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A Journey of Twenty-Five Years Through the Ecological Biochemistry of Flavonoidsthis Review Was Written in Response to the Auth

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A Journey of Twenty-Five Years Through the Ecological Biochemistry of Flavonoidsthis Review Was Written in Response to the Auth 70028 (RV-8) Biosci. Biotechnol. Biochem., 71, 70028-1–18, 2007 Award Review A Journey of Twenty-Five Years through the Ecological Biochemistry of Flavonoids Satoshi TAHARA Laboratory of Ecological Chemistry, Graduate School of Agriculture, Hokkaido University, Kita-ku, Sapporo 060-8589, Japan Online Publication, June 7, 2007 [doi:10.1271/bbb.70028] The ecological biochemistry of flavonoids, in which I 3 have been engaged for 25 years, is summarized in this 2 3 1 review article. The review covers (1) a survey of rare 1 2 bio-active flavonoids in higher plants; (2) the fungal metabolism of prenylated flavonoids; (3) flavonoids anti- Flavonoid skeleton Isoflavonoid skeleton in the narrow sense (1,2-diphenylpropane) doting against benzimidazole fungicides; (4) dihydro- (1,3-diphenylpropane) flavonolAdvance ampelopsin in Salix sacharinensis as a View feeding stimulant towards willow beetles; and (5) flavones as Flavonoid skeletons in the broad sense signaling substances in the life-cycle development of the 3' 8 1 2' 9 O phytopathogenic Peronosporomycete Aphanomyces co- 4' 7 2 chlioides, a cause of spinach root rot and sugar beet 8 1 1' B A C 2' 9 O 5' 6 1' 7 10 3 3' damping-off diseases. Finally recent trends in the eco- A C 2 6' 5 4 B 6 3 4' logical biochemistry of flavonoids are briefly described. 10 6' 5 4 5' 2-phenylchroman 3-phenylchroman Key words: flavonoids; ecological biochemistry; secon- dary metabolites; signal substance; allelo- Fig. 1. ProofsCarbon Skeletons of Flavonoids. chemicals skeletons that can be subdivided into some 10 classes I. General Introduction according to their oxidation levels and variations in the complexity of carbon skeletons caused by alk(en)yl- One of the representative classes of plant secondary ation, glycosylation, oligomerization, and so on. metabolites, the flavonoids (C6–C3–C6) consist of two The functional diversity of flavonoids is due to their main groups, flavonoids in the narrow sense and structural diversity and their general properties as poly- isoflavonoids. The isoflavonoids are structurally distinct phenols with structural similarity to steroids. Due to the from other flavonid classes in that they contain a C15 great numbers of known flavonoids (estimated to be skeleton based on 1,2-diphenylpropane, whereas the about 10,000) and their diverse bioactivities, for exam- flavonoid classes consist of another C15 skeleton based ple, as polyphenols (antioxidative, active oxygen scav- on 1,3-diphenylpropane. The great majority of flavo- enging, UV-absorbing, protein denaturing, chelate form- noids have a 2- or 3-phenylchroman skeleton, and the ing, etc.), as steroid analogs (estrogenic, cell-membrane former skeleton results in phenyl group migration from dysfunctioning, and cell proliferation regulating), as C-2 to C-3 on ring C (Fig. 1). Nine carbons consisting plant defensive agents (antifungal, insecticidal, and alle- of B- and C-rings originate from that of cinnamate lopathic), as signal substances between autotrophs and biosynthesized via the shikimate pathway, while six heterotrophs (symbiosis, pathogenesis, feeding, and ovi- carbons of the A-ring are supplied by three cycles of the positing), as antidotes against fungicides, herbicides, polyketide chain elongation reaction using p-coumaroyl- and snake venoms, and as miscellaneous enzyme inhib- S-CoA as a starter. The structural diversity of natural itors, it is impossible to cover all of them here, but flavonoids is mainly due to two fundamental carbon details of the biological and chemical aspects of fla- This review was written in response to the author’s receipt of The Japan Bioscience, Biotechnology, and Agrochemistry Society Senior Scientist Award in 2006. Address correspondence to; Tel: +81-11-706-3840; Fax: +81-11-706-4182; E-mail: [email protected] 70028-2 S. TAHARA vonoids are to be found in general reference books,1–8) a optically active components using optically active 2- handbook of natural flavonoids,9) analytical books,10–15) methyl-2-trifluoromethyl-2-phenylacetic acid so that the monographs,16–21) and diverse review articles (not con- relationship between the absolute stereochemistry and tained in the references mentioned above).22–35) CD Cotton effects could be determined.29) This review looks back over the path of my studies Four coumaranochroman-4-ones (9–12) belonging to of flavonoids over the past 25 years. My studies of the a new class of isoflavonoids, lupinols A (9) and B (10) ecological biochemistry of flavonoids started in Sep- from Lupinus albus, lupinol C (11) from L. luteus, and tember 1981 when I was accepted as a visiting research piscerythrol (12) from