Cananga latifolia 수피의 식물 유래 곤충 유충 호르몬 유도체 성분
Plant-derived juvenile hormone III analogues from the stem bark of Cananga latifolia
- 약학대학 약학과
- Issue Date
- 서울대학교 대학원
- 학위논문 (석사)-- 서울대학교 대학원 : 약학과, 2013. 2. 성상현.
- Juvenile hormone III (JH III) regulates important physiological development such as metamorphosis and reproduction in insect species. Since JH III was first to be isolated from the plant, Cyperus iria, the discovery of JH III has not been reported in other plants. In the present study, we succeeded in gaining a proof of the existence of JH III and its mimics from Cananga latifolia.
From 80% MeOH extract of C.latifolia stem bark, six new compounds (4-5, 8-11) were isolated along with ten known compounds (1-3, 6-7, 12-16). Six compounds were determined as (2E, 6E, 10R)-11-butoxy-10-hydroxy-3, 7, 11-trimethyldodeca-2, 6-dienoic acid methyl ester (4), (2E, 6E)-3, 7, 11-trimethyl-10-oxododeca-2, 6-dienoic acid methyl ester (5), (2E)-3-methyl-5-[(1S, 2R, 6R)-1, 2, 6-trimethyl-3-oxocyclohexyl]-pent-2-enoic acid methyl ester (8), 1β-hydroxy-3-oxo-4β, 5α, 7α-H-eudesmane 11-O-α-L-rhamnopyranoside (9), aubergenone 11-O-2′, 3′-di-O-acetyl-α-L-rhamnopyranoside (10) and aubergenone 11-O-2′, 4′-di-O-acetyl-α-L-rhamnopyranoside (11) by spectroscopy analysis.Three known compounds, methyl-10R-hydroxy-3, 7, 11-trimethyl-2E, 6E, 10E-dodecatrienoate (6), (2E, 6E, 10R)-10, 11-dihydroxy-3, 7, 11-trimethyldodeca-2, 6-dienoic acid (3) and (2E, 6S)-3-methyl-6-hydroxy-6-[(2R, 5R)-5-(2-hydroxypropan-2-yl)-2-methyltetrahydrofuran-2-yl]-hex-2-enoaic acid methyl ester (7), were also reported for the first time from the plants, not the insects or synthetic chemistry.
By analysis of the chemical constituents of C. latifolia using an UPLC-QTOF/MS system, Juvenile Hormone Ⅲ (1) and (2E, 6E, 10R)-10, 11-dihydroxy-3, 7, 11-trimethyldodeca-2, 6-dienoaic acid methyl ester (2) were predominantly present in the 80% MeOH extract of C.latifolia.