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, pesticides, expl ...

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 (biology), family Orchidaceae (), a diverse and widespread group of flowering plants with blooms that are often colourful and fragrant. Orchids are cosmopolitan distribution, cosmopolitan plants that ...

, and a few in the families Dioscoreaceae,

Combretaceae The Combretaceae, often called the white mangrove family, are a family of flowering plant Flowering plants are plants that bear flowers and fruits, and form the clade Angiospermae (). The term angiosperm is derived from the Ancient Greek, G ...

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 ...

, as well as in the lower plant class

Marchantiophyta Liverworts are a group of non-vascular plant, non-vascular embryophyte, land plants forming the division Marchantiophyta (). They may also be referred to as hepatics. Like mosses and hornworts, they have a gametophyte-dominant life cycle, in wh ...

(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 ...

'' 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 ''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 Epiphyte, epiphytic and Lithophyte, lithophytic orchids in the Family (biology), family Orchidaceae. It is a very large genus, containing more than 1,800 species that are found in diverse habitats throughout m ...

'', ''

Bulbophyllum ''Bulbophyllum'' is a genus of mostly Epiphyte, epiphytic and Lithophyte, lithophytic orchids in the Family (biology), family Orchidaceae. It is the largest genus in the orchid family and one of the List of the largest genera of flowering plants, ...

'', ''

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 Plants of the World On ...

'', ''

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 ...

'', ''

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

'', ''

Coelogyne ''Coelogyne'' is a genus of 594 species, which are 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 fro ...

'', ''

Cymbidium ''Cymbidium'' , commonly known as boat orchids, is a genus of evergreen flowering plants in the orchid Family (biology), family Orchidaceae. Orchids in this genus are Epiphyte, epiphytic, Lithophyte, lithophytic, Terrestrial plant, terrestrial o ...

'', '' 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 language, Greek ''επί, epi'' an ...

''. 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''. 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 Gymnopusin is a phenanthrenediol produced by the orchid '' Bulbophyllum gymnopus''. It is also found in '' Bulbophyllum reptans'' and '' Maxillaria densa''.Phytotoxicity and ultrastructural effects of gymnopusin from the orchid Maxillaria densa on ...

. '' Bulbophyllum reptans'' 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 w ...

'' 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

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 Crystal, crystalline solid with a characteristic odor that is detectable at concentrations as low as 0.08 Parts-per notation ...

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 production of the red dye alizarin and other dyes, as a scintil ...

degradation.

References

External links

* {{Phenanthrenoid

Phenanthrols

Chemistry

Natural occurrences

In orchids

Glycosides

Metabolism

See also

References

External links