Publication Cover
Natural Product Research
Formerly Natural Product Letters
Volume 24, 2010 - Issue 5
436
Views
29
CrossRef citations to date
0
Altmetric
Review article

The chemical structures, plant origins, ethnobotany and biological activities of homoisoflavanones

, &
Pages 457-490 | Received 20 May 2009, Accepted 08 Oct 2009, Published online: 17 Mar 2010

References

  • Adinolfi , M , Aquila , T , Barone , G , Lanzetta , R and Parrilli , M . 1989 . Homoisoflavanones from Bellevalia romana . Phytochemistry , 28 ( 11 ) : 3244 – 3246 .
  • Adinolfi , M , Barone , G , Belardini , M , Lanzetta , R , Laonigro , G and Parrilli , M . 1984 . 3-Benzyl-4-chromanones from Muscari comosum . Phytochemistry , 23 ( 9 ) : 2091 – 2093 .
  • Adinolfi , M , Barone , G , Belardini , M , Lanzetta , R , Laonigro , G and Parrilli , M . 1985 . Homoisoflavanones from Muscari comosum bulbs . Phytochemistry , 24 ( 10 ) : 2423 – 2426 .
  • Adinolfi , M , Corsaro , MM , Lanzetta , R , Laonigro , G , Mangoni , L and Parrilli , M . 1987 . Ten homoisoflavanones from two Muscari species . Phytochemistry , 26 ( 1 ) : 285 – 290 .
  • Adinolfi , M , Lanzetta , R , Laonigro , G , Parrilli , M and Breitmaier , E . 1986 . 1H and 13C chemical shift assignments of homoisoflavanones . Magnetic Resonance in Chemistry , 24 : 663 – 667 .
  • Amschler , G , Frahm , AW , Hatzelmann , A , Kilian , U , Muller-Doblies , D and Muller-Doblies , U . 1996 . Constituents of Veltheimia viridifolia. I. Homoisoflavanones of the bulbs . Planta Medica , 62 ( 6 ) : 534 – 539 .
  • Bangani , V , Crouch , NR and Mulholland , DA . 1999 . Homoisoflavanones and stilbenoids from Scilla nervosa . Phytochemistry , 51 ( 7 ) : 947 – 951 .
  • Barone , G , Corsaro , MM , Lanzetta , R and Parrilli , M . 1988 . Homoisoflavanones from Muscari neglectum . Phytochemistry , 27 ( 3 ) : 921 – 923 .
  • Böhler , P and Tamm , C . 1967 . The homo-isoflavones, a new class of natural product. Isolation and structure of eucomin and eucomol . Tetrahedron Letters , 8 ( 36 ) : 3479 – 3483 .
  • Camarda , L , Merlini , L and Nasini , G . 1983 . Dragon's blood from Dracaena draco, structure of novel homoisoflavonoids . Heterocycles , 20 ( 1 ) : 39 – 43 .
  • Chen , P and Yang , J-S . 2007 . Flavonol galactoside caffeiate ester and homoisoflavones from Caesalpinia millettii Hook . et Arn. Chemical & Pharmaceutical Bulletin (Tokyo) , 55 : 655 – 657 .
  • Corsaro , MM , Lanzetta , R , Mancino , A and Parrilli , M . 1992 . Homoisoflavanones from Chionodoxa luciliae . Phytochemistry , 31 ( 4 ) : 1395 – 1397 .
  • Crouch , NR , Bangani , V and Mulholland , DA . 1999 . Homoisoflavanones from three South African Scilla species . Phytochemistry , 51 ( 7 ) : 943 – 946 .
  • Della Loggia , R. , Del Negro , P. , Tubaro , A. , Barone , G. and Parrilli , M. 1989 . Homoisoflavanones as anti-inflammatory principles of Muscari comosum . Planta Medica , 55 : 587 – 588 .
  • Dlamini , B . (1981). Swaziland flora: Their local names and uses. Ministry of Agriculture and Co-operatives, Forestry Section. Mbabane, Swaziland
  • Duke , JA . 2002 . Handbook of medicinal herbs , London : CRC Press .
  • Du Toit , K , Elgorashi , EE , Malan , SF , Drewes , SE , van Staden , J Crouch , NR . 2005 . Anti-inflammatory activity and QSAR studies of compounds isolated from Hyacinthaceae species and Tachiadenus longiflorus Griseb (Gentianaceae) . Bioorganic & Medicinal Chemistry , 13 : 2561 – 2568 .
