Eurifoloids A–R, Structurally Diverse Diterpenoids from Euphorbia neriifolia

Abstract

Eighteen new diterpenoids, named eurifoloids A-R (1-18), including ingenane (1 and 2), abietane (3-7), isopimarane (8-12), and ent-atisane (13-18) types, along with four known analogues were isolated from Euphorbia neriifolia. Eurifoloid M (13) represents a rare class of ent-atisane-type norditerpenoid. Eurifoloids E (5) and F (6) exhibited significant anti-HIV activities, with EC50 values of 3.58 ± 0.31 (SI = 8.6) and 7.40 ± 0.94 μM (SI = 10.3), respectively.

Terpenes from Euphorbia antiquorum and Their in Vitro Anti‐HIV Activity

“…To evaluate the anti‐HIV activities of the compounds isolated from E. antiquorum , we tested them on HIV‐1 NL4‐3 infected MT4 cells in vitro ( Table ) and compound 7 showed a moderate activity, with an EC 50 value of 1.38 ± 0.45 (SI = 7.61). The eight known diterpenoids were separated and identified to be (3 R ,12 R )‐3,12‐dihydroxy‐ ent ‐isopimara‐8(14),15‐dien‐18‐al ( 4 ), eurifoloid I ( 5 ), ent ‐kaurane‐3‐oxo‐16 β ,17‐diol ( 6 ), 8‐ O ‐methylingol‐3,12‐diacetate‐7‐benzoate ( 7 ), ingol‐3,8,12‐triacetate 7‐tiglate ( 8 ), 3,8,12‐ O ‐triacetylingol 7‐benzoate ( 9 ), euphorantin I ( 10 ) and 3,12‐ O ‐diacetyl‐7‐ O ‐angeloyl‐8‐methoxyingol ( 11 ) by comparing the spectroscopic data with those reported.…”

Diterpenoids from Euphorbia neriifolia and Their Related Anti‐HIV and Cytotoxic Activity

“…Compounds 4 – 15 were elucidated to be ent ‐16 α ,17‐dihydroxyatisan‐3‐one ( 4 ), eurifoloid R ( 5 ), ent‐ atisane‐3 α ,16 α ,17‐triol ( 6 ), ent ‐atisane‐3 β ,16 α ,17‐triol ( 7 ), ent ‐atisane‐1 β ,16 α ,17‐triol ( 8 ), 4,13 β ‐dihydroxy‐14‐oxo‐3,4‐secoatis‐16‐en‐3‐oic acid methyl ester ( 9 ), eurifoloid M ( 10 ), ent ‐3 S ‐hydroxyatis‐16(17)‐en‐1,14‐dione ( 11 ), ent ‐3 α ,13 S ‐dihydroxyatis‐16‐en‐14‐one ( 12 ), ent ‐3 β ,13 S ‐dihydroxyatis‐16‐en‐14‐one ( 13 ), ent ‐13 S ‐hydroxyatis‐16‐ene‐3,14‐dione ( 14 ), and (4 R ,5 S ,8 S ,9 R ,10 S ,13 R ,16 S )‐ ent ‐16 α ,17‐dihydroxy‐19‐tigloyloxykauran‐3‐one ( 15 ) ( Figure ) through spectroscopic data by comparison with those of literature values.…”

“…Euphorbia neriifolia Linn . (Euphorbiaceae), a poisonous plant, is native to India and also cultivated in south and southwest of China . It has been reported that various parts, stems, leaves, roots and milky latex of E. neriifolia have several ethnomedicinal uses.…”

“…It has been reported that various parts, stems, leaves, roots and milky latex of E. neriifolia have several ethnomedicinal uses. For example, the milky latex is rated as laxative and expectorant . A number of structurally diverse diterpenoids have been reported from the title plant, several of which exhibited anti‐HIV, cytotoxic, immunomodulatory, and anti‐inflammatory activities…”

(±)‐Hippolide J – A Pair of Unusual Antifungal Enantiomeric Sesterterpenoids from the Marine Sponge Hippospongia lachne

“…[24,25] The 1 H NMR spectrum displayed resonances of four olefinic protons at δ H = 5.86, 5.66, 5.06, and 5.08 ppm; three methine protons at δ H = 2.13, 2.72, and 2.87 ppm; two oxygenated methylene groups at δ H = 4.04 and 4.64 ppm; and four methyl singlets at δ H = 1.08, 1.58, 1.60, and 1.68 ppm ( Table 1). The molecular formula C 25 H 36 O 3 with eight degrees of unsaturation was deduced from the molecular ESI-HRMS ion peak at m/z = 407.2563 [M + Na] + .…”