3-Epi-cyclolaudenol and known triterpenes from euphorbia caudicifolia

Govardhan, Ch.; Reddy, Ravisekhara P.; Sundararamaiah, T.

doi:10.1016/s0031-9422(00)80342-8

Cited by 19 publications

(11 citation statements)

References 4 publications

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“…Its latex is used in the folk medicine as purgative, rubefacient, and expectorant, while the root is antispasmodic (1,2). A literature survey shows that terpenoidal constituents have so far been reported from various parts (3,4). We now report the results of studies on the fresh and undried latex, with the isolation of two further cyclopropane triterpenes 1 and 2 which have not been reported previously from this species.…”

Section: Planta Medica 1988mentioning

confidence: 62%

Triterpenoids from the Latex ofEuphorbia caudicifolia

Afza¹,

Khan²,

Malik³

et al. 1988

Planta Med

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Euphorbia caudicifolia Haines (Euphorbiaceae) is a short shrub growing mainly in the dry regions of India and Pakistan. Its latex is used in the folk medicine as purgative, rubefacient, and expectorant, while the root is antispasmodic (1, 2). A literature survey shows that terpenoidal constituents have so far been reported from various parts (3,4). We now report the results of studies on the fresh and undried latex, with the isolation of two further cyclopropane triterpenes 1 and 2 which have not been reported previously from this species. Compounds 1 and 2 were identified as cyclotrichosantol and cycloeucalenol, respectively, by physical and spectroscopic data. This is only the second report of the natural occurrence of compound 1 following earlier isolation from Trichosantes palmata (5).The fresh latex (1 kg) was collected from Karachi, dissolved in acetone (11), and the coagulated residue was filtered. The filtrate was kept overnight in the cold whereupon a thick crystallizate settled out. The crystals were recrystallized from moist acetone, and then subjected to column chromatography over silica gel, eluting with a mixture of hexane and chloroform. The eluate obtained from hexane: chloroform (80:20) yielded compound! {m.p. 141-142°C; Ref. (5) m.p. 143-144°C; [a]D: +41°; Ref. (5)[a]0 +42°}; yield: 80mg. Compound 2 was obtained from hexane : chloroform (75 :25) {m.p. 138°C; Ref. (6) m.p. 138-139°C; [a]0: + 44.5°, Ref. (5, 6) [aID: + 45°}; yield: 120 mg.

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Section: Planta Medica 1988mentioning

confidence: 62%

Triterpenoids from the Latex ofEuphorbia caudicifolia

Afza¹,

Khan²,

Malik³

et al. 1988

Planta Med

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“…Apparently, K. pinnata is another example of a plant in which sterol biosynthesis has become complicated: different mechanisms for the formation of the same side chain seem to be operating parallel and at the same time. The A2S-sterols, 2m,n and 3m,n, are epimeric mixtures because different mechanisms do not necessarily result in the formation of the same epimer at C- 24.…”

Section: Resultsmentioning

confidence: 99%

“…Other examples of 24-alkyl-A25-sterols from higher plants. In cases where the configuration at C-24 has been firmly established, h25-unsaturated 24-alkylsterols isolated from seed-bearing plants always were reported to have the 24S/f~stereochemistry (4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19)(20)(23)(24)(25)(26)(27)(28)(29)31). Thus, this study constitutes the first example of the isolation of 24R-alkyl-A25-sterols, 2m and 3m, from the seedbearing plants, and, also, the first demonstration of the c~occurrence of C-24 epimeric 24-alkyl-A25-sterols (2m/2n and 3m/3n) in a non-marine organism.…”

Section: Resultsmentioning

confidence: 99%

Sterols ofKalanchoe pinnata: First report of the isolation of both C‐24 epimers of 24‐alkyl‐Δ²⁵‐sterols from a higher plant

