4-deoxyphorbol and 4α-deoxyphorbol aldehydes new diterpenes and their esters

Antimycobacterial Activity of Phorbol Esters from the Fruits of Sapium indicum

“…The IR spectrum showed the presence of carbonyls (1724, 1687 cm -1 ), and the UV spectrum (λ max 253, 360 nm) suggested the presence of a conjugated enone and benzoyl chromophores. 12 The 1 H and 13 C NMR spectra (Tables 1-3), analyzed by the aid of 1 H-1 H COSY and HMQC experiments, showed patterns similar to those of known compounds (3, 5, and 7) 3,4 (Tables 1-3), with signals at δ 7.59 for H-1 (C-1 at δ 60.0), 5.25 for H-7 (C-7 at δ 125.7), and 1.05 for H-14 (C-14 at δ 35.8).…”

“…Previous phytochemical studies on S . indicum have resulted in the isolation of several phorbol esters. − Recently, several phorbol esters were found to inhibit HIV-1 . As part of our continuing chemical studies on Thai medicinal plants, − we describe herein the chromatographic separation of a hexane extract of the fruits of S. indicum , which resulted in the isolation of three new phorbol esters, 12-(2- N -methylaminobenzoyl)-4 β ,5,20-trideoxyphorbol-13-acetate ( 1 ), 12-(2- N -methylaminobenzoyl)-4 α ,5,20-trideoxyphorbol-13-acetate ( 2 ), and 12-(2- N -methylaminobenzoyl)-4 α ,20-dideoxy-5-hydroxyphorbol-13-acetate ( 6 ), along with six known phorbol esters.…”

“…Compounds 1-9 were evaluated for their antimycobacterial activity against Mycobacterium tuberculosis H37Ra. 11 Six compounds of previously known structure were isolated from the hexane extract of the fruits of S. indicum, as described in the Experimental Section, and were identified, in turn, as sapintoxin A (3), 3 R-sapinine (4), 3 sapintoxin C (5), 4 sapintoxin B (7), 4 12-(2′-N-methylaminobenzoyl)-4R-deoxy-5,20-dihydroxyphorbol-13-acetate (8), 2 and 12-(2methylaminobenzoyl)-4-deoxyphorbaldehyde-13-acetae (9), 3 by comparison of their physical and spectral data with reported values. The 13 C NMR spectral data of these known isolates are reported herein for the first time.…”

Diterpenoids from the Roots of Euphorbia fischeriana

“…It is rare to find an aldehyde group present at C-20 in the tigliane nucleus. The first example was 12-[2-methylaminobenzoyl]-4-deoxyphorbaldehyde-13-acetate . On the basis of the above spectroscopic information, the structure of 5 was deduced as 12-deoxyphorbaldehyde-13-acetate.…”

Alienusolin, a New 4α-Deoxyphorbol Ester Derivative, and Crotonimide C, a New Glutarimide Alkaloid from the Kenyan Croton alienus

“…The acetate group and two acyl groups were attached via oxygen at C-13, C-12, and C-20, respectively. The acetate group was determined to be attached to C-13 due to correlations observed in the NOESY spectrum between H 3 -16 and the acetoxy methyl group proton resonance, supported by the downfield shift of H-12 at δ 5.47, characteristic of esters that exhibit the presence of an acyl group at C-12 and an acetate group at C-13 [20,21]. Acid hydrolysis of compound 1 and subsequent analysis of the resulting products using GC/MS suggested that the acyl groups attached to C-12 and C-20 were the same and were determined to be decanoyl moieties.…”