επί, epi'' and ''δένδρο ...

''. 3,4,8-Trimethoxyphenanthrene-2,5-diol is one of the 17 phenanthrenes found in the extract of the stems of the orchid ''

Dendrobium nobile ''Dendrobium nobile'', commonly known as the noble dendrobium, is a member of the family Orchidaceae. It has become a popular cultivated decorative house plant, because it produces colourful blooms in winter and spring, at a time when little el ...

''. Three phenanthrenes can be isolated from the stems of the orchid ''

Flickingeria fimbriata ''Dendrobium plicatile'' is an Asia, Asian orchid species, a member of the genus ''Dendrobium, Dendobium''. It was formerly described as ''Flickingeria fimbriata.'' Distribution The orchid's native regions include Southeast Asia, the Himalayas, ...

''. 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 Plicatol A is one of the three phenanthrenes that can be isolated from the stems of the orchid ''Dendrobium plicatile ''Dendrobium plicatile'' is an Asian orchid species, a member of the genus '' Dendobium''. It was formerly described as ''Flicki ...

, 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 ''Bulbophyllum gymnopus'' is a species of orchid in the genus ''Bulbophyllum''. The plant produces the phenanthrenediol gymnopusin Gymnopusin is a phenanthrenediol produced by the orchid '' Bulbophyllum gymnopus''. It is also found in '' Bulbo ...

'' produces the phenanthrenediol

gymnopusin Gymnopusin is a phenanthrenediol produced by the orchid ''Bulbophyllum gymnopus''. It is also found in ''Bulbophyllum reptans'' and ''Maxillaria densa ''Maxillaria densa'', the crowded maxillaria, is a species of orchid ranging from Mexico sout ...

. ''

Bulbophyllum reptans ''Bulbophyllum reptans'' is a species of orchid in the genus ''Bulbophyllum''. ''B. reptans'' contains the phenanthrenediol gymnopusin (2,7-dihydroxy-3,4,9-trimethoxyphenanthrene), the phenanthrenes Phenanthrenoids are chemical compounds formed ...

'' contains

, 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 ''Coelogyne cristata'' is an epiphytic orchid that comes from cool, moist areas of the eastern Himalayas and Vietnam. It blooms every spring, before the snow begins to melt. Its genus name ''Coelogyne'' originates from two Greek language, Greek ...

'' contains coeloginanthridin (3,5,7-trihydroxy-1,2-dimethoxy-9,10-dihydrophenanthrene), a 9,10-dihydrophenanthrene derivative, and

coeloginanthrin Coeloginanthrin is a phenanthrenoid found in the orchid ''Coelogyne cristata ''Coelogyne cristata'' is an epiphytic orchid that comes from cool, moist areas of the eastern Himalayas and Vietnam. It blooms every spring, before the snow begins to ...

(3,5,7-trihydroxy-1,2-dimethoxyphenanthrene), the corresponding phenanthrene analogue,

coelogin Coelogin is a phenanthrenoid found in the high altitude Himalayan orchid ''Coelogyne cristata ''Coelogyne cristata'' is an epiphytic orchid that comes from cool, moist areas of the eastern Himalayas and Vietnam. It blooms every spring, before t ...

and

coeloginin Coeloginin is a phenanthrenoid found in the high altitude Himalayan orchid ''Coelogyne cristata ''Coelogyne cristata'' is an epiphytic orchid that comes from cool, moist areas of the eastern Himalayas and Vietnam. It blooms every spring, before ...

. 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 ''Maxillaria densa'', the crowded maxillaria, is a species of orchid ranging from Mexico south to Nicaragua. Gymnopusin Gymnopusin is a phenanthrenediol produced by the orchid '' Bulbophyllum gymnopus''. It is also found in '' Bulbophyllum rep ...

''. 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

Cis-3,4-dihydrophenanthrene-3,4-diol dehydrogenase is an enzyme that uses (+)-cis- 3,4-dihydrophenanthrene-3,4-diol and NAD+ to produce phenanthrene-3,4-diol, NADH and H+. This enzyme participates in

naphthalene Naphthalene is an organic compound with formula . It is the simplest polycyclic aromatic hydrocarbon, and is a white crystalline solid with a characteristic odor that is detectable at concentrations as low as 0.08 ppm by mass. As an aromati ...

and

anthracene Anthracene is a solid polycyclic aromatic hydrocarbon (PAH) of formula C14H10, consisting of three fused benzene rings. It is a component of coal tar. Anthracene is used in the Economic production, production of the red dye alizarin and other dyes ...

degradation.

References

External links

* {{Phenanthrenoid

Phenanthrols

Chemistry

Natural occurrences

In orchids

Glycosides

Metabolism

See also

References

External links