Corymbol, a new diterpenic alcohol

Pérez-Amador, MC; Jiménez, Federico García

doi:10.1016/s0040-4020(01)82267-5

Cited by 10 publications

(6 citation statements)

References 5 publications

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“…21 Compound 5 (C 20 H 34 O 3 , m/z 322.2090) showed the presence of one or more hydroxyl groups (3374 cm -1 ) in its IR spectrum. The 1D NMR spectral data of 5 (Table 2) along with the 2D NMR spectra (COSY-45°, HMQC, HMBC) supported an ent-kaurane-6,16,17-triol skeleton as reported for corymbol, isolated from Turbina corymbosa 22 and Calibrachoa parviflora. 23 However the optical rotation, [R] D 25 -9°(c 0.0425, pyridine), of 5 was found to be different from the reported value of [R] D 25 -38°(pyridine), 23 which suggested that compound 5 might be a stereoisomer of corymbol.…”

Section: Resultssupporting

confidence: 61%

Six New Diterpenoids from Suregada multiflora

et al. 2004

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Six new diterpenoids were isolated from a CH(2)Cl(2)-MeOH extract of the bark of Suregada multiflora. The structures were established on the basis of one- and two-dimensional NMR and other spectroscopic studies and chemical derivatizations. Two compounds, suregadolides C (1) and D (2), were identified as new diterpene lactones of two antipodal series, containing a cyclopropane ring bridging C-3 and C-4 of the basic abietane skeleton. Suremulide A (3) was found to be a new abietene diterpene lactone. Bannaringaolide A (4), a diterpene lactone, based on a novel carbon skeleton with a seven-membered ring, possibly formed by the rearrangement of the exocyclic C-17 in ring C of an ent-pimarane framework, has also been isolated. A kaurane triol, suremulol A (5), and a kaurane diol, suremulol B (6), were also identified as new metabolites.

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Section: Resultssupporting

confidence: 61%

Six New Diterpenoids from Suregada multiflora

et al. 2004

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“…The CHCl 3 extract of stems of C. kusanoi exhibited significant cytotoxic activity against several cancer cell lines. Bioactivity-guided fractionation has led to isolation of two new terpenoids, 3β-hydroxy-11,14-oxo-abieta-8,12-diene ( 1 ) and 3β- trans -(3,4-dihydroxycinnamoyloxy)-11α-methoxy-12-ursene ( 2 ), and four known compounds, including 28-hydroxy-β-amyrone , , erythrodiol ( 3 ) , coniferaldehyde , and β-sitosteryl-3β-glucopyranoside-6′- O -palmitate , from the CHCl 3 extract of stems of C. kusanoi . In this work, structure elucidation of 1 and 2 and the cytotoxic activities of 1−3 (Figure ) are reported.…”

Section: Introductionmentioning

confidence: 99%

Terpenoids Induce Cell Cycle Arrest and Apoptosis from the Stems of Celastrus kusanoi Associated with Reactive Oxygen Species

Chen

Lin

Huang

et al. 2010

J. Agric. Food Chem.

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Bioguided fractionation of the CHCl(3) extracts obtained from Celastrus kusanoi stems led to isolation of two new terpenoids, 3beta-hydroxy-11,14-oxo-abieta-8,12-diene (1) and 3beta-trans-(3,4-dihydroxycinnamoyloxy)-11alpha-methoxy-12-ursene (2), and four known compounds characterized by spectroscopic methods. Compounds 1 and 2 and known triterpenoid erythrodiol (3) exhibited cytotoxic activity against bladder cancer cells (NTUB1) with IC(50) values of 58.2 +/- 2.3, 160.1 +/- 60.9, and 18.3 +/- 0.5 microM, respectively. Exposure of NTUB1 to 3 (5 and 10 microM) for 24 h significantly increased the level of production of reactive oxygen species (ROS). Flow cytometric analysis showed that treatment of NTUB1 with 3 led to the cell cycle arrest at G0/G1 accompanied by an increase in the extent of apoptotic cell death after 24 h. These data suggest that the presentation of G1 phase arrest and apoptosis in 3-treated NTUB1 for 24 h was mediated through an increased amount of ROS in cells exposed to 3.