  • Du Toit , K , Elgorashi , EE , Malan , SF , Mulholland , DA , Drewes , SE and Van Staden , J . 2007 . Antibacterial activity and QSAR of homoisoflavanones isolated from six Hyacinthaceae species . South African Journal of Botany , 73 : 236 – 241 .
  • Finckh , RE and Tamm , C . 1970 . Homo-isoflavones. III. Isolation and structure of punctatin, 3,9-dihydropunctatin, 4′–O–methyl-3,9-dihydropunctatin, 4′-demethyleucomin and 4′-demethyl-5-O-methyl-3,9-dihydroeucomin . Experientia , 26 ( 5 ) : 472 – 473 .
  • Fukai , T , Wang , Q-H , Inami , R and Nomura , T . 1990 . Structures of prenylated dihydrochalcone, Gancaonin J and homoisoflavanone, Gancaonin K from Glycyrrhiza pallidiflora . Heterocycles , 31 ( 4 ) : 643 – 650 .
  • Gerstner , J . 1939 . A preliminary check list of Zulu names of plants . Bantu studies , 13 : 131 – 149 .
  • Gerstner , J . 1941 . A preliminary check list of Zulu names of plants with short notes . Bantu studies , 15 : 369 – 383 .
  • Grancaiova , Z , Masterová , I and Suchy , V . 1992 . Constituents of Muscari armeniacum . Fitoterapia , LXIII ( 4 ) : 380
  • Heller , W , Andermatt , P , Schaad , W and Tamm , C . 1976 . Helvetica Chimica Acta , 59 : 2048 – 2058 .
  • Heller , W and Tamm , C . 1978 . 5,7-Dihydroxy-8-methoxy-chroman-4-on aus dem Zwiebelwachs von Eucomis comosa . Helvetica Chimica Acta , 61 ( 124 ) : 1257 – 1261 .
  • Heller , W and Tamm , C . 1981 . Homoisoflavanones and biogenetically related compounds . Fortschritte der Chemie Organischer Naturstoffe , 40 : 105 – 152 .
  • Hoang Anh , N , Van Sung , T , Porzel , A , Franke , K and Wessjohann , LA . 2003 . Homoisoflavanoids from Ophiopogon japonicus Ker-Gawl . Phytochemistry , 62 : 1153 – 1158 .
  • Huang , P-L , Gan , K-H , Wu , R-R and Lin , C-N . 1997 . Benzoquinones, a homoisoflavanone and other constituents from Polygonatum alte-lobatum . Phytochemistry , 44 ( 7 ) : 1369 – 1373 .
  • Hutchings , A , Scott , A , Lewis , G and Cunningham , AB . (1996). Zulu medicinal plants: An inventory. South Africa: University of KwaZulu-Natal Press
  • Jacot Guillarmod , A . 1971 . Flora of Lesotho , Lehre : Verlag von Cramer .
  • Jain , SC , Sharma , SK , Kumar , R , Rajwanshi , VK and Ravindra Babu , B . 1997 . A homoisoflavanone from Pterocarpus marsupium . Phytochemistry , 44 ( 4 ) : 765 – 766 .
  • Jaspal , S and Grover , S . 2004 . An improved synthesis of homoisoflavanones . Indian Journal of Chemistry , 43B : 1782 – 1783 .
  • Kim , JH , Kim , KH , Kim , JH , Yu , YS , Kim , Y-M Kim , K-W . 2007 . Homoisoflavanone inhibits retinal neovascularization through cell cycle arrest with decrease of cdc2 expression . Biochemical and Biophysical Research Communications , 362 ( 4 ) : 848 – 852 .
  • Kim , JH , Yu , YS , Jun , HO , Kwon , HJ , Park , KH and Kim , KW . 2008 . Inhibition of choroidal neovascularization by homoisoflavanone, a new angiogenesis inhibitor . Molecular Vision , 14 : 556 – 561 .
  • Kirkiacharian , B , Gomis , M , Tongo , HG , Mahuteau , J and Brion , J . 1984 . The 13C NMR spectra of homoisoflavonoids . Organic Magnetic Resonance , 22 ( 2 ) : 106 – 108 .
  • Koorbanally , NA , Crouch , NR , Harilal , A , Pillay , B and Mulholland , DA . 2006c . Coincident isolation of a novel homoisoflavonoid from Resnova humifusa and Eucomis montana (Hyacinthoideae: Hyacinthaceae) . Biochemical Systematics and Ecology , 34 ( 2 ) : 114 – 118 .
