Extractives from Cedrela odorata L. The structure of methyl angolensate

Chan, Wai-Shing; Magnus, K. E.; Mootoo, Baldwin S.

doi:10.1039/j39670000171

Cited by 18 publications

(22 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Cineracipadesin A (1), with both a 9,11-epoxide ring and an 8,30-epoxide ring, is the second example of such a limonoid found in nature. 13 The molecular formula C 31 14 2D NMR analysis confirmed this suggestion and provided detailed information on its structure. The HMBC correlations of H-2/C-2-OAc and H-3/ C-3-OAc identified two O-acetyl groups at C-2 and C-3, respectively.…”

supporting

confidence: 67%

Tetranortriterpenoids from the Leaves of Cipadessa cinerascens

Fang

et al. 2009

J. Nat. Prod.

View full text Add to dashboard Cite

Seven known and six new tetranortriterpenoids, cineracipadesins A-F (1-6), were isolated from the leaves of Cipadessa cinerascens. Compound 1 has a mexicanolide-type structural skeleton with a rare 9alpha,11alpha-epoxide ring; compound 2 has a methyl angolensate-type structure with 9,11-dihydroxy groups, representing the first example of a precursor of a trijugin-type limonoid; and 3 is the first reported methyl angolensate-type limonoid with a ketone group at ring C. Their structures were determined with extensive spectroscopic analysis. X-ray crystallography confirmed the structure of 1. The ability of compounds 1-7 to inhibit the growth of the P-388 murine leukemia cell line was evaluated.

show abstract

supporting

confidence: 67%

Tetranortriterpenoids from the Leaves of Cipadessa cinerascens

Fang

et al. 2009

J. Nat. Prod.

View full text Add to dashboard Cite

show abstract

“…Methyl angolensate ( 24 ) is the most common limonoid in the genus Entandrophragma and is widely distributed in the family Meliaceae . The structure of 24 was established by spectroscopic analysis and chemical transformations, and finally confirmed by X‐ray analysis . Some limonoids belonging to this class have been reported from the species E. angolense (Figure a and b; Table ).…”

Section: Limonoidsmentioning

confidence: 99%

Phytochemistry and pharmacology of the genusEntandrophragmaover the 50 years from 1967 to 2018: a ‘golden’ overview

Happi

Ngadjui

Green

et al. 2018

Journal of Pharmacy and Pharmacology

View full text Add to dashboard Cite

show abstract

mentioning

confidence: 99%

“…HMBC experiment (Fig. 2) showed that 3 was methyl angolensate type limonoid, 10,11) characterized by a six-membered ring C connected with ring A by C-9 and C-10. The structure of 3 was determined by NMR data in DMSO-d 6 signed as HO-9a on the basis of its correlations with C-8, C-9, C-10 and C-11 in HMBC experiment, and with H-11a in NOESY experiment (Fig.…”

mentioning

confidence: 99%

Three New Limonoids from Cipadessa cinerascens

Yuan

et al. 2007

CHEMICAL & PHARMACEUTICAL BULLETIN

View full text Add to dashboard Cite

The leaves and roots of Cipadessa cinerascens (PELL.) HAND-MAZZ (Meliaceae), a shrub distributed in Southwest China, are used for the treatment of rheumatism, malaria, scald and skin itch.1) From the leaves of C. cinerascens flavonoids and their glucosides were isolated. [2][3][4] From the leaves and bark of C. cinerascens, novel limonoids, cipadesins A-C, were obtained during our study.5) The continued study led to the isolation of three new limonoids, cipadesins D-F (1-3), together with 8,15-dihydroxy-13E-labdane, 6) b-sitosterol and b-daucosterol. 168.8, 170.4, 170.8), the left twenty six 13 C-NMR signals indicated that 1 may be a limonoid. The presence of b-substituted furan ring (d H 6.42, 7.44, 7.59; d C 108.8, 121.1, 140.4, 143.4) and four tertiary methyl groups as well as the HMBC experiment ( Fig. 2) showed that 1 was trijugin type limonoid, [7][8][9] characterized by a five-membered ring C with an exocyclic carbonyl at C-9. Three acetyl groups were located at C-2, C-3 and C-12 by the HMBC cross signals between H-2 (d H 5.25), OAc (d C 170.4), between H-3 (d H 5.14), OAc (d C 170.8), and between H-12 (d H 5.55), OAc (d C 168.8). The relative stereochemistry of 1 was determined by NOESY experiments (Fig. 2). X-Ray crystallographic analysis of 1 (Fig. 3) confirmed the structure.The UV, IR, 1 H-and 13 C-NMR spectral data of cipadesins E, F (2, 3) were similar to those of 1, suggesting they are all limonoids.Cipadesin E (2) was isolated as white powder. Its molecular formula C 31 H 38 O 12 was provided by the quasi-molecular ion peak at m/z 625.2283 [MϩNa] ϩ in the HR-ESI-MS. The presence of a ketonic carbonyl group and four ester carbonyl groups were recognized from the IR peak at 1746 cm Ϫ1 , and 7) showed that 2 was trijugin type limonoid (Fig. 2). A hydroxyl group resonated at d 4.72 gave HMBC correlations with C-9 and C-11, and NOESY correlation with H-12a, allowing it to be assigned to C-11a. The remaining structure was confirmed by HMBC and NOESY experiments (Fig. 2).Cipadesin F (3) was isolated as white powder. Its molecular formula C 31 H 40 O 11 was concluded from the quasi-molecular ion peak at m/z 611.2471 [MϩNa] ϩ in the HR-ESI-MS. Four ester carbonyl groups were revealed by the IR peak at 1739 cm Ϫ1 and 13 C-NMR signals at d 175.0, 170.7, 170.2 and 169.9. HMBC experiment (Fig. 2) showed that 3 was methyl angolensate type limonoid, 10,11) characterized by a six-membered ring C connected with ring A by C-9 and C-10. The structure of 3 was determined by NMR data in DMSO-d 6 . The hydroxyl group resonated at d 4.72 was as- D-F (1-3), together with 8,15-dihydroxy-13E-labdane, b b-sitosterol and b b-daucosterol, were isolated from the leaves and bark of Cipadessa cinerascens. Their structures were elucidated by spectral evidence. X-Ray crystallographic analysis confirmed the structure of 1.

show abstract

Extractives from Cedrela odorata L. The structure of methyl angolensate

Cited by 18 publications

References 0 publications

Tetranortriterpenoids from the Leaves of Cipadessa cinerascens

Tetranortriterpenoids from the Leaves of Cipadessa cinerascens

Phytochemistry and pharmacology of the genusEntandrophragmaover the 50 years from 1967 to 2018: a ‘golden’ overview

Three New Limonoids from Cipadessa cinerascens

Contact Info

Product

Resources

About