Homoisoflavonoid

Homoisoflavones can be synthesized from 2'-hydroxydihydrochalcones.{{Cite journal|url=http://www.arkat-usa.org/get-file/25518/|doi=10.3998/ark.5550190.0009.b28|title=New efficient synthesis and bioactivity of homoisoflavonoids|journal=Arkivoc|volume=2008|issue=11|pages=285–294|year=2008|doi-access=free|hdl=2027/spo.5550190.0009.b28|hdl-access=free |last1=Rao |first1=Vallabhaneni Madhava |last2=Damu |first2=Guri Lakshmi Vasantha |last3=Sudhakar |first3=Dega |last4=Siddaiah |first4=Vidavaluri |last5=Rao |first5=Chunduri Venkata }}

Homoisoflavanones can be synthesized{{Cite journal|doi=10.1016/S0040-4020(01)91433-4|title=A new synthesis of homoisoflavanones (3-benzyl-4-chromanones)|journal=Tetrahedron|volume=41|issue=24|pages=5933–5937|year=1985|last1=Jain|first1=Amolak C.|last2=Anita Mehta (née Sharma)|first2=(Mrs)}} from 3,5-methoxy phenols via chroman-4-one in three steps{{Cite journal|doi=10.1007/s11224-010-9703-x|title=Synthesis and NMR elucidation of homoisoflavanone analogues|journal=Structural Chemistry|volume=22|pages=161–166|year=2010|last1=Shaikh|first1=Mahidansha|last2=Petzold|first2=Katja|last3=Kruger|first3=Hendrik G.|last4=Du Toit|first4=Karen}} or from phloroglucinol.{{Cite journal|doi=10.1016/S0040-4039(00)94146-7|title=Synthesis of scillascillin, a naturally occurring benzocyclobutene|journal=Tetrahedron Letters|volume=24|issue=50|pages=5581–5584|year=1983|last1=Rawal|first1=Viresh H.|last2=Cava|first2=Michael P.}}

;Conversion

Homoisoflavanes can be obtained from the conversion of homoisoflavonoids.{{Cite journal|pmid=19003606|year=2008|last1=Zhang|first1=L|title=Synthesis of (+/-) homoisoflavanone and corresponding homoisoflavane|journal=Journal of Asian Natural Products Research|volume=10|issue=9–10|pages=909–913|last2=Zhang|first2=W. G.|last3=Kang|first3=J|last4=Bao|first4=K|last5=Dai|first5=Y|last6=Yao|first6=X. S.|doi=10.1080/10286020802217499}}

The homoisoflavonoids portulacanones A, B, C and D can be found in Portulaca oleracea (common purslane, Caryophyllales, Portulacaceae).{{Cite journal|doi=10.1016/j.phytochem.2012.05.014|pmid=22683318|title=Homoisoflavonoids from the medicinal plant Portulaca oleracea|journal=Phytochemistry|volume=80|pages=37–41|year=2012|last1=Yan|first1=Jian|last2=Sun|first2=Li-Rong|last3=Zhou|first3=Zhong-Yu|last4=Chen|first4=Yu-Chan|last5=Zhang|first5=Wei-Min|last6=Dai|first6=Hao-Fu|last7=Tan|first7=Jian-Wen}}

The 3,4-dihydroxyhomoisoflavans sappanol, episappanol, 3'-deoxysappanol, 3'-O-methylsappanol and 3'-O-methylepisappanol can be found in Caesalpinia sappan.{{Cite journal|url=http://ci.nii.ac.jp/naid/110006281320/|doi=10.1248/cpb.35.2761|title=Homoisoflavonoids and related compounds. II. Isolation and absolute configurations of 3,4-dihydroxylated homoisoflavans and brazilins from Caesalpinia sappan L|journal=Chemical & Pharmaceutical Bulletin|volume=35|issue=7|pages=2761–2773|year=1987|last1=Namikoshi|first1=Michio|last2=Nakata|first2=Hiroyuki|last3=Yamada|first3=Hiroyuki|last4=Nagai|first4=Minako|last5=Saitoh|first5=Tamotsu|doi-access=free}}

