# Phenanthrenoid

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[[File:Gymnopusin.svg|thumb|right|Chemical structure of [gymnopusin](/source/gymnopusin), a chemical compound found in [orchid](/source/orchid)s]]
'''Phenanthrenoids''' are chemical compounds formed with a [phenanthrene](/source/phenanthrene) backbone. These compounds occur naturally in plants, although they can also be synthesized.<ref>{{cite journal | last1 = Evans | first1 = David A. | last2 = Cain | first2 = Paul A. | last3 = Wong | first3 = Rayman Y. | year = 1977 | title = A general approach to the synthesis of phenanthrenoid compounds. An alternative to oxidative phenolic coupling | journal = J. Am. Chem. Soc. | volume = 99 | issue = 21| pages = 7083–7085 | doi = 10.1021/ja00463a063 | bibcode = 1977JAChS..99.7083E }}</ref>

== Phenanthrols ==
Phenanthrols are any of five isomeric phenols derived from phenanthrene ([1-phenanthrol](/source/1-phenanthrol), [2-phenanthrol](/source/2-phenanthrol), [3-phenanthrol](/source/3-phenanthrol), [4-phenanthrol](/source/4-phenanthrol), [9-phenanthrol](/source/9-phenanthrol)). These molecules can be biomarkers of smoking and/or PAH worker exposure.<ref>{{cite journal | last1 = Serdar | first1 = B | last2 = Waidyanatha | first2 = S | last3 = Zheng | first3 = Y | last4 = Rappaport | first4 = SM | year = 2003 | title = Simultaneous determination of urinary 1- and 2-naphthols, 3- and 9-phenanthrols, and 1-pyrenol in coke oven workers | journal = Biomarkers | volume = 8 | issue = 2| pages = 93–109 | pmid = 12775495 | doi=10.1080/1354750021000046570}}</ref>

== Chemistry ==
Under [UV irradiation, stilbene and its derivatives undergo intramolecular cyclization](/source/Stilbene_photocyclization) to form [dihydrophenanthrenes](/source/dihydrophenanthrenes).

== Natural occurrences ==
Phenanthrenes have been reported from flowering plants, mainly in the family [Orchidaceae](/source/Orchidaceae), and a few in the families [Dioscoreaceae](/source/Dioscoreaceae), [Combretaceae](/source/Combretaceae) and [Betulaceae](/source/Betulaceae), as well as in the lower plant class [Marchantiophyta](/source/Marchantiophyta) (liverworts).<ref name=Kovacs>{{cite journal | last1 = Kovács | first1 = Adriána | last2 = Vasas | first2 = Andrea | last3 = Hohmann | first3 = Judit | year = 2008 | title = Natural phenanthrenes and their biological activity | journal = Phytochemistry | volume = 69 | issue = 5| pages = 1084–1110 | doi = 10.1016/j.phytochem.2007.12.005 | pmid = 18243254 | bibcode = 2008PChem..69.1084K }}</ref>

The rhizome of ''[Dioscorea communis](/source/Dioscorea_communis)'' contains phenanthrenes ([7-hydroxy-2,3,4,8-tetramethoxyphenanthrene](/source/7-hydroxy-2%2C3%2C4%2C8-tetramethoxyphenanthrene), [2,3,4-trimethoxy-7,8-methylenedioxyphenanthrene](/source/2%2C3%2C4-trimethoxy-7%2C8-methylenedioxyphenanthrene), [3-hydroxy-2,4,-dimethoxy-7,8-methylenedioxyphenanthrene](/source/3-hydroxy-2%2C4%2C-dimethoxy-7%2C8-methylenedioxyphenanthrene), [2-hydroxy-3,5,7-trimethoxyphenanthrene](/source/2-hydroxy-3%2C5%2C7-trimethoxyphenanthrene) and [2-hydroxy-3,5,7-trimethoxy-9,10-dihydrophenanthrene](/source/2-hydroxy-3%2C5%2C7-trimethoxy-9%2C10-dihydrophenanthrene)).<ref>{{cite journal | last1 = Kovácsa | first1 = Adriána | last2 = Forgob | first2 = Peter | last3 = Zupkóc | first3 = István | last4 = Réthyc | first4 = Borbála | last5 = Falkayc | first5 = György | last6 = Szabód | first6 = Pál | last7 = Hohmanna | first7 = Judit | year = 2007 | title = Phenanthrenes and a dihydrophenanthrene from Tamus communis and their cytotoxic activity | journal = Phytochemistry | volume = 68 | issue = 5| pages = 687–691 | doi = 10.1016/j.phytochem.2006.10.028 | pmid = 17166530 | bibcode = 2007PChem..68..687K }}</ref>

