Mass spectrometry of kaurene derivatives—I. The mass spectra of some (−)‐kauran‐16‐ols

Kalinovsky, A. I.; Serebryakov, É. P.; Zolotarev, B. M.; Simolin, A. V.; Kucherov, V. F.; Chizhov, O. S.

doi:10.1002/oms.1210031107

Cited by 11 publications

(4 citation statements)

References 5 publications

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“…= 290 [M] + (11), 123 (100), 94 (77), 105 (77), 272 (71), 134 (61), 232 (60). The mass spectra obtained matched with those for (-)-16a-hydroxykaurane as published by Hunek (1968) and Kalinowsky et al (1970). Since the mass spectra of the 16-a and ß-hydroxy-isomers are different, we were thus able to confirm the 16a-hydroxy configuration.…”

Section: Gc-ms Studiessupporting

confidence: 80%

The moss Physcomitrella patens releases a tetracyclic diterpene

2004

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The presence of the tetracyclic diterpene 16alpha-hydroxykaurane (16alpha-hydroxy-ent-kaurane, C20H34O, CAS 5524-17-4) was detected in sterile cell cultures of the moss Physcomitrella patens (Hedw.) B.S.G. using gas chromatography and mass spectrometry. 16alpha-hydroxykaurane was found to be a major lipid compound in P. patens, with an estimated intracellular concentration of up to 0.84 mmol/l and an extracellular concentration of up to 9.3 micromol/l. The overall content of 16alpha-hydroxykaurane (in milligrams) produced per culture reached 0.37-fold that of chlorophyll a+b. In agar cultures with low air exchange, 16alpha-hydroxykaurane forms needle-like crystals on tissue and on the inner surface of the culture vessels, indicating that it is being released into the atmosphere. Solid phase microextraction confirmed the air-bound release of 16alpha-hydroxykaurane. To our knowledge this is the first report on the release of a plant-derived tetracyclic diterpene into the air.

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Section: Gc-ms Studiessupporting

confidence: 80%

The moss Physcomitrella patens releases a tetracyclic diterpene

2004

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“…(C,,H,,O). Its fragmentation pattern [6] and PMR [7] spectrum aggreed exactly with data published for 16-ahydroxy-kauran.…”

Section: Introductionsupporting

confidence: 82%

“…The second product (11) was eluted by benzene-ethyl acetate (2:l) and it crystallized from hexanelethyl acetate, m.p. 170-174', The physical constants and mass spectrum of this compound aggreed with those reported for 16-a-hydroxykauran-19al [6].. To establish the configuration of the aldehyde group, compound I1 was reduced with LiAlH, in ethereal solution. A diol, m.p.…”

Section: Chromatographysupporting

confidence: 53%

“…The mass spectrum of IIIa shows fragments at m/e91,105,117,131,141, 159, 197, 289 and 285 (lOOO/o). This fragmentation pattern is different from that characteristic of the 16-a-hydroxykaurans [6]. In fact, after an initial loss of water (M+-H,O) the mass spectrum of IIIa is practically identical with the mass spectrum of (-)-kaur-9(11)-16diene-19-oic acid isolated from Espeletia schultzii as-shown in Fig.…”

Section: Chromatographymentioning

confidence: 73%

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Kauranoid Diterpenes in Ruilopezia margarita

Usubillaga¹,

Nakano²

1979

Planta Med

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Pl;nta ad medica ~b n t ~esearch Abstract Four kauranoid diterpenes have been isolated from the leaves and bud stalks of Ruilopezia margarita CUAT. A light petroleum extract was treated with diluted N a O H solution to obtain neutral and acidic fractions. Silica gel/column chromatography rendered 16-ahydroxy-kauran and 16-a-hydroxykauran-19-a1 from the neutral fraction. The acidic fraction yielded 16-a-hydroxy-kauran-19-oic acid and 16-a-hydroxy-kaur-9(11)-ene-19-oic acid. The latter was dehydrated with SOCI,/Pyridine to yield a mixture of A 15 and A 16 kaur-dienes which upon hydrogenation with Pd / MeOH rendered (-)kaur-9(11)-ene-19-oic acid. The name Ruilopezic acid is proposed for this new kaurenic acid.

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Characterization and mass spectral analysis of some grayanotoxin derivatives

Jawad

Kinghorn

Doorenbos

et al. 1977

Biol. Mass Spectrom.

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The mass spectra of grayanotoxin III and some of its mono-, di, and tri-ester derivatives are discussed. Some of the physiological responses of this compound class are also presented. The extraction of this material from a natural source is discussed as well as the schemes for ester derivatization and spectral characterization of all compounds studied. High resolution mass spectral analysis and comparison of the mass spectra of similar compounds were used to define possible fragmentation mechanisms.

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Mass spectrometry of kaurene derivatives—I. The mass spectra of some (−)‐kauran‐16‐ols

Cited by 11 publications

References 5 publications

The moss Physcomitrella patens releases a tetracyclic diterpene

The moss Physcomitrella patens releases a tetracyclic diterpene

Kauranoid Diterpenes in Ruilopezia margarita

Characterization and mass spectral analysis of some grayanotoxin derivatives

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