Is phototridachiahydropyrone a true natural product?

Gavagnin, Margherita; Mollo, Ernesto; Cimino, Guido

doi:10.1016/j.bjp.2015.07.028

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Original Articles • Rev. bras. farmacogn. 25 (6) • Dec 2015 • https://doi.org/10.1016/j.bjp.2015.07.028 copy

Is phototridachiahydropyrone a true natural product?^☆ ☆ Dedicated to Prof. Rosângela De Almeida Epifanio's memory. She spent one year in our institute giving, with her enthusiasm, culture, will, and rigorous work, relevant contributions to marine chemistry.

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Abstract

The occurrence of (−)-phototridachiahydropyrone (5) in nature has been proven. This compound has been now identified as minor component of the extract of marine sacoglossan mollusk Elysia crispata from which the main (−)-tridachiahydropyrone (4) was previously described. Synthetic (±)-5 was formerly obtained by Moses’ group by biomimetic photochemical conversion of (±)-tridachiahydropyrone (4). The same authors suggested that compound 5 had to be a natural product derived from precursor 4 “yet to be discovered”. Comparison of CD profiles of natural (−)-4 and (−)-5 indicated the same absolute configuration for both compounds. This evidence is in agreement with the concerted mechanism proposed for the photochemical conversion.

Keywords
Marine natural products; Polypropionates; Sacoglossans; Tridachiahydropyrones

Carbon	δ_H (mult, J)	δ _C	m	HMBC (C→H)
1	–	165.7	s	H3-20; OMe
2	–	87.9	s	H3-20
3	–	194.8	s	H-9; H3-17; H3-20
4	–	44.6	s	H-7; H-9; H3-17
5	–	145.0	s	H-7; H-9; H3-17; H3-19
6	–	117.4	s	H-7; H3-19
7	3.08 (s)	57.5	d	H-9; H-11; H3-18; H3-19
8	–	131.8	s	H-7; H3-18
9	5.95 (s)	12.8	d	H-7, H3-17; H3-18
10	–	133.4	s	H-7; H2-12; H3-16
11	5.41 (bt, 7.1)	129.2	d	H-7; H2-12; H3-16
12	1.96 (dd, 7.1, 6.9)	37.4	t	H-11; H3-14; H3-15
13	1.65 (m)	28.9	d	H2-12; H3-14; H3-15
14	0.91 (d, 6.6)	22.4	q	H2-12
15	0.91 (d, 6.6)	22.4	q	H2-12
16	1.38 (bs)	11.9	q	H-7; H-11
17	1.34 (s)	27.6	q	H-7
18	1.60 (s)	21.0	q	H-7; H-9
19	1.64 (s)	13.1	q	H-7
20	1.64 (s)	6.7	q	–
OMe	3.99 (s)	55.0	q	–

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[1] * Corresponding author. E-mail:mgavagnin@icb.cnr.it (M. Gavagnin).

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Is phototridachiahydropyrone a true natural product?☆ ☆ Dedicated to Prof. Rosângela De Almeida Epifanio's memory. She spent one year in our institute giving, with her enthusiasm, culture, will, and rigorous work, relevant contributions to marine chemistry.

Abstract

Is phototridachiahydropyrone a true natural product?^☆ ☆ Dedicated to Prof. Rosângela De Almeida Epifanio's memory. She spent one year in our institute giving, with her enthusiasm, culture, will, and rigorous work, relevant contributions to marine chemistry.