Terpenes of Podocarpus lambertius

Campello, Jayr de Paiva; Fonseca, S.F.; Chang, Ching-Jer; Wenkert, Ernest

doi:10.1016/0031-9422(75)85047-3

Cited by 27 publications

(2 citation statements)

References 11 publications

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“…been isolated (197)(198)(199)(200)(201)(202)(203)(204)(205)(206)(207)(208)(209)(210), the biological gain for their producers remains still unknown. Structurally and biosynthetically interesting are the toxic (211) ergochromes, e.g.…”

Section: Bi-and Polyphenylsmentioning

confidence: 99%

Fortschritte der Chemie organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products

Bringmann

Günther

Ochse

et al. 2001

Fortschritte Der Chemie Organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products

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Section: Bi-and Polyphenylsmentioning

confidence: 99%

Fortschritte der Chemie organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products

Bringmann

Günther

Ochse

et al. 2001

Fortschritte Der Chemie Organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products

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“…species (16,(18)(19)(20), suggests that important phytochemical differences between these genera do not exist.…”

mentioning

confidence: 99%

Norditerpene Dilactones from Decussocarpus rospigliosii

Amaro-Luis¹,

Carroz²

1988

J. Nat. Prod.

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Decussocarpus rospigliosii (Pilger) De Laubenfels (Podocarpaceae) is a tree found in Venezuela throughout the rain forest zone of the Andes (1). Taxonomically, this species had been included previously in the genus Podocarpus, but it eventually has been reclassified in the genus Decussocarpus (2).Recently, we reported the isolation and identification of four diterpenes in the phenolic fraction of the CHClj extract from the bark of the same species (3). We now report the isolation of nagilactone E, nagilactone F, nagilactone G, ß-sitosterol, and ß-sitosterol 3--ß-D-glucopyranoside from the neutral fraction of this extract.These compounds were identified by comparison of spectroscopic data with literature values (4-6). We also obtained and assigned the 13C-nmr spectrum of nagilactone G; this spectrum has not been published previously.Nagilactone E has only been isolated from Podocarpus nagi Zoll et Moritzi (5), while nagilactones F and G have been reported from several Podocarpus species (5-8).Within the genus Podocarpus sensu stricto, norditerpene dilactones, which exhibit interesting biological and pharmacological activity (9)(10)(11)(12)(13)(14), appear to be especially abundant (7). This fact suggests that the occurrence of similar compounds in D. rospigliosii could be important from the taxonomic and pharmacological point of view.The isolation of some phenolic diterpenes from Decussocarpus species (3,(15)(16)(17), which also occur in Podocarpus

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Chemical Transformations of Phyllocladane (=13β‐Kaurane) Diterpenoids

Liu

Müller

Rüedi

2003

Helvetica Chimica Acta

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Earlier phytochemical work on Plectranthus ambiguus (Lamiaceae) afforded a series of tetracyclic phyllocladane-type ( 13b-kaurane) diterpenoids (see 1a ± f). In the course of investigations concerning the reaction behavior of this rare natural-products, a new constituent of P. ambiguus was isolated, (2S,3R,16R)-phyllocladane-2,3,16,17-tetrol 2,3-diacetate (1g), and another eighteen new phyllocladanes were prepared by chemical transformations and characterized. The main constituent 1b of P. ambiguus was chemically transformed to the known natural diterpenoid calliterpenone ( (16R)-16,17-dihydroxyphyllocladan-3-one; 2) thus unambiguously establishing its structure (Scheme 1). Epimerization at C(16) via the epoxy derivative 20 yielded 16-epicalliterpenone (21), 17-hydroxyphylloclad-15-ene-3-one (22), and (16R)-3-oxophyllocladan-17-al (23) (Scheme 6). Comparing this reaction sequence with the corresponding one starting from diastereoisomeric (16R)-16,17-dihydroxy-ent-kauran-3-one ( abbeokutone; 27) showed basically the same outcome (Scheme 7). Furthermore, three new C(16)-substituted ent-kauran-3-ones were characterized.Reliable spectroscopic arguments for the determination of the configuration at C(16) in phyllocladanes and kauranes as well as for the differentiation of the diastereoisomeric skeletons are presented.

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Terpenes of Podocarpus lambertius

Cited by 27 publications

References 11 publications

Fortschritte der Chemie organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products

Fortschritte der Chemie organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products

Norditerpene Dilactones from Decussocarpus rospigliosii

Chemical Transformations of Phyllocladane (=13β‐Kaurane) Diterpenoids

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