New Triterpenes from the Bark of Western White Pine (<i>Pinus monticola</i> D<scp>OUGL</scp>.)

Kutney, James P.; Eigendorf, Guenter K.; Worth, Brian R.; Conner, Anthony H.; Nagasampagi, B. A.

doi:10.1002/hlca.19810640424

Cited by 19 publications

(4 citation statements)

References 16 publications

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“…The NOESY spectrum showed NOE correlations between H-5 and Me-28α and H-1α; and H-9 and Me-18β and Me-19β, respectively. The configuration of the hydroxyl group at position 24 was established by CD using 2% Eu(dpm) 3 in CCl 4 as the solvent. , The CD spectrum of 3 exhibited a positive Cotton effect curve at 285 nm (Δε −1.34) and 310 nm (Δε +1.21), indicating S -configuration of the hydroxyl group at C-24. Accordingly, 3 was elucidated as 3-oxolanost-9β H -7-en-24 S ,25-diol.…”

Section: Resultsmentioning

confidence: 99%

Triterpenoid Constituents Isolated from the Bark of Abies sachalinensis

2002

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Three new lanostane-type triterpenoids (1-3) were isolated from the bark of Abies sachalinensis along with a known compound (4). The structures of 1-4 were characterized by spectroscopic methods including NMR and MS. Compound 4 and some derivatives were tested for inhibitory effects on in vitro DNA topoisomerases I and II and found to be selective catalytic inhibitors of topoisomerase II activity with IC(50) values in the range 43-76 microM.

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Section: Resultsmentioning

confidence: 99%

Triterpenoid Constituents Isolated from the Bark of Abies sachalinensis

2002

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“…The above data implied that 3 was a tetracyclic triterpene. Careful analysis of 1D-and 2D-NMR data revealed that compound 3 was very similar to (24S)-3b-methoxy-5a-lanost-9(11)-ene-24,25-diol (4) [9], which was also isolated in this investigation, except for the replacement of a Me group by an Obearing CH 2 group in 3. The HMBCs of Me(27) to the three O-bearing C-atoms (C(24), C(25), and C(26) at d(C) 79.3, 73.9, and 67.7) enabled us to locate the Obearing CH 2 C-atom as C(26) (Fig.…”

Section: Results Andmentioning

confidence: 89%

“…Besides these three new compounds, five known compounds, angustanoic acid D [10], 7,8-epoxy-1(12)-caryophyllen-9b-ol [11], junicedric acid [12], 12-hydroxydehydroabietic acid [13], and (24S)-3b-methoxy-5a-lanost-9(11)-ene-24,25-diol [9] were isolated and identified by means of spectroscopic methods. …”

Section: Results Andmentioning

confidence: 99%

Three New Terpenoids from Pinus yunnanensis

Wang

et al. 2010

Helvetica Chimica Acta

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A new abietatrienoid, 15-methoxydidehydroabietic acid (1), a new ring B-seco abietatrienoid, 10-hydroxy-9,10-secoabieta-8,11,13-trien-18-oic acid (2), and a new tetracyclic triterpenoid, pinusyunnanol (3), together with five known compounds, were obtained from the twigs and needles of Pinus yunnanensis. The structures of the new compounds were elucidated by means of extensive spectroscopic analyses.Introduction. -The genus Pinus is known to be a rich resource of terpenoids [1 -4] and fatty acids [5], some of which exhibited antimicrobial [6] and antiviral [7] activities. Pinus yunnanensis (Pinaceae) is an evergreen tall tree distributed in the southwest of China [8]. In our present work, three new compounds, 15-methoxydehydroabietic acid (1), 10-hydroxy-9,10-secoabieta-8,11,13-trien-18-oic acid (2), and pinusyunnanol (3), along with five known compounds, angustanoic acid D, 7,8-epoxy-1(12)-caryophyllen9b-ol, junicedric acid, 12-hydroxydehydroabietic acid, and (24S)-3b-methoxy-5a-lanost-9(11)-ene-24,25-diol (4), were isolated from the EtOH extracts of the twigs and needles of P. yunnanensis. We report here the isolation and structure elucidation of these compounds by means of extensive spectroscopic analyses.

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“…This was confirmed by HMBC spectral data (see Supporting Information). The relative configuration of the hydroxy group at C-24 was assigned by comparison of the 1 H-NMR spectrum of 2 with that of the known compound [3]. Thus, 2 was lanost-9(11),25-diene-3b,24b-diol.…”

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confidence: 99%

Triterpenoids and Sesquiterpenes fromMulgedium tataricum

Wang¹,

Lin²,

Jia³

2006

Planta Med

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The chemical investigation of Mulgedium tataricum afforded six new compounds which were identified as lanost-9(11),23 Z(24)-diene-3beta,25-diol (1), lanost-9(11),25-diene-3beta,24beta-diol (2), ursane-20-ene-3beta,22alpha-diol (3), 4 E,10 E-3beta,11beta-dihydroxygermacra-4(5),10(1)-dien-12,6alpha-olide (4), 4 E-1beta-hydroperoxy-3beta,11beta-dihydroxygermacra-4(5),10(14)-dien-12,6alpha-olide (5) and lactucin-8-O-P-methoxyphenyl acetate (6) by using a combination of MS and NMR techniques. Compound 6 exhibited significant cytotoxicity against cultured human hepatoma cells (SMMC-7721) and human acute promyelocytic leukemia cells (HL60). The antibacterial activity study indicated that 1 and 2 strongly inhibited the growth of Escherichia coli.

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New Triterpenes from the Bark of Western White Pine (Pinus monticola DOUGL.)

Abstract: SummaryEleven new triterpenes with the lanostene-type skeleton were isolated from the benzene extract of western white pine bark. Their structures were determined mainly on the basis of physical and spectral data.

Cited by 19 publications

References 16 publications

Triterpenoid Constituents Isolated from the Bark of Abies sachalinensis

Triterpenoid Constituents Isolated from the Bark of Abies sachalinensis

Three New Terpenoids from Pinus yunnanensis

Triterpenoids and Sesquiterpenes fromMulgedium tataricum

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