Humulenes and Other Constituents of Ferula latipinna

González, Antonio G.; Bermejo, Jaime; Dı́az, Jesús; Arancibia, Luis; Paz, Pedro Perez de

doi:10.1021/np50060a015

Cited by 15 publications

(9 citation statements)

References 16 publications

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“…The biosynthetic pathway proposed to 10 should involve a himachalane derivative which was not detected in this study, but has been isolated from Ferula latipinna (Umbelliferae), 10 which could be formed by cyclization of bicyclogermacrene ( Figure 1). In the volatile oil, the absence of 10 and the reduced amount of 7 (3.0%) could be explained by the predominance of germacrene-D (37.8%) and bicyclogermacrene (27.5%).…”

Section: Resultsmentioning

confidence: 81%

Macrocarpane, a new sesquiterpene skeleton from the leaves of Porcelia macrocarpa

Chaves¹,

Lago

Roque³

2003

J. Braz. Chem. Soc.

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Section: Resultsmentioning

confidence: 81%

Macrocarpane, a new sesquiterpene skeleton from the leaves of Porcelia macrocarpa

Chaves¹,

Lago

Roque³

2003

J. Braz. Chem. Soc.

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“…The control mice were given 0.3 ml of cottonseed oil only. with those of -humulene derivatives such as 15-CH2OAc or 15-C02H (19,20). The location of the epoxide group in 4 was determined by the analysis of its proton spectrum.…”

Section: Sesquiterpenes From Clove (Eugenia Caryophyllata)mentioning

confidence: 99%

Sesquiterpenes from Clove (Eugenia caryophyllata) as Potential Anticarcinogenic Agents

Zheng¹,

Kenney²,

Lam³

1992

J. Nat. Prod.

317

148

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Bioassay-directed fractionation of clove terpenes from the plant Eugenia caryophyllata has led to the isolation of the following five active known compounds: beta-caryophyllene [1], beta-caryophyllene oxide [2], alpha-humulene [3], alpha-humulene epoxide I [4], and eugenol [5]. Their structures were determined on the basis of spectral analysis (hreims, 1H and 13C nmr). These compounds showed significant activity as inducers of the detoxifying enzyme glutathione S-transferase in the mouse liver and small intestine. The ability of natural anticarcinogens to induce detoxifying enzymes has been found to correlate with their activity in the inhibition of chemical carcinogenesis. Thus, these sesquiterpenes show promise as potential anticarcinogenic agents.

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“…high-performance liquid chromatography (HPLC)). The following 15 sesquiterpene coumarin ethers were isolated from the aforementioned fractions: conferone (1) [26], conferol (2) [27], feselol (3) [27], badrakemone (4) [28], mogoltadone (5) [29], farnesiferol A (6) [30], farnesiferol A acetate (7) [31], gummosin (8) [32], ferukrin (9) [33], ferukrin acetate (10) [33], deacetylkellerin (11) [34], kellerin (12) [35], samarcandone (13) [36], samarcandin (14) [37], and samarcandin acetate (15) (Figure 1). Due to the availability of limited NMR data for the isolated cytotoxic coumarins in the literature, extensive 2D NMR spectroscopic techniques, such as 2D 1 H-1 H correlation spectroscopy (COSY), nuclear Overhauser effect spectroscopy (NOESY), heteronuclear single-quantum coherence (HSQC), heteronuclear multiple-bond connectivity (HMBC), (Supplementary Materials Figures S2-S91) as well as high-resolution mass spectroscopy (HRMS) and optical rotation measurements (Supplementary Materials Table S1), were used for the confirmation of their structures.…”

Section: Bioactivity-directed Isolation and Structure Elucidation Of ...mentioning

confidence: 99%

“…Ferula species are rich sources of sesquiterpene esters and coumarins [ 8 , 9 , 10 , 11 ]. While certain sesquiterpene esters of Ferula species show cytotoxic activity on resistant cancer cell lines [ 12 ], sesquiterpene coumarins through the competitive inhibition of the p-glycoprotein transport mechanism reverse the p-glycoprotein-mediated multidrug-resistant cancer cell lines [ 13 , 14 ].…”

Section: Introductionmentioning

confidence: 99%

Sesquiterpene Coumarin Ethers with Selective Cytotoxic Activities from the Roots of Ferula huber-morathii Peşmen (Apiaceae) and Unequivocal Determination of the Absolute Stereochemistry of Samarcandin

Eruçar,

Kuran,

Altıparmak Ülbegi

et al. 2023

Pharmaceuticals

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Ancient physicians frequently used the resin of Ferula species to treat cancer. Today, some folkloric recipes used for cancer treatment also contain the resin of Ferula species. The dichloromethane extract of the roots of Ferula huber-morathii exhibited cytotoxic activities against COLO 205 (colon), K-562 (lymphoblast), and MCF-7 (breast) cancer cell lines (IC50 = 52 µg/mL, 72 µg/mL, and 20 µg/mL, respectively). Fifteen sesquiterpene coumarin ethers with cytotoxic activity were isolated from the dichloromethane extract of the roots of F. huber-morathii using bioactivity-directed isolation studies. Extensive spectroscopic analyses and chemical transformations have elucidated the structures of these sesquiterpene coumarin ethers as conferone (1), conferol (2), feselol (3), badrakemone (4), mogoltadone (5), farnesiferol A (6), farnesiferol A acetate (7), gummosin (8), ferukrin (9), ferukrin acetate (10), deacetylkellerin (11), kellerin (12), samarcandone (13), samarcandin (14), and samarcandin acetate (15). The absolute configuration of samarcandin (14) was unequivocally determined by the X-ray crystallographic analysis of the semi-synthetic (R)-MTPA ester of samarcandin (24). Conferol (2) and mogoltadone (5) were found to be the most potent cytotoxic compounds against all three cancer cell lines; furthermore, these compounds exhibit low cytotoxic activity against the non-cancerous human umbilical vein epithelial cells (HUVEC) cell line. Investigation of the biological activity mechanisms of mogoltadone (5) revealed that while suppressing the levels of Bcl-XL and procaspase-3 in the COLO 205 cancer cell line, it did not have a significant effect on the Bcl-XL, caspase-3, and β-catenin protein levels of the HUVEC cell line, which may explain the cytotoxic selectivity of mogoltadone (5) on cancer cell lines.

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Humulenes and Other Constituents of Ferula latipinna

Cited by 15 publications

References 16 publications

Macrocarpane, a new sesquiterpene skeleton from the leaves of Porcelia macrocarpa

Macrocarpane, a new sesquiterpene skeleton from the leaves of Porcelia macrocarpa

Sesquiterpenes from Clove (Eugenia caryophyllata) as Potential Anticarcinogenic Agents

Sesquiterpene Coumarin Ethers with Selective Cytotoxic Activities from the Roots of Ferula huber-morathii Peşmen (Apiaceae) and Unequivocal Determination of the Absolute Stereochemistry of Samarcandin

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