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Phenanthrenoid

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

Chemical structure of gymnopusin, a chemical compound found in orchids

Phenanthrols

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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

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

Natural occurrences

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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

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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

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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

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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

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References

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  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. doi: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. doi:10.1080/1354750021000046570. PMID 12775495.
  3. ^ a b Kovács, Adriána; Vasas, Andrea; Hohmann, Judit (2008). "Natural phenanthrenes and their biological activity". Phytochemistry. 69 (5): 1084–1110. Bibcode:2008PChem..69.1084K. doi:10.1016/j.phytochem.2007.12.005. PMID 18243254.
  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. Bibcode:2007PChem..68..687K. doi:10.1016/j.phytochem.2006.10.028. PMID 17166530.
  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. doi:10.1080/14786419.2012.662759. PMID 22360833.{{cite journal}}: CS1 maint: numeric names: authors list (link)
  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. doi: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. doi:10.1016/j.bmcl.2010.04.054.
  8. ^ Yang, H.; Sang, H.S.; Young, C.K. (2007). "Antifibrotic phenanthrenes of Dendrobium nobile stems". Journal of Natural Products. 70 (12): 1925–1929. doi:10.1021/np070423f. PMID 18052323.
  9. ^ Honda, Chie; Yamaki, Masae (2000). "Phenanthrenes from Dendrobium plicatile". Phytochemistry. 53 (8): 987–990. Bibcode:2000PChem..53..987H. doi:10.1016/S0031-9422(99)00497-5.
  10. ^ Bhandari, S (1985). "Nudol, a phenanthrene of the orchids Eulophia nuda, Eria carinata and Eria stricta". Phytochemistry. 24 (4): 801–804. Bibcode:1985PChem..24..801B. doi:10.1016/S0031-9422(00)84898-0.
  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. doi:10.1016/j.jep.2009.12.031. PMID 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). doi: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. doi:10.1039/P19890001787.
  14. ^ Majumder, P.L; Pal, S; Majumder, S (1999). "Dimeric phenanthrenes from the orchid Bulbophyllum reptans". Phytochemistry. 50 (5): 891–897. Bibcode:1999PChem..50..891M. doi:10.1016/S0031-9422(98)00609-8.
  15. ^ Leong Y-W, KAng C-C; Harrison, LJ; Powell, AD (1997). "Phenanthrenes, dihydrophenanthrenes and bibenzyls from the orchid Bulbophyllum vaginatum". Phytochemistry. 44 (1): 157–165. Bibcode:1997PChem..44..157L. doi:10.1016/s0031-9422(96)00387-1. INIST 2557322.
  16. ^ Majumder, PL; Sen, S; Majumder, S (Oct 2001). "Phenanthrene derivatives from the orchid Coelogyne cristata". Phytochemistry. 58 (4): 581–6. Bibcode:2001PChem..58..581M. doi:10.1016/s0031-9422(01)00287-4. PMID 11576602.
  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. doi:10.1086/337458. JSTOR 2474721.
  18. ^ Estrada, Samuel; Toscano, Rubén A.; Mata, Rachel (1999). "New Phenanthrene Derivatives from Maxillaria densa". J. Nat. Prod. 62 (8): 1175–1178. doi:10.1021/np990061e. PMID 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. Bibcode:1990PChem..29..271M. doi:10.1016/0031-9422(90)89048-E.
  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. Bibcode:2013PChL....6..640L. doi:10.1016/j.phytol.2013.08.003.
  21. ^ M. Toyota; T. Yoshida; Y. Kan; S. Takaoka; Y. Asakawa (1996). "(+)-Cavicularin: A Novel Optically Active Cyclic Bibenzyl-Dihydrophenanthrene Derivative from the Liverwort Cavicularia densa Steph". Tetrahedron Letters. 37 (27): 4745–4748. doi:10.1016/0040-4039(96)00956-2.[dead link]
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