Isolation and Structure of Bryostatins 12 and 13

George Pettit; John E. Leet; Cherry L. Herald; Yoshiaki Kamano; Fred E. Boettner; Lubomir Baczynskyj; Ronald A. Nieman

doi:10.1021/jo00389a037

Isolation and Structure of Bryostatins 12 and 13

George Pettit, John E. Leet, Cherry L. Herald, Yoshiaki Kamano, Fred E. Boettner, Lubomir Baczynskyj, Ronald A. Nieman

Research output: Contribution to journal › Article › peer-review

53 Scopus citations

Abstract

Bryostatins 12 (4, 3.7 mg) and 13 (5, 0.7 mg) were isolated from ~1000 kg of the marine bryozoan Bugula neritina (Linnaeus) found in the Eastern Pacific Ocean (California). The new bryostatins led to strong cell growth inhibitory (PS cell line ED₅₀0.014 and 0.0054 μg/mL) and antineoplastic activity (for bryostatin 12, a 47-68% increase in life extension at 30–50 μg/kg) against the marine P388 lymphocytic leukemia (PS system). In addition to the previously known constituents (bryostatins 1–3) of Bugula neritina from this ocean area the presence of bryostatins 8 (13.2 mg) and 9 (16.4 mg) was also established. A detailed series of ¹H-¹H-1 COSY, 2D-J-resolved,¹H-¹³C 2D-shift correlated, and ¹H-[^lH] NOE difference¹H NMR experiments combined with¹³C NMR and SP-SIMS studies were employed to elucidate the structures of bryostatins 12 and 13.

Original language	English (US)
Pages (from-to)	2854-2860
Number of pages	7
Journal	Journal of Organic Chemistry
Volume	52
Issue number	13
DOIs	https://doi.org/10.1021/jo00389a037
State	Published - Jun 1 1987

ASJC Scopus subject areas

Organic Chemistry

Access to Document

10.1021/jo00389a037

Cite this

@article{cdcc400b513f4534b4fbfe39f530769b,

title = "Isolation and Structure of Bryostatins 12 and 13",

abstract = "Bryostatins 12 (4, 3.7 mg) and 13 (5, 0.7 mg) were isolated from ~1000 kg of the marine bryozoan Bugula neritina (Linnaeus) found in the Eastern Pacific Ocean (California). The new bryostatins led to strong cell growth inhibitory (PS cell line ED500.014 and 0.0054 μg/mL) and antineoplastic activity (for bryostatin 12, a 47-68% increase in life extension at 30–50 μg/kg) against the marine P388 lymphocytic leukemia (PS system). In addition to the previously known constituents (bryostatins 1–3) of Bugula neritina from this ocean area the presence of bryostatins 8 (13.2 mg) and 9 (16.4 mg) was also established. A detailed series of 1H-1H-1 COSY, 2D-J-resolved,1H-13C 2D-shift correlated, and 1H-[lH] NOE difference1H NMR experiments combined with13C NMR and SP-SIMS studies were employed to elucidate the structures of bryostatins 12 and 13.",

author = "George Pettit and Leet, {John E.} and Herald, {Cherry L.} and Yoshiaki Kamano and Boettner, {Fred E.} and Lubomir Baczynskyj and Nieman, {Ronald A.}",

year = "1987",

month = jun,

day = "1",

doi = "10.1021/jo00389a037",

language = "English (US)",

volume = "52",

pages = "2854--2860",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "13",

}

TY - JOUR

T1 - Isolation and Structure of Bryostatins 12 and 13

AU - Pettit, George

AU - Leet, John E.

AU - Herald, Cherry L.

AU - Kamano, Yoshiaki

AU - Boettner, Fred E.

AU - Baczynskyj, Lubomir

AU - Nieman, Ronald A.

PY - 1987/6/1

Y1 - 1987/6/1

N2 - Bryostatins 12 (4, 3.7 mg) and 13 (5, 0.7 mg) were isolated from ~1000 kg of the marine bryozoan Bugula neritina (Linnaeus) found in the Eastern Pacific Ocean (California). The new bryostatins led to strong cell growth inhibitory (PS cell line ED500.014 and 0.0054 μg/mL) and antineoplastic activity (for bryostatin 12, a 47-68% increase in life extension at 30–50 μg/kg) against the marine P388 lymphocytic leukemia (PS system). In addition to the previously known constituents (bryostatins 1–3) of Bugula neritina from this ocean area the presence of bryostatins 8 (13.2 mg) and 9 (16.4 mg) was also established. A detailed series of 1H-1H-1 COSY, 2D-J-resolved,1H-13C 2D-shift correlated, and 1H-[lH] NOE difference1H NMR experiments combined with13C NMR and SP-SIMS studies were employed to elucidate the structures of bryostatins 12 and 13.

AB - Bryostatins 12 (4, 3.7 mg) and 13 (5, 0.7 mg) were isolated from ~1000 kg of the marine bryozoan Bugula neritina (Linnaeus) found in the Eastern Pacific Ocean (California). The new bryostatins led to strong cell growth inhibitory (PS cell line ED500.014 and 0.0054 μg/mL) and antineoplastic activity (for bryostatin 12, a 47-68% increase in life extension at 30–50 μg/kg) against the marine P388 lymphocytic leukemia (PS system). In addition to the previously known constituents (bryostatins 1–3) of Bugula neritina from this ocean area the presence of bryostatins 8 (13.2 mg) and 9 (16.4 mg) was also established. A detailed series of 1H-1H-1 COSY, 2D-J-resolved,1H-13C 2D-shift correlated, and 1H-[lH] NOE difference1H NMR experiments combined with13C NMR and SP-SIMS studies were employed to elucidate the structures of bryostatins 12 and 13.

UR - http://www.scopus.com/inward/record.url?scp=0000204755&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0000204755&partnerID=8YFLogxK

U2 - 10.1021/jo00389a037

DO - 10.1021/jo00389a037

M3 - Article

AN - SCOPUS:0000204755

SN - 0022-3263

VL - 52

SP - 2854

EP - 2860

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 13

ER -

Isolation and Structure of Bryostatins 12 and 13

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this