Homoisoflavonoid

Homoisoflavonoids (3-benzylidenechroman-4-ones) are a type of phenolic compounds[1] occurring naturally in plants.

Chemical structure of the 3,4-dihydroxyhomoisoflavan sappanol.

Chemically, they have the general structure of a 16-carbon skeleton, which consists of two phenyl rings (A and B) and heterocyclic ring (C).

Synthesis

Homoisoflavones can be synthetized from 2'-hydroxydihydrochalcones.[2]

Homoisoflavanones can be synthetized[3] from 3,5-methoxy phenols via chroman-4-one in three steps[4] or from phloroglucinol.[5]

Conversion

Homoisoflavanes can be obtained from the conversion of homoisoflavonoids.[6]

Natural occurrences

The homoisoflavonoids portulacanones A, B, C and D can be found in Portulaca oleracea (common purslane, Caryophyllales, Portulacaceae).[7]

The 3,4-dihydroxyhomoisoflavans sappanol, episappanol, 3'-deoxysappanol, 3'-O-methylsappanol and 3'-O-methylepisappanol can be found in Caesalpinia sappan.[8]

The homoisoflavones scillavones A and B can be isolated from the bulbs of Scilla scilloides (Barnardia japonica).[9]

Homoisoflavanones
Chemical structure of sappanone A.

Homoisoflavanones (3-Benzyl-4-chromanones[10]) can be found in various plants,[11] notably in Hyacinthaceae (Scilloideae).[12]

Sappanone A can be found in Caesalpinia sappan.[13]

C-Methylated homoisoflavanones (3-(4'-methoxy-benzyl)-5,7-dihydroxy-6-methyl-8-methoxy-chroman-4-one, 3-(4'-methoxy-benzyl)-5,7-dihydroxy-6,8-dimethyl-chroman-4-one, 3-(4'-hydroxy-benzyl)-5,7-dihydroxy-6,8-dimethyl-chroman-4-one, 3-(4'-hydroxy-benzyl)-5,7-dihydroxy-6-methyl-8-methoxy-chroman-4-one and 3-(4'-hydroxy-benzyl)-5,7-dihydroxy-6-methyl-chroman-4-one) can be found in the rhizomes of Polygonum odoratum.[14]

5,7-Dihydroxy-3-(3-hydroxy-4-methoxybenzyl)-chroman-4-one, a homoisoflavanone extracted from Cremastra appendiculata (Orchidaceae), has anti-angiogenic activities and inhibits UVB-induced skin inflammation through reduced cyclooxygenase-2 expression and NF-?B nuclear localization.[15]

In Asparagaceae

3-(4'-Methoxybenzyl)-7,8-methylenedioxy-chroman-4-one, a homoisoflavanone with antimycobacterial activity, can be isolated from Chlorophytum inornatum (Asparagaceae, Agavoideae).[6]

5,7-Dihydroxy-3-(4-methoxybenzyl)-chroman-4-one, 7-hydroxy-3-(4-hydroxybenzyl)-chroman-4-one and 4’-demethyl-3,9-dihydro-punctatin can be isolated from Agave tequilana (Asparagaceae, Agavoideae).[16]

in Scilloideae (Hyacinthaceae)

7-O-α-Rhamnopyranosyl-(1→6)-β-glucopiranosyl-5-hydroxy-3-(4-methoxybenzyl)-chroman-4-one, 7-O-α-rhamnopyranosyl-(1→6)-β-glucopiranosyl-5-hydroxy-3-(4′-hydroxybenzyl)-chroman-4-one, 5,7-dihydroxy-3-(4′-methoxybenzyl)-chroman-4-one (3,9-dihidroeucomin), 5,7-dihydroxy-6-methoxy-3-(4′-methoxybenzyl)-chroman-4-one, 5,7-dihydroxy 3-(4′-hydroxybenzyl)-chroman-4-one (4,4′-demethyl-3,9-dihydropuctatin), 5,7-dihydroxy-3-(4′-hydroxybenzyl)-6-methoxy-chroman-4-one (3,9-dihydroeucomnalin) and 7-hydroxy-3-(4′-hydroxybenzyl)-5-methoxy-chroman-4-one can be isolated from the bulbs of Ledebouria floribunda (tribe Hyacintheae).[17] Other compounds can be found in Ledebouria revoluta, a plant widely used as an ethnomedicinal in southern Africa.[10]

The homoisoflavanone glycosides (-)-7-O-methyleucomol 5-O-beta-D-glucopyranoside, (-)-7-O-methyleucomol 5-O-beta-rutinoside and (-)-7-O-methyleucomol 5-O-beta-neohesperidoside can be isolated from the bulbs of Ornithogalum caudatum (tribe Ornithogaloideae).[18]

Scillascillin-type homoisoflavanones (3-hydroxy-type homoisoflavonoids) can be isolated from Drimiopsis maculata (tribe Hyacintheae, Massoniinae).[19]

