Phenanthrenoid Explained

Phenanthrenoids are chemical compounds formed with a phenanthrene backbone. These compounds occur naturally in plants, although they can also be synthesized.[1]

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.[2]

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, 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]

In orchids

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]

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.[20]

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 and anthracene degradation.

See also

External links

Notes and References

  1. Evans . David A. . Cain . Paul A. . Wong . Rayman Y. . 1977 . A general approach to the synthesis of phenanthrenoid compounds. An alternative to oxidative phenolic coupling . J. Am. Chem. Soc. . 99 . 21. 7083–7085 . 10.1021/ja00463a063 .
  2. Serdar . B . Waidyanatha . S . Zheng . Y . Rappaport . SM . 2003 . Simultaneous determination of urinary 1- and 2-naphthols, 3- and 9-phenanthrols, and 1-pyrenol in coke oven workers . Biomarkers . 8 . 2. 93–109 . 12775495 . 10.1080/1354750021000046570.
  3. Kovács . Adriána . Vasas . Andrea . Hohmann . Judit . 2008 . Natural phenanthrenes and their biological activity . Phytochemistry . 69 . 5. 1084–1110 . 10.1016/j.phytochem.2007.12.005 . 18243254 . 2008PChem..69.1084K .
  4. Kovácsa . Adriána . Forgob . Peter . Zupkóc . István . Réthyc . Borbála . Falkayc . György . Szabód . Pál . Hohmanna . Judit . 2007 . Phenanthrenes and a dihydrophenanthrene from Tamus communis and their cytotoxic activity . Phytochemistry . 68 . 5. 687–691 . 10.1016/j.phytochem.2006.10.028 . 17166530 . 2007PChem..68..687K .
  5. FA1 . Behery . Naeem . ZE . Maatooq . GT . Amer . MM . Ahmed . AF . 2013 . A novel antioxidant phenanthrenoid dimer from Juncus acutus L. . Nat Prod Res . 27 . 2. 155–163 . 10.1080/14786419.2012.662759 . 22360833 .
  6. Mahmud . Zurinah . Khan . Mohammad N. . Lajis . Nordin H. . Toia . Robert F. . 1992 . Perakensol: A Phenanthrenoid Isolated from Alseodaphne perakensis . J. Nat. Prod. . 55 . 4. 533–535 . 10.1021/np50082a027 .
  7. Hwang . JS . Lee . SA . Hong . SS . Han . XH . Lee . C . Kang . SJ . Lee . D . Kim . Y . Hong . JT . Lee . MK . Hwang . BY . 2010 . Phenanthrenes from Dendrobium nobile and their inhibition of the LPS-induced production of nitric oxide in macrophage RAW 264.7 cells . Bioorg Med Chem Lett . 20 . 12. 3785–7 . 10.1016/j.bmcl.2010.04.054 .
  8. Yang . H. . Sang . H.S. . Young . C.K. . 2007 . Antifibrotic phenanthrenes of Dendrobium nobile stems . . 70 . 12. 1925–1929 . 10.1021/np070423f . 18052323.
  9. Honda . Chie . Yamaki . Masae . 2000 . Phenanthrenes from Dendrobium plicatile . Phytochemistry . 53 . 8. 987–990 . 10.1016/S0031-9422(99)00497-5 . 2000PChem..53..987H .
  10. Bhandari . S . 1985 . Nudol, a phenanthrene of the orchids Eulophia nuda, Eria carinata and Eria stricta . Phytochemistry . 24 . 4. 801–804 . 10.1016/S0031-9422(00)84898-0 . 1985PChem..24..801B .
  11. Shriram . Varsha . Kumar . Vinay . Kishor . P B Kavi . Suryawanshi . Sharad B . Upadhyay . Ankur K . Bhat . Manoj K . 2010 . Cytotoxic activity of 9,10-dihydro-2,5-dimethoxyphenanthrene-1,7-diol from Eulophia nuda against human cancer cells . Journal of Ethnopharmacology . 128 . 1. 251–253 . 10.1016/j.jep.2009.12.031 . 20045453.
  12. Ropi Mukhtar . Mat . Azlan Nafiah . Mohd . Awang . Khalijah . Hadi . A. Hamid A. . Weng Ng . Seik . 2008 . 2,7-Dihydroxy-3,6-dimethoxyphenanthrene from Dehaasia longipedicellata . Acta Crystallographica E . 64 . 6. 10.1107/S1600536808014451/bt2712Isup2.hkl .
  13. Hughes . Andrew B. . Sargent . Melvyn V. . 1989 . Structure and synthesis of gymnopusin, a novel phenanthrenediol from the orchid Bulbophyllum gymnopus . J. Chem. Soc. . 1 . 10. 1787–1791 . 10.1039/P19890001787 .
  14. Majumder . P.L . Pal . S . Majumder . S . 1999 . Dimeric phenanthrenes from the orchid Bulbophyllum reptans . Phytochemistry . 50 . 5. 891–897 . 10.1016/S0031-9422(98)00609-8 . 1999PChem..50..891M .
  15. Leong Y-W . KAng C-C . Harrison . LJ . Powell . AD . 1997 . Phenanthrenes, dihydrophenanthrenes and bibenzyls from the orchid Bulbophyllum vaginatum . 10.1016/s0031-9422(96)00387-1 . Phytochemistry . 44 . 1. 157–165 . 1997PChem..44..157L . .
  16. 11576602 . 58 . 4 . Phenanthrene derivatives from the orchid Coelogyne cristata. . Oct 2001 . Phytochemistry . 581–6 . 10.1016/s0031-9422(01)00287-4 . Majumder . PL . Sen . S . Majumder . S. 2001PChem..58..581M .
  17. Hills . Katherine A. . Stoessl . Albert . Oliva . Allison P. . Arditti . Joseph . 1984 . Effects of Orchinol, Loroglossol, Dehydroorchinol, Batatasin III, and 3,4'- Dihydroxy-5-Methoxydihydrostilbene on Orchid Seedlings . Botanical Gazette . 145 . 3. 298–301 . 2474721 . 10.1086/337458.
  18. Estrada . Samuel . Toscano . Rubén A. . Mata . Rachel . 1999 . New Phenanthrene Derivatives from Maxillaria densa . J. Nat. Prod. . 62 . 8. 1175–1178 . 10.1021/np990061e . 10479332 .
  19. Majumder . P.L. . Pal . Anjali . Joardar . Mukta . 1990 . Cirrhopetalanthrin, a dimeric phenanthrene derivative from the orchid Cirrhopetalum maculosum . Phytochemistry . 29 . 1. 271–274 . 10.1016/0031-9422(90)89048-E . 1990PChem..29..271M .
  20. Li . Fu . Pan . Hong-Mei . Liu . Xin . Chen . Bin . Tang . Ya-Xiong . Xi . Xing-Jun . Wang . Ming-Kui . 2013 . New phenanthrene glycosides from Dendrobium denneanum and their cytotoxic activity . Phytochemistry Letters . 6 . 4. 640–644 . 10.1016/j.phytol.2013.08.003 . 2013PChL....6..640L .
  21. (+)-Cavicularin: A Novel Optically Active Cyclic Bibenzyl-Dihydrophenanthrene Derivative from the Liverwort Cavicularia densa Steph . M. Toyota . T. Yoshida . Y. Kan . S. Takaoka . Y. Asakawa . Tetrahedron Letters . 1996 . 4745–4748 . 10.1016/0040-4039(96)00956-2 . 37 . 27.

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