Stereochemistry of terpenoid coumarins. Crystal and molecular structure of samarcandin

Nasirov, S. M.; Saidkhodzhaev, Ashraf I.; Khasanov, T. Kh.; Yagudaev, M. R.; Malikov, V. M.

doi:10.1007/bf00714905

Cited by 6 publications

(4 citation statements)

References 3 publications

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“…165 In the mass spectra of such compounds the 3'-acyloxy group is split out preferentially as the carboxylic acid, the 4'acyloxy group being eliminated mainly as the carboxyl radical and much less as the acid.' Osthenol (7-hydroxy-8-prenylcoumarin) readily undergoes cyclodehydrogenation to seselin (1 68) with trityl tetrafluoroborate.166 173 The absolute configuration of (1 74) from Amyris elemifera has been shown to be the same as that of the co-occurring marmesin acetate (63).loo The stereochemistries of elemiferone (175), its monoacetate (I 76) and diacetate (177) are as yet ~nassigned,'~~ but that of swietenocoumarin H (1 78) is…”

Section: C-substituted 7-oxygenated Coumarinsmentioning

confidence: 99%

Coumarins

Murray¹

1989

Nat. Prod. Rep.

122

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Section: C-substituted 7-oxygenated Coumarinsmentioning

confidence: 99%

Coumarins

Murray¹

1989

Nat. Prod. Rep.

122

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“…Nevertheless, the stereochemistry of samarcandin proposed in these publications was incorrect. The relative stereochemistry of samarcandin ( 14 ) was established with a single crystal X-ray crystallographic analysis [ 61 ]; however, without providing any supporting evidence, the relative stereochemistry was proposed as the absolute stereochemistry of samarcandin in this paper. In a more recent publication, the stereochemistry of samarcandin ( 14 ) was reinvestigated by computational chemistry methods and X-ray crystallographic analysis.…”

Section: Resultsmentioning

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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“…In 1985, the absolute configuration of samarcandin (86) has been established by Nasirov et al 140 O n the basis of the res ult of the X-Ray inves tigation, the abs olute configurations of badrakemin (51), and colladonin (54), conferol (74), isos amarcandin (89), nevskin (= episamarcandin) (91), and feshurin (95) have been defined. The pres ent inves tigation has shown the molecular structure of samarcandin (86) and the fact that the substituent (CH 2 OAr, where Ar is a coumarin residue) at C-9 is present in the equatorial orientation.…”

Section: Ferulamentioning

confidence: 99%

Terpenoid Coumarins of the Genus Ferula

El‐Razek¹,

Ohta²,

Hirata³

2003

HETEROCYCLES

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Chemical studies on the plants of the genus Ferula (Apiaceae) show the presence of many compounds belonging mainly to the groups of monoterpene coumarins, sesquiterpene coumarins, sesquiterpenes, furanocoumarins and aromatic compounds. Biological studies reveal significant activities, such as an anti-HIV activity, inhibition of cytokine release and early events of carcinogenesis. Extracts of some species of Ferula have long been used in folk medicine for treating various diseases, possess an antimicrobial and estrogenic actions, and are natural plant growth inhibitors and stimulators.

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Stereochemistry of terpenoid coumarins. Crystal and molecular structure of samarcandin

Cited by 6 publications

References 3 publications

Coumarins

Coumarins

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

Terpenoid Coumarins of the Genus Ferula

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