P. erythrina, were reported in associate by Professor Jeffrey B. Harborne at the 1991 for the first time (see reference 29 and studies cited Phytochemical Unit in the Plant Science Laboratories therein). Compound 12 was easily dehydrated with of the University of Reading, UK. I studied at the sulfuric acid to yield lisetin (13), the first coumarono- laboratories on a research project concerning the analy- chromone isolated from P. erythrina in 1956, and from sis and evaluation of antifungal isoflavones in lupins, P. communis in 1966. Compounds 9 and 11 were sim- proposed by Professor Harborne and supervised by Dr. ilarly dehydrated to yielded lupinalbins F (14) and B John L. Ingham. (15) respectively. The second naturally occurring cou- maronochromone found in Millettia auriculata was II. Survey of Rare Flavonoids in Higher millettin (16). A 3-hydroxycoumaranochroman-4-one Plants (erysenegalensin J, 17) corresponding to the hydrate of 16 was reported from Erythrina senegalensis by Wandji The number of flavonoids known at the end of 2004 et al. in 1995.40) 20-Hydroxyisoflavones, viz.,20-hydrox- was reported to be 8,150 (including 1,609 isoflavo- ylupalbigenin (18), luteone (19), piscerythrone (20), and noids),8) but these numbers are approximate. For ex- auriculatin (21), structurally related to these coumara- ample,Advance the coumaronochromones, a small class ofView isofla- nochroman-4-ones (9, 11, 12, and 17), were also isolated vonoids, included 39 (three of which should be elim- from leguminous plants. The schematic relationships inated from the list due to unconformity of their carbon among 20-hydroxyisoflavone, coumaranochromanone, skeletons with that of coumaronochromone),8) but the and coumaronochromone are shown in Fig. 2. list clearly missed at least eight compounds isolated by The chemical structure of a complex estrogenic iso- our group.36–39) flavone, kwakhurin (22), isolated from Pueraria mirifica In our survey of isoflavonoidal constituents in the root known as a rejuvenating plant in Thailand, was bark of the Jamaican dogwood (Piscidia erythrina (L.) established by spectroscopic analysis of diverse deriv- Sarg.), known to be fish-poisoning and rich in isofla- atives.18,41) Recently, a total synthesis of 22 with its vones, with a highly substituted B-ring, two 40-amino- triisopropyl etherProofs was reported.42,43) substituted isoflavones and one with an oxazole ring Two novel isoflavone dimers belonging to a new class were isolated.29) Their exotic structures were estab- of biflavonoids, 5,7,40-trihydroxycoumaranochroman-4- lished as 40-amino-5,7,30-trihydroxy-50-methoxy-20,60- one-(3 ! 5000)-500,700,2000,4000-tetrahydroxyisoflavone (lu- di-(3,3-dimethylallyl)isoflavone (1), 40-amino-5,7,30-tri- pinalbisone A, 23) and 5,7,40-trihydroxycoumarano- hydroxy-50-methoxy-8,20-di-(3,3-dimethylallyl)isoflavone chroman-4-one-(3 ! 800)-500,700,2000,4000-tetrahydroxyiso- (2), and 7-hyroxy-50-methoxy-20-(3,3-dimethylallyl)-ox- flavone (lupinalbisone B, 24), were isolated from the azolo-[4000,5000:40,30]-isoflavone (3) by spectroscopic and partly senesced roots of L. albus, and their structures chemical methods. The first one (1) was chemically including relative stereochemistry were elucidated by converted to a compound which was also obtained from spectroscopic methods.44) An enzymatic reaction using the corresponding 40-hydroxyisoflavone, erythbigenin horseradish peroxidase and 20-hydroxygenistein (25)as (4).29) Nitrogenous plant secondary metabolites occur a substrate yielded these dimers together with 5,7,40- widely in nature, but to our knowledge no naturally trihydroxycoumaronochromone (lupinalbin A, 26). It occurring flavonoids directly nitrogenated on the C6– has been shown that dimerization of 25 results in a C3–C6 skeleton have been described. remarkable increase in fungitoxicity. A class of naturally Further unusual flavonoids in P. erythrina were two occurring fungitoxins such as 23 and 24 are supposed to pairs of isoflavone atropisomers, erythbigenones A (5) be produced from less fungitoxic precursors in bio- and B (6), and erythbigenols A (7) and B (8), each of logically and/or mechanically injured or stressed plants which possessed a fully(penta)-substituted B-ring.29) by the aid of constitutive enzymes in the relevant plant. The isoflavones composing each pair were diastereoiso- These fungitoxic products, 23 and 24, showing intensi- meric due to two asymmetric factors (a rotationally fied antifungal activity may be classified as members of hindered C3–C10 axis and an asymmetric carbon at C– the post-inhibitins.45) They play significant roles in the 200) and were separated by TLC. The relative stereo- defense systems of plants in emergencies when the structures of these atropdiastereoisomers were estab- plants are biologically or physically stressed, especially lished by a combination of spectroscopic and chemical during the lag phase prior to de novo biosynthesis of methods.
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