Phenanthrenoids are chemical compounds formed with a phenanthrene backbone. These compounds occur naturally in plants, although they can also be synthesized. [1]
Phenanthrenoids are chemical compounds formed with a phenanthrene backbone. These compounds occur naturally in plants, although they can also be synthesized. [1]
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. [2]
Under UV irradiation, stilbene and its derivatives undergo intramolecular cyclization to form dihydrophenanthrenes.
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). [3]
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). [4]
The dimeric phenanthrenoid 8,8'-bidehydrojuncusol and the monomeric dehydrojuncusol can be isolated from Juncus acutus . [5]
Perakensol is a phenanthrenoid that can be isolated from Alseodaphne perakensis . [6]
Phenanthrenes have been reported in species of Dendrobium , Bulbophyllum , Eria , Maxillaria , Bletilla , Coelogyne , Cymbidium , Ephemerantha and Epidendrum . [3]
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 . [7] [8]
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. [9]
Nudol is a phenanthrene from the orchids Eulophia nuda , Eria carinata and Eria stricta . [10] 9,10-Dihydro-2,5-dimethoxyphenanthrene-1,7-diol is a phenanthrene from Eulophia nuda . This compound shows cytotoxic activity against human cancer cells. [11]
2,7-Dihydroxy-3,6-dimethoxyphenanthrene is a phenanthrene from Dehaasia longipedicellata . [12]
Bulbophyllum gymnopus produces the phenanthrenediol gymnopusin. [13]
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. [14]
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. [15]
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. [16]
Orchinol and loroglossol have a phytoalexin effect and reduce the growth of Cattleya aurantiaca seedlings. [17]
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 . [18]
Cirrhopetalanthrin is a dimeric phenanthrene derivative from Cirrhopetalum maculosum . [19]
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 . [20]
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 and anthracene degradation.
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.
Dendrobium nobile, commonly known as the noble dendrobium, is a member of the family Orchidaceae. Dendrobium nobile is one of the most widespread ornamental members of the orchid family. It is the state flower of Sikkim.
Bulbophyllum umbellatum is a species of orchid. It is native to tropical parts of South Asia, from the west central Himalayas to Taiwan and Indo-China.
Bulbophyllum vaginatum is a species of orchid.
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 words, koilos ("hollow") and gyne ("woman"), because of the orchid's pistil. Cristata takes its species name from crista, the Latin word for "comb", because of the look of the flower's lip.
Cryptochilus acuminatus, synonym Eria carinata, is a species of orchid. It is native to Nepal, Bhutan, Assam, Thailand, Vietnam and peninsular Malaysia.
Maxillaria densa, the crowded maxillaria, is a species of orchid ranging from Mexico south to Nicaragua.
Bulbophyllum reptans is a species of orchid in the genus Bulbophyllum.
The flavans are benzopyran derivatives that use the 2-phenyl-3,4-dihydro-2H-chromene skeleton. They may be found in plants. These compounds include the flavan-3-ols, flavan-4-ols and flavan-3,4-diols (leucoanthocyanidin).
Dihydrostilbenoids (bibenzyls) are natural phenols formed from the dihydrostilbene (bibenzyl) backbone.
Plicatol A is one of the three phenanthrenes that can be isolated from the stems of the orchid Dendrobium plicatile.
Plicatol B is one of the three phenanthrenes that can be isolated from the stems of the orchid Flickingeria fimbriata. It can also be isolated from Dendrobium densiflorum, D. loddigesii, D. moschatum, D. rotundatum and Bulbophyllum kwangtungense
Plicatol C is one of the three phenanthrenes that can be isolated from the stems of the orchid Dendrobium plicatile.
Nudol is a phenanthrenoid of the orchids Eulophia nuda, Eria carinata, Eria stricta and Maxillaria densa.
Orchinol is a 9,10-dihydrophenanthrene, a type of phenanthrenoid. It can be isolated from infected Orchis militaris and infected Loroglossum hircinum with Rhizoctonia repens. This molecule has a phytoalexin effect. It reduces the growth of Cattleya aurantiaca seedlings and has an antifungal activity.
Coelogin is a phenanthrenoid found in the high altitude Himalayan orchid Coelogyne cristata. This molecule has a phenanthro[4,5-bcd]pyran structure.
Coeloginin is a phenanthrenoid found in the high altitude Himalayan orchid Coelogyne cristata. This molecule has a phenanthro[4,5-bcd]pyrone structure.
Juncusol is a 9,10-dihydrophrenathrene found in Juncus species such as J. acutus, J. effusus or J. roemerianus.
Coeloginanthrin is a phenanthrenoid found in the orchid Coelogyne cristata.
Confusarin is a phenanthrenoid found in the orchids Eria confusa and Bulbophyllum reptans. It can also be synthesized.
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The dictionary definition of phenanthrol at Wiktionary