请输入您要查询的百科知识：

　

词条 Phenanthrenoid
释义

  1. Phenanthrols

  2. Chemistry

  3. Natural occurrences

      In orchids    Glycosides  

  4. Metabolism

  5. See also

  6. References

  7. External links

Phenanthreoids are chemical compounds formed with a phenanthrene backbone. Those compound are naturally occurring in plants, although they can also be synthetized.[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 higher plants, mainly in the Orchidaceae family. A few phenanthrenes have been found in the Hepaticae class and Dioscoreaceae, Combretaceae and Betulaceae families.[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]

From the stems of the orchid Flickingeria fimbriata, three phenanthrenes can be isolated. 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 of 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

  • (+)-Cavicularin, a cyclic bibenzyl-dihydrophenanthrene derivative[21]

References

1. ^{{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 | url = | journal = J. Am. Chem. Soc. | volume = 99 | issue = 21| pages = 7083–7085 | doi = 10.1021/ja00463a063 }}
2. ^{{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 | url = | journal = Biomarkers | volume = 8 | issue = 2| pages = 93–109 | pmid = 12775495 | doi=10.1080/1354750021000046570}}
3. ^1 {{cite journal | last1 = Kovács | first1 = Adriána | last2 = Vasas | first2 = Andrea | last3 = Hohmann | first3 = Judit | year = 2008 | title = Natural phenanthrenes and their biological activity | url = | journal = Phytochemistry | volume = 69 | issue = 5| pages = 1084–1110 | doi = 10.1016/j.phytochem.2007.12.005 }}
4. ^{{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 | url = | journal = Phytochemistry | volume = 68 | issue = 5| pages = 687–691 | doi = 10.1016/j.phytochem.2006.10.028 }}
5. ^{{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. | url = | journal = Nat Prod Res | volume = 27 | issue = 2| pages = 155–163 | doi = 10.1080/14786419.2012.662759 | pmid = 22360833 }}
6. ^{{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 | url = | journal = J. Nat. Prod. | volume = 55 | issue = 4| pages = 533–535 | doi = 10.1021/np50082a027 }}
7. ^{{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 | url = | journal = Bioorg Med Chem Lett | volume = 20 | issue = 12| pages = 3785–7 | doi = 10.1016/j.bmcl.2010.04.054 }}
8. ^{{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 | url = | journal = Journal of Natural Products | volume = 70 | issue = 12| pages = 1925–1929 | doi=10.1021/np070423f}}
9. ^{{cite journal | last1 = Honda | first1 = Chie | last2 = Yamaki | first2 = Masae | year = 2000 | title = Phenanthrenes from Dendrobium plicatile | url = | journal = Phytochemistry | volume = 53 | issue = 8| pages = 987–990 | doi = 10.1016/S0031-9422(99)00497-5 }}
10. ^{{cite journal | last1 = Bhandari | first1 = S | year = 1985 | title = Nudol, a phenanthrene of the orchids Eulophia nuda, Eria carinata and Eria stricta | url = | journal = Phytochemistry | volume = 24 | issue = 4| pages = 801–804 | doi = 10.1016/S0031-9422(00)84898-0 }}
11. ^{{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 | url = | journal = Journal of Ethnopharmacology | volume = 128 | issue = 1| pages = 251–253 | doi = 10.1016/j.jep.2009.12.031 | pmid=20045453}}
12. ^{{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 | url = | journal = Acta Crystallographica E | volume = 64 | issue = 6| pages = | doi = 10.1107/S1600536808014451/bt2712Isup2.hkl }}
13. ^{{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 | url = | journal = J. Chem. Soc. | volume = 1 | issue = 10| pages = 1787–1791 | doi = 10.1039/P19890001787 }}
14. ^{{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 | url = | journal = Phytochemistry | volume = 50 | issue = 5| pages = 891–897 | doi = 10.1016/S0031-9422(98)00609-8 }}
15. ^{{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 | id={{INIST|2557322}} }}
16. ^{{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}}
17. ^{{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}}
18. ^{{cite journal | last1 = Estrada | first1 = Samuel | last2 = Toscano | first2 = Rubén A. | last3 = Mata | first3 = Rachel | year = 1999 | title = New Phenanthrene Derivatives from Maxillaria densa | url = | journal = J. Nat. Prod. | volume = 62 | issue = 8| pages = 1175–1178 | doi = 10.1021/np990061e }}
19. ^{{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 | url = | journal = Phytochemistry | volume = 29 | issue = 1| pages = 271–274 | doi = 10.1016/0031-9422(90)89048-E }}
20. ^{{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 | url = | journal = Phytochemistry Letters | volume = 6 | issue = 4| pages = 640–644 | doi = 10.1016/j.phytol.2013.08.003 }}
21. ^{{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 | url = http://www.sciencedirect.com/science?_ob=ArticleURL&_udi=B6THS-3V99257-14&_user=1065764&_handle=V-WA-A-W-CD-MsSAYVA-UUA-U-AAWAUAUZVD-AAAYCEAVVD-AZVWVYEDB-CD-U&_fmt=summary&_coverDate=07%2F01%2F1996&_rdoc=32&_orig=browse&_srch=%23toc%235290%231996%23999629972%2339771!&_cdi=5290&view=c&_acct=C000051225&_version=1&_urlVersion=0&_userid=1065764&md5=4e93161113dd5af8dad768dd3c3d842a | doi = 10.1016/0040-4039(96)00956-2 | volume = 37 | issue = 27}}{{dead link|date=March 2019|bot=medic}}{{cbignore|bot=medic}}

External links

  • {{wiktionary-inline|phenanthrol}}
{{stilbenoids}}{{clear right}}{{Phenanthrenoid}}

1 : Phenanthrenoids
随便看

　

开放百科全书收录14589846条英语、德语、日语等多语种百科知识，基本涵盖了大多数领域的百科知识，是一部内容自由、开放的电子版国际百科全书。

　

Copyright © 2023 OENC.NET All Rights Reserved
京ICP备2021023879号 更新时间：2024/11/13 18:12:16