New Homoisoflavanes, a New Alkaloid and Spirostane Steroids from the Roots of Herreria montevidensis Klotzsch ex Griseb. (Herreriaceae)

Dutra-Behrens, M.; Schmeda-Hirschmann, Guillermo

doi:10.3390/molecules21111589

Cited by 5 publications

(3 citation statements)

References 22 publications

(40 reference statements)

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“…Six novel homoisoflavans, namely, (3 R )-7-methoxy-3-(4-hydroxybenzyl)chroman, (3 R )-7-hydroxy-5-methoxy-6-methyl-3-(4-hydroxybenzyl)chroman, (3 R )-7-hydroxy-5-methoxy-6-methyl-3-(4-hydroxybenzyl)chroman, and (3 R )-7-methoxy-3-(4-hydroxybenzyl)chroman, along with two known homoisoflavans, have been isolated and characterized from the CHCl 3 -soluble fractions by applying HPLC (mobile phase: H 2 O–MeOH 5:5, 3:7). Moreover, two novel homoisoflavans, 7-hydroxy-8-methoxy-3-(4-hydroxybenzyl)-3-chromen and 7-hydroxy-8-methoxy-3-(4-hydroxybenzyl)-3-chromen, could be isolated from the methanolic extract [ 84 ].…”

Section: Chemotaxonomy Of Homoisoflavonoidsmentioning

confidence: 99%

A Comprehensive Review on Chemotaxonomic and Phytochemical Aspects of Homoisoflavonoids, as Rare Flavonoid Derivatives

Mottaghipisheh

Stuppner

2021

IJMS

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Homoisoflavonoids (3-benzylidene-4-chromanones) are considered as an infrequent flavonoid class, possessing multi-beneficial bioactivities. The present study gives an overview on phytochemical aspects of homoisoflavonoids, including utilized plant species, parts, extracts, and separation techniques. Overall, these compounds have mainly been isolated and identified from bulbs and rhizomes of the plants belonging to Asparagaceae and Fabaceae families, particularly the genera of Ophiopogon, Dracaena, Scilla, Polygonatum, and Caesalpinia.

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Section: Chemotaxonomy Of Homoisoflavonoidsmentioning

confidence: 99%

A Comprehensive Review on Chemotaxonomic and Phytochemical Aspects of Homoisoflavonoids, as Rare Flavonoid Derivatives

Mottaghipisheh

Stuppner

2021

IJMS

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“…36 Zhao et al 37 reported the isolation of the 3-benzylchromen 20 (Figure 4) from C. sappan and observed that this may have been the first natural product possessing a double bond located at C-3 and C-4 of a homoisoflavan system. In 2016 came a further report on the isolation of 3 more similar Δ 3,4 -unsaturated compounds, but with additional hydroxy and methoxy substituents 38,39 from Caesalpina spinosa and Herreria montevidensis, respectively. Interestingly, He et al also reported 2 more compounds 23 and 24 from the same plant, which contain a carbonyl group at C-2.…”

Section: Novel Structures Containing the Hif Skeletonmentioning

confidence: 99%

Naturally Occurring Homoisoflavonoids: Phytochemistry, Biological Activities, and Synthesis (Part II)

Abegaz

Kinfe

2019

Natural Product Communications

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This review documents all the new homoisoflavonoids (HIFs) that have been reported since 2007, whose total number has grown from 159 in 2007 to 295 at the present time. This review contains their structures, biological sources, plant parts they are obtained from, and, if reported, their optical rotations and melting points. The same classification is followed as an earlier review to ease reference to both reviews. This review takes note of the recent revision of plant families that were known to contain HIFs that have now been merged into one big family, Asparagaceae. Homoisoflavonoids also occur in Fabaceae and others. Two taxa, Ophiopogoan japonicus (Asparagaceae) and Caesalpinia sappan (Fabaceae), have been the source of many HIFs. These are briefly summarized. The biological properties of HIFs are also reviewed under the topics such as antioxidant, anti-inflammatory, antimicrobial, antidiabetic, and cytotoxic. The review also surveys the total synthesis of natural HIFs. All new compounds are classified and tabulated following the same style as the previous review. Dedicated to Professor Andrew Paul Krapcho on the occasion of his 87th Birthday.

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“…A total of 15 homoisoflavanes has been reported to date since the discovery of ( S )-3-(4-hydroxybenzyl)chroman-7-ol (Figure ). − The new homoisoflavane dracaeconolide B, 3-(4-hydroxybenzyl)-7-hydroxy-5,8-dimethoxychromane, has been recently isolated from the red resin of Dracaena cochinchinensis (Lour.) S.C. Chen (Liliaceae) .…”

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confidence: 99%

Synthesis and Structure Revision of Naturally Occurring Homoisoflavane (+)-Dracaeconolide B

et al. 2022

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Dracaeconolide B (1), a naturally occurring homoisoflavane, was isolated from the red resin of Dracaena cochinchinensis. Efforts have been made to elucidate the exact structure of compound 1 since it was confirmed that dracaeconolide B did not contain a 7-hydroxy-5,8-dimethoxy moiety. The structure of dracaeconolide B was revised by synthesis of three homoisoflavanes containing a 5,6,7-trioxygenated moiety each and analysis by NMR spectroscopy. The revised structure of dracaeconolide B was proposed as 3-(4-hydroxybenzyl)-7-hydroxy-5,6-dimethoxychromane. Noyori's Ru-catalyzed asymmetric transfer hydrogenation was used to synthesize (+)-dracaeconolide B. The absolute configuration of the compound was revised to S based on the results obtained by the electronic circular dichroism calculation. We examined the antiangiogenic activity of (S)-and (R)dracaeconolide B and of synthetic 5,6,7-and 5,7,8-trioxygenated homoisoflavanes. The results can potentially help in the synthesis of related natural products and support drug discovery to treat neovascular eye diseases.

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New Homoisoflavanes, a New Alkaloid and Spirostane Steroids from the Roots of Herreria montevidensis Klotzsch ex Griseb. (Herreriaceae)

Cited by 5 publications

References 22 publications

A Comprehensive Review on Chemotaxonomic and Phytochemical Aspects of Homoisoflavonoids, as Rare Flavonoid Derivatives

A Comprehensive Review on Chemotaxonomic and Phytochemical Aspects of Homoisoflavonoids, as Rare Flavonoid Derivatives

Naturally Occurring Homoisoflavonoids: Phytochemistry, Biological Activities, and Synthesis (Part II)

Synthesis and Structure Revision of Naturally Occurring Homoisoflavane (+)-Dracaeconolide B

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