  • Koorbanally , C , Crouch , NR , Langlois , A , Du Toit , K , Mulholland , DA and Drewes , SE . 2006a . Homoisoflavanones and spirocyclic nortriterpenoids from three Eucomis species: E. comosa, E. schijffii and E. pallidiflora subsp. pole-evansii (Hyacinthaceae) . South African Journal of Botany , 72 ( 3 ) : 428 – 433 .
  • Koorbanally , C , Crouch , NR and Mulholland , DA . 2001 . Scillascillin-type homoisoflavanones from Drimiopsis maculata (Hyacinthaceae) . Biochemical Systematics and Ecology , 29 ( 5 ) : 539 – 541 .
  • Koorbanally , C , Mulholland , DA and Crouch , NR . 2005a . A novel 3-hydroxy-3-benzyl-4-chromanone-type homoisoflavonoid from Albuca fastigiata (Ornithogaloideae: Hyacinthaceae) . Biochemical Systematics and Ecology , 33 : 545 – 549 .
  • Koorbanally , C , Mulholland , DA and Crouch , NR . 2005b . A novel homoisoflavonoid from Drimia delagoensis (Urgineoideae: Hyacinthaceae) . Biochemical Systematics and Ecology , 33 ( 7 ) : 743 – 748 .
  • Koorbanally , C , Mulholland , DA and Crouch , NR . 2006b . Norlignans and homoisoflavanones from two South African Drimiopsis species (Hyacinthaceae: Hyacinthoideae) . Biochemical Systematics and Ecology , 34 ( 7 ) : 588 – 592 .
  • Koorbanally , C , Sewjee , S , Mulholland , DA , Crouch , NR and Dold , A . 2007 . Homoisoflavanones from Pseudoprospero firmifolium of the monotypic tribe Pseudoprospereae (Hyacinthaceae: Hyacinthoideae) . Phytochemistry , 68 ( 22–24 ) : 2753 – 2756 .
  • Kouno , I , Komori , T and Kawasaki , T . 1973 . Zur struktur der neuen typen homo-isoflavanone aus bulben von . Tetrahedron Letters , 14 ( 46 ) : 4569 – 4572 .
  • Likhitwitayawuid , K , Sawasdee , K and Kirtikara , K . 2002 . Flavonoids and stilbenoids with COX-1 and COX-2 inhibitory activity from Dracaena loureiri . Planta Medica , 68 ( 9 ) : 841 – 843 .
  • López , SN , Sierra , MG , Gattuso , SJ , Furlan , RL and Zacchino , SA . 2006 . An unusual homoisoflavanone and a structurally-related dihydrochalcone from Polygonum ferrugineum (Polygonaceae) . Phytochemistry , 67 ( 19 ) : 2152 – 2158 .
  • Maheswara , M , Siddaiah , V and Venkata Rao , C . 2006 . Two new homoisoflavonoids from Caesalpinia pulcherrima . Chemical & Pharmaceutical Bulletin (Tokyo) , 54 ( 8 ) : 1193 – 1195 .
  • Mander , M . (1997). Marketing of indigenous medicinal plants in South Africa. Investigational Report 164. Institute of Natural Resources, South Africa
  • Masterová , I , Suchy , V , Uhrin , D , Ubik , K , Grancaiova , Z and Bobovnicky , B . 1991 . Homoisoflavanones and other constituents from Muscari racemosum . Phytochemistry , 30 ( 2 ) : 713 – 714 .
  • Miadoková , E , Masterová , I , Vlcková , V , Dúhová , V and Tóth , J . 2002 . Antimutagenic potential of homoisoflavonoids from Muscari racemosum . Journal of Ethnopharmacology , 81 ( 3 ) : 381 – 386 .
  • Mimaki , Y , Kanmoto , T , Sashida , Y , Nishino , A , Satomi , Y and Nishino , H . 1996 . Steroidal saponins from the underground parts of Chlorophytum comosum and their inhibitory activity on tumour promoter-induced phospholipids metabolism of hela cells . Phytochemistry , 41 ( 5 ) : 1405 – 1410 .
  • Moodley , N , Crouch , NR , Mulholland , DA , Slade , D and Ferreira , D . 2006 . 3-Benzyl-4-chromanones (homoisoflavanones) from bulbs of the ethnomedicinal geophyte Ledebouria revoluta (Hyacinthaceae) . South African Journal of Botany , 72 ( 4 ) : 517 – 520 .
