Rearranged (4→2)-abeo-clerodane and clerodane diterpenes from Aristolochia chamissonis

Bomm, Mauro Dionei; Zukerman-Schpector, Júlio; Lopes, Lucia Maria Xavier

doi:10.1016/s0031-9422(98)00583-4

Cited by 32 publications

(31 citation statements)

References 18 publications

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“…The optical rotation values and spectral characteristics ( 1 H and 13 C NMR, MS and IR) of 5 and 6 agreed with those of kolavelool 8,11 and kolavenol, 8,12 respectively. The first was already obtained from Guarea trichilioides 13 Thus compound 7 is reported for the first time as a genuine natural product.…”

Section: Resultssupporting

confidence: 63%

“…A previous chemical study of the aerial parts of a specimen of Guarea kunthiana found in Ecuador resulted in the isolation of the limonoid ecuadorin. 2 No limonoids were detected in the leaves of the specimen investigated in the present work which provided, on the other hand, one new, ent-kaur-16-en-2-one (3) and three known, ent-kaur-16-ene (1), ent-3β-and 3α-hydroxykaur-16-ene (2, 4) kaurenoids, three known ent-clerodane diterpenes, kolavelool (5), kolavenol (6) and kolavenal (7), the cembranoid (-)-nephthenol (8) and ent-13-epimanoyloxide (9) in addition to four known sesquiterpenes, spathulenol (10) alismol (11), alismoxide (12), and (-)-4β,10α-aromadendranediol (13), polyprenol-12 (14) and α-and δ-tocopherols (15,16). Kolavenal has now been reported for the first time from nature, while it was known earlier as a derivative by synthesis from kolavenol.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Terpenoid constituents from leaves of Guarea kunthiana

Garcez¹,

Garcez²,

Silva³

et al. 2004

J. Braz. Chem. Soc.

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sesquiterpenos (alismol, alismóxido, espatulenol e 4β,10α-aromadendranodiol), poliprenol-12 e α-e δ-tocoferóis. Kolavenal está sendo relatado pela primeira vez como produto natural, assim como a ocorrência de diterpenos do tipo cembrano e ent-caurano na família Meliaceae.From leaves of Guarea kunthiana one new kaurene diterpene (ent-kaur-16-en-2-one) was isolated along with eight known diterpenes (ent-kaur-16-ene, ent-3α-and 3β-hydroxykaur-16-ene, kolavelool, kolavenol, kolavenal, ent-13-epi-manoyloxide and (-)-nephthenol), four sesquiterpenes (alismol, alismoxide, spathulenol and 4β,10α-aromadendranediol), polyprenol-12 and α-and δ-tocopherols. Kolavenal is reported for the first time as a natural product, as well as the occurrence of cembrane-and ent-kaurane-type diterpenes in the Meliaceae.

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Section: Resultssupporting

confidence: 63%

Section: Introductionmentioning

confidence: 99%

Terpenoid constituents from leaves of Guarea kunthiana

Garcez¹,

Garcez²,

Silva³

et al. 2004

J. Braz. Chem. Soc.

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“…243 A clerodane peroxide, 15(16)-peroxy-3,13-clerodadien-18-oic acid 404, was isolated from the Taiwanese liverwort Schistochila acuminata, 244 and the structurally related 2β-hydroperoxykolavelool 405 was reported from Aristolochia chamissonis. 245 The plant Casearia arguta afforded further members of the series, argutins F-H 406-408. 246 The aerial parts of Aster oharai contained two labdane peroxides 409 and 410, of which compound 409 showed moderate cytotoxicity against several human tumor cell lines with ED 50 values ranging from 1.1 to 7.7 μg/mL.…”

mentioning

confidence: 99%

Peroxy natural products

Liu

2013

Nat. Prod. Bioprospect.

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“…The molecular formula of 1 was revealed as C 19 gest that 1 has a clerodane-type skeleton [4,5]. The data also indicated that 1 is partially similar to 2 and 3, except for the side chain at C-11 [6,7], ( [6 -9] (Fig. 2).…”

Section: Resultsmentioning

confidence: 90%