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. 2001 Mar 9;28(45):5461–5464. doi: 10.1016/S0040-4039(00)96754-6

Reiswigins A and B, novel antiviral diterpenes from a deepwater sponge

Y Kashman 1,2, S Hirsch 1,2, F Koehn 1,2, S Cross 1,2
PMCID: PMC7127280  PMID: 32287434

Abstract

The structures of reiswigins A(1) and B(2), new reduced azulene diterpene enones have been determined by combined one and two dimensional NMR and mass spectral techniques.

The structures of reiswigins A(1) and B(2) have been determined by combined one and two dimensional NMR and mass spectral techniques.

graphic file with name gr1.jpg

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References

  • 1.Taxonomic identification of the sponge was made by S. Pomponi and C. Diaz. M.C. Diaz, B. Alvarez, and R.W.M. VanSoest, New Species of Demospongiae(Porifera) from the National Park “Archipelago de los Roques,” Venezuela. Bijdr. Dierk., In Press.
  • 2.Antiviral assays for herpes simplex virus type 1 (HSV-1) and vesicular stomatitis virus (VSV) were plaque reduction tests in infected CV-1 monkey kidney cells. Coronavirus strain A59 inhibitions were measured by reduction in cell fusion and cytopathic effects in NCTC 1469 mouse liver cells. Readings in these assays range from “-” for no observable viral inhibition, to “3+”, denoting complete inhibition of virus by the test compound. Reiswigin A(1) was nontoxic at 2μg and completely inhibited HSV-1 and VSV. A59 was partially inhibited at 20μg with a 2+ reading. Reiswigin B(2) showed the same activity as 1 against HSV-1 and A-59.
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  • 5.Reiswigin B(2): MS(HREI) m/z 302,0.5%) C20H30O2, 1H NMR(360 MHz,CDCl3)δ 6.04sht(1H,H-17,J=1.3), 5.82s(1H,H-3), 2.41m(2H,H-15), 2.27m(2H,H-5), 2.20m(1H,H-13), 2.13s(3H,Me-20), 1.88s(6H,Me-19,Me-12). 1.82m(1H,H-10) 1.74m(1H,H-8), 1.68m(3H,H-6,H-10), 1.64dt(1H,H-7,J=9.3,1.5), 1.32m(2H,H-9), 1.11s(3H,Me-11), 0.93d(3H,Me-14,J=6.5), 13C NMR(90 MHz, CDCl3): 207.9s, 201.3s, 155.6s, 153.2s, 127.8d, 124.8d, 57.1s, 48.6d, 47.0t, 45.8d, 35.7t, 35.3t, 30.8t, 29.1q, 28.2q, 25.2t, 22.8t, 21.2q, 20.6q, 20.4q, IR(CHCl3): 2900br, 1650, 1605 cm−1, UV(heptane): 234nm(ε=6700) optical rotation [α]D20 =−20° (c= 0.1,CHCl3)
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