The homoisoflavones scillavones A and B can be isolated from the bulbs of Scilla scilloides (Barnardia japonica).{{Cite journal|pmid=18591825|year=2008|last1=Nishida|first1=Y|title=A new homostilbene and two new homoisoflavones from the bulbs of Scilla scilloides|journal=Chemical & Pharmaceutical Bulletin|volume=56|issue=7|pages=1022–5|last2=Eto|first2=M|last3=Miyashita|first3=H|last4=Ikeda|first4=T|last5=Yamaguchi|first5=K|last6=Yoshimitsu|first6=H|last7=Nohara|first7=T|last8=Ono|first8=M|doi=10.1248/cpb.56.1022|doi-access=free}}

File:Sappanone A.svg]]

Homoisoflavanones (3-Benzyl-4-chromanones{{Cite journal|doi=10.1016/j.sajb.2006.01.004|title=3-Benzyl-4-chromanones (homoisoflavanones) from bulbs of the ethnomedicinal geophyte Ledebouria revoluta (Hyacinthaceae)|journal=South African Journal of Botany|volume=72|issue=4|pages=517–520|year=2006|last1=Moodley|first1=N.|last2=Crouch|first2=N.R.|last3=Mulholland|first3=D.A|last4=Slade|first4=D.|last5=Ferreira|first5=D.|doi-access=free}}) can be found in various plants,{{Cite journal|doi=10.1080/14786410903335174|pmid=20306368|title=The chemical structures, plant origins, ethnobotany and biological activities of homoisoflavanones|journal=Natural Product Research|volume=24|issue=5|pages=457–490|year=2010|last1=Du Toit|first1=Karen|last2=Drewes|first2=Siegfried E.|last3=Bodenstein|first3=Johannes}} notably in Hyacinthaceae (Scilloideae).{{Cite journal|doi=10.1016/j.sajb.2007.01.002|title=Antibacterial activity and QSAR of homoisoflavanones isolated from six Hyacinthaceae species|journal=South African Journal of Botany|volume=73|issue=2|pages=236–241|year=2007|last1=Du Toit|first1=K.|last2=Elgorashi|first2=E.E.|last3=Malan|first3=S.F.|last4=Mulholland|first4=D.A.|last5=Drewes|first5=S.E.|last6=Van Staden|first6=J.|doi-access=free}}

Sappanone A can be found in Caesalpinia sappan.{{Cite journal|pmc=3431864|year=2012|last1=Chang|first1=T. S.|title=Melanogenesis Inhibition by Homoisoflavavone Sappanone a from Caesalpinia sappan|journal=International Journal of Molecular Sciences|volume=13|issue=8|pages=10359–10367|last2=Chao|first2=S. Y.|last3=Ding|first3=H. Y.|doi=10.3390/ijms130810359|pmid=22949866 |doi-access=free }}

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.{{Cite journal|pmid=19384735|year=2009|last1=Wang|first1=D|title=A new C-methylated homoisoflavanone and triterpenoid from the rhizomes of Polygonatum odoratum|journal=Natural Product Research|volume=23|issue=6|pages=580–9|last2=Li|first2=D|last3=Zhu|first3=W|last4=Peng|first4=P|doi=10.1080/14786410802560633}}

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.{{Cite journal|doi=10.1016/j.jdermsci.2010.07.001|pmid=20724116|title=Homoisoflavanone inhibits UVB-induced skin inflammation through reduced cyclooxygenase-2 expression and NF-κB nuclear localization|journal=Journal of Dermatological Science|volume=59|issue=3|pages=163–169|year=2010|last1=Hur|first1=Seulgi|last2=Lee|first2=Yun Sang|last3=Yoo|first3=Hyun|last4=Yang|first4=Jeong-Hee|last5=Kim|first5=Tae-Yoon}}

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

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).{{Cite journal|doi=10.3390/molecules15053295|pmid=20657479|title=Homoisoflavanones from Agave tequilana Weber|journal=Molecules|volume=15|issue=5|pages=3295–3301|year=2010|last1=Morales-Serna|first1=José Antonio|last2=Jiménez|first2=Armando|last3=Estrada-Reyes|first3=Rosa|last4=Marquez|first4=Carmen|last5=Cárdenas|first5=Jorge|last6=Salmón|first6=Manuel|pmc=6263332 |doi-access=free }}

; 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).{{Cite journal|doi=10.1016/j.fitote.2008.10.006|pmid=19027834|title=Homoisoflavanones from Ledebouria floribunda|journal=Fitoterapia|volume=80|issue=2|pages=96–101|year=2009|last1=Calvo|first1=María Isabel}} Other compounds can be found in Ledebouria revoluta, a plant widely used as an ethnomedicinal in southern Africa.