Akihisa

Kokke

Tamura

et al. 1991

Lipids

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Eighteen sterols were isolated from the aerial parts ofKalanchoe pinnata (Crassulaceae) including four novel sterols,viz. (24R)‐stigmasta‐5,25‐dien‐3β‐ol (24‐epiclerosterol), (24R)‐5α‐stigmasta‐7,25‐dien‐3β‐ol, 5α‐stigmast‐24‐en‐3β‐ol, and 25‐methyl‐5α‐ergost‐24(28)‐en‐3β‐ol. 24‐Epiclerosterol and its Δ7‐analog occur together with their 24S/β‐epimers in the same plant making this the first report of the isolation of both C‐24 epimers of Δ25‐unsaturated 24‐alkylsterols from a non‐marine organism. Iodine‐catalyzed isomerization of stigmasta‐5,24‐dien‐3β‐ol (24‐ethyldesmosterol), the main sterol ofK. pinnata, yielded 24‐epiclerosterol among other products.

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“…Isolation of some of the natural molecules like euphol, caducinol etc. from different species of the genus Euphorbia has been reported in the literatures [2][3][4][5][6][7]. Based on the composition analysis some genera are termed xerophytic [8].…”

Section: Introductionmentioning

confidence: 99%

“…Although isolation of some of the molecules from the latex of this Euphorbia caducifolia Haines has already been done, but any report describing complete technical analysis and characterization of the masses and foretelling their various industrial applications is rare [2][3][4][5][6][7]. Most of the rubber compounding ingredients are crude based and therefore, is non renewable in nature.…”

Section: Introductionmentioning

confidence: 99%

Technical Analysis of Euphorbia caducifolia Haines Latex of South-East Asian Origin - Part I

Bhattacharyya

Kar

Chakraborty

et al. 2013

Polymers from Renewable Resources

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Identification and characterization of the latex from Euphorbia caducifolia Haines has been thoroughly described in this article. The average total solid content (TSC) of the latex was 27% and pH was found to vary between 6 to 7. About 70% by weight of the whole coagulum (Cog) was found soluble in toluene; rest was insoluble. Toluene soluble portion (TE) was mainly composed of terpenes and terpenoids of three different molecular weights; the lowest molecular weight fraction being the dominant (82%) one. Presence of about 8% natural rubber (NR, a polyterpene), mostly of cis configuration, was also identified from the composition analysis of that portion. Due to dominant low molecular weight mass, it was tackier as compared to Cog portion when manually felt. Thermal characterization showed a low temperature melting behavior (starting at 70°C for Cog and at 104°C for TE), ideal for a tackifier resin. Both Cog and TE portions were found to exhibit high thermal decomposition temperature ensuring high process safety. The ash was rich in magnesium oxide and has a great potential to be used as the cure retarder in certain rubber compounds. Absence of any deleterious metals like copper, manganese etc. was also a great positive point towards its application standpoint.

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3-Epi-cyclolaudenol and known triterpenes from euphorbia caudicifolia

Cited by 19 publications

References 4 publications

Triterpenoids from the Latex ofEuphorbia caudicifolia

Triterpenoids from the Latex ofEuphorbia caudicifolia

Sterols ofKalanchoe pinnata: First report of the isolation of both C‐24 epimers of 24‐alkyl‐Δ²⁵‐sterols from a higher plant

Technical Analysis of Euphorbia caducifolia Haines Latex of South-East Asian Origin - Part I

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3-Epi-cyclolaudenol and known triterpenes from euphorbia caudicifolia

Cited by 19 publications

References 4 publications

Triterpenoids from the Latex ofEuphorbia caudicifolia

Triterpenoids from the Latex ofEuphorbia caudicifolia

Sterols ofKalanchoe pinnata: First report of the isolation of both C‐24 epimers of 24‐alkyl‐Δ25‐sterols from a higher plant

Technical Analysis of Euphorbia caducifolia Haines Latex of South-East Asian Origin - Part I

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Sterols ofKalanchoe pinnata: First report of the isolation of both C‐24 epimers of 24‐alkyl‐Δ²⁵‐sterols from a higher plant