Hapalosiphon

Welwitindolinone A isonitrile (117) from the blue-green alga Hapalosiphon welwiischii is active against Aspergillus oryzae, Penicillium notation, Saccharomyces cerevisiae, and Trichophyton mentagrophytes [93]. 

Klein D, Daloze D, Braekman JC, Hoffmann L, Demoulin V (1995) New Hapalindoles from the Cyanophyte Hapalosiphon laingii. J Nat Prod 58 1781... 

Huber U, Moore RE, Patterson GML (1998) Isolation of a Nitrile-Containing Indole Alkaloid from the Terrestrial Blue-Green Alga Hapalosiphon delicatulus. J Nat Prod 61 ... 

Hapalosiphon Republic, Denmark, Egypt, England, Finland, France, Germany, Greece, Japan, Korea, Latvia, Norway, Philippines, Portugal, Slovenia, Switzerland, Taiwan, Thailand, USA... 

There are at least 12 different species of cyanobacteria that have been shown to produce toxins, often several different toxins per species. The main toxin-producing species include Anabaena, Aphanizome-non, Cylindrospermopsis raciborskii, Gloeotrichia, Hapalosiphon, Lyngbia, Nodularia, Nostoc, Oscil-latoria, Schizothrix, Spirulina, Synechocystis, and Microcystis. 

Stratmann K, Moore RE, Bonjouklian R, Deeter JB, Patterson GML, Shaffer S, Smith CD, Smitka TA (1994) Welwitindolinones, unusual alkaloids from the blue-green algae Hapalosiphon welwitschii and westiella intricata. Relationship to fischerindoles and hapa-lindoles. J Am Chem Soc 116 9935-9942... 

C28H43NO6, Mr 489.65, [a]D-49.2 (CH2CI2). A cyclic depsipeptide antibiotic from the blue alga (cyanobacterium) Hapalosiphon welwitschii. H. is able to counteract the resistance of certain tumor cells to cytostatic agents and thus (experimentally) potentiates the action of anti-cancer drugs. 

Depsipeptide antibiotic. Isol. from the blue-green alga Hapalosiphon welwitschii. Shows multidrug-resistance reversing activity. Solid. [a],j -49.2 (c, 0.35 in CH2CI2). 

C21H21CIN2O2S M 400.928 Alkaloid from the blue-green algae Hapalosiphon welwitschii (freshwater) and Westiella intricata (terrestrial). 

Moore RE, Cheuk C, Patterson GML (1984) Hapalindoles - New Alkaloids from the Blue-Green Alga Hapalosiphon fontinalis. J Am Chem Soc 106 6456... 

Moore RE, Cheuk C, Yang XQG, Patterson GML, Bonjoukhan R, Smitka TA, Mynderse JS, Foster RS, Jones ND, Swartzendruber JK, Deeter JB (1987) Hapalindoles, Antibacterial and Antimycotic Alkaloids from the Cyanophyte Hapalosiphon fontinalis. J Org Chem 52 1036... 

Welwitindolinone A Isonitrile 3 is the first of a family of oxindole natural products isolated from the cyanobacteria Hapalosiphon welwischii and Westiella intricate on the basis of their activity for reversing multiple drug resistance (MDR). A key transformation in the total synthesis of 3 reported (J. Am. Chem. Soc. 2008,130, 2087) by John L. Wood, now at Colorado State University, was the chlorination of 1, that in one step established both the axial secondary chloro substituent and the flanking chiral quaternary center. 

Stigonematales Stigonemataceae Hapalosiphon, Kirtuthrix, Stigonema, Umezakia, Westiellopsis... 

Hapalindole O (Rj = NCS, R2 = OH) Hapalosiphonfontinalis, Hapalosiphon laingii Moore, Chuck, and Patterson, 1984b ... 

New hapalindoles from the cyanophyte Hapalosiphon laingii. J. Nat. Prod., 58,1781-1785. 

---