Eucomin, eucomol,[20] (E)-7-O-methyl-eucomin, (—)-7-O-methyleucomol, (+)-3,9-dihydro-eucomin and 7-O-methyl-3,9-dihydro-eucomin[21] can be isolated from the bulbs of Eucomis bicolor (tribe Hyacintheae, Massoniinae). 4′-o-Methyl-punctatin, autumnalin and 3,9-dihydro-autumnalin can be found in Eucomis autumnalis.[22]

Five homoisoflavanones, 3,5-dihydroxy-7,8-dimethoxy-3-(3',4'-dimethoxybenzyl)-4-chromanone, 3,5-dihydroxy-7-methoxy-3-(3',4'-dimethoxybenzyl)-4-chromanone, 3,5-dihydroxy-7,8-dimethoxy-3-(3'-hydroxy-4'-methoxybenzyl)-4-chromanone, 3,5,6-trihydroxy-7-methoxy-3-(3'-hydroxy-4'-methoxybenzyl)-4-chromanone and 3,5,7-trihydroxy-3-(3'-hydroxy-4'methoxybenzyl)-4-chromanone, can be isolated from the dichloromethane extract of the bulbs of Pseudoprospero firmifolium (tribe Hyacintheae, subtribe Pseudoprospero).[23]

A homoisoflavanone can also be found in Albuca fastigiata (tribe Ornithogaleae).[24]

The same molecule, 5,6-dimethoxy-7-hydroxy-3-(4′-hydroxybenzyl)-4-chromanone, can be found in the bulbs of Resnova humifusa and Eucomis montana (tribe Hyacintheae, subtribe Massoniinae).[25]

Uses

The homoisoflavonoids portulacanones A, B, C and D show in vitro cytotoxic activities towards four human cancer cell lines.[7]

gollark: Well, can't say no to more xenowyrms.
gollark: It was accepted for some reason?
gollark: Huh. I offered a CB Red and Celestial on a trade for a CB Thalassa.
gollark: I can store hatchlings too.
gollark: I tend to go to whichever has fewest people, since I mostly want multibiomey ones.

See also

References
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  2. "New efficient synthesis and bioactivity of homoisoflavonoids". Arkivoc. 2008 (11): 285–294. 2008. doi:10.3998/ark.5550190.0009.b28.
  3. Jain, Amolak C.; Anita Mehta (née Sharma), (Mrs) (1985). "A new synthesis of homoisoflavanones (3-benzyl-4-chromanones)". Tetrahedron. 41 (24): 5933–5937. doi:10.1016/S0040-4020(01)91433-4.
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  5. Rawal, Viresh H.; Cava, Michael P. (1983). "Synthesis of scillascillin, a naturally occurring benzocyclobutene". Tetrahedron Letters. 24 (50): 5581–5584. doi:10.1016/S0040-4039(00)94146-7.
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  13. Chang, T. S.; Chao, S. Y.; Ding, H. Y. (2012). "Melanogenesis Inhibition by Homoisoflavavone Sappanone a from Caesalpinia sappan". International Journal of Molecular Sciences. 13 (8): 10359–10367. doi:10.3390/ijms130810359. PMC 3431864. PMID 22949866.
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  15. Hur, Seulgi; Lee, Yun Sang; Yoo, Hyun; Yang, Jeong-Hee; Kim, Tae-Yoon (2010). "Homoisoflavanone inhibits UVB-induced skin inflammation through reduced cyclooxygenase-2 expression and NF-κB nuclear localization". Journal of Dermatological Science. 59 (3): 163–169. doi:10.1016/j.jdermsci.2010.07.001. PMID 20724116.
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  23. Koorbanally, C; Sewjee, S; Mulholland, D. A.; Crouch, N. R.; Dold, A (2007). "Homoisoflavanones from Pseudoprospero firmifolium of the monotypic tribe Pseudoprospereae (Hyacinthaceae: Hyacinthoideae)". Phytochemistry. 68 (22–24): 2753–6. doi:10.1016/j.phytochem.2007.08.005. PMID 17884116.
  24. Koorbanally, Chantal; Mulholland, Dulcie A.; Crouch, Neil R. (2005). "A novel 3-hydroxy-3-benzyl-4-chromanone-type homoisoflavonoid from Albuca fastigiata (Ornithogaloideae: Hyacinthaceae)". Biochemical Systematics and Ecology. 33 (5): 545–549. doi:10.1016/j.bse.2004.08.009.
  25. Koorbanally, Neil A.; Crouch, Neil R.; Harilal, Avinash; Pillay, Bavani; Mulholland, Dulcie A. (2006). "Coincident isolation of a novel homoisoflavonoid from Resnova humifusa and Eucomis montana (Hyacinthoideae: Hyacinthaceae)". Biochemical Systematics and Ecology. 34 (2): 114–118. doi:10.1016/j.bse.2005.08.003.
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