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“…Compound 8 treated similarly gave methyl 2-methyl butyrate and monoacetate 4. ent-Kaurane-7a.,16$,17-triol [9].-From fraction I, followed by Dynamax C-18 (21.4 X 250 mm) 30% H20 in MeCN, elution volume 125-140 ml, yield 750 ppm. Mp 220-221°(EtOAc); [ ] (X nm) + 3°(589), +3°(578), +4°( 546), +8°(436), +16°(365) (95% EtOH, r= 1.0); *H nmr (CD3OD) 0.83 (s, H3-19), 0.85 (s, H3-18), 1.06 (s, H3-20), 3.58 (d,J= 12 Hz, 1/2 H2-17), ca. 3.60 (m, H-7), 3.70 (d, J= 12, 1/2 H2-17); 13C nmr see Table 2; eims m!z [M]+ 322.2507 (C20H34O3 requires 322.2509).…”

Section: Interconversions Of Compoundsmentioning

confidence: 99%

“…7-Keto-etxx.-kaurane-16$, 17-dial [12],-From fraction I, followed by Dynamax C-18 (21.4 X 250 mm) 30% H20 in MeCN, elution volume 140-160 ml, yield 70 ppm. Mp 168-170°( heptane); [ ] (X nm)-12°(589), -12°(578), -10°(546), +24°(436), +198°(365); irvmax(CHCl3)cm™13600, 3450 br, 1695; *H nmr (CDC13) 0.86 (s, H3-18, -19), 1.19(H3-20), 3.73 (m, H2-17); 13C nmr see Table 2;…”

Section: Interconversions Of Compoundsmentioning

confidence: 99%

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Diterpenes of Calibrachoa parviflora

Elliger¹,

Wong²,

Benson³

et al. 1992

J. Nat. Prod.

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Califi.n& 94710 hSTRACT.-hVeS of Calibraha pawrflwa gave the huranoids corymbl 6-monuacetate [4} and corymbl 17-monoacetate [5], corymbl 17-(2-methylbutyrate) [6], and corymbl 6-acetate-17-(2-methylbutyrate) 181. Other new kauranoids were ent-hurane-7a, 16@,17-triol 191, its 7-acetate [lo], and its 7-acetate-17-(2-methylburyrate) [ll], the corresponding 7-ketcdiol [12]and its 17-acetate 1133. New pimaranes were 15R, 16dihydroxy-cnt-isopimar-8( 14)-en-7-one 1141 and the ring-closed analogues, 14a, 16-oxido-mt-isopimar-7-en-15a-ol [17j and 14a, 16-oxidoart-isopimar-7-ene-6a, 15a-diol [ZO]. The known diterpenes, entkaurane-l6~,17diol, its 17-acetate, ent-hurane-&, 16p,l?-triol (corymbl), and its 6,17-diacetate were also obtained. C . p a w i f i a did not yield any of the ergostanoids that are characteristic of Petunia species, rhus supporting its recent reassignment into a separate genus.In a continuing investigation of plant resistance toward insect herbivores, we have shown that foliage of various Petunia (Solanaceae) species is toxic to certain insects, and that this effect can be related to the presence in the leaves of a large number of steroidal substances which we have termed petuniasterones and petuniolides (1,2). More recently (3), we reported the occurrence in Petunia infita of a set of novel pyridine ringcontaining analogues of these steroids (petunianines) which are also agents that inhibit insect growth and development. While evaluating plants that are closely related to Petunia it was of interest to examine the allied species Calibrachoa pawtfia (=Petunia pawifia) Jess. (Solanaceae), which has the same range in South America as Petunia and is found in Mexico, Cuba, and the United States as far north as New Jersey. The plants of C. pawifia have 2n = 2x = 18 chromosomes, in contrast to all species of Petunia with 2n= 2x= 14 (4), and this genus has recently been distinguished from that of Petunia ( 5 ) . RESULTS AND DISCUSSIONIn the present study, larvae of the lepidopteran Helic-a zeu (=Hehothis zeu Boddie) survived well on fresh stems and leaves of C. pawifia, and it was, therefore, of interest to determine if any steroids similar to those responsible for toxicity in Petunia occurred in Calibraha, and if so, whether differing structure lessened toxicity. No steroidal substances of the Petunia type were isolated from C. pawifia; however, numerous diterpenes were present including several previously undescribed kauranoids and pimaranes. These findings support the conclusion that C. pawifia is correctly assigned in a genus distinct from Petunia.KAuRANES.-Compounds 1-13 belong to the ent-kaurane series. Diol 1 has been isolated previously from Croton and other genera, and its acetate 2 has been prepared (7,8). The 13C-nmr spectra of 1 and 2 (Table 1) were in agreement with shifts reported for kauranoid systems (9,lO) in general, and with values observed for the relevant carbons of abbeokutone acetate (1 1).Compound 3 has the structure ascribed to corymbol isolated from Turbina cwymbosa (12), but the observ...

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Corymbol, a new diterpenic alcohol

Cited by 10 publications

References 5 publications

Six New Diterpenoids from Suregada multiflora

Six New Diterpenoids from Suregada multiflora

Terpenoids Induce Cell Cycle Arrest and Apoptosis from the Stems of Celastrus kusanoi Associated with Reactive Oxygen Species

Diterpenes of Calibrachoa parviflora

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