  • Mulholland , DA , Crouch , NR , Koorbanally , C , Moodley , N and Pohl , T . 2006 . Infraspecific chemical variation in Scilla zebrina (Hyacinthaceae) . Biochemical Systematics and Ecology , 34 ( 3 ) : 251 – 255 .
  • Mulholland , DA , Crouch , NR , Pohl , TL and Ndlovu , E . 2004 . A homoisoflavanone from Ornithogalum longibracteatum (Ornithogaloideae: Hyacinthaceae) . Biochemical Systematics and Ecology , 32 ( 5 ) : 499 – 502 .
  • Mutanyatta , J , Matapa , BG , Shushu , DD and Abegaz , BM . 2003 . Homoisoflavonoids and xanthones from the tubers of wild and in vitro regenerated Ledebouria graminifolia and cytotoxic activities of some of the homoisoflavonoids . Phytochemistry , 62 ( 5 ) : 797 – 804 .
  • Nguyen , AT , Fontaine , J , Malonne , H and Duez , P . 2006 . Homoisoflavanones from Disporopsis aspera . Phytochemistry , 67 ( 19 ) : 2159 – 2163 .
  • Nishida , Y , Eto , M , Miyashita , H , Ikeda , T , Yamaguchi , K Yoshimitshu , H . 2008 . A new homostilbene and two new homoisoflavones from the bulbs of Scilla scilloides . Chemical & Pharmaceutical Bulletin (Tokyo) , 56 ( 7 ) : 1022 – 1025 .
  • O'Donnell , G , Bucar , F and Gibbons , S . 2006 . Phytochemistry and antimycobacterial activity of Chlorophytum inornatum . Phytochemistry , 67 ( 2 ) : 178 – 182 .
  • Osbaldeston , TA and Wood , RPA . 2000 . Dioscorides – de materia medica , Johannesburg : IBIDIS Press .
  • Pao-Lin , H , Kim-Hong , G , Ru-Rong , W and Chun-Nan , L . 1997 . Benzoquinones, a homoisoflavanone and other constituents from Polygonatum alte-lobatum . Phytochemistry , 44 ( 7 ) : 1369 – 1373 .
  • Pohl , T , Crouch , N and Mulholland , D . 2000 . Southern African Hyacinthaceae: Chemistry, bioactivity and ethnobotany . Current Organic Chemistry , 4 : 1287 – 1324 .
  • Pohl , T , Koorbanally , C , Crouch , N and Mulholland , D . 2001 . Secondary metabolites of Scilla plumbea, Ledebouria cooperi and Ledebouria ovatifolia (Hyacinthaceae) . Biochemical Systematics and Ecology , 29 ( 8 ) : 857 – 860 .
  • Purushothaman , K , Kalyani , K , Subramaniam , K and Shanmughanathan , S . 1982 . Structure of bonducellin – a new homoisoflavone from Caesalpinia bonducella . Indian Journal of Chemistry , 21B : 383
  • Rafi , MM and Vastano , BC . 2007 . Identification of a structure specific Bcl-2 phosphorylating homoisoflavone molecule from Vietnamese coriander (Polygonatum odoratum) that induced apoptosis and G2/M cell cycle arrest in breast cancer cell lines . Food Chemistry , 104 ( 1 ) : 332 – 340 .
  • Rao , YK , Fang , S-HF and Tzeng , Y-M . 2005 . Anti-inflammatory activities of flavonoids isolated from Caesalpinia pulcherrima . Journal of Ethnopharmacology , 100 : 249 – 253 .
  • Rawal , VH and Cava , MP . 1983 . Synthesis of scillascillin, a naturally occurring benzocyclobutene . Tetrahedron Letters , 24 ( 50 ) : 5581 – 5584 .
  • Saitoh , T , Shigemi , S , Hiroyuki , N , Takashi , S , Junei , K Yamahara , J . 1986 . 3-Benzylchroman derivatives related to brazilin from Sappan lignum . Chemical & Pharmaceutical Bulletin (Tokyo) , 34 ( 6 ) : 2506 – 2511 .
  • Shim , JS , Kim , JH , Lee , J , Kim , SN and Kwon , HJ . 2004 . Anti-angiogenic activity of a homoisoflavanone from Cremastra appendiculata . Planta Medica , 70 ( 2 ) : 171 – 173 .
