Polyketides and Steroids

Jiaju Zhou

• Publisher: De Gruyter
• Year: 2019
• ISBN:
  9783110653717
• Edition: 1
• Topic: Physical Sciences
• Subtopic: Clinical Chemistry

This 8-volume set provides a systematic description on 8, 350 active marine natural products from 3, 025 various kinds of marine organisms. The diversity of structures, biological resources and pharmacological activities are discussed in detail. Molecular structural classification system with 264 structural types are developed as well. The 5th volume mainly illustrates the molecular formula and structures of polyketides and steroids.

1 Polyketides

1.1 Linear Polyketides

1 Balticolid

Type: Linear polyketides nobranched. C₁₂H₁₆O₄ Colorless oil, [α]_D²² = +135.2° (c = 0.35, MeOH). Source: An unidentified ascomycetous fungus (drift-wood, Greifswalder Bodden, Baltic Sea, Germany). Pharm: Anti-HSV-1 (IC₅₀ = 0.45 μmol/L). Ref: M. A. M. Shushni, et al, Mar. Drugs, 2011, 9, 844│S. Z. Moghadamtousi, et al, Mar. Drugs, 2015, 13, 4520 (rev)

2 Aureoverticillactam

Type: Linear polyketides monobranched. C₂₈H₃₉NO₄ Amorph. solid. Source: Marine-derived streptomycete Streptomyces aureoverticillatus NPS001583. Pharm: Cytotoxic (HT29, EC₅₀ = (3.6 ± 2.6)μmol/L; B16-F-10, EC₅₀ = (2.2 ± 0.9)μmol/L; JurKat, EC₅₀ = (2.3 ± 1.1)μmol/L). Ref: S. S. Mitchell, et al, JNP, 2004, 67, 1400

3 Cyanolide A

Type: Linear polyketides dibranched. C₄₂H₇₂O₁₆ Oil, [α]_D²³ = −59° (c = 0.6, CHCl₃). Source: Cyanobacterium Lyngbya bouillonii (Pigeon I., Papua New Guinea). Pharm: Molluscacidal (snail vector Biomphalaria glabrata, LC₅₀ = 1.2 μmol/L, very potent; molluscacides play a critical role in control of schistosomiasis transmission); toxic (brine shrimp, LC₅₀ = 10.8 μmol/L). Ref: H. Kim, et al, Org. Lett., 2010, 12, 2880│A. R. Pereira, et al, JNP, 2010, 73, 217

4 Formosalide A

Type: Linear polyketides dibranched. C₃₂H₅₀O₉ Amorph. solid, [α]_D²⁵ = +17.3° (c = 0.01, MeOH). Source: Dinoflagellate Prorocentrum sp. (seaweed washings, South Bay, Taiwan). Pharm: Cytotoxic (CCRF-CEM, LD₅₀ = 0.54 μg/mL, DLD-1, LD₅₀ > 40 μg/mL). Ref: C. -K. Lu, et al, Tet. Lett., 2009, 50, 1825

5 Formosalide B

Type: Linear polyketides dibranched. C₃₃H₅₂O₉ Amorph. solid, [α]_D²⁴ = +18.8° (c = 0.04, MeOH). Source: Dinoflagellate Prorocentrum sp. (seaweed washings, South Bay, Taiwan). Pharm: Cytotoxic (CCRF-CEM, LD₅₀ = 0.43 μg/mL, DLD-1, LD₅₀ = 2.73 μg/mL). Ref: C. -K. Lu, et al, Tet. Lett., 2009, 50, 1825

6 Koshikalide

Type: Linear polyketides dibranched. C₁₇H₂₆O₄ Oil, [α]_D²² = +156° (c = 0.03, MeOH). Source: Cyanobacterium Lyngbya sp. Pharm: Cytotoxic (HeLa-S3 cells, IC₅₀ = 42 μg/mL, weak). Ref: A. Iwasaki, et al, Tet. Lett., 2010, 51, 959

7 Colopsinol A

Type: Linear polyketides tribranched. C₇₂H₁₂₀O₂₅S [α]_D²⁰ = −11° (c = 0.35, MeOH). Source: Dinoflagellate Amphidinium sp. Y-5. Pharm: DNA polymerase α inhibitor (IC₅₀ = 13 μmol/L). DNA polymerase β inhibitor (IC₅₀ = 7 μmol/L). Ref: J. Kobayashi, et al, JOC, 1999, 64, 1478│T. Kubota, et al, JCS Perkin I, 1999, 3483│J. Kobayashi, et al, Pure Appl Chem, 2003, 75:337

8 Colopsinol C

Type: Linear polyketides tribranched. C₆₂H₁₀₄O₂₀S ...