Kulinone

Planta Med. 2011 Jun;77(9):922-8.

Cytotoxic triterpenoids and steroids from the bark of Melia azedarach.[Pubmed: 21243584]

METHODS AND RESULTS:
Two new triterpenoids (1, 2) and two new steroids (3, 4) along with twelve related known compounds (5-16) were isolated from the bark of Melia azedarach. The new structures were elucidated by means of spectroscopic methods and molecular modeling studies and found to be 21,24-cycloeupha-7-ene-3 β,16 β,21 α,25-tetrol (1), 3 β-acetoxy-12 β-hydroxy-eupha-7,24-dien-21,16 β-olide (2), 29-hydroperoxy-stigmasta-7,24(28) E-dien-3 β-ol (3), and 24 ξ-hydroperoxy-24-vinyl-lathosterol (4). All isolated compounds were tested for their cytotoxic activity against three human cancer cell lines (A549, H460, HGC27) using the CellTiter Glo™ luminescent cell viability assay.
CONCLUSIONS:
Among them, compounds 2- 4, 24 ξ-hydroperoxy-24-vinyl-cholesterol (6), Kulinone (7), meliastatin 3 ( 8), 3-oxo-olean-12-en-28-oic acid (10), and (22 E,24 S)-5 α,8 α-epidioxy-24-methyl-cholesta-6,22-dien-3 β-ol (12) were found to have cytotoxic effects, with IC₅₀ values of 5.6-21.2 μg/mL.

J Nat Prod. 2002 Dec;65(12):1886-91.

Antineoplastic agents. 489. Isolation and structures of meliastatins 1-5 and related euphane triterpenes from the tree Melia dubia.[Pubmed: 12502333 ]

The bark of the giant neem tree Melia dubia was found to contain 11 euphane-type triterpenes.
METHODS AND RESULTS:
Five new compounds, meliastatins 1-5 (1-5), proved to inhibit growth of the P388 lymphocytic leukemia cell line (ED(50) 1.7-5.6 microg/mL). Four of the others, the previously known methyl kulonate (8), Kulinone (9), 16-hydroxybutyrospermol (10), and kulactone (11), were also found to inhibit (ED(50) 2.5-6.2 microg/mL) the P388 cancer cell line. In addition, two new euphane triterpenes were isolated and named dubione A (6) and dubione B (7).
CONCLUSIONS:
Structures for each of the 11 euphane triterpenes were established by spectral techniques that included HRMS and 2D NMR.