The dimeric phenanthrenoid [8,8'-bidehydrojuncusol](/source/8%2C8'-bidehydrojuncusol) and the monomeric [dehydrojuncusol](/source/dehydrojuncusol) can be isolated from ''[Juncus acutus](/source/Juncus_acutus)''.<ref>{{cite journal | last1 = FA1 | first1 = Behery | last2 = Naeem | first2 = ZE | last3 = Maatooq | first3 = GT | last4 = Amer | first4 = MM | last5 = Ahmed | first5 = AF | year = 2013 | title = A novel antioxidant phenanthrenoid dimer from Juncus acutus L. | journal = Nat Prod Res | volume = 27 | issue = 2| pages = 155–163 | doi = 10.1080/14786419.2012.662759 | pmid = 22360833 }}</ref>

[Perakensol](/source/Perakensol) is a phenanthrenoid that can be isolated from ''[Alseodaphne perakensis](/source/Alseodaphne_perakensis)''.<ref>{{cite journal | last1 = Mahmud | first1 = Zurinah | last2 = Khan | first2 = Mohammad N. | last3 = Lajis | first3 = Nordin H. | last4 = Toia | first4 = Robert F. | year = 1992 | title = Perakensol: A Phenanthrenoid Isolated from Alseodaphne perakensis | journal = J. Nat. Prod. | volume = 55 | issue = 4| pages = 533–535 | doi = 10.1021/np50082a027 | bibcode = 1992JNAtP..55..533M }}</ref>

=== In orchids ===
Phenanthrenes have been reported in species of ''[Dendrobium](/source/Dendrobium)'', ''[Bulbophyllum](/source/Bulbophyllum)'', ''[Eria](/source/Eria)'', ''[Maxillaria](/source/Maxillaria)'', ''[Bletilla](/source/Bletilla)'', ''[Coelogyne](/source/Coelogyne)'', ''[Cymbidium](/source/Cymbidium)'', ''[Ephemerantha](/source/Ephemerantha)'' and ''[Epidendrum](/source/Epidendrum)''.<ref name=Kovacs/>

[3,4,8-Trimethoxyphenanthrene-2,5-diol](/source/3%2C4%2C8-Trimethoxyphenanthrene-2%2C5-diol) is one of the 17 phenanthrenes found in the extract of the stems of the orchid ''[Dendrobium nobile](/source/Dendrobium_nobile)''.<ref>{{cite journal | last1 = Hwang | first1 = JS | last2 = Lee | first2 = SA | last3 = Hong | first3 = SS | last4 = Han | first4 = XH | last5 = Lee | first5 = C | last6 = Kang | first6 = SJ | last7 = Lee | first7 = D | last8 = Kim | first8 = Y | last9 = Hong | first9 = JT | last10 = Lee | first10 = MK | last11 = Hwang | first11 = BY | year = 2010 | title = Phenanthrenes from Dendrobium nobile and their inhibition of the LPS-induced production of nitric oxide in macrophage RAW 264.7 cells | journal = Bioorg Med Chem Lett | volume = 20 | issue = 12| pages = 3785–7 | doi = 10.1016/j.bmcl.2010.04.054 | pmid = 20483604 }}</ref><ref>{{cite journal | last1 = Yang | first1 = H. | last2 = Sang | first2 = H.S. | last3 = Young | first3 = C.K. | year = 2007 | title = Antifibrotic phenanthrenes of Dendrobium nobile stems | journal = [Journal of Natural Products](/source/Journal_of_Natural_Products) | volume = 70 | issue = 12| pages = 1925–1929 | doi=10.1021/np070423f | pmid = 18052323 | bibcode = 2007JNAtP..70.1925Y }}</ref>

Three phenanthrenes can be isolated from the stems of the orchid ''[Flickingeria fimbriata](/source/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](/source/plicatol_A), [B](/source/Plicatol_B) and [C](/source/Plicatol_C).<ref>{{cite journal | last1 = Honda | first1 = Chie | last2 = Yamaki | first2 = Masae | year = 2000 | title = Phenanthrenes from Dendrobium plicatile | journal = Phytochemistry | volume = 53 | issue = 8| pages = 987–990 | doi = 10.1016/S0031-9422(99)00497-5 | pmid = 10820817 | bibcode = 2000PChem..53..987H }}</ref>

