A novel 3-benzylchromone from the South African Lachenalia rubida (Hyacinthaceae)

Langlois, A.; Mulholland, Dulcie A.; Duncan, Graham; Crouch, Neil R.; Edwards, T. J.

doi:10.1016/j.bse.2005.01.003

Cited by 6 publications

(6 citation statements)

References 16 publications

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“…( R ) - 5-Hydroxy-3-(4-hydroxybenzyl)-7-methoxy-4-chromanone 1 and 5-hydroxy-3-(4-hydroxybenzyl)-7-methoxy-4-chromone 2 have been isolated previously from Lachenalia rubida Jacq. [21]. This species, like Massonia pustulata , is from the subfamily Hyacinthoideae and endemic to the dry areas of South Africa and Namibia.…”

Section: Resultsmentioning

confidence: 99%

Antiangiogenic Activity and Cytotoxicity of Triterpenoids and Homoisoflavonoids from Massonia pustulata and Massonia bifolia

et al. 2018

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The Hyacinthaceae family ( APGII), with approximately 900 species in around 70 genera, plays a significant role in traditional medicine in Africa as well as across Europe and the Middle and Far East. The dichloromethane extract of the bulbs of (Hyacinthaceae APGII) yielded two known homoisoflavonoids, ()-5-hydroxy-3-(4-hydroxybenzyl)-7-methoxy-4-chromanone 1: and 5-hydroxy-3-(4-hydroxybenzyl)-7-methoxy-4-chromone 2: and four spirocyclic nortriterpenoids, eucosterol 3: , 28-hydroxyeucosterol 4: and two previously unreported triterpenoid derivatives, ()-17,23-epoxy-3,22,29-trihydroxylanost-8-en-27,23-olide 5: , and ()-17,23-epoxy-28,29-dihydroxylanost-8-en-3-on-27,23-olide 6: . Compounds 1, 2, 3: , and 5: were assessed for cytotoxicity against CaCo-2 cells using a neutral red uptake assay. Compounds 1, 2: , and 5: reduced cell viability by 70% at concentrations of 30, 100, and 100 µM, respectively. yielded three known homoisoflavonoids, ()(4'-hydroxy)-5-hydroxy-7-methoxy-4-chromanone 1: , ()-(4'-hydroxy)-5,7-dihydroxy-4-chromanone 7: and ()(3'-hydroxy-4'-methoxy)-5,7-dihydroxy-4-chromanone 9: , two previously unreported homoisoflavonoids, ()3-benzylidene-(3',4'-dihydroxy)-5-hydroxy-7-methoxy-4-chromanone 8: and ()(3',4'-dihydroxy)-5-hydroxy-7-methoxy-4-chromanone 10,: and a spirocyclic nortriterpenoid, 15-deoxoeucosterol 11: . Compounds 1, 1AC, 7, 8, 9,: and 10: were screened for antiangiogenic activity against human retinal microvascular endothelial cells. Some compounds showed dose-dependent antiproliferative activity and blocked endothelial tube formation, suggestive of antiangiogenic activity.

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Section: Resultsmentioning

confidence: 99%

Antiangiogenic Activity and Cytotoxicity of Triterpenoids and Homoisoflavonoids from Massonia pustulata and Massonia bifolia

et al. 2018

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“…A further interesting feature of the Caesalpinia metabolism is the production of homoisoflavan-3,4-diols (3-benzyl-3,4-dihydroxychromans). Seven such compounds (85)(86)(87)(88)(89)(90)(91) have been reported to date and all of them were found in two species of one genus, C. sappan and C. japonica [18, 26a, 26b, 26d]. These are the unsaturated analogs of the 3-benzylchroman-4-ones discussed earlier.…”

Section: -Benzylflavansmentioning

confidence: 99%

“…Therefore, the absolute stereochemistry at C-4 had to be R, and thus epi-sappanol (87) had to be (3R, 4R)-3-(3,4dihydroxybenzyl)-3,3,7-trihydroxychroman. The absolute stereochemistry of 3′-deoxysappanol (85) was deduced from the observed negative cotton effect of the CD curve of its dimethyl ether similar to that of the methyl ether of sappanol (86). This led to the conclusion that 87 must be (3R, 4S)-3-(4hydroxybenzyl)-3,4,7-trihydroxychroman.…”

Section: Absolute Configuration and Stereochemistrymentioning

confidence: 99%

Naturally Occurring Homoisoflavonoids: Phytochemistry, Biological Activities and Synthesis