  • Siddaiah , V , Maheswara , M , Venkata Rao , C , Venkateswarlu , S and Subbaraju , GV . 2007 . Synthesis, structural revision, and antioxidant activities of antimutagenic homoisoflavonoids from Hoffmanosseggia intricata . Bioorganic & Medicinal Chemistry Letters , 17 ( 5 ) : 1288 – 1290 .
  • Siddaiah , V , Rao , CV , Venkateswarlu , S , Krishnaraju , AV and Subbaraju , GV . 2006 . Synthesis, stereochemical assignments, and biological activities of homoisoflavonoids . Bioorganic & Medicinal Chemistry , 14 ( 8 ) : 2545 – 2551 .
  • Sidwell , WTL and Tamm , C . 1970 . The homo-isoflavones. III. Isolation and structure of 4′-o-methyl-punctatin, autumnalin and 3,9-dihydro-autumnalin . Tetrahedron Letters , 11 ( 7 ) : 475 – 478 .
  • Silayo , A , Ngadjui , BT and Abegaz , BM . 1999 . Homoisoflavonoids and stilbenes from the bulbs of Scilla nervosa subsp. rigidifolia . Phytochemistry , 52 ( 5 ) : 947 – 955 .
  • Simon , C and Lamla , M . 1991 . Merging pharmacopoeia: Understanding the historical origins of incorporative pharmacopoeial processes among Xhosa healers in southern Africa . Journal of Ethnopharmacology , 33 : 237 – 242 .
  • Speta , F . (1998). The families and genera of vascular plants. III. Flowering plants. Monocotyledons. Liliaceae (except Orchidaceae). Berlin: Springer-Verlag
  • Srinivas , K , Rao , Y , Mahender , I , Das , B , Krishna , K Kishore , K . 2003 . Flavanoids from Caesalpinia pulcherrima . Phytochemistry , 63 : 789 – 793 .
  • Tait , S , Salvati , AL , Desideri , N and Fiore , L . 2006 . Antiviral activity of substituted homoisoflavonoids on enteroviruses . Antiviral Research , 72 ( 3 ) : 252 – 255 .
  • Tang , Y , Yu , B , Hu , J , Wu , T and Hui , H . 2002 . Three new homoisoflavanone glycosides from the bulbs of Ornithogalum caudatum . Journal of Natural Products , 65 ( 2 ) : 218 – 220 .
  • Tinto , WF , Simmons-Boyce , JL , McLean , S and Reynolds , WF . 2005 . Constituents of Agave americana and Agave barbadensis . Fitoterapia , 76 : 594 – 597 .
  • Van Wyk , B-E , Van Oudtshoorn , B and Gericke , N . 1997 . Medicinal plants of South Africa , Pretoria : Briza Publications .
  • Van Wyk , B-E and Wink , M . 2004 . Medicinal plants of the world , Oregon : Timber Press .
  • Wall , ME , Wani , MC , Manikumar , G , Taylor , H and McGivney , R . 1989 . Plant antimutagens, 6. Intricatin and intricatinol, new antimutagenic homoisoflavonoids from Hoffmanosseggia intricata . Journal of Natural Products , 52 ( 4 ) : 774 – 778 .
  • Watt , J and Breyer-Brandwijk , M . 1962 . The medicinal and poisonous plants of southern and eastern Africa , Edinburgh : Livingston .
  • Ye , M , Guo , D , Ye , G and Huang , C . 2004 . Analysis of homoisoflavanones in Opiopogon japonicus by HPLC-DAD-ESI-MS . Journal of the American Society for Mass Spectrometry , 16 ( 2 ) : 234 – 243 .
  • Zhao , H , Bai , H , Wang , Y , Li , W and Koike , K . 2008 . A new homoisoflavan from Caesalpinia sappan . Natural Medicine (Tokyo) , 62 ( 3 ) : 325 – 327 .
  • Zhao , P , Iwamoto , Y , Kouno , I , Egami , Y and Yamamoto , H . 2004 . Stimulating the production of homoisoflavonoids in cell suspension cultures of Caesalpinia pulcherrima using cork tissue . Phytochemistry , 65 ( 17 ) : 2455 – 2461 .
  • Zhu , Y , Yan , K and Tu , G . 1987 . Two homoisoflavones from Ophiopogon japonicus . Phytochemistry , 26 ( 10 ) : 2873 – 2874 .

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.