[Nudol](/source/Nudol) is a phenanthrene from the orchids ''[Eulophia nuda](/source/Eulophia_nuda)'', ''[Eria carinata](/source/Eria_carinata)'' and ''[Eria stricta](/source/Eria_stricta)''.<ref>{{cite journal | last1 = Bhandari | first1 = S | year = 1985 | title = Nudol, a phenanthrene of the orchids Eulophia nuda, Eria carinata and Eria stricta | journal = Phytochemistry | volume = 24 | issue = 4| pages = 801–804 | doi = 10.1016/S0031-9422(00)84898-0 | bibcode = 1985PChem..24..801B }}</ref> [9,10-Dihydro-2,5-dimethoxyphenanthrene-1,7-diol](/source/9%2C10-Dihydro-2%2C5-dimethoxyphenanthrene-1%2C7-diol) is a phenanthrene from ''[Eulophia nuda](/source/Eulophia_nuda)''. This compound shows cytotoxic activity against human cancer cells.<ref>{{cite journal | last1 = Shriram | first1 = Varsha | last2 = Kumar | first2 = Vinay | last3 = Kishor | first3 = P B Kavi | last4 = Suryawanshi | first4 = Sharad B | last5 = Upadhyay | first5 = Ankur K | last6 = Bhat | first6 = Manoj K | year = 2010 | title = Cytotoxic activity of 9,10-dihydro-2,5-dimethoxyphenanthrene-1,7-diol from Eulophia nuda against human cancer cells | journal = Journal of Ethnopharmacology | volume = 128 | issue = 1| pages = 251–253 | doi = 10.1016/j.jep.2009.12.031 | pmid=20045453}}</ref>

[2,7-Dihydroxy-3,6-dimethoxyphenanthrene](/source/2%2C7-Dihydroxy-3%2C6-dimethoxyphenanthrene) is a phenanthrene from ''[Dehaasia longipedicellata](/source/Dehaasia_longipedicellata)''.<ref>{{cite journal | last1 = Ropi Mukhtar | first1 = Mat | last2 = Azlan Nafiah | first2 = Mohd | last3 = Awang | first3 = Khalijah | last4 = Hadi | first4 = A. Hamid A. | last5 = Weng Ng | first5 = Seik | year = 2008 | title = 2,7-Dihydroxy-3,6-dimethoxyphenanthrene from Dehaasia longipedicellata | journal = Acta Crystallographica E | volume = 64 | issue = 6| doi = 10.1107/S1600536808014451/bt2712Isup2.hkl }}</ref>

''[Bulbophyllum gymnopus](/source/Bulbophyllum_gymnopus)'' produces the phenanthrenediol [gymnopusin](/source/gymnopusin).<ref>{{cite journal | last1 = Hughes | first1 = Andrew B. | last2 = Sargent | first2 = Melvyn V. | year = 1989 | title = Structure and synthesis of gymnopusin, a novel phenanthrenediol from the orchid Bulbophyllum gymnopus | journal = J. Chem. Soc. | volume = 1 | issue = 10| pages = 1787–1791 | doi = 10.1039/P19890001787 }}</ref>

''[Bulbophyllum reptans](/source/Bulbophyllum_reptans)'' contains [gymnopusin](/source/gymnopusin), [confusarin](/source/confusarin) (2,7-dihydroxy-3,4,8-trimethoxyphenanthrene), [2,7-dihydroxy-3,4,6-trimethoxyphenanthrene](/source/2%2C7-dihydroxy-3%2C4%2C6-trimethoxyphenanthrene) and its [9,10-dihydro derivative](/source/9%2C10-dihydro-2%2C7-dihydroxy-3%2C4%2C6-trimethoxyphenanthrene), [flavanthrinin](/source/flavanthrinin) (2,7-dihydroxy-4-methoxyphenanthrene) and its 9,10-dihydro derivative ([coelonin](/source/coelonin)), [cirrhopetalanthrin](/source/cirrhopetalanthrin) (2,2′,7,7′-tetrahydroxy-4,4′-dimethoxy-1,1′-biphenanthryl), its 9,9′,10,10′-tetrahydro derivative ([flavanthrin](/source/flavanthrin)) and the dimeric phenanthrenes [reptanthrin](/source/reptanthrin) and [isoreptanthrin](/source/isoreptanthrin).<ref>{{cite journal | last1 = Majumder | first1 = P.L | last2 = Pal | first2 = S | last3 = Majumder | first3 = S | year = 1999 | title = Dimeric phenanthrenes from the orchid Bulbophyllum reptans | journal = Phytochemistry | volume = 50 | issue = 5| pages = 891–897 | doi = 10.1016/S0031-9422(98)00609-8 | bibcode = 1999PChem..50..891M }}</ref>

