Studies on constituents of Abies grandis

Kutney, James P.; Grierson, D. S.; Knowles, G. D.; Westcott, Neil D.; Rogers, I. H.

doi:10.1016/s0040-4020(01)99370-6

Cited by 27 publications

(6 citation statements)

References 11 publications

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“…During the course of our work, five groups of investigators have reported the isolation and the structure elucidation of several highly oxygenated lanostanes, 9ß-3 5 3 5, cycloartanes, and some of their analogues from the bark and needles of Abies alba Mill. (7,8), the bark of A. granáis (9), the seeds of both A. mariesii and A. firma (10,11), and the bark and needles of Abies sibilica (12,13).…”

mentioning

confidence: 99%

9β-Lanostane-Type Triterpene Lactones from the Stem Bark of Abies veitchii

Tanaka¹,

Matsunaga²

1991

J. Nat. Prod.

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Two new tetracyclic triterpene lactones were isolated, together with two known compounds, 3-oxo-93-lanosta-7,24-dien-26,23R-olide [2] and 3ß-1^ ^-9ßlanosta-7,24-dien-26,23R-olide [31, from the stem bark of Abies veitchii. The structures of the new compounds were established as 3ot-hydroxy-9ß-lanosta-7,24-dien-26,23f?-olide [6] and 3ce-methoxylanosta-7,9( 1 l),24-trien-26,23R-olide [7], respectively, on the basis of chemical and spectral evidence.Abies veitchii Lindl. (Pinaceae) (Japanese name: Shirabiso) is a tall evergreen tree growing deep in the mountains from central to northern Japan (1). Our previous studies on the chemical constituents of Abies species have revealed a tetracyclic triterpene lactone, abieslactone [1] (3 -methoxy-9ß-lanosta-7,24-dien-26,23f?-olide) (2,3), from the bark and leaves oí Abies mariesii Mast., Abies amabilis (Dougl.) Forbes, and Abies procera Rehd., a mixture of five «-alkyl ferulates bearing alkyl moieties from C-22 to C-26, a mixture of campesterol and ß-sitosterol, 3--9ß-5 3-7,24-dien-26,23f?-olide [2] (4), 3ß-hyd Oxy-9ß-lanosta-7,24-dien-26,23R-olide [31, and 27-hydroxy-3-oxo-9ß-lanosta-7,24-dien-26,23/?-olide [4l (5) from the bark of Abies firma Sieb. et Zuce.,

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mentioning

confidence: 99%

9β-Lanostane-Type Triterpene Lactones from the Stem Bark of Abies veitchii

Tanaka¹,

Matsunaga²

1991

J. Nat. Prod.

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“…[27] It is noteworthy that the configuration of C23 in the biogenetic precursor can either be R or S because both configurations are commonly found in five-membered a,b-unsatuated-glactone rings in nature. [28] These conclusions are very significant for our new biogenetic pathway. The remaining question is whether or not 1 and 4 can be formed through this route as there are two possible intramolecular dehydration products formed between the two OH groups of each hydrated intermediate (26,28,30,33, 36, 39; Scheme 3).…”

mentioning

confidence: 88%

“…[28] These conclusions are very significant for our new biogenetic pathway. The remaining question is whether or not 1 and 4 can be formed through this route as there are two possible intramolecular dehydration products formed between the two OH groups of each hydrated intermediate (26,28,30,33, 36, 39; Scheme 3).…”

mentioning

confidence: 88%

Structure Elucidation and Theoretical Investigation of Key Steps in the Biogenetic Pathway of Schisanartane Nortriterpenoids by Using DFT Methods

Xiao

Lei

Ren

et al. 2008

Chemistry A European J

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Rubrifloradilactone C (4), a novel bioactive nortriterpenoid, along with four other nortriterpenoids (1-3, 5) were isolated from Schisandra rubriflora. The structure of 4 was determined by extensive NMR spectral analysis, computational evidence by using the GIAO method at the B3LYP/6-311++G(2d,p)//B3LYP/6-31G(d) levels, and X-ray analysis. DFT at the B3LYP/6-311+G(d,p) level was selected to clarify the key mechanistic steps in the formation of 1 and 4 through transition-state (TS) investigations. The effect of enzymes on the TS barriers was considered by using the polarized continuum model. Other possible products based on the new mechanism were predicted.

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“…145 (20), 141 (lo), 135 (33), 133 (24), 127 (lo), 125 (ll), 123 (17), 121 (39, 119 (36). 111 (7). 109 (37), 107 (35) 4, 481.0, 470.4, 468.7.…”

Section: (=Viii)unclassified

“…Recrystallization from hexane provided an analytical sample of (24S)-24,25[2H~]isopropylidinediox~v-5a-lanost-9(1l)-en-3~-ol (17), 484 (7), 483 (7), 469 (71, 468 (12). 467 (35), 466 (211, 453 (6), 451 (21), 424 (3, 423 (9, 410 (6), 409 (19), 407 ( I I ) , 392 (7), 391 (23), 357 (6), 356 (27), 355 (loo), 309 (7), 301 (6), 297 (9), 295 (21), 288 (5), 285 (5). 283 ( 5 ) , 281 (7), 271 (5), 269 (8), 257 (6), 255 (17), 253 (7), 243 (6), 241 (14), 239 (9), 229 (14), 227 (15), 225 (6), 215 (19).…”

Section: (=Viii)mentioning

confidence: 99%