Neolignans from Nectandra puberula

José C. Moro, João B. Fernandes, Paulo C. Vieira, Massayoshi Yoshida, Otto R. Gottlieb, Hugo E. Gottlieb

Research output: Contribution to journalArticlepeer-review

22 Scopus citations

Abstract

The trunk wood of Nectandra puberula was found to contain 1,6-geranylgeranodioic acid besides five neolignans, the known veraguensin and the novel 7-hydroxy- and 7-oxo-3,4,3′,4′-tetraoxy-8.8′-neolignans, all with the (8S,8′R)-absolute configuration.

Original languageEnglish
Pages (from-to)269-272
Number of pages4
JournalPhytochemistry
Volume26
Issue number1
DOIs
StatePublished - 23 Dec 1986
Externally publishedYes

Bibliographical note

Funding Information:
-6300. [O],“p,-2 100. [U]z= Moo. (7S,8S,8’R~3.4,3’.4’-~eframefhox~7.6’.8.8’-neo/i~na(nIO ). To compound 5 (I5 mg) in CH,CI, (3 ml). ptolucnaulpbonic acid (I mg) in CH,CI, was added. The soln was kept for I hr at room temp.. and then. after rhe addition of more CHIC&. was ncutralizal with aq. NaHCO,. The organic layer was dried (MgSO,). fil~crcd and evaporated. Recrystalluat~on of the rc-sldue from Et,0 gave 10 (13.3 mg), mp 128-130 . III. mp 132.8 133.6 [IO]. IR v$,&cm I: 1593. 1474 (Ar). 774; UVigHnm. 230. 281 (c 19650. 69200);M S. see rcf [l3]. ‘H NMR(60 M~CCl.t66.47.6.18.5.89(tpch~,res~tlnly2. 2 and I aromatic protons). 3.67.3.63,3.39( eachs . respozlivcly I. 2, I OMe), 3.25 (d,J - 9 Hz_ H-7’). I.65 I.30 (m,2 H-8.8’). 2.63 (d,J = 7 Hz. 2H-7h 1.02( d,J = 5 Hz. 3H-9).0.80 (d. J - 5 Ht, 3H-9’); [a]; - IS’ (~0.80. M&H). III. [IO] - 8.5; ORD (~0.80: MaHI t~l,,.O.1416-. l4m. t4laoO.C bl!!, + 17 150 [.$I?.. +5550, [&]\c-+6250 CD (c 0110. .McOHr. [0]E,I -8430. [U] p: + 5550. [U] 3 - 1800. [U] z:,’ + 8700 Ac~nowled~nrr-This work was supported by FINEP (grant). CNPq (fellowships IO J.B.F. and M.Y. and grant). CAPES and FAPESP (graduate fellowships to J.C.M. and granb).

Funding

-6300. [O],“p,-2 100. [U]z= Moo. (7S,8S,8’R~3.4,3’.4’-~eframefhox~7.6’.8.8’-neo/i~na(nIO ). To compound 5 (I5 mg) in CH,CI, (3 ml). ptolucnaulpbonic acid (I mg) in CH,CI, was added. The soln was kept for I hr at room temp.. and then. after rhe addition of more CHIC&. was ncutralizal with aq. NaHCO,. The organic layer was dried (MgSO,). fil~crcd and evaporated. Recrystalluat~on of the rc-sldue from Et,0 gave 10 (13.3 mg), mp 128-130 . III. mp 132.8 133.6 [IO]. IR v$,&cm I: 1593. 1474 (Ar). 774; UVigHnm. 230. 281 (c 19650. 69200);M S. see rcf [l3]. ‘H NMR(60 M~CCl.t66.47.6.18.5.89(tpch~,res~tlnly2. 2 and I aromatic protons). 3.67.3.63,3.39( eachs . respozlivcly I. 2, I OMe), 3.25 (d,J - 9 Hz_ H-7’). I.65 I.30 (m,2 H-8.8’). 2.63 (d,J = 7 Hz. 2H-7h 1.02( d,J = 5 Hz. 3H-9).0.80 (d. J - 5 Ht, 3H-9’); [a]; - IS’ (~0.80. M&H). III. [IO] - 8.5; ORD (~0.80: MaHI t~l,,.O.1416-. l4m. t4laoO.C bl!!, + 17 150 [.$I?.. +5550, [&]\c-+6250 CD (c 0110. .McOHr. [0]E,I -8430. [U] p: + 5550. [U] 3 - 1800. [U] z:,’ + 8700 Ac~nowled~nrr-This work was supported by FINEP (grant). CNPq (fellowships IO J.B.F. and M.Y. and grant). CAPES and FAPESP (graduate fellowships to J.C.M. and granb).

FundersFunder number
Conselho Nacional de Desenvolvimento Científico e Tecnológico
Financiadora de Estudos e Projetos

    Keywords

    • Lauraceae
    • Nectandra puberula
    • diaryidimethyl-n-butanones.
    • geranylgeranodioic acid
    • neolignans

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