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).{{Cite journal|pmid=11858761|year=2002|last1=Tang|first1=Y|title=Three new homoisoflavanone glycosides from the bulbs of Ornithogalum caudatum|journal=Journal of Natural Products|volume=65|issue=2|pages=218–20|last2=Yu|first2=B|last3=Hu|first3=J|last4=Wu|first4=T|last5=Hui|first5=H|doi=10.1021/np010466a}}

Scillascillin-type homoisoflavanones (3-hydroxy-type homoisoflavonoids) can be isolated from Drimiopsis maculata (tribe Hyacintheae, Massoniinae).{{Cite journal|pmid=11274776|year=2001|last1=Koorbanally|first1=C|title=Scillascillin-type homoisoflavanones from Drimiopsis maculata (Hyacinthaceae)|journal=Biochemical Systematics and Ecology|volume=29|issue=5|pages=539–541|last2=Crouch|first2=N. R.|last3=Mulholland|first3=D. A.|doi=10.1016/s0305-1978(00)00073-9}}

Eucomin, eucomol,{{Cite book|doi=10.1007/978-3-7091-8611-4_3|chapter=Homoisoflavanones and Biogenetically Related Compounds|title=Fortschritte der Chemie organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products|volume=40|pages=105–152|year=1981|last1=Heller|first1=W.|last2=Tamm|first2=Ch.|isbn=978-3-7091-8613-8}} (E)-7-O-methyl-eucomin, (—)-7-O-methyleucomol, (+)-3,9-dihydro-eucomin and 7-O-methyl-3,9-dihydro-eucomin{{Cite journal|doi=10.1002/hlca.19760590618|pmid=1017955|title=Homoisoflavanone. IV. Neue Inhaltsstoffe der Eucomin-Reihe von Eucomis bicolor|journal=Helvetica Chimica Acta|volume=59|issue=6|pages=2048–2058|year=1976|last1=Heller|first1=Werner|last2=Andermatt|first2=Paul|last3=Schaad|first3=Werner A.|last4=Tamm|first4=Christoph}} 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.{{Cite journal|doi=10.1016/0040-4039(70)89003-7|title=The homo-isoflavones II1). Isolation and structure of 4′-o-methyl-punctatin, autumnalin and 3,9-dihydro-autumnalin|journal=Tetrahedron Letters|volume=11|issue=7|pages=475–478|year=1970|last1=Sidwell|first1=W.T.L.|last2=Tamm|first2=Ch.}}

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).{{Cite journal|pmid=17884116|year=2007|last1=Koorbanally|first1=C|title=Homoisoflavanones from Pseudoprospero firmifolium of the monotypic tribe Pseudoprospereae (Hyacinthaceae: Hyacinthoideae)|journal=Phytochemistry|volume=68|issue=22–24|pages=2753–6|last2=Sewjee|first2=S|last3=Mulholland|first3=D. A.|last4=Crouch|first4=N. R.|last5=Dold|first5=A|doi=10.1016/j.phytochem.2007.08.005}}

A homoisoflavanone can also be found in Albuca fastigiata (tribe Ornithogaleae).{{Cite journal|doi=10.1016/j.bse.2004.08.009|title=A novel 3-hydroxy-3-benzyl-4-chromanone-type homoisoflavonoid from Albuca fastigiata (Ornithogaloideae: Hyacinthaceae)|journal=Biochemical Systematics and Ecology|volume=33|issue=5|pages=545–549|year=2005|last1=Koorbanally|first1=Chantal|last2=Mulholland|first2=Dulcie A.|last3=Crouch|first3=Neil R.}}

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).{{Cite journal|doi=10.1016/j.bse.2005.08.003|title=Coincident isolation of a novel homoisoflavonoid from Resnova humifusa and Eucomis montana (Hyacinthoideae: Hyacinthaceae)|journal=Biochemical Systematics and Ecology|volume=34|issue=2|pages=114–118|year=2006|last1=Koorbanally|first1=Neil A.|last2=Crouch|first2=Neil R.|last3=Harilal|first3=Avinash|last4=Pillay|first4=Bavani|last5=Mulholland|first5=Dulcie A.}}

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

• Flavonoids and isoflavonoids, related chemicals with a 15-carbon skeleton

{{reflist}}

{{Homoisoflavonoid}}