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).

Keywords

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

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