''[Bulbophyllum vaginatum](/source/Bulbophyllum_vaginatum)'' contains the two phenanthrenes [4,9-dimethoxyphenanthrene-2,5-diol](/source/4%2C9-dimethoxyphenanthrene-2%2C5-diol) and [4,6-dimethoxyphenanthrene-2,3,7-triol](/source/4%2C6-dimethoxyphenanthrene-2%2C3%2C7-triol), and the two dihydrophenanthrenes [4-methoxy-9,10-dihydrophenanthrene-2,3,7-triol](/source/4-methoxy-9%2C10-dihydrophenanthrene-2%2C3%2C7-triol) and [4,6-dimethoxy-9,10-dihydrophenanthrene-2,3,7-triol](/source/4%2C6-dimethoxy-9%2C10-dihydrophenanthrene-2%2C3%2C7-triol).<ref>{{cite journal | last1 = Leong Y-W | first1 = KAng C-C | last2 = Harrison | first2 = LJ | last3 = Powell | first3 = AD | year = 1997 | title = Phenanthrenes, dihydrophenanthrenes and bibenzyls from the orchid Bulbophyllum vaginatum | doi = 10.1016/s0031-9422(96)00387-1 | journal = Phytochemistry | volume = 44 | issue = 1| pages = 157–165 | bibcode = 1997PChem..44..157L | url = http://scholarbank.nus.edu.sg/handle/10635/76744 | id={{INIST|2557322}} }}</ref>

''[Coelogyne cristata](/source/Coelogyne_cristata)'' contains [coeloginanthridin](/source/coeloginanthridin) (3,5,7-trihydroxy-1,2-dimethoxy-9,10-dihydrophenanthrene), a 9,10-dihydrophenanthrene derivative, and [coeloginanthrin](/source/coeloginanthrin) (3,5,7-trihydroxy-1,2-dimethoxyphenanthrene), the corresponding phenanthrene analogue, [coelogin](/source/coelogin) and [coeloginin](/source/coeloginin).<ref>{{cite journal | pmid = 11576602 | volume=58 | issue=4 | title=Phenanthrene derivatives from the orchid Coelogyne cristata. | date=Oct 2001 | journal=Phytochemistry | pages=581–6 | doi=10.1016/s0031-9422(01)00287-4 | last1 = Majumder | first1 = PL | last2 = Sen | first2 = S | last3 = Majumder | first3 = S| bibcode=2001PChem..58..581M }}</ref>

[Orchinol](/source/Orchinol) and [loroglossol](/source/loroglossol) have a phytoalexin effect and reduce the growth of ''[Cattleya aurantiaca](/source/Cattleya_aurantiaca)'' seedlings.<ref>{{cite journal | last1 = Hills | first1 = Katherine A. | last2 = Stoessl | first2 = Albert | last3 = Oliva | first3 = Allison P. | last4 = Arditti | first4 = Joseph | year = 1984 | title = Effects of Orchinol, Loroglossol, Dehydroorchinol, Batatasin III, and 3,4'- Dihydroxy-5-Methoxydihydrostilbene on Orchid Seedlings | journal = Botanical Gazette | volume = 145 | issue = 3| pages = 298–301 | jstor=2474721 | doi=10.1086/337458| url = https://escholarship.org/uc/item/7qk082wt | url-access = subscription }}</ref>

