Ferulsinaic acid, a sesquiterpene coumarin with a rare carbon skeleton from Ferula species

Ahmed, Ahmed A.; Hegazy, Mohamed‐Elamir F.; Zellagui, Amar; Rhouati, Salah; Mohamed, Tarik A.; Sayed, Ahmed Rabee; Abdella, Mohamed A.; Ohta, Shigeru; Hirata, Toshifumi

doi:10.1016/j.phytochem.2006.12.011

Cited by 32 publications

(19 citation statements)

References 22 publications

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“…The species Ferula asafoetida has been reported to exhibit anti-carcinogenic properties and to afford protection against freeradical-mediated diseases (Saleem, Alam, & Sultana, 2001) and exhibited anti-leishmanial activity against promastigotes (Iranshahi et al, 2007). Previous phytochemical studies of plants from this genus revealed that the main constituents are sesquiterpenes and sesquiterpene coumarins (reviewed in Ahmed et al, 2007).…”

Section: Introductionmentioning

confidence: 99%

“…In our recent communication, we reported the isolation and structure elucidation of two new sesquiterpene coumarins (Ahmed et al, 2007;Lahouel et al, 2007) from a methylene chloride extract of F. vesceritensis. It is evident from the literature and previous investigations that the genus Ferula possesses high biological activities (Ahmed et al, 2007), which prompts us to study the anti-cancer activity for the major isolated compound, lapiferin, from F. vesceritensis with different extraction methods.…”

Section: Introductionmentioning

confidence: 99%

“…It is evident from the literature and previous investigations that the genus Ferula possesses high biological activities (Ahmed et al, 2007), which prompts us to study the anti-cancer activity for the major isolated compound, lapiferin, from F. vesceritensis with different extraction methods.…”

Section: Introductionmentioning

confidence: 99%

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A crystal lapiferin derived from Ferula vesceritensis induces apoptosis pathway in MCF-7 breast cancer cells

Gamal‐Eldeen¹,

Hegazy

2010

Natural Product Research

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Ferula vesceritensis is a plant that is used in the traditional medicine in Algeria. Chromatographic investigation of the methylene chloride/methanol extract of the aerial parts of F. vesceritensis afforded a crystal carotene sesquiterpene designed lapiferin (10alpha-acetoxy-6alpha-angeloyloxy-8alpha,9alpha-epoxy-trans-caxotan-4beta-ol) for the first time from this species. The structure was determined by comprehensive NMR studies, including DEPT, COSY, NOE, HMQC, HMBC and HRMS, and X-ray data of lapiferin. We report here for the first time the isolation of lapiferin from F. vesceritensis as a new natural source, and we additionally report the first X-ray data for lapiferin. We also report for the first time the specific anti-cancer activity of lapiferin against human breast cancer cells (MCF-7), which is due to apoptosis and not necrosis. Moreover, we have identified for the first time the cell death pathway induced by lapiferin in human breast cancer cells, and also that lapiferin evokes multiple consequences that trigger apoptotic cell death, involving the enhancement of DNA fragmentation, the activation of caspases and the induction of histone acetylation in MCF-7 cells. In conclusion, we record here F. vesceritensis as a new natural source of lapiferin and its first X-ray analysis, and the promising specific anti-cancer activity against human breast cancer of lapiferin and accordingly F. vesceritensis extract.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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A crystal lapiferin derived from Ferula vesceritensis induces apoptosis pathway in MCF-7 breast cancer cells

Gamal‐Eldeen¹,

Hegazy

2010

Natural Product Research

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“…Mogoltacin (47) was described to significantly enhanced the cytotoxicity of vincristine (by 32.8%) towards human transitional cell carcinoma without causing any toxic effects on the cells (Rassouli et al 2009). The resins of F. vesceritensis and F. sinaica afforded many sesquiterpene coumarins including a compound with rare carbon skeletonferulsinaic acid (51) (Ahmed et al 2007). Ferulsinaic acid (51) …”

Section: Sesquiterpene Umbelliferyl (7-hydroxycoumarin) Ethersmentioning

confidence: 99%

“…Accordingly, plants producing sesquiterpene coumarins may express such squalene epoxidaselike enzymes for the epoxidation of 7-O farnesylated coumarins and the generation of a carbocation analogous to the protosteryl or dammarenyl cation in triterpene biosynthesis (Phillips et al 2006). Following this assumption, biogenetic patterns have been outlined for several natural sesquiterpene coumarins (Appendino et al 1994;Gohar and El-Bassuony 2007;Ahmed et al 2007;Kojima et al 2000;Isaka et al 2001, Nagatsu et al 2002Motai and Kitanaka 2004). Nevertheless, the evidence for these biosynthetic steps was primarily inferred from related terpene pathways and needs further experimental support in case of the sesquiterpene coumarins.…”

Section: Farnesyl Diphosphatementioning

confidence: 99%

Sesquiterpene coumarins

Gliszczyńska

Brodelius

2011

Phytochem Rev

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Plants have a long history as therapeutic tools in the treatment of human diseases and have been used as a source of medicines for ages. In search of new biologically active natural products, many plants and herbs used in traditional medicine are screened for natural products with pharmacological activity. In this paper, we present a group of natural products, the sesquiterpene coumarins isolated from plants, and describe their wide range of biological activity. Sesquiterpene coumarins are found in some plants of the families Apiaceae (Umbelliferae), Asteraceae (Compositae) and Rutaceae. The coumarin moiety is often umbelliferone (7-hydroxycoumarin) but scopoletin (7-hydroxy-6-methoxycoumarin) and isofraxidin (7-hydroxy-6,8-dimethoxycoumarin) are also found. These coumarins are linked to a C 15 terpene moiety through an ether linkage. Another group of sesquiterpene coumarins is the prenylated 4-hydroxycoumarins where the link between the coumarin and the C 15 terpene moiety is a C-C-bond at carbon 3 of the coumarin moiety. Finally, the prenyl-furocoumarintype sesquiterpenoids are a separate group of sesquiterpene coumarins based on the suggested biosynthetic pathway. Our relatively limited knowledge on the biosynthesis of sesquiterpene coumarins is reviewed.

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Two New Sesquiterpene Derivatives from the Tunisian Endemic Ferula tunetanaPom.

Jabrane

Jannet

Mighri

et al. 2010

Chemistry & Biodiversity

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A new sesquiterpene ester, tunetanin A (1), a new sesquiterpene coumarin, tunetacoumarin A (2), together with eight known compounds, i.e., coladin (3), coladonin (4), isosmarcandin (5), 13-hydroxyfeselol (6), umbelliprenin (7) propiophenone (8), beta-sitosterol (9), and stigmasterol (10), were isolated from the roots of Ferula tunetana. Their structures were elucidated on the basis of extensive spectroscopic methods, including 1D- and 2D-NMR experiments and MS analysis, as well as by comparison with published data. The cytotoxicity of compounds 1-7 towards two human colon cancer cell lines, HT-29 and HCT 116, was evaluated. Compounds 3, 4, and 6 showed weak cytotoxic activities.

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Ferulsinaic acid, a sesquiterpene coumarin with a rare carbon skeleton from Ferula species

Cited by 32 publications

References 22 publications

A crystal lapiferin derived from Ferula vesceritensis induces apoptosis pathway in MCF-7 breast cancer cells

A crystal lapiferin derived from Ferula vesceritensis induces apoptosis pathway in MCF-7 breast cancer cells

Sesquiterpene coumarins

Two New Sesquiterpene Derivatives from the Tunisian Endemic Ferula tunetanaPom.

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