Journal
PHYTOCHEMISTRY REVIEWS
Volume 14, Issue 5, Pages 835-847Publisher
SPRINGER
DOI: 10.1007/s11101-014-9380-2
Keywords
Cowpea; Germination; Stereochemistry; Striga gesnerioides; Strigolactone
Categories
Funding
- Asia Africa Science Platform Program of the Japan Society for the Promotion of Science
- JST/JICA
- Science and Technology Research Partnership for Sustainable Development (SATREPS)
- Ministry of Education, Science, and Culture of Japan [11J01777, 23405023, 24658111, 25292065]
- Grants-in-Aid for Scientific Research [23405023, 24658111] Funding Source: KAKEN
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Alectrol was first isolated from root exudates of cowpea (Vigna unguiculata), a genuine host of a root parasitic weed Striga gesnerioides, as a germination stimulant for seeds of the parasite. The proposed structure, an isomer of strigol, was disproven by chemical synthesis. Recently, another structure, namely orobanchyl acetate, was proposed. Surprisingly, however, the synthetic compound having this proposed structure for alectrol was not active in inducing germination of S. gesnerioides seeds although it was active toward seeds of other root parasitic weeds such as S. hermonthica and Orobanche minor. Detailed studies on H-1 NMR, mass and CD spectra of naturally occurring alectrol, re-isolated from cowpea root exudates, revealed that the genuine structure of the germination stimulant is not orobanchyl acetate but its stereoisomer ent-2'-epi-orobanchyl acetate. Accordingly, the structure of natural orobanchol was revised to ent-2'-epi-orobanchol 12 years after a tentative structure of orobanchol was proposed. Strict stereochemical requirements of strigolactones for germination induction of S. gesnerioides seeds, authentic samples of synthetic strigolactones and advanced analytical instruments made the structural assignment possible, thus ending a 20 years controversy concerning the true structure of alectrol.
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