Rhodestrin: A Novel Indole Terpenoid Phytohormone from Rhodobacter sphaeroides

Abstract

A new phytohormone was isolated as a metabolite of anthranilate photobiotransformation by Rhodobacter sphaeroides OU5. It was identified by MS and NMR ((1)H, (13)C) as an indole terpenoid ester [(2E,4E,6E,8E,10E,12E,14E,16E,18E)24-hydroxy-2,6,10,14,19 pentamethyl tetrecosa-2,4,6,8,10,12,14,16,18 nonenyl-2(hydroxy methyl)-1H-indole-3-carboxylate] and is named as rhodestrin. Rhodestrin at 50 nM: gave positive test in auxin bioassay and initiated more profuse and early rooting in tissue-cultured plants than other auxins at 5 microM.

Rhodethrin: a novel indole terpenoid ether produced by Rhodobacter sphaeroides has cytotoxic and phytohormonal activities

“…A UV spectral peak of the metabolite at 270 nm confirmed the indole nucleus and a peak at 419 nm indicated the presence of a terpenoid. This compound differs from sphestrin (Sunayana et al 2005a) or rhodestrin (Sunayana et al 2005b) 3414, 2959, 2926, 1716, 1614, 1456, 1414, 1277, 1246, 1089, 742 and 497 (asymmetrical C-O-C stretches band at 1275-1200 [7.84-8.33 nm] confirm the aryl alkyl ether); EIMS m/z 279 [M] + ; anal. C 64.2% and H 6.8%, calcd.…”

“…Further, root initiation was observed with in 8-10 days in rhodethrin-treated plants, while with IAA it was observed only after 12-15 days. Rhodethrintreated plants had increased root length and thus it differs from rhodestrin, where profuse rooting was observed (Sunayana et al 2005b). …”

“…Infra-red (IR) analysis was done on a Shimadzu FT/IR 5300 spectrophotometer and mass analysis using a Mass VG 70-70H analyzer. Auxin coleoptile bioassay and rooting effects in tissue culture (Sunayana et al 2005b), cytotoxic activity against Sup-T 1 lymphoma and Colo-125 cancer cell lines (Mosman 1983) and COX-2 inhibitory (Copeland et al 1994) studies were done using standard protocols.…”

“…These bacteria are gaining importance with respect to the production of novel metabolites. Indole terpenoid esters, including sphestrin (Sunayana et al 2005a) and rhodestrin (Sunayana et al 2005b), have been reported from these bacteria. Sphestrin had no biological activity though rhodestrin had good phytohormonal activity, while neither compound had cytotoxicity.…”

Mass Cultivation and Secondary Metabolite Analysis of Rhodobacter capsulatus PS-2

“…농축산용 미생물제제로 활용되는 광합성세균 중 홍색비유 황세균 (purple nonsulfur bacteria, PSB)은 혐기·광 조건이나 호기·암 조건에서 생장이 가능하며 여러 유기물과 무기물을 이용하여 다양한 대사활동을 한다 [4]. 또한 균체 성분 중 비 타민과 아미노산 함량이 높고 식물생장촉진 효과가 있는 것 으로 알려져 있다 [5]. 9 cfu/mL로 측정되었다 (Fig.…”