Abegaz

Mutanyatta-Comar

Nindi

2007

Natural Product Communications

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This review covers the phytochemical, biological properties, and synthesis of naturally occurring homoisoflavonoids. Homoisoflavonoids are a very important class of secondary metabolites whose numbers have grown from 20 in 1981 to 157 at the present time. They are found to occur in seven plant families. For the purpose of this review they are classified into five groups: 3-benzylchroman-4-ones, 3-benzylflavans, Δ3,9 and Δ2,3 3-benzylchroman-4-ones, benzocyclobutenes (scillascillins) and rearranged homoisoflavonoids (brazilin and related compounds). Biosynthetically, the 3-benzylchroman-4-ones and the 3-hydroxy-derivatives have been shown to arise from a chalcone precursor (sappanchalcone) and there is strong evidence that this isolable intermediate can be converted into the diverse structures such as the benzocyclobutenes (scillascillins) and the rearranged, brazilin-type compounds. Homoisoflavonoids possess a wide range of biological activities, including, antimicrobial, antimutagenic, anti-inflammatory, antidiabetic, etc, properties. The review also surveys the chemical synthesis of natural homoisoflavonoids. Analytical methods for the determination of these important metabolites are also reviewed. The last section is devoted to a brief review of the diagnostic NMR spectroscopic features of homoisoflavonoids. A comprehensive Table has also been compiled listing all known metabolites, their sources, melting points and optical rotation values (where available) and references.

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“…73 Ledebouria oribunda (Baker) Jessop is used by traditional healers in the Eastern Cape of South Africa to treat skin disorders, tuberculosis, urinary tract infections and gastroenteritis. Three homoisoavanones, with unusual substituents at C-6, -7 and -8 (163)(164)(165) have been isolated from the bulbs as well as two 7-O-diglycosides (166)(167) and ve additional homoiso-avanones (10,30,50,62,168). These latter seven homoiso-avanones have shown good antioxidant activity against the DPPH radical (IC 50 of 31-273 mg ml À1 ) and in the b-carotene/ linoleic acid system (antioxidant activity of up to 79% aer 120 min) as did 164 and 165 against the DPPH radical (IC 50 of 23.2 and 28.7 mg ml À1 respectively).…”

mentioning

confidence: 99%

“…has yielded avone sulphates (luteolin-3 0 -sulphate and -7,3 0 -disulphate, tricetin-3 0 -sulphate and -7,3 0 disulphate, diosmetin-3 0 -sulphate and -7,3 0 -disulphate) 166 while the bulbs of L. rubida Jacq., collected from the Western Cape, South Africa, were found to contain the homoisoavanones 402 and 403. 165 The bulbs of Pseudoprospero rmifolium (Baker) Speta have been found to contain ve 3-hydroxy-3-benzyl-4-chromanone type homoisoavanones, all as racemic mixtures (404)(405)(406)(407)(408) as well as the spirocyclic nortriterpenoid, 15-deoxoeucosterol. 167 A subsequent study on the bulbs of Pseudoprospero rmifolium subsp.…”

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confidence: 99%

The chemistry and biological activity of the Hyacinthaceae

2013

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The Hyacinthaceae (sensu APGII), with approximately 900 species in about 70 genera, can be divided into three main subfamilies, the Hyacinthoideae, the Urgineoideae and the Ornithogaloideae, with a small fourth subfamily the Oziroëoideae, restricted to South America. The plants included in this family have long been used in traditional medicine for a wide range of medicinal applications. This, together with some significant toxicity to livestock has led to the chemical composition of many of the species being investigated. The compounds found are, for the most part, subfamily-restricted, with homoisoflavanones and spirocyclic nortriterpenoids characterising the Hyacinthoideae, bufadienolides characterising the Urgineoideae, and cardenolides and steroidal glycosides characterising the Ornithogaloideae. The phytochemical profiles of 38 genera of the Hyacinthaceae will be discussed as well as any biological activity associated with both crude extracts and compounds isolated. The Hyacinthaceae of southern Africa were last reviewed in 2000 (T. S. Pohl, N. R. Crouch and D. A. Mulholland, Curr. Org. Chem., 2000, 4, 1287-1324; ref. 1); the current contribution considers the family at a global level.

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A novel 3-benzylchromone from the South African Lachenalia rubida (Hyacinthaceae)

Cited by 6 publications

References 16 publications

Antiangiogenic Activity and Cytotoxicity of Triterpenoids and Homoisoflavonoids from Massonia pustulata and Massonia bifolia

Antiangiogenic Activity and Cytotoxicity of Triterpenoids and Homoisoflavonoids from Massonia pustulata and Massonia bifolia

Naturally Occurring Homoisoflavonoids: Phytochemistry, Biological Activities and Synthesis

The chemistry and biological activity of the Hyacinthaceae

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