Four New Insect Antifeedant neo-Clerodane Diterpenoids, Ajugacumbins A, B, C and D, from Ajuga decumbens

• Published in: Chemical & pharmaceutical bulletin Vol. 37; no. 9; pp. 2505 - 2508
• Main Authors: MIN, Zhi-da, WANG, Shi-qiang, ZHENG, Qi-tai, WU, Binrg, MIZUNO, Mizuo, TANAKA, Toshiyuki, IINUMA, Munekazu
• Format: Journal Article
• Language: English
• Published: Tokyo The Pharmaceutical Society of Japan 1989; Maruzen; Japan Science and Technology Agency
• Subjects: Ajuga decumbens; ajugacumbin A; ajugacumbin B; ajugacumbin C; ajugacumbin D; Analytical, structural and metabolic biochemistry; Biological and medical sciences; Fundamental and applied biological sciences. Psychology; insect antifeedant activity; Labiatae; neo-clerodane; Other biological molecules; Terpenes, steroids. Hormones; X-ray analysis; Characterization; Terpenoid; Molecular structure; Labiatae; Dicotyledones; Angiospermae; Isolation; Spermatophyta; Spectrophotometry; X ray diffraction
• ISSN: 0009-2363; 1347-5223
• DOI: 10.1248/cpb.37.2505

From the ethanol extract of whole herbs of Ajuga decumbens (Labiatae), four new neo-clerodane diterpenoids, named ajugacumbins A, B, C and D (1-4), were isolated. The configuration of 1 was determined to be 6α-acetoxy-4, 17-epoxy-18-tigloyloxy-neo-cleroda-13-en-15, 16-olide by X-ray analysis. THe other structures were also determined by spectroscopic analysis to be 4, 17-epoxy-6α-hydroxy-18-tigloyloxy-neo-cleroda-13-en-15, 16-olide (2), 1α, 3β, 6α-triacetoxy-4, 17-epoxy-18-tigloyloxy-neo-cleroda-13-en-15, 16-olide (3) and 6α-acetoxy-4, 17-epoxy-3β-hydroxy-18-tigloyloxy-neo-cleroda-13-en-15, 16-olide (4). These compounds displayed insect antifeedant activity.