Pyrrolizidine alkaloids from Cryptantha species

Stermitz, Frank R.; Pass, Michael A.; Kelley, Ronald B.; Liddell, James R.

doi:10.1016/0031-9422(93)85524-u

Cited by 19 publications

(31 citation statements)

References 12 publications

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“…Other pyrrolizidine alkaloids esterified with 2,3‐dihydroxy‐2‐methylbutanoic acid have been isolated from Ipomoea hederifolia (Jenett‐Siems et al ., ), Senecio caudatus (Bohlmann et al ., ) and Cryptantha clevelandii (Stermitz et al ., ) but only two, one each from S . caudatus and C .…”

Section: Resultsmentioning

confidence: 99%

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Dehydropyrrolizidine Alkaloids in Two Cryptantha Species: Including Two New Open Chain Diesters One of Which is Amphoteric

Colegate

Gardner

Davis

et al. 2012

Phytochemical Analysis

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The retronecine-based alkaloids detected in both Cryptantha species herein investigated aligns them within the Krynitzkia subgenus. The dehydropyrrolizidine alkaloids detected are expected to be toxic but the low levels in the plants potentially mitigate the risk. The identification of the amphoteric echiuplatine provides a cautionary note with respect to the analysis of total dehydropyrrolizidine alkaloid content.

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Section: Resultsmentioning

confidence: 99%

“…Similarly, the relevant 1 H chemical shifts observed for cryptanthine (H19, 20 and 21) are almost identical to those reported by Stermitz et al . () and therefore cryptanthine can be described as 9‐angeloyl‐7‐ threo ‐2,3‐dihydroxy‐2‐methylbutanoylretronecine ( 5 ).…”

Section: Resultsmentioning

confidence: 99%

Dehydropyrrolizidine Alkaloids in Two Cryptantha Species: Including Two New Open Chain Diesters One of Which is Amphoteric

Colegate

Gardner

Davis

et al. 2012

Phytochemical Analysis

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“…Intermedine, 3'-acetylintermedine, 7-acetylintemedine, lycopsamine, 3'-acetyllycopsamine, 7-acetyllycopsamine [63] …”

Section: Virgatamentioning

confidence: 99%

“…[66] C. leiocarpa 7-Angeloylretronecine, 9-angeloylretronecine, echiumine, intermedine, 3'-acetylintermedine, 2'',3''-epoxyechiumine, thero-2',3'-dihydroxyechiumine, erytho-3''-chloro-2''-hydroxyechiumine [63] C. thyrsiflora Intermedine, 3'-acetylintermedine, 7-acetylintemedine, lycopsamine, 3'-acetyllycopsamine, 7-acetyllycopsamine [63] …”

Section: Flavamentioning

confidence: 99%

Diversity of Pyrrolizidine Alkaloids in the Boraginaceae Structures, Distribution, and Biological Properties

2014

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Among the diversity of secondary metabolites which are produced by plants as means of defence against herbivores and microbes, pyrrolizidine alkaloids (PAs) are common in Boraginaceae, Asteraceae and some other plant families. Pyrrolizidine alkaloids are infamous as toxic compounds which can alkylate DNA und thus cause mutations and even cancer in herbivores and humans. Almost all genera of the family Boraginaceae synthesize and store this type of alkaloids. This review reports the available information on the present status (literature up to early 2014) of the pyrrolizidine alkaloids in the Boraginaceae and summarizes the topics structure, distribution, chemistry, chemotaxonomic significance, and biological properties.

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“…[1][2][3] These metabolites have been isolated from a wide variety of plants, especially from genera belonging to the Boraginaceae family. [4][5][6] The genus Heliotropium, a well-known source of such alkaloids [7][8][9] and other minor compounds, such as flavonoids and geranyl aromatic derivatives, is constituted of about 250 species represented by herbs and shrubs, distributed throughout the terrestrial globe. 10 In the course of a search for novel and biologically active compounds from plants the EtOH extract from the roots of Heliotropium indicum L., popularly known as fedegoso, found abundantly in the region of northeast Brazil, was investigated.…”

Section: Introductionmentioning

confidence: 99%

Pyrrolizidine alkaloids from Heliotropium indicum

Souza¹,

Machado²,

Pessoa³

et al. 2005

J. Braz. Chem. Soc.

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Um novo alcalóide denominado Helindicina (1), e o conhecido licopsamina (2) foram isolados das raízes de Heliotropium indicum (Boraginaceae). As estruturas foram estabelecidas tendo como base um amplo estudo de 1D e 2D RMN (COSY, HMBC, HMQC, NOESY) e HREIMS. Este representa o primeiro relato de um alcalóide contendo um anel lacônico no gênero Heliotropium. Estes alcalóides mostraram moderada atividade antioxidante.Helindicine (1), a new pyrrolizidine alkaloid with unusual structural features, together with the known lycopsamine (2), were isolated from the roots of Heliotropium indicum (Boraginaceae). The structures were established by a combination of 1D and 2D NMR methods (COSY, HMQC, HMBC, and NOESY) and HREIMS. This is the first report of a lactone pyrrolizidine alkaloid in the genus Heliotropium. Compounds 1 and 2 were assayed for antioxidant activity and showed moderate activity.

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Pyrrolizidine alkaloids from Cryptantha species

Cited by 19 publications

References 12 publications

Dehydropyrrolizidine Alkaloids in Two Cryptantha Species: Including Two New Open Chain Diesters One of Which is Amphoteric

Dehydropyrrolizidine Alkaloids in Two Cryptantha Species: Including Two New Open Chain Diesters One of Which is Amphoteric

Diversity of Pyrrolizidine Alkaloids in the Boraginaceae Structures, Distribution, and Biological Properties

Pyrrolizidine alkaloids from Heliotropium indicum

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