The phenanthrenes [2,5-dihydroxy-3,4-dimethoxyphenanthrene](/source/2%2C5-dihydroxy-3%2C4-dimethoxyphenanthrene), [9,10-dihydro-2,5-dihydroxy-3,4-dimethoxyphenanthrene](/source/9%2C10-dihydro-2%2C5-dihydroxy-3%2C4-dimethoxyphenanthrene), 2,7-dihydroxy-3,4-dimethoxyphenanthrene ([nudol](/source/nudol)), [9,10-dihydro-2,7-dihydroxy-3,4-dimethoxyphenanthrene](/source/9%2C10-dihydro-2%2C7-dihydroxy-3%2C4-dimethoxyphenanthrene), [2,5-dihydroxy-3,4,9-trimethoxyphenanthrene](/source/2%2C5-dihydroxy-3%2C4%2C9-trimethoxyphenanthrene) and [2,7-dihydroxy-3,4,9-trimethoxyphenanthrene](/source/2%2C7-dihydroxy-3%2C4%2C9-trimethoxyphenanthrene) can be isolated from ''[Maxillaria densa](/source/Maxillaria_densa)''.<ref>{{cite journal | last1 = Estrada | first1 = Samuel | last2 = Toscano | first2 = Rubén A. | last3 = Mata | first3 = Rachel | year = 1999 | title = New Phenanthrene Derivatives from Maxillaria densa | journal = J. Nat. Prod. | volume = 62 | issue = 8| pages = 1175–1178 | doi = 10.1021/np990061e | pmid = 10479332 | bibcode = 1999JNAtP..62.1175E }}</ref>

[Cirrhopetalanthrin](/source/Cirrhopetalanthrin) is a dimeric phenanthrene derivative from ''[Cirrhopetalum maculosum](/source/Cirrhopetalum_maculosum)''.<ref>{{cite journal | last1 = Majumder | first1 = P.L. | last2 = Pal | first2 = Anjali | last3 = Joardar | first3 = Mukta | year = 1990 | title = Cirrhopetalanthrin, a dimeric phenanthrene derivative from the orchid Cirrhopetalum maculosum | journal = Phytochemistry | volume = 29 | issue = 1| pages = 271–274 | doi = 10.1016/0031-9422(90)89048-E | bibcode = 1990PChem..29..271M }}</ref>

==== Glycosides ====
Five phenanthrene glycosides, [denneanoside A](/source/denneanoside_A), [B](/source/denneanoside_B), [C](/source/denneanoside_C), [D](/source/denneanoside_D) and [E](/source/denneanoside_E) and one 9,10-dihydrophenanthrene glycoside, [denneanoside F](/source/denneanoside_F), can be isolated from the stem of ''[Dendrobium denneanum](/source/Dendrobium_denneanum)''.<ref>{{cite journal | last1 = Li | first1 = Fu | last2 = Pan | first2 = Hong-Mei | last3 = Liu | first3 = Xin | last4 = Chen | first4 = Bin | last5 = Tang | first5 = Ya-Xiong | last6 = Xi | first6 = Xing-Jun | last7 = Wang | first7 = Ming-Kui | year = 2013 | title = New phenanthrene glycosides from Dendrobium denneanum and their cytotoxic activity | journal = Phytochemistry Letters | volume = 6 | issue = 4| pages = 640–644 | doi = 10.1016/j.phytol.2013.08.003 | bibcode = 2013PChL....6..640L }}</ref>

== Metabolism ==
[Cis-3,4-dihydrophenanthrene-3,4-diol dehydrogenase](/source/Cis-3%2C4-dihydrophenanthrene-3%2C4-diol_dehydrogenase) is an enzyme that uses (+)-cis-[3,4-dihydrophenanthrene-3,4-diol](/source/3%2C4-dihydrophenanthrene-3%2C4-diol) and NAD<small>+</small> to produce [phenanthrene-3,4-diol](/source/phenanthrene-3%2C4-diol), NADH and H<small>+</small>. This enzyme participates in [naphthalene](/source/naphthalene) and [anthracene](/source/anthracene) degradation.

== See also ==
* (+)-[Cavicularin](/source/Cavicularin), a cyclic bibenzyl-dihydrophenanthrene derivative<ref>{{cite journal | title = (+)-Cavicularin: A Novel Optically Active Cyclic Bibenzyl-Dihydrophenanthrene Derivative from the Liverwort Cavicularia densa Steph |author1=M. Toyota |author2=T. Yoshida |author3=Y. Kan |author4=S. Takaoka |author5=Y. Asakawa | journal = Tetrahedron Letters | year = 1996 | pages = 4745–4748 | doi = 10.1016/0040-4039(96)00956-2 | volume = 37 | issue = 27}}{{dead link|date=March 2019|bot=medic}}{{cbignore|bot=medic}}</ref>

== References ==
{{reflist}}

== External links ==
* {{wiktionary-inline|phenanthrol}}

{{stilbenoids}}{{clear right}}
{{Phenanthrenoid}}

Category:Phenanthrenoids

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Adapted from the Wikipedia article [Phenanthrenoid](https://en.wikipedia.org/wiki/Phenanthrenoid) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